$136+ Cheap flights from San Francisco (SFO) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Sep 9 — Sep 161
Round-trip
1 adult, Economy
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Find cheap flights from San Francisco to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Francisco to Chicago are usually found in September or February, booked 67 days in advance, depart on a Wednesday or Tuesday and return on a Thursday
Cheap flight deals from San Francisco to Chicago
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Cheapest flights from San Francisco to ChicagoExplore the most affordable flight options available from San Francisco to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
Explore the most affordable flight options available from San Francisco to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
This CheapOair deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:58 pm -
1 stop10h 01m
Sun 9/206:25 am -
1 stop15h 23m
Deal found 8/9![Frontier logo]()
$276
This Cheapflightsfares deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:30 pm -
1 stop16h 06m
Tue 9/19:20 pm -
1 stop25h 26m
Deal found 8/7![Frontier logo]()
$276
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:05 am -
1 stop6h 43m
Tue 10/61:27 pm -
1 stop6h 50m
Deal found 8/7![Delta logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:18 am -
2 stops24h 09m
Sun 10/189:33 pm -
1 stop28h 18m
Deal found 8/7![Multiple Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:00 am -
1 stop6h 55m
Wed 1/62:55 pm -
1 stop7h 23m
Deal found 8/6![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:20 pm -
1 stop6h 30m
Tue 9/296:40 am -
1 stop6h 10m
Deal found 8/9![Southwest logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:06 pm -
1 stop11h 21m
Sun 10/189:33 pm -
1 stop28h 18m
Deal found 8/9![Multiple Airlines logo]()
$278
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/209:42 am -
1 stop12h 41m
Sun 9/278:55 pm -
1 stop13h 19m
Deal found 8/7![Frontier logo]()
$278
This Cheapflightsfares deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:05 pm -
1 stop6h 32m
Tue 9/12:41 pm -
1 stop23h 31m
Deal found 8/6![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:01 am -
1 stop8h 30m
Thu 9/311:50 am -
1 stop9h 36m
Deal found 8/5![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:17 am -
1 stop7h 22m
Sun 9/139:29 pm -
1 stop12h 45m
Deal found 8/5![Multiple Airlines logo]()
$280
This Cheapflightsfares deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:22 am -
1 stop21h 20m
Mon 10/126:50 am -
1 stop19h 01m
Deal found 8/5![Frontier logo]()
$280
Best flights from San Francisco to ChicagoDiscover carefully curated flight deals from San Francisco to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
Discover carefully curated flight deals from San Francisco to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:06 pm -
1 stop11h 21m
Sun 10/189:33 pm -
1 stop28h 18m
Deal found 8/9![Multiple Airlines logo]()
$278
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:55 am -
2 stops7h 50m
Sat 10/176:45 am -
1 stop7h 00m
Deal found 8/4![Southwest logo]()
$282
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:10 am -
Nonstop4h 35m
Tue 10/67:44 am -
Nonstop4h 46m
Deal found 8/7![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:59 pm -
1 stop6h 51m
Mon 11/235:25 pm -
1 stop8h 32m
Deal found 8/4![Delta logo]()
$365
This Alaska Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/204:23 pm -
1 stop18h 55m
Sun 11/222:16 pm -
1 stop8h 29m
Deal found 8/9![Alaska Airlines logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:22 am -
2 stops27h 05m
Sun 10/189:33 pm -
1 stop12h 50m
Deal found 8/5![Multiple Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:40 am -
2 stops9h 30m
Thu 9/244:55 pm -
1 stop8h 15m
Deal found 8/7![Southwest logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:17 am -
1 stop7h 22m
Sun 9/139:29 pm -
1 stop12h 45m
Deal found 8/9![Multiple Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:35 pm -
Nonstop4h 29m
Sun 10/46:07 am -
Nonstop4h 38m
Deal found 8/9![United Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:07 pm -
2 stops28h 04m
Sun 9/209:29 pm -
1 stop12h 45m
Deal found 8/6![Multiple Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:10 am -
2 stops10h 20m
Fri 9/115:00 pm -
2 stops7h 50m
Deal found 8/5![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
Nonstop4h 29m
Mon 9/286:07 am -
Nonstop4h 38m
Deal found 8/8![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:40 pm -
Nonstop4h 10m
Wed 9/307:05 pm -
Nonstop4h 35m
Deal found 8/9![Southwest logo]()
$337
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:00 am -
Nonstop4h 25m
Thu 10/156:07 am -
Nonstop4h 38m
Deal found 8/9![United Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:10 pm -
1 stop20h 17m
Sun 10/49:36 pm -
1 stop15h 19m
Deal found 8/4![Multiple Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:05 am -
1 stop8h 45m
Mon 9/2810:15 am -
Nonstop4h 35m
Deal found 8/8![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:35 pm -
Nonstop4h 26m
Wed 9/164:00 pm -
Nonstop4h 49m
Deal found 8/5![United Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:17 am -
1 stop7h 22m
Thu 9/179:29 pm -
1 stop12h 45m
Deal found 8/5![Multiple Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:38 pm -
Nonstop4h 21m
Sat 10/102:32 pm -
Nonstop4h 48m
Deal found 8/7![United Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:06 pm -
1 stop11h 21m
Sun 10/258:53 pm -
2 stops18h 19m
Deal found 8/9![Multiple Airlines logo]()
$330
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:35 pm -
1 stop7h 30m
Mon 10/128:25 pm -
1 stop6h 15m
Deal found 8/9![Southwest logo]()
$370
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:35 am -
Nonstop4h 21m
Wed 9/164:00 pm -
Nonstop4h 49m
Deal found 8/5![United Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:22 am -
2 stops27h 05m
Sun 10/119:33 pm -
1 stop12h 50m
Deal found 8/5![Multiple Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:10 pm -
1 stop7h 20m
Mon 9/2111:05 am -
2 stops8h 50m
Deal found 8/4![Southwest logo]()
$375
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:38 pm -
Nonstop4h 21m
Mon 9/76:00 am -
Nonstop4h 38m
Deal found 8/9![United Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:22 am -
1 stop11h 51m
Sun 10/258:53 pm -
1 stop28h 58m
Deal found 8/5![Multiple Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:40 pm -
Nonstop4h 10m
Sun 10/116:30 am -
1 stop8h 00m
Deal found 8/5![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/41:40 pm -
2 stops8h 25m
Wed 10/712:15 pm -
1 stop10h 05m
Deal found 8/4![Southwest logo]()
$391
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:38 pm -
Nonstop4h 21m
Mon 9/76:00 am -
Nonstop4h 38m
Deal found 8/6![United Airlines logo]()
$401
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:35 pm -
Nonstop4h 26m
Sun 8/308:40 am -
Nonstop4h 45m
Deal found 8/9![United Airlines logo]()
$405
Last-minute flights from San Francisco to ChicagoDiscover last-minute flight deals from San Francisco to Chicago. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco to Chicago. Data last updated August 10, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:05 pm -
1 stop6h 32m
Tue 9/12:41 pm -
1 stop23h 31m
Deal found 8/6![Frontier logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:29 am -
2 stops12h 40m
Sun 8/309:35 pm -
1 stop13h 08m
Deal found 8/6![Multiple Airlines logo]()
$281
This Frontier deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:01 am -
1 stop8h 30m
Thu 9/311:50 am -
1 stop9h 36m
Deal found 8/5![Frontier logo]()
$280
This Cheapflightsfares deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:30 pm -
1 stop16h 06m
Tue 9/19:20 pm -
1 stop25h 26m
Deal found 8/7![Frontier logo]()
$276
This Cheapflightsfares deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:23 pm -
1 stop7h 54m
Tue 9/89:20 pm -
1 stop15h 02m
Deal found 8/9![Frontier logo]()
$280
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:15 am -
2 stops9h 35m
Sat 9/51:45 pm -
2 stops7h 50m
Deal found 8/7![Southwest logo]()
$277
This Priceline deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:35 pm -
1 stop10h 15m
Fri 9/1112:54 pm -
1 stop11h 34m
Deal found 8/5![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:17 am -
1 stop7h 22m
Sun 9/139:29 pm -
1 stop12h 45m
Deal found 8/5![Multiple Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:35 am -
Nonstop4h 05m
Mon 9/147:00 am -
1 stop8h 30m
Deal found 8/9![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:15 pm -
1 stop8h 15m
Fri 9/182:50 pm -
1 stop8h 55m
Deal found 8/9![Southwest logo]()
$278
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/209:42 am -
1 stop12h 41m
Sun 9/278:55 pm -
1 stop13h 19m
Deal found 8/7![Frontier logo]()
$278
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:05 am -
1 stop6h 33m
Sat 9/263:40 pm -
1 stop10h 17m
Deal found 8/7![Delta logo]()
$277
One-way flights from San Francisco to ChicagoSearch for one-way flight options from San Francisco to Chicago. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
Search for one-way flight options from San Francisco to Chicago. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Trip.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:58 pm -
1 stop10h 01m
Deal found 8/6![Frontier logo]()
$136
This Super.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:35 pm -
1 stop10h 20m
Deal found 8/7![Frontier logo]()
$137
This Frontier deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:42 am -
1 stop10h 41m
Deal found 8/9![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:31 pm -
2 stops42h 48m
Deal found 8/6![Multiple Airlines logo]()
$138
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:35 am -
1 stop8h 25m
Deal found 8/7![Southwest logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/54:31 pm -
2 stops42h 46m
Deal found 8/6![Multiple Airlines logo]()
$139
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am -
1 stop8h 51m
Deal found 8/7![Delta logo]()
$139
This Trip.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:35 pm -
1 stop10h 20m
Deal found 8/6![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:52 pm -
2 stops28h 33m
Deal found 8/7![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:00 pm -
2 stops16h 01m
Deal found 8/7![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:10 pm -
1 stop22h 07m
Deal found 8/9![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/204:31 pm -
2 stops29h 52m
Deal found 8/8![Frontier logo]()
$142
Find flight deals from San Francisco to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Francisco (SFO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $276 (CheapOair) |
One-way from | $136 (Trip.com) |
Popular in | July |
Cheapest in | September |
Average price | $400 |
Good round-trip deal | $360 or less |
Good one-way deal | $213 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Francisco to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 10, 2026.
Use the filters below to find and compare flights from San Francisco to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San FranciscoChicago
SFO San Francisco - RFD Chicago Greater Rockford
SFORFD
San Francisco
Thu 10/15
10:06 pm-11:27 am
1 stop11h 21m
Chicago Greater Rockford
Sun 10/18
9:33 pm-11:51 pm
1 stop28h 18m
$278
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Wed 10/14
6:55 am-4:45 pm
2 stops7h 50m
Chicago Midway
Sat 10/17
6:45 am-11:45 am
1 stop7h 00m
$282
San FranciscoChicago
SFO San Francisco - RFD Chicago Greater Rockford
SFORFD
San Francisco
Thu 10/8
6:22 am-11:27 am
2 stops27h 05m
Chicago Greater Rockford
Sun 10/18
9:33 pm-8:23 am
1 stop12h 50m
$284
San FranciscoChicago
SFO San Francisco - RFD Chicago Greater Rockford
SFORFD
San Francisco
Thu 9/10
11:17 am-8:39 pm
1 stop7h 22m
Chicago Greater Rockford
Sun 9/13
9:29 pm-8:14 am
1 stop12h 45m
$293
San FranciscoChicago
SFO San Francisco - RFD Chicago Greater Rockford
SFORFD
San Francisco
Thu 9/17
12:07 pm-6:11 pm
2 stops28h 04m
Chicago Greater Rockford
Sun 9/20
9:29 pm-8:14 am
1 stop12h 45m
$296
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Sun 10/4
6:10 am-12:45 pm
Nonstop4h 35m
Chicago O'Hare Intl
Tue 10/6
7:44 am-10:30 am
Nonstop4h 46m
$297
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Tue 9/22
5:40 am-5:10 pm
2 stops9h 30m
Chicago Midway
Thu 9/24
4:55 pm-11:10 pm
1 stop8h 15m
$322
San FranciscoChicago
SFO San Francisco - RFD Chicago Greater Rockford
SFORFD
San Francisco
Thu 10/1
1:10 pm-11:27 am
1 stop20h 17m
Chicago Greater Rockford
Sun 10/4
9:36 pm-10:55 am
1 stop15h 19m
$322
San FranciscoChicago
SFO San Francisco - RFD Chicago Greater Rockford
SFORFD
San Francisco
Thu 9/10
11:17 am-8:39 pm
1 stop7h 22m
Chicago Greater Rockford
Thu 9/17
9:29 pm-8:14 am
1 stop12h 45m
$329
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Sat 9/5
6:10 am-6:30 pm
2 stops10h 20m
Chicago Midway
Fri 9/11
5:00 pm-10:50 pm
2 stops7h 50m
$330
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from San Francisco to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Francisco to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on San Francisco-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Francisco-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Francisco-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Francisco-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Francisco-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from San Francisco to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Francisco with our price prediction graph.
SFO-CHI
SFO-RFD
SFO-MDW
SFO-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Francisco to Chicago
SFO-CHI
SFO-RFD
SFO-MDW
SFO-ORD
What is the cheapest month to book a flight from San Francisco to Chicago?
Currently, September is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $347). Flying from San Francisco to Chicago in June is currently the most expensive (average of $484). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SFO to CHI?
Find hourly flight availability from San Francisco to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 10, 2026.
One of the essential ways to save on airfare from San Francisco to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 11% on airfare.
Weekly flight availability from San Francisco to Chicago
Explore weekly flight availability from San Francisco to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 10, 2026.
The most flights from SFO to CHI are scheduled on a Friday (86 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (35 on average).
How much does it cost to fly round-trip from San Francisco to Chicago?
Airfare is below average for this route at the moment.
San Francisco to Chicago flights typically cost between $327 and $531 in September.The cheapest round-trip price found within the last 5 days was $276 on Frontier (Sep 18-Sep 20).
What’s the top layover airport for flights from San Francisco to Chicago?
Share of 1-stop round-trip flights from San Francisco to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Las Vegas (LAS) – chosen by Cheapflights users on 40% of 1-stop itineraries from San Francisco to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from San Francisco to Chicago?
Average round-trip fare for 1-stop flights from San Francisco to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $153.
What’s the fastest layover option from San Francisco to Chicago?
Shortest average travel time for 1-stop one-way flights from San Francisco to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via San Diego (SAN) have the shortest average one-way travel time for 1-stop routes: 7h 01m.
Which airport typically offers the quickest layover for flights from San Francisco to Chicago?
Average layover duration for 1-stop one-way flights from San Francisco to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via San Diego (SAN) offer the fastest connection on this route, with an average layover time of 0h 57m.
How often are flights from San Francisco to Chicago delayed?
About 11% of weekly flights between San Francisco and Chicago have experienced delays in the past year, with the average delay time being 190 minutes.
What is the most punctual flight time for San Francisco to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on San Francisco to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
How far ahead should I book a flight from San Francisco to Chicago?
The best time to book flights from San Francisco to Chicago is 66 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from San Francisco to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Francisco to Chicago. Price data was last updated on August 8, 2026.
Travelers seeking maximum savings on their San Francisco to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for San Francisco to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Francisco to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 10, 2026.
Read through reviews of airlines operating flights from San Francisco to Chicago, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from San Francisco to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 10, 2026.
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San Francisco and Chicago flights
Browse other San Francisco and Chicago flight options. Last updated on August 10, 2026.
Other flights from San Francisco
Browse through other flights departing from San Francisco. Flights are based on user searches made on Cheapflights and were last updated on August 10, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from San Francisco to Chicago
Discover the top 7 airlines that operate flights from San Francisco to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$122 | Average$387 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$283 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$195 | Average$382 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$222 | Average$408 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$224 | Average$298 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$252 | Average$479 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$432 | FlexibilityNo cancel fee | On-time63% |