$123+ Cheap flights from San Francisco (SFO) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
SFO — CHI
Oct 27 — Nov 31
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 February or September, booked 65 days in advance, depart on a Wednesday or Thursday 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 September 27, 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 September 27, 2026.
This Expedia deal was found by Cheapflights users on 9/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2011:59 pm -
1 stop12h 36m
Tue 10/2712:27 pm -
1 stop12h 02m
Deal found 9/22![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 9/23. 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.
Tue 10/2010:14 pm -
1 stop11h 18m
Tue 10/2710:40 am -
1 stop13h 49m
Deal found 9/23![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 9/25. 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.
Sat 10/176:00 am -
1 stop16h 24m
Sat 10/2412:37 pm -
1 stop11h 48m
Deal found 9/25![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/137:25 pm -
1 stop9h 09m
Tue 10/276:30 am -
2 stops13h 49m
Deal found 9/22![Frontier logo]()
$260
This Mytrip deal was found by Cheapflights users on 9/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:39 am -
2 stops17h 55m
Wed 10/218:01 pm -
1 stop15h 53m
Deal found 9/23![Frontier logo]()
$261
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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.
Thu 10/228:58 am -
1 stop19h 36m
Sun 10/256:30 am -
1 stop19h 45m
Deal found 9/22![Frontier logo]()
$262
This Mytrip deal was found by Cheapflights users on 9/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:25 pm -
1 stop9h 09m
Tue 10/206:30 am -
2 stops16h 08m
Deal found 9/24![Frontier logo]()
$263
This Super.com deal was found by Cheapflights users on 9/23. 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.
Mon 10/1911:59 pm -
1 stop12h 36m
Wed 10/213:30 pm -
1 stop8h 55m
Deal found 9/23![Frontier logo]()
$264
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 10/237:25 pm -
1 stop9h 09m
Mon 10/263:30 pm -
1 stop24h 50m
Deal found 9/23![Frontier logo]()
$264
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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.
Wed 10/147:25 pm -
1 stop9h 09m
Sat 10/1712:37 pm -
1 stop11h 48m
Deal found 9/22![Frontier logo]()
$265
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 10/1611:59 pm -
1 stop12h 36m
Wed 10/2812:27 pm -
1 stop12h 02m
Deal found 9/23![Frontier logo]()
$267
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 11/611:52 pm -
1 stop7h 43m
Mon 11/96:30 am -
1 stop6h 47m
Deal found 9/22![Frontier logo]()
$267
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 September 27, 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 September 27, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/26. 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.
Sat 10/245:45 pm -
1 stop9h 55m
Wed 10/287:00 am -
2 stops12h 00m
Deal found 9/26![Alaska Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/276:35 am -
Nonstop4h 26m
Mon 11/29:57 pm -
Nonstop4h 56m
Deal found 9/22![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/25. 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 10/1711:40 pm -
Nonstop4h 10m
Sat 10/245:10 am -
1 stop9h 05m
Deal found 9/25![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 9/25. 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 10/2312:10 am -
1 stop6h 43m
Sat 10/244:30 pm -
1 stop7h 45m
Deal found 9/25![Delta logo]()
$357
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Thu 10/155:00 am -
Nonstop4h 25m
Mon 10/196:07 am -
Nonstop4h 38m
Deal found 9/22![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 9/26. 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 10/2311:40 pm -
Nonstop4h 10m
Mon 10/269:25 pm -
Nonstop4h 45m
Deal found 9/26![Southwest logo]()
$350
This Alaska Airlines deal was found by Cheapflights users on 9/26. 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.
Sat 10/177:03 am -
1 stop9h 50m
Sat 10/247:20 am -
2 stops12h 50m
Deal found 9/26![Alaska Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 9/22. 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 10/156:15 pm -
1 stop8h 15m
Mon 10/195:25 am -
1 stop7h 40m
Deal found 9/22![Southwest logo]()
$370
This Delta deal was found by Cheapflights users on 9/24. 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.
Mon 10/268:58 pm -
2 stops9h 55m
Thu 10/297:35 am -
1 stop6h 49m
Deal found 9/24![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 9/24. 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 11/65:15 am -
2 stops10h 20m
Mon 11/95:20 pm -
2 stops8h 05m
Deal found 9/24![Southwest logo]()
$393
This United Airlines deal was found by Cheapflights users on 9/26. 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
Sat 10/178:40 am -
Nonstop4h 45m
Deal found 9/26![United Airlines logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 9/23. 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 12/184:12 pm -
1 stop19h 07m
Mon 12/287:58 pm -
1 stop14h 54m
Deal found 9/23![Alaska Airlines logo]()
$457
This Southwest deal was found by Cheapflights users on 9/25. 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 12/66:30 pm -
1 stop7h 55m
Sat 12/1210:15 am -
Nonstop4h 50m
Deal found 9/25![Southwest logo]()
$397
This United Airlines deal was found by Cheapflights users on 9/22. 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 11/206:42 pm -
Nonstop4h 17m
Fri 11/276:00 am -
Nonstop4h 44m
Deal found 9/22![United Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 9/26. 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 11/511:35 pm -
Nonstop4h 25m
Sun 11/811:00 am -
Nonstop4h 50m
Deal found 9/26![Southwest logo]()
$400
This United Airlines deal was found by Cheapflights users on 9/26. 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 10/1111:30 pm -
Nonstop4h 29m
Sat 10/173:35 pm -
Nonstop4h 49m
Deal found 9/26![United Airlines logo]()
$469
This Alaska Airlines deal was found by Cheapflights users on 9/24. 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.
Tue 12/222:02 pm -
1 stop7h 57m
Sun 12/277:58 pm -
1 stop14h 54m
Deal found 9/24![Alaska Airlines logo]()
$517
This Southwest deal was found by Cheapflights users on 9/26. 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 10/2112:15 pm -
1 stop8h 00m
Sun 10/256:30 am -
1 stop8h 00m
Deal found 9/26![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 9/25. 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 12/46:00 am -
Nonstop4h 15m
Sun 12/69:55 am -
1 stop6h 40m
Deal found 9/25![Southwest logo]()
$410
This Southwest deal was found by Cheapflights users on 9/24. 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 10/1411:40 pm -
Nonstop4h 10m
Wed 10/215:45 am -
1 stop6h 45m
Deal found 9/24![Southwest logo]()
$445
This Southwest deal was found by Cheapflights users on 9/25. 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 10/125:35 am -
Nonstop4h 10m
Sat 10/247:05 pm -
Nonstop4h 45m
Deal found 9/25![Southwest logo]()
$469
Last-minute flights from San Francisco to ChicagoDiscover last-minute flight deals from San Francisco to Chicago. Data last updated September 27, 2026 and is based on user searches.
Discover last-minute flight deals from San Francisco to Chicago. Data last updated September 27, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 10/611:17 am -
1 stop16h 21m
Tue 10/138:01 pm -
1 stop26h 37m
Deal found 9/22![Frontier logo]()
$295
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 10/1311:59 pm -
1 stop12h 36m
Sat 10/173:30 pm -
1 stop8h 55m
Deal found 9/22![Frontier logo]()
$286
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 10/1611:59 pm -
1 stop12h 36m
Wed 10/2812:27 pm -
1 stop12h 02m
Deal found 9/23![Frontier logo]()
$267
This Frontier deal was found by Cheapflights users on 9/23. 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 10/1611:59 pm -
1 stop12h 36m
Wed 10/216:21 am -
1 stop13h 34m
Deal found 9/23![Frontier logo]()
$271
This Frontier deal was found by Cheapflights users on 9/24. 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 10/1611:59 pm -
1 stop12h 36m
Fri 10/236:15 am -
1 stop13h 40m
Deal found 9/24![Frontier logo]()
$284
This Super.com deal was found by Cheapflights users on 9/23. 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.
Mon 10/1911:59 pm -
1 stop12h 36m
Wed 10/213:30 pm -
1 stop8h 55m
Deal found 9/23![Frontier logo]()
$264
This Expedia deal was found by Cheapflights users on 9/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2011:59 pm -
1 stop12h 36m
Tue 10/2712:27 pm -
1 stop12h 02m
Deal found 9/22![Frontier logo]()
$258
This Trip.com deal was found by Cheapflights users on 9/26. 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.
Tue 10/2011:59 pm -
1 stop12h 36m
Sat 10/317:25 am -
1 stop12h 45m
Deal found 9/26![Frontier logo]()
$273
This Trip.com deal was found by Cheapflights users on 9/22. 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 10/2111:59 pm -
1 stop10h 18m
Tue 10/279:53 am -
1 stop10h 17m
Deal found 9/22![Frontier logo]()
$281
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 10/2311:59 pm -
1 stop12h 36m
Fri 10/3012:20 pm -
1 stop12h 09m
Deal found 9/23![Frontier logo]()
$280
This Trip.com deal was found by Cheapflights users on 9/23. 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.
Mon 10/2611:59 pm -
1 stop9h 23m
Sat 10/317:25 am -
1 stop12h 45m
Deal found 9/23![Frontier logo]()
$268
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Mon 10/2611:59 pm -
1 stop9h 23m
Wed 10/286:16 am -
1 stop13h 54m
Deal found 9/23![Frontier logo]()
$270
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 September 27, 2026.
Search for one-way flight options from San Francisco to Chicago. Find affordable one-way fares based on user searches. Data last updated September 27, 2026.
This Mytrip deal was found by Cheapflights users on 9/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:02 pm -
1 stop10h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$123
This Super.com deal was found by Cheapflights users on 9/23. 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.
Wed 10/217:25 pm -
1 stop9h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$124
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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.
Wed 10/147:25 pm -
1 stop9h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$125
This Super.com deal was found by Cheapflights users on 9/22. 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.
Tue 11/311:52 pm -
1 stop9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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.
Wed 11/1111:52 pm -
1 stop7h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$127
This Frontier deal was found by Cheapflights users on 9/24. 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.
Tue 10/2711:52 pm -
1 stop9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/207:11 pm -
2 stops33h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$129
This CheapOair deal was found by Cheapflights users on 9/22. 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.
Mon 10/2611:59 pm -
1 stop9h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$130
This CheapOair deal was found by Cheapflights users on 9/25. 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.
Tue 10/2711:52 pm -
1 stop7h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$130
This Super.com deal was found by Cheapflights users on 9/22. 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.
Mon 10/1911:59 pm -
1 stop12h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$131
This Super.com deal was found by Cheapflights users on 9/23. 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.
Mon 11/22:21 pm -
1 stop12h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$131
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Wed 10/2811:52 pm -
1 stop9h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$132
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 September 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Orbitz) |
One-way from | $123 (Mytrip) |
Popular in | July |
Cheapest in | February |
Average price | $372 |
Good round-trip deal | $377 or less |
Good one-way deal | $209 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 7,457,451 searches. Data last updated September 27, 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 - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Mon 11/23
8:25 am-8:03 pm
1 stop9h 38m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Wed 11/11
8:43 am-11:59 pm
2 stops13h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$167
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Thu 12/3
6:00 am-12:15 pm
Nonstop4h 15m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Sat 11/14
11:30 am-11:36 pm
1 stop10h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
San FranciscoChicago
SFO San Francisco - ORD Chicago O'Hare Intl
SFOORD
San Francisco
Wed 10/21
6:38 pm-12:55 am
Nonstop4h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Tue 11/10
11:35 pm-6:00 am
Nonstop4h 25m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
Quickest round-trip
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Mon 10/26
5:35 am-11:45 am
Nonstop4h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Sat 10/24
11:40 pm-5:50 am
Nonstop4h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Mon 11/2
10:25 pm-10:43 am
1 stop10h 18m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
San FranciscoChicago
SFO San Francisco - MDW Chicago Midway
SFOMDW
San Francisco
Mon 11/23
6:00 am-4:39 pm
1 stop8h 39m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
Showing 1-10 of 42 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 September.
| 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 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-ORD
SFO-MDW
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-ORD
SFO-MDW
What is the cheapest month to book a flight from San Francisco to Chicago?
Currently, February is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $369). 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 September 27, 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 September 27, 2026.
The most flights from SFO to CHI are scheduled on a Friday (96 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (61 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 $309 and $521 in February.The cheapest round-trip price found within the last 5 days was $257 on Frontier (Feb 4-Feb 8).
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 67% 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.
Dallas (DFW) is the most affordable 1-stop option, with an average round-trip price of $285.
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 Dallas (DFW) have the shortest average one-way travel time for 1-stop routes: 9h 04m.
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 Dallas (DFW) offer the fastest connection on this route, with an average layover time of 4h 15m.
How often are flights from San Francisco to Chicago delayed?
About 9% of weekly flights between San Francisco and Chicago have experienced delays in the past year, with the average delay time being 185 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 Monday 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 9% 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 September 26, 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 September 27, 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.
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
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 September 27, 2026.
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San Francisco and Chicago flights
Browse other San Francisco and Chicago flight options. Last updated on September 27, 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 September 27, 2026.
Popular flight searches
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 7,457,451 searches. Data last updated September 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$122 | Average$376 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$157 | Average$300 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$204 | Average$402 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$224 | Average$306 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$237 | Average$416 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$263 | Average$486 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$433 | FlexibilityNo cancel fee | On-time63% |