$109+ Cheap flights from Oakland, CA (OAK) 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Oct 6 — Oct 131
Round-trip
1 adult, Economy
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Find cheap flights from Oakland 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 Oakland to Chicago are usually found in February or May, booked 72 days in advance, depart on a Tuesday or Monday and return on a Thursday
Cheap flight deals from Oakland to Chicago
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Best
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Cheapest flights from Oakland to ChicagoExplore the most affordable flight options available from Oakland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
Explore the most affordable flight options available from Oakland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
This Frontier deal was found by Cheapflights users on 9/2. 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 9/246:51 pm -
1 stop8h 47m
Thu 10/18:55 pm -
1 stop14h 27m
Deal found 9/2![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 9/2. 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.
Thu 9/2410:17 am -
1 stop17h 21m
Mon 9/288:55 pm -
1 stop16h 56m
Deal found 9/2![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Fri 10/305:55 pm -
1 stop9h 18m
Mon 11/25:15 pm -
1 stop20h 38m
Deal found 9/6![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Mon 11/3011:24 am -
1 stop22h 22m
Thu 12/312:51 pm -
1 stop10h 37m
Deal found 9/4![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/295:55 pm -
1 stop9h 18m
Mon 11/25:15 pm -
1 stop20h 38m
Deal found 9/6![Frontier logo]()
$241
This CheapOair deal was found by Cheapflights users on 9/1. 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 10/712:47 pm -
1 stop14h 30m
Mon 10/123:30 pm -
1 stop22h 22m
Deal found 9/1![Frontier logo]()
$252
This Expedia deal was found by Cheapflights users on 9/1. 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.
Wed 9/2312:47 pm -
1 stop14h 51m
Wed 9/302:18 pm -
1 stop9h 10m
Deal found 9/1![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Fri 11/65:55 pm -
1 stop9h 18m
Sun 11/85:15 pm -
1 stop25h 45m
Deal found 9/5![Frontier logo]()
$254
This Southwest deal was found by Cheapflights users on 9/2. 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 11/211:50 pm -
Nonstop4h 05m
Thu 11/59:55 pm -
Nonstop4h 40m
Deal found 9/2![Southwest logo]()
$257
This CheapOair deal was found by Cheapflights users on 9/2. 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.
Thu 9/2410:17 am -
1 stop17h 21m
Fri 9/258:55 pm -
1 stop16h 56m
Deal found 9/2![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/110:17 am -
1 stop17h 21m
Sun 10/48:55 pm -
1 stop14h 27m
Deal found 9/3![Frontier logo]()
$262
This Travelocity deal was found by Cheapflights users on 9/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:46 pm -
1 stop7h 54m
Fri 11/135:15 pm -
1 stop20h 38m
Deal found 9/2![Multiple Airlines logo]()
$264
Best flights from Oakland to ChicagoDiscover carefully curated flight deals from Oakland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
Discover carefully curated flight deals from Oakland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
This Southwest deal was found by Cheapflights users on 9/1. 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 10/2311:55 pm -
Nonstop4h 00m
Mon 10/269:30 pm -
Nonstop4h 45m
Deal found 9/1![Southwest logo]()
$268
This Alaska Airlines deal was found by Cheapflights users on 9/1. 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 11/1010:00 am -
1 stop6h 59m
Wed 11/112:15 pm -
1 stop9h 18m
Deal found 9/1![Alaska Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 10/1412:47 pm -
1 stop29h 26m
Sun 10/189:33 pm -
1 stop13h 32m
Deal found 9/2![Multiple Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/2. 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 10/2112:41 pm -
1 stop7h 24m
Sat 10/245:27 am -
2 stops12h 55m
Deal found 9/2![Delta logo]()
$320
This Alaska Airlines deal was found by Cheapflights users on 9/3. 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.
Wed 10/217:02 am -
1 stop7h 48m
Tue 10/275:46 pm -
1 stop19h 39m
Deal found 9/3![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 9/3. 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 10/311:55 pm -
Nonstop4h 00m
Sat 10/107:30 pm -
Nonstop4h 40m
Deal found 9/3![Southwest logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/1510:17 am -
1 stop7h 56m
Sun 10/189:33 pm -
1 stop13h 32m
Deal found 9/3![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/2910:18 am -
1 stop7h 12m
Sun 11/18:53 pm -
1 stop14h 30m
Deal found 9/6![Multiple Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 9/1. 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.
Sun 10/116:00 am -
2 stops10h 29m
Wed 10/147:15 pm -
1 stop6h 41m
Deal found 9/1![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 9/2. 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 1/48:20 pm -
1 stop7h 20m
Sat 1/92:15 pm -
Nonstop4h 45m
Deal found 9/2![Southwest logo]()
$311
This Alaska Airlines deal was found by Cheapflights users on 9/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:29 pm -
1 stop8h 30m
Tue 10/63:49 pm -
1 stop9h 06m
Deal found 9/4![Alaska Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/2410:17 am -
1 stop8h 22m
Sun 9/279:29 pm -
1 stop13h 53m
Deal found 9/2![Multiple Airlines logo]()
$310
This Alaska Airlines deal was found by Cheapflights users on 9/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:02 am -
1 stop20h 38m
Sat 10/107:00 am -
1 stop17h 55m
Deal found 9/5![Alaska Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 9/3. 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 12/163:00 pm -
2 stops7h 10m
Sat 1/96:25 am -
2 stops8h 05m
Deal found 9/3![Southwest logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 11/510:18 am -
1 stop7h 44m
Sun 11/88:37 pm -
1 stop22h 23m
Deal found 9/5![Multiple Airlines logo]()
$314
This Southwest deal was found by Cheapflights users on 9/5. 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.
Mon 10/511:55 pm -
Nonstop4h 00m
Sat 10/107:30 pm -
Nonstop4h 40m
Deal found 9/5![Southwest logo]()
$345
This Alaska Airlines deal was found by Cheapflights users on 9/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:04 am -
1 stop28h 21m
Wed 10/77:00 am -
1 stop13h 54m
Deal found 9/6![Alaska Airlines logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 9/2312:47 pm -
1 stop29h 52m
Sun 9/279:29 pm -
1 stop13h 53m
Deal found 9/2![Multiple Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 9/3. 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 10/1811:55 pm -
Nonstop4h 00m
Sat 10/245:05 pm -
1 stop6h 25m
Deal found 9/3![Southwest logo]()
$347
This Alaska Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 11/1910:00 am -
1 stop6h 59m
Sun 11/222:16 pm -
1 stop11h 09m
Deal found 9/3![Alaska Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/225:20 pm -
2 stops16h 07m
Sun 10/258:53 pm -
1 stop14h 12m
Deal found 9/3![Multiple Airlines logo]()
$333
This Alaska Airlines deal was found by Cheapflights users on 9/3. 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 10/137:04 am -
1 stop9h 49m
Mon 10/197:20 am -
1 stop9h 14m
Deal found 9/3![Alaska Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 9/5. 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.
Tue 12/83:00 pm -
2 stops7h 10m
Tue 12/1510:10 am -
2 stops8h 15m
Deal found 9/5![Southwest logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 9/1710:17 am -
1 stop8h 22m
Sun 9/209:29 pm -
1 stop13h 53m
Deal found 9/5![Multiple Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 9/4. 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.
Tue 10/2711:55 pm -
Nonstop4h 00m
Thu 11/55:20 am -
2 stops8h 15m
Deal found 9/4![Southwest logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 9/2. 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.
Thu 9/243:13 pm -
1 stop6h 46m
Mon 9/286:00 am -
2 stops19h 10m
Deal found 9/2![Alaska Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Wed 9/1612:47 pm -
1 stop29h 52m
Sun 9/209:29 pm -
1 stop22h 27m
Deal found 9/5![Multiple Airlines logo]()
$367
This Alaska Airlines deal was found by Cheapflights users on 9/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:59 am -
1 stop6h 54m
Wed 10/143:49 pm -
2 stops21h 41m
Deal found 9/4![Alaska Airlines logo]()
$389
This Southwest deal was found by Cheapflights users on 9/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/118:20 pm -
1 stop7h 20m
Sun 12/139:55 pm -
Nonstop4h 40m
Deal found 9/6![Southwest logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 12/910:23 pm -
1 stop11h 34m
Sun 12/1312:47 pm -
1 stop10h 41m
Deal found 9/2![Multiple Airlines logo]()
$369
Last-minute flights from Oakland to ChicagoDiscover last-minute flight deals from Oakland to Chicago. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chicago. Data last updated September 6, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 9/1. 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.
Wed 9/2312:47 pm -
1 stop14h 51m
Wed 9/302:18 pm -
1 stop9h 10m
Deal found 9/1![Multiple Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 9/1. 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 9/2311:55 pm -
Nonstop4h 00m
Wed 9/308:35 pm -
Nonstop4h 35m
Deal found 9/1![Southwest logo]()
$257
This Frontier deal was found by Cheapflights users on 9/2. 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 9/246:51 pm -
1 stop8h 47m
Thu 10/18:55 pm -
1 stop14h 27m
Deal found 9/2![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 9/2. 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.
Thu 9/2410:17 am -
1 stop17h 21m
Mon 9/288:55 pm -
1 stop16h 56m
Deal found 9/2![Frontier logo]()
$228
This CheapOair deal was found by Cheapflights users on 9/2. 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.
Thu 9/2410:17 am -
1 stop17h 21m
Fri 9/258:55 pm -
1 stop16h 56m
Deal found 9/2![Frontier logo]()
$259
This Expedia deal was found by Cheapflights users on 9/3. 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.
Thu 9/2410:17 am -
1 stop17h 21m
Sun 9/278:55 pm -
1 stop23h 01m
Deal found 9/3![Frontier logo]()
$268
This Southwest deal was found by Cheapflights users on 9/2. 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 9/2811:55 pm -
Nonstop4h 00m
Fri 10/29:30 pm -
Nonstop4h 40m
Deal found 9/2![Southwest logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/110:17 am -
1 stop17h 21m
Sun 10/48:55 pm -
1 stop14h 27m
Deal found 9/3![Frontier logo]()
$262
This Expedia deal was found by Cheapflights users on 9/2. 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 10/612:47 pm -
1 stop14h 51m
Fri 10/167:49 pm -
1 stop17h 41m
Deal found 9/2![Multiple Airlines logo]()
$270
This CheapOair deal was found by Cheapflights users on 9/1. 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 10/712:47 pm -
1 stop14h 30m
Mon 10/123:30 pm -
1 stop22h 22m
Deal found 9/1![Frontier logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/295:55 pm -
1 stop9h 18m
Mon 11/25:15 pm -
1 stop20h 38m
Deal found 9/6![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Fri 10/305:55 pm -
1 stop9h 18m
Mon 11/25:15 pm -
1 stop20h 38m
Deal found 9/6![Frontier logo]()
$237
One-way flights from Oakland to ChicagoSearch for one-way flight options from Oakland to Chicago. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
Search for one-way flight options from Oakland to Chicago. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
This Priceline deal was found by Cheapflights users on 9/2. 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.
Thu 10/16:51 pm -
1 stop8h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 9/1. 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 10/85:20 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$115
This Frontier deal was found by Cheapflights users on 9/2. 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.
Mon 10/265:20 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$116
This CheapOair deal was found by Cheapflights users on 9/3. 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 10/712:47 pm -
1 stop14h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$120
This Southwest deal was found by Cheapflights users on 9/3. 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 10/1011:55 pm -
Nonstop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$129
This Priceline deal was found by Cheapflights users on 9/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:51 pm -
1 stop8h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$133
This Alaska Airlines deal was found by Cheapflights users on 9/2. 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 10/69:59 am -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Alaska Airlines logo]()
$139
This Frontier deal was found by Cheapflights users on 9/2. 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.
Mon 10/195:20 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$140
This Alaska Airlines deal was found by Cheapflights users on 9/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:53 pm -
1 stop7h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Alaska Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 9/1. 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 9/245:20 am -
2 stops7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Southwest logo]()
$144
This Alaska Airlines deal was found by Cheapflights users on 9/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/97:00 am -
1 stop14h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Alaska Airlines logo]()
$147
This Alaska Airlines deal was found by Cheapflights users on 9/3. 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 9/257:51 pm -
1 stop8h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Alaska Airlines logo]()
$150
Find flight deals from Oakland to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) 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 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $218 (Frontier) |
One-way from | $109 (Priceline) |
Popular in | November |
Cheapest in | February |
Average price | $422 |
Good round-trip deal | $418 or less |
Good one-way deal | $270 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland 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 6, 2026.
Use the filters below to find and compare flights from Oakland to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Mon 10/12
11:55 pm-5:55 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$129
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Tue 10/20
7:53 pm-5:40 am
1 stop7h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$142
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Tue 10/27
7:02 am-4:50 pm
1 stop7h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$142
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Mon 10/26
8:10 pm-5:45 am
2 stops7h 35m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$144
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 11/26
5:55 am-1:44 pm
1 stop5h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$158
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Sat 10/17
12:41 pm-10:05 pm
1 stop7h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$158
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Sat 10/10
12:41 pm-10:05 pm
1 stop7h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$158
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Mon 3/1
8:00 pm-5:40 am
1 stop7h 40m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$163
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Wed 10/28
6:00 am-7:11 pm
2 stops11h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$163
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Sat 10/3
12:39 pm-10:00 pm
1 stop7h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$168
Showing 1-10 of 58 resultsSorted by cheapest first
Compare providers for flights from Oakland 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 Oakland to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Oakland, California-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Oakland, California-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 Oakland, California-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 Oakland to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Oakland with our price prediction graph.
OAK-CHI
OAK-ORD
OAK-MDW
OAK-RFD
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 Oakland to Chicago
OAK-CHI
OAK-ORD
OAK-MDW
OAK-RFD
What is the cheapest month to book a flight from Oakland, California to Chicago?
Currently, February is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $364). Flying from Oakland, California to Chicago in July is currently the most expensive (average of $544). 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 OAK to CHI?
Find hourly flight availability from Oakland 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 6, 2026.
One of the essential ways to save on airfare from Oakland, California to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 60% on airfare.
Weekly flight availability from Oakland, California to Chicago
Explore weekly flight availability from Oakland 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 6, 2026.
The most flights from OAK to CHI are scheduled on a Thursday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Oakland, California to Chicago?
Airfare is below average for this route at the moment.
Oakland, California to Chicago flights typically cost between $347 and $537 in September.The cheapest round-trip price found within the last 5 days was $218 on Frontier (Sep 24-Oct 1).
How far ahead should I book a flight from Oakland, California to Chicago?
The best time to book flights from Oakland, California to Chicago is 59 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.
The best insider tips for Oakland 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 Oakland 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 6, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andUnited Airlines from Oakland to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
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 Oakland 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
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Complete your trip
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Oakland and Chicago flights
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Other flights from Oakland
Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on September 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Oakland to Chicago
Discover the top 4 airlines that operate flights from Oakland 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 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$271 | Average$407 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$272 | Average$522 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$275 | Average$440 | FlexibilityNo cancel fee | On-time63% |