$131+ Cheap flights from Chicago (CHI) to Oakland, CA (OAK)
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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
Oct 25 — Nov 11
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Oakland 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.Cheap flight deals from Chicago to Oakland
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Cheapest flights from Chicago to OaklandExplore the most affordable flight options available from Chicago to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
Explore the most affordable flight options available from Chicago to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:21 am -
1 stop7h 12m
Mon 12/712:28 pm -
1 stop14h 33m
Deal found 9/24![Frontier logo]()
$259
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 12/106:21 am -
1 stop7h 12m
Mon 12/1412:28 pm -
1 stop14h 33m
Deal found 9/20![Frontier logo]()
$266
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:15 pm -
1 stop20h 38m
Mon 11/1610:18 am -
1 stop16h 55m
Deal found 9/24![Frontier logo]()
$273
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.
Thu 10/295:15 pm -
1 stop18h 08m
Mon 11/210:18 am -
1 stop16h 55m
Deal found 9/23![Frontier logo]()
$274
This CheapOair deal was found by Cheapflights users on 9/21. 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 12/16:21 am -
1 stop7h 12m
Wed 12/212:28 pm -
1 stop14h 31m
Deal found 9/21![Frontier logo]()
$280
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 11/55:15 pm -
1 stop18h 08m
Mon 11/95:55 pm -
1 stop9h 18m
Deal found 9/20![Frontier logo]()
$281
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 10/305:15 pm -
1 stop20h 38m
Mon 11/210:18 am -
1 stop16h 55m
Deal found 9/22![Frontier logo]()
$283
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 11/176:30 am -
2 stops31h 23m
Tue 12/112:28 pm -
1 stop14h 31m
Deal found 9/22![Frontier logo]()
$285
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 12/46:21 am -
1 stop7h 12m
Mon 12/712:28 pm -
1 stop14h 33m
Deal found 9/20![Frontier logo]()
$288
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 11/195:15 pm -
1 stop19h 14m
Sun 11/222:34 pm -
1 stop12h 36m
Deal found 9/20![Frontier logo]()
$290
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:30 pm -
Nonstop4h 45m
Sat 10/2411:55 pm -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/21. 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 10/199:30 pm -
Nonstop4h 45m
Wed 10/2111:55 pm -
Nonstop4h 00m
Deal found 9/21![Southwest logo]()
$343
Best flights from Chicago to OaklandDiscover carefully curated flight deals from Chicago to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
Discover carefully curated flight deals from Chicago to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
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.
Thu 10/159:30 pm -
Nonstop4h 45m
Sat 10/2411:55 pm -
Nonstop4h 00m
Deal found 9/24![Southwest logo]()
$337
This Alaska Airlines deal was found by Cheapflights users on 9/19. 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 10/297:20 am -
1 stop9h 14m
Mon 11/22:44 pm -
1 stop7h 05m
Deal found 9/19![Alaska Airlines logo]()
$357
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:35 am -
1 stop6h 26m
Mon 11/25:02 pm -
2 stops14h 23m
Deal found 9/23![Delta logo]()
$374
This Alaska Airlines deal was found by Cheapflights users on 9/20. 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 10/205:46 pm -
1 stop19h 39m
Thu 11/56:12 pm -
1 stop17h 05m
Deal found 9/20![Alaska Airlines logo]()
$357
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:45 am -
1 stop6h 40m
Wed 10/287:15 am -
2 stops7h 30m
Deal found 9/23![Southwest logo]()
$362
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:55 pm -
2 stops12h 01m
Wed 11/412:41 pm -
1 stop7h 24m
Deal found 9/22![Delta logo]()
$374
This Alaska Airlines deal was found by Cheapflights users on 9/19. 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 10/287:20 am -
1 stop9h 14m
Wed 11/410:00 am -
1 stop6h 59m
Deal found 9/19![Alaska Airlines logo]()
$357
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.
Tue 10/273:40 pm -
2 stops10h 16m
Wed 10/2812:41 pm -
1 stop7h 24m
Deal found 9/24![Delta logo]()
$374
This Southwest deal was found by Cheapflights users on 9/21. 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 11/59:55 pm -
Nonstop4h 45m
Sun 11/85:35 am -
Nonstop4h 00m
Deal found 9/21![Southwest logo]()
$387
This Alaska Airlines deal was found by Cheapflights users on 9/19. 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 10/297:20 am -
1 stop9h 14m
Thu 11/510:00 am -
1 stop6h 59m
Deal found 9/19![Alaska Airlines logo]()
$357
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.
Wed 10/2810:12 am -
2 stops8h 10m
Sat 10/316:00 am -
2 stops8h 47m
Deal found 9/24![Delta logo]()
$380
This Alaska Airlines deal was found by Cheapflights users on 9/19. 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 10/303:49 pm -
1 stop9h 06m
Mon 11/22:44 pm -
1 stop7h 05m
Deal found 9/19![Alaska Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 9/21. 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 11/65:20 pm -
2 stops7h 20m
Sun 11/811:50 pm -
Nonstop4h 05m
Deal found 9/21![Southwest logo]()
$415
This Delta deal was found by Cheapflights users on 9/19. 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 10/307:15 pm -
1 stop6h 41m
Tue 11/36:00 am -
2 stops8h 32m
Deal found 9/19![Delta logo]()
$391
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.
Tue 12/110:10 am -
2 stops8h 10m
Mon 12/73:00 pm -
2 stops7h 10m
Deal found 9/24![Southwest logo]()
$437
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:17 pm -
1 stop6h 38m
Fri 11/275:55 am -
2 stops8h 23m
Deal found 9/22![Delta logo]()
$404
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:20 am -
1 stop8h 44m
Sat 11/216:49 am -
1 stop15h 00m
Deal found 9/22![Alaska Airlines logo]()
$418
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.
Mon 10/267:15 pm -
1 stop7h 25m
Tue 10/2711:55 pm -
Nonstop4h 00m
Deal found 9/22![Southwest logo]()
$447
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.
Tue 10/206:35 am -
2 stops11h 47m
Wed 11/412:41 pm -
1 stop7h 24m
Deal found 9/24![Delta logo]()
$421
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.
Tue 10/2710:15 am -
2 stops8h 20m
Thu 10/295:00 am -
1 stop6h 25m
Deal found 9/22![Southwest logo]()
$462
This Southwest deal was found by Cheapflights users on 9/20. 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 11/236:05 pm -
1 stop6h 55m
Sun 11/299:10 pm -
1 stop6h 35m
Deal found 9/20![Southwest logo]()
$482
Last-minute flights from Chicago to OaklandDiscover last-minute flight deals from Chicago to Oakland. Data last updated September 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oakland. Data last updated September 25, 2026 and is based on user searches.
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 10/138:01 pm -
2 stops39h 21m
Thu 10/225:20 pm -
1 stop9h 56m
Deal found 9/22![Frontier logo]()
$314
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 10/137:20 am -
1 stop9h 14m
Thu 10/225:20 pm -
1 stop9h 56m
Deal found 9/22![Multiple Airlines logo]()
$319
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:30 pm -
Nonstop4h 45m
Sat 10/2411:55 pm -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$337
This Cheapflightsfares deal was found by Cheapflights users on 9/21. 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 10/163:30 pm -
1 stop22h 22m
Thu 12/1012:28 pm -
1 stop14h 33m
Deal found 9/21![Frontier logo]()
$315
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:30 pm -
Nonstop4h 45m
Mon 10/2611:55 pm -
Nonstop4h 00m
Deal found 9/23![Southwest logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/193:30 pm -
1 stop22h 22m
Wed 10/2112:47 pm -
2 stops18h 34m
Deal found 9/21![Frontier logo]()
$291
This Southwest deal was found by Cheapflights users on 9/21. 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 10/199:30 pm -
Nonstop4h 45m
Wed 10/2111:55 pm -
Nonstop4h 00m
Deal found 9/21![Southwest logo]()
$343
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.
Fri 10/233:30 pm -
1 stop22h 22m
Mon 10/265:20 pm -
2 stops29h 01m
Deal found 9/22![Frontier logo]()
$324
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.
Thu 10/295:15 pm -
1 stop18h 08m
Mon 11/210:18 am -
1 stop16h 55m
Deal found 9/23![Frontier logo]()
$274
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:15 pm -
1 stop18h 08m
Sun 11/15:55 pm -
1 stop9h 18m
Deal found 9/24![Frontier logo]()
$303
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 10/305:15 pm -
1 stop20h 38m
Mon 11/210:18 am -
1 stop16h 55m
Deal found 9/22![Frontier logo]()
$283
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:15 pm -
1 stop20h 38m
Sun 11/110:18 am -
1 stop16h 55m
Deal found 9/24![Frontier logo]()
$312
One-way flights from Chicago to OaklandSearch for one-way flight options from Chicago to Oakland. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
Search for one-way flight options from Chicago to Oakland. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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.
Mon 10/263:30 pm -
1 stop22h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$131
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 12/106:21 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$133
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.
Thu 12/36:21 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 9/21. 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 12/16:21 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$136
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.
Mon 10/193:30 pm -
1 stop22h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$139
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 12/116:21 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$140
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:15 pm -
1 stop25h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 11/176:16 am -
2 stops31h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 10/203:30 pm -
2 stops22h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$151
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.
Thu 10/224:20 pm -
2 stops18h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$159
This Cheapflightsfares deal was found by Cheapflights users on 9/21. 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 11/215:19 am -
1 stop7h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$160
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/261:12 pm -
2 stops24h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$163
Find flight deals from Chicago to Oakland
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Oakland (OAK). 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 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $259 (Cheapflightsfares) |
One-way from | $131 (Cheapflightsfares) |
Popular in | November |
Cheapest in | April |
Average price | $332 |
Good round-trip deal | $345 or less |
Good one-way deal | $181 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Oakland 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 25, 2026.
Use the filters below to find and compare flights from Chicago to Oakland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Sat 11/21
9:30 pm-12:15 am
Nonstop4h 45m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$169
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Wed 10/21
7:20 am-2:34 pm
1 stop9h 14m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Wed 10/14
6:05 am-12:05 pm
1 stop8h 00m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Thu 10/22
5:25 am-11:35 am
1 stop8h 10m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Wed 11/11
7:17 pm-11:55 pm
1 stop6h 38m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$185
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Tue 11/3
1:55 pm-9:58 pm
2 stops10h 03m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$190
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Tue 3/23
2:05 pm-6:55 pm
1 stop6h 50m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$193
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Tue 12/1
8:45 pm-11:35 pm
Nonstop4h 50m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$202
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Mon 12/21
9:25 pm-12:15 am
Nonstop4h 50m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$202
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Tue 12/22
5:10 am-10:55 am
1 stop7h 45m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$212
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Chicago to Oakland
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 Chicago to Oakland in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Oakland, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Oakland, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Oakland, California flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Oakland, California 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 Chicago-Oakland, California 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 Chicago to Oakland
Have a flexible travel schedule? Discover the best time to fly to Oakland from Chicago with our price prediction graph.
CHI-OAK
MDW-OAK
ORD-OAK
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 Chicago to Oakland
CHI-OAK
MDW-OAK
ORD-OAK
What is the cheapest month to book a flight from Chicago to Oakland, California?
Currently, April is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $327). Flying from Chicago to Oakland, California in December is currently the most expensive (average of $504). 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 CHI to OAK?
Find hourly flight availability from Chicago to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 25, 2026.
It’s typically best to fly out from Chicago to Oakland, California in the afternoon. Doing so could potentially save you 49% on the flight price compared to flying in the morning, which is usually more expensive.
How much does it cost to fly round-trip from Chicago to Oakland, California?
Airfare is below average for this route at the moment.
Chicago to Oakland, California flights typically cost between $293 and $458 in December.The cheapest round-trip price found within the last 5 days was $259 on Frontier (Dec 1-Dec 7).
How often are flights from Chicago to Oakland delayed?
About 26% of weekly flights between Chicago and Oakland have experienced delays in the past year, with the average delay time being 106 minutes.
What is the most punctual flight time for Chicago to Oakland flights?
Historically, flights departing in the early afternoon 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?
Thursday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Oakland flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 32% of flights being delayed.
The best insider tips for Chicago to Oakland 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 Chicago to Oakland trip
Our travel experts
Reviews of airlines servicing Oakland
Get insights into the airlines that provide service to Oakland. 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 Oakland. Reviews last updated September 25, 2026.
Get a feel of what it's like to fly with Southwest and Alaska Airlines from Chicago to Oakland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Other flights to Oakland
Explore flights to Oakland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 25, 2026.
Chicago and Oakland flights
Browse other Chicago and Oakland flight options. Last updated on September 25, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 25, 2026.
Popular flight searches
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Consider these flights traveling from Chicago to Oakland.
Top 3 airlines flying from Chicago to Oakland
Discover the top 3 airlines that operate flights from Chicago to Oakland. 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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$165 | Average$354 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$177 | Average$377 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$274 | Average$429 | FlexibilityNo cancel fee | On-time63% |