$126+ Cheap flights from Illinois 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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Oct 26 — Nov 21
Round-trip
1 adult, Economy
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Find cheap flights from Illinois 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
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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 Illinois to Oakland
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Cheapest flights from Illinois to OaklandExplore the most affordable flight options available from Illinois to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2026.
Explore the most affordable flight options available from Illinois to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 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 9/21. 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.
Thu 12/106:21 am -
1 stop7h 12m
Mon 12/1412:28 pm -
1 stop14h 33m
Deal found 9/21![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 9/21. 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.
Thu 11/55:15 pm -
1 stop18h 08m
Mon 11/95:55 pm -
1 stop9h 18m
Deal found 9/21![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 9/23. 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 12/46:21 am -
1 stop7h 12m
Mon 12/712:28 pm -
1 stop14h 33m
Deal found 9/23![Frontier logo]()
$288
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 11/195:15 pm -
1 stop19h 14m
Sun 11/222:34 pm -
1 stop12h 36m
Deal found 9/22![Frontier logo]()
$290
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 9/23. 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
Best flights from Illinois to OaklandDiscover carefully curated flight deals from Illinois to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 26, 2026.
Discover carefully curated flight deals from Illinois to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 26, 2026.
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 10/136:05 am -
1 stop6h 30m
Thu 10/226:55 pm -
1 stop7h 35m
Deal found 9/22![Southwest logo]()
$357
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:07 pm -
1 stop9h 12m
Mon 11/910:00 am -
1 stop6h 59m
Deal found 9/25![Alaska Airlines logo]()
$357
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.
Wed 10/217:35 am -
1 stop6h 26m
Sat 10/245:02 pm -
2 stops13h 37m
Deal found 9/25![Delta logo]()
$364
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.
Mon 1/257:40 am -
1 stop8h 16m
Thu 2/41:18 pm -
1 stop8h 41m
Deal found 9/22![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 9/24. 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 11/179:59 am -
2 stops8h 18m
Wed 12/25:55 am -
2 stops11h 10m
Deal found 9/24![Delta logo]()
$380
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:49 pm -
1 stop9h 06m
Wed 11/46:12 am -
1 stop10h 47m
Deal found 9/25![Alaska Airlines logo]()
$357
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 10/197:15 pm -
1 stop7h 25m
Wed 10/216:35 am -
2 stops7h 30m
Deal found 9/21![Southwest logo]()
$368
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:18 pm -
1 stop6h 45m
Mon 12/75:07 pm -
2 stops14h 15m
Deal found 9/26![Delta logo]()
$386
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 10/207:00 am -
1 stop13h 54m
Thu 11/510:00 am -
1 stop6h 59m
Deal found 9/24![Alaska Airlines logo]()
$357
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.
Tue 12/18:45 pm -
Nonstop4h 50m
Wed 12/27:10 am -
1 stop8h 15m
Deal found 9/21![Southwest logo]()
$380
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 12/212:00 pm -
1 stop6h 25m
Tue 12/299:35 pm -
1 stop6h 10m
Deal found 9/21![Southwest logo]()
$385
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/162:08 pm -
1 stop7h 31m
Mon 1/189:57 am -
1 stop25h 18m
Deal found 9/21![Alaska Airlines logo]()
$390
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.
Wed 10/218:35 pm -
Nonstop4h 45m
Sun 10/2511:55 pm -
Nonstop4h 00m
Deal found 9/25![Southwest logo]()
$387
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.
Fri 11/69:55 pm -
Nonstop4h 45m
Sun 11/811:50 pm -
Nonstop4h 05m
Deal found 9/22![Southwest logo]()
$400
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 11/1910:10 am -
2 stops8h 10m
Sun 11/228:30 pm -
1 stop5h 55m
Deal found 9/21![Southwest logo]()
$412
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 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 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 10/2710:00 am -
Nonstop4h 40m
Thu 10/298:10 pm -
2 stops7h 35m
Deal found 9/22![Southwest logo]()
$452
Last-minute flights from Illinois to OaklandDiscover last-minute flight deals from Illinois to Oakland. Data last updated September 26, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Oakland. Data last updated September 26, 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
Sat 10/2411:55 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 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.
Thu 10/223:30 pm -
1 stop19h 35m
Sun 10/255:20 pm -
2 stops23h 11m
Deal found 9/24![Frontier logo]()
$325
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 Illinois to OaklandSearch for one-way flight options from Illinois to Oakland. Find affordable one-way fares based on user searches. Data last updated September 26, 2026.
Search for one-way flight options from Illinois to Oakland. Find affordable one-way fares based on user searches. Data last updated September 26, 2026.
This Cheapflightsfares 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 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$126
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 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 9/22. 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 10/2712:27 pm -
2 stops25h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![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.
Tue 10/203:30 pm -
2 stops22h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$152
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 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.
Sun 10/253:30 pm -
1 stop26h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$163
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 Illinois to Oakland
Keep the following information in mind while searching for Illinois to Oakland flight deals. Data was last updated September 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $259 (Cheapflightsfares) |
One-way from | $126 (Cheapflightsfares) |
Popular in | June |
Cheapest in | September |
Average price | $337 |
Good round-trip deal | $335 or less |
Good one-way deal | $209 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois 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 26, 2026.
Use the filters below to find and compare flights from Illinois 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
Mon 11/2
9:55 pm-12:35 am
Nonstop4h 40m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$169
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Sat 10/24
7:30 pm-10:10 pm
Nonstop4h 40m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$175
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Sat 10/17
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
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
Sat 11/14
4:00 pm-10:02 pm
1 stop8h 02m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$180
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
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Mon 10/19
7:20 am-11:30 am
1 stop30h 10m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$197
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Fri 1/1
4:07 pm-11:59 pm
1 stop9h 52m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$202
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Fri 11/20
7:26 am-3:15 pm
1 stop9h 49m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$202
Showing 1-10 of 37 resultsSorted by cheapest first
Best time to book a flight from Illinois to Oakland
Have a flexible travel schedule? Discover the best time to fly to Oakland from Illinois with our price prediction graph.
ORD-OAK
MDW-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 Illinois to Oakland
USIL-OAK
ORD-OAK
MDW-OAK
What is the cheapest month to book a flight from Illinois to Oakland, California?
Currently, April is the cheapest month in which you can book a flight from Illinois to Oakland, California (average of $327). Flying from Illinois 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 IL to OAK?
Find hourly flight availability from Illinois 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 26, 2026.
One of the essential ways to save on airfare from Illinois to Oakland, California is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 49% on airfare.
How much does it cost to fly round-trip from Illinois to Oakland, California?
Airfare is below average for this route at the moment.
Illinois to Oakland, California flights typically cost between $328 and $491 in December.The cheapest round-trip price found within the last 5 days was $259 on Frontier (Dec 1-Dec 7).
Related info for your journey
Find useful and relevant information for your journey from Illinois to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Illinois to Oakland
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Complete your trip
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Search flights from Illinois to Oakland by cabin class
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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 26, 2026.
Illinois and Oakland flights
Browse other Illinois and Oakland flight options. Last updated on September 26, 2026.
Popular flight searches
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Illinois to Oakland flights
Consider these flights traveling from Illinois to Oakland.
Top 3 airlines flying from Illinois to Oakland
Discover the top 3 airlines that operate flights from Illinois 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 26, 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% |