$126+ Cheap flights from Oakland, CA (OAK) to Illinois
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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Oct 31 — Nov 71
Round-trip
1 adult, Economy
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Find cheap flights from Oakland to Illinois 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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Cheapest flights from Oakland to IllinoisExplore the most affordable flight options available from Oakland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 1, 2026.
Explore the most affordable flight options available from Oakland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/55:55 pm -
1 stop9h 18m
Mon 11/95:15 pm -
1 stop20h 38m
Deal found 9/27![Frontier logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/2210:17 am -
1 stop16h 59m
Mon 10/263:30 pm -
1 stop22h 23m
Deal found 9/29![Frontier logo]()
$254
This Frontier deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:56 pm -
1 stop11h 14m
Thu 11/265:19 am -
1 stop7h 10m
Deal found 9/30![Frontier logo]()
$258
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/812:28 pm -
1 stop14h 33m
Thu 12/106:21 am -
1 stop7h 12m
Deal found 9/29![Frontier logo]()
$259
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/295:55 pm -
1 stop9h 18m
Thu 11/55:15 pm -
1 stop25h 45m
Deal found 9/27![Frontier logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/3010:18 am -
1 stop16h 55m
Mon 11/25:15 pm -
1 stop20h 38m
Deal found 9/29![Frontier logo]()
$266
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.
Mon 11/210:18 am -
1 stop16h 55m
Fri 11/65:15 pm -
1 stop20h 38m
Deal found 9/25![Frontier logo]()
$267
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/222:34 pm -
1 stop12h 36m
Thu 11/265:19 am -
1 stop7h 10m
Deal found 9/29![Frontier logo]()
$276
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/2311:24 am -
1 stop15h 46m
Tue 12/16:21 am -
1 stop7h 12m
Deal found 9/29![Frontier logo]()
$278
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:17 am -
1 stop16h 59m
Sun 10/253:30 pm -
1 stop19h 35m
Deal found 9/26![Frontier logo]()
$284
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/1911:55 pm -
Nonstop4h 00m
Wed 10/218:35 pm -
Nonstop4h 45m
Deal found 9/28![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/2611:55 pm -
Nonstop4h 00m
Thu 10/296:15 pm -
1 stop6h 25m
Deal found 9/30![Southwest logo]()
$343
Best flights from Oakland to IllinoisDiscover carefully curated flight deals from Oakland to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
Discover carefully curated flight deals from Oakland to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
This CheapOair deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:20 pm -
1 stop9h 56m
Mon 10/263:30 pm -
1 stop22h 23m
Deal found 9/25![Frontier logo]()
$330
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/2812:20 pm -
1 stop7h 55m
Tue 11/310:00 am -
1 stop7h 00m
Deal found 9/27![Southwest logo]()
$352
This Alaska Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/122:44 pm -
1 stop7h 05m
Tue 11/172:15 pm -
1 stop8h 45m
Deal found 9/27![Alaska Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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
Tue 10/271:23 pm -
2 stops12h 33m
Deal found 9/29![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/2611:55 pm -
Nonstop4h 00m
Fri 10/306:15 pm -
1 stop6h 25m
Deal found 9/29![Southwest logo]()
$356
This Alaska Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 stop8h 45m
Deal found 9/27![Alaska Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/115:55 am -
2 stops8h 23m
Wed 11/187:17 pm -
1 stop6h 38m
Deal found 9/27![Delta logo]()
$364
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.
Mon 11/1610:00 am -
1 stop6h 59m
Tue 11/177:20 am -
1 stop29h 32m
Deal found 9/25![Alaska Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/105:00 pm -
2 stops14h 22m
Mon 11/167:17 pm -
1 stop6h 38m
Deal found 9/27![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:10 pm -
2 stops7h 35m
Tue 11/310:15 am -
2 stops9h 00m
Deal found 9/26![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/293:20 pm -
2 stops7h 40m
Thu 11/55:20 am -
2 stops8h 15m
Deal found 9/27![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/115:55 am -
2 stops10h 09m
Wed 11/181:05 pm -
2 stops12h 50m
Deal found 9/27![Delta logo]()
$370
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.
Tue 10/209:59 am -
1 stop6h 54m
Fri 10/237:20 am -
1 stop9h 14m
Deal found 9/25![Alaska Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/115:55 am -
2 stops10h 09m
Tue 11/176:00 am -
2 stops12h 17m
Deal found 9/27![Delta logo]()
$370
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/198:10 pm -
2 stops7h 35m
Tue 10/2710:15 am -
2 stops8h 20m
Deal found 9/28![Southwest logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/710:36 am -
1 stop6h 24m
Sat 12/127:27 am -
1 stop10h 48m
Deal found 9/29![Alaska Airlines logo]()
$380
This Alaska Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/269:59 am -
1 stop6h 54m
Thu 10/293:49 pm -
1 stop9h 06m
Deal found 9/27![Alaska Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 2/26:40 am -
Nonstop4h 00m
Sun 2/73:50 pm -
Nonstop4h 45m
Deal found 9/30![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/37:45 am -
1 stop7h 00m
Sun 11/89:55 pm -
Nonstop4h 45m
Deal found 9/27![Southwest logo]()
$397
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.
Tue 10/209:59 am -
1 stop6h 54m
Sun 10/257:20 am -
1 stop30h 10m
Deal found 9/25![Alaska Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/1911:30 am -
1 stop8h 30m
Wed 11/256:30 pm -
1 stop6h 45m
Deal found 9/28![Southwest logo]()
$405
Last-minute flights from Oakland to IllinoisDiscover last-minute flight deals from Oakland to Illinois. Data last updated October 1, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Illinois. Data last updated October 1, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/1911:55 pm -
Nonstop4h 00m
Wed 10/218:35 pm -
Nonstop4h 45m
Deal found 9/28![Southwest logo]()
$337
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/2210:17 am -
1 stop16h 59m
Mon 10/263:30 pm -
1 stop22h 23m
Deal found 9/27![Frontier logo]()
$253
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:17 am -
1 stop16h 59m
Sun 10/253:30 pm -
1 stop19h 35m
Deal found 9/26![Frontier logo]()
$284
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/235:20 pm -
1 stop9h 56m
Mon 10/263:30 pm -
1 stop22h 23m
Deal found 9/29![Frontier logo]()
$304
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/265:20 pm -
1 stop9h 56m
Fri 10/305:15 pm -
1 stop20h 38m
Deal found 9/29![Frontier logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/265:20 pm -
1 stop9h 56m
Wed 10/287:15 am -
2 stops28h 08m
Deal found 9/29![Frontier logo]()
$305
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/2611:55 pm -
Nonstop4h 00m
Thu 10/296:15 pm -
1 stop6h 25m
Deal found 9/30![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/2611:55 pm -
Nonstop4h 00m
Mon 11/25:20 am -
2 stops8h 15m
Deal found 9/30![Southwest logo]()
$348
This Frontier deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:48 pm -
2 stops22h 03m
Wed 10/288:13 pm -
2 stops22h 47m
Deal found 9/29![Frontier logo]()
$302
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/295:55 pm -
1 stop9h 18m
Thu 11/55:15 pm -
1 stop25h 45m
Deal found 9/27![Frontier logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/3010:18 am -
1 stop16h 55m
Mon 11/25:15 pm -
1 stop20h 38m
Deal found 9/29![Frontier logo]()
$266
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/3010:18 am -
1 stop16h 55m
Sun 11/15:15 pm -
1 stop25h 45m
Deal found 9/29![Frontier logo]()
$297
One-way flights from Oakland to IllinoisSearch for one-way flight options from Oakland to Illinois. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
Search for one-way flight options from Oakland to Illinois. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
This Expedia deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/510:18 am -
1 stop16h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$126
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/2210:17 am -
1 stop16h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/112:28 pm -
2 stops18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/2812:48 pm -
2 stops32h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/2712:48 pm -
2 stops32h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$140
This Expedia deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/242:34 pm -
1 stop12h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/2812:48 pm -
2 stops18h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$145
This Priceline deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/265:20 pm -
1 stop9h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 12/212:28 pm -
2 stops24h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:20 pm -
2 stops35h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$155
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/131:18 pm -
1 stop8h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Alaska Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:50 am -
2 stops23h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$162
Find flight deals from Oakland to Illinois
Keep the following information in mind while searching for Oakland to Illinois flight deals. Data was last updated October 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $246 (Cheapflightsfares) |
One-way from | $126 (Expedia) |
Popular in | July |
Cheapest in | February |
Average price | $411 |
Good round-trip deal | $437 or less |
Good one-way deal | $256 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland to Illinois 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 October 1, 2026.
Use the filters below to find and compare flights from Oakland to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 11/5
5:55 pm-5:13 am
1 stop9h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$135
Quickest round-trip
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sat 10/24
11:55 pm-5:55 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Wed 10/21
7:04 am-6:53 pm
1 stop9h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Wed 10/28
11:50 am-9:05 pm
1 stop7h 15m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Sat 11/7
12:57 pm-11:59 pm
1 stop9h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Wed 11/11
10:00 am-6:59 pm
1 stop6h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Tue 10/20
7:04 am-6:53 pm
1 stop9h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Fri 10/23
11:55 pm-5:55 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$182
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Fri 12/25
11:50 pm-5:55 am
Nonstop4h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$182
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Fri 11/6
11:50 pm-5:55 am
Nonstop4h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$182
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from Oakland to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Oakland with our price prediction graph.
OAK-ORD
OAK-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Oakland to Illinois
OAK-USIL
OAK-ORD
OAK-MDW
What is the cheapest month to book a flight from Oakland, California to Illinois?
Currently, February is the cheapest month in which you can book a flight from Oakland, California to Illinois (average of $364). Flying from Oakland, California to Illinois in November is currently the most expensive (average of $556). 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 IL?
Find hourly flight availability from Oakland to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 1, 2026.
When flying from Oakland, California to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 61% versus a flight in the afternoon.
How much does it cost to fly round-trip from Oakland, California to Illinois?
Airfare is below average for this route at the moment.
Oakland, California to Illinois flights typically cost between $462 and $607 in November.The cheapest round-trip price found within the last 5 days was $246 on Frontier (Nov 5-Nov 9).
How far ahead should I book a flight from Oakland, California to Illinois?
Booking 61 days in advance of your planned departure date is, on average, the best time to get cheap flights from Oakland, California to Illinois. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated October 1, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta from Oakland to Illinois by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
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Alternative routes for Oakland to Illinois
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Complete your trip
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Oakland and Illinois flights
Browse other Oakland and Illinois flight options. Last updated on October 1, 2026.
Popular flight searches
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Oakland to Illinois flights
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Top 3 airlines flying from Oakland to Illinois
Discover the top 3 airlines that operate flights from Oakland to Illinois. 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 October 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$272 | Average$516 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$275 | Average$441 | FlexibilityNo cancel fee | On-time63% |