$88+ 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 21 — Oct 281
Round-trip
1 adult, Economy
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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 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 21, 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 21, 2026.
This Orbitz deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz 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 9/16![Frontier logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/25:15 pm -
1 stop20h 38m
Thu 11/510:18 am -
1 stop16h 55m
Deal found 9/18![Frontier logo]()
$206
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/910:18 am -
1 stop16h 55m
Deal found 9/17![Frontier logo]()
$214
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:30 pm -
Nonstop4h 40m
Sat 10/3110:55 pm -
Nonstop4h 10m
Deal found 9/17![Southwest logo]()
$231
This Expedia deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/125:15 pm -
1 stop25h 45m
Mon 11/165:55 pm -
1 stop9h 18m
Deal found 9/18![Frontier logo]()
$234
This Priceline deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Wed 10/143:49 pm -
1 stop9h 06m
Mon 10/195:20 pm -
1 stop9h 56m
Deal found 9/16![Multiple Airlines logo]()
$242
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/209:00 am -
1 stop11h 54m
Wed 11/410:00 am -
1 stop6h 59m
Deal found 9/16![Alaska Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/205:45 am -
1 stop6h 40m
Wed 11/43:05 pm -
1 stop7h 10m
Deal found 9/17![Southwest logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/148:01 pm -
2 stops39h 04m
Mon 10/195:20 pm -
1 stop9h 56m
Deal found 9/16![Frontier logo]()
$255
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/229:30 pm -
Nonstop4h 45m
Tue 10/2711:50 am -
1 stop7h 10m
Deal found 9/17![Southwest logo]()
$257
This Priceline deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:20 am -
1 stop9h 14m
Mon 10/265:20 pm -
1 stop9h 56m
Deal found 9/17![Multiple Airlines logo]()
$258
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/299:30 pm -
Nonstop4h 45m
Mon 11/25:35 am -
Nonstop4h 00m
Deal found 9/17![Southwest logo]()
$263
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 21, 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 21, 2026.
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/205:45 am -
1 stop6h 40m
Wed 11/43:05 pm -
1 stop7h 10m
Deal found 9/17![Southwest logo]()
$251
This Alaska Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:27 am -
1 stop17h 59m
Wed 12/161:36 pm -
1 stop8h 23m
Deal found 9/17![Alaska Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/172:44 pm -
2 stops11h 11m
Wed 12/25:55 am -
2 stops8h 48m
Deal found 9/16![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/155:25 am -
1 stop6h 45m
Mon 10/2611:55 pm -
Nonstop4h 00m
Deal found 9/17![Southwest logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/262:21 pm -
1 stop11h 21m
Thu 10/299:59 am -
1 stop6h 54m
Deal found 9/16![Alaska Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/102:21 pm -
2 stops11h 34m
Thu 11/125:00 pm -
1 stop5h 40m
Deal found 9/18![Delta logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/227:20 am -
1 stop9h 14m
Sun 10/257:04 am -
1 stop28h 21m
Deal found 9/16![Alaska Airlines logo]()
$343
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.
Thu 11/1210:05 am -
Nonstop4h 40m
Thu 11/129:30 pm -
1 stop6h 10m
Deal found 9/20![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/175:30 am -
2 stops12h 47m
Tue 12/15:55 am -
2 stops16h 20m
Deal found 9/16![Delta logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/237:26 am -
1 stop9h 49m
Thu 12/310:36 am -
1 stop6h 24m
Deal found 9/18![Alaska Airlines logo]()
$357
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/146:10 am -
2 stops8h 05m
Mon 1/185:45 am -
Nonstop4h 00m
Deal found 9/19![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/412:34 pm -
1 stop7h 22m
Deal found 9/18![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/25:20 am -
2 stops8h 15m
Thu 11/511:50 pm -
Nonstop4h 05m
Deal found 9/18![Southwest logo]()
$360
This Delta 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 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 9/21![Delta logo]()
$391
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/246:57 pm -
1 stop19h 19m
Thu 12/312:51 pm -
1 stop20h 28m
Deal found 9/16![Alaska Airlines logo]()
$394
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.
Tue 10/135:50 pm -
1 stop6h 20m
Fri 10/166:55 pm -
1 stop7h 35m
Deal found 9/20![Southwest logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/197:20 am -
1 stop8h 44m
Tue 12/16:52 pm -
2 stops20h 57m
Deal found 9/16![Alaska Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/165:29 pm -
2 stops24h 48m
Wed 12/25:55 am -
2 stops8h 55m
Deal found 9/16![Delta logo]()
$416
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/306:05 am -
2 stops7h 50m
Tue 11/39:30 am -
2 stops8h 20m
Deal found 9/18![Southwest logo]()
$380
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.
Wed 2/108:00 am -
2 stops10h 17m
Tue 2/167:00 am -
1 stop8h 01m
Deal found 9/20![Alaska Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/176:00 am -
2 stops12h 17m
Tue 12/112:34 pm -
2 stops27h 27m
Deal found 9/16![Delta logo]()
$423
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 12/179:55 am -
1 stop7h 00m
Fri 12/1811:50 pm -
Nonstop4h 05m
Deal found 9/16![Southwest logo]()
$421
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/212:03 pm -
1 stop11h 53m
Wed 10/286:00 am -
2 stops8h 32m
Deal found 9/16![Delta logo]()
$426
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/287:02 am -
1 stop13h 52m
Thu 10/297:02 am -
1 stop14h 57m
Deal found 9/16![Alaska Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/311:55 am -
1 stop7h 20m
Sun 2/72:25 pm -
2 stops7h 05m
Deal found 9/16![Southwest logo]()
$426
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:00 pm -
1 stop6h 56m
Sun 11/16:00 am -
1 stop5h 32m
Deal found 9/16![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:00 pm -
1 stop6h 56m
Wed 10/145:02 pm -
1 stop5h 42m
Deal found 9/16![Delta logo]()
$471
This Alaska Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:04 am -
1 stop8h 12m
Fri 1/16:00 am -
1 stop7h 34m
Deal found 9/17![Alaska Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/1511:08 am -
2 stops14h 48m
Tue 10/205:02 pm -
2 stops15h 16m
Deal found 9/17![Delta logo]()
$1,039
Last-minute flights from Illinois to OaklandDiscover last-minute flight deals from Illinois to Oakland. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Oakland. Data last updated September 21, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/28:55 pm -
1 stop16h 56m
Tue 10/612:47 pm -
1 stop14h 51m
Deal found 9/17![Frontier logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/71:21 pm -
1 stop22h 01m
Mon 10/125:20 pm -
2 stops29h 04m
Deal found 9/17![Frontier logo]()
$266
This Priceline deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Wed 10/143:49 pm -
1 stop9h 06m
Mon 10/195:20 pm -
1 stop9h 56m
Deal found 9/16![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/148:01 pm -
2 stops39h 04m
Mon 10/195:20 pm -
1 stop9h 56m
Deal found 9/16![Frontier logo]()
$255
This Priceline deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:20 am -
1 stop9h 14m
Mon 10/265:20 pm -
1 stop9h 56m
Deal found 9/17![Multiple Airlines logo]()
$258
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/209:00 am -
1 stop11h 54m
Wed 11/410:00 am -
1 stop6h 59m
Deal found 9/16![Alaska Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/205:45 am -
1 stop6h 40m
Wed 11/43:05 pm -
1 stop7h 10m
Deal found 9/17![Southwest logo]()
$251
This Alaska Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/213:49 pm -
1 stop9h 06m
Mon 10/263:14 pm -
1 stop6h 45m
Deal found 9/16![Alaska Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/229:30 pm -
Nonstop4h 45m
Tue 10/2711:50 am -
1 stop7h 10m
Deal found 9/17![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:30 pm -
Nonstop4h 40m
Sat 10/3110:55 pm -
Nonstop4h 10m
Deal found 9/17![Southwest logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Sat 10/244:41 pm -
2 stops18h 41m
Mon 10/265:20 pm -
1 stop9h 56m
Deal found 9/16![Frontier logo]()
$271
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/299:30 pm -
Nonstop4h 45m
Mon 11/25:35 am -
Nonstop4h 00m
Deal found 9/17![Southwest logo]()
$263
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 21, 2026.
Search for one-way flight options from Illinois to Oakland. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/16:21 am -
1 stop31h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$88
This Cheapflightsfares deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 9/18![Frontier logo]()
$103
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/288:35 pm -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$116
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/1710:00 am -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$121
This Alaska Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:20 am -
1 stop9h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Alaska Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 9/17![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/186:16 am -
2 stops29h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/126:21 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$130
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 Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/2710:12 am -
2 stops8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$131
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/168:45 pm -
Nonstop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$132
This Frontier 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 Frontier 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 9/19![Frontier logo]()
$135
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 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (Orbitz) |
One-way from | $88 (Kiwi.com) |
Popular in | June |
Cheapest in | September |
Average price | $337 |
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 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 21, 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
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Tue 10/13
7:20 am-2:34 pm
1 stop9h 14m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$126
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Wed 1/6
2:11 pm-7:25 pm
1 stop7h 14m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$126
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Wed 10/14
3:49 pm-10:55 pm
1 stop9h 06m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$126
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Tue 12/15
12:39 pm-12:03 am
2 stops13h 24m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$131
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Mon 11/16
8:45 pm-11:35 pm
Nonstop4h 50m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$132
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Sat 12/12
12:39 pm-10:09 pm
2 stops11h 30m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$147
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Thu 1/7
7:00 am-4:32 pm
2 stops11h 32m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$171
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Sat 11/21
5:00 am-11:25 am
1 stop8h 25m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Tue 10/20
7:40 am-12:05 pm
1 stop6h 25m
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 10/24
2:14 pm-7:37 pm
1 stop7h 23m
Oakland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
Showing 1-10 of 59 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.
MDW-OAK
ORD-OAK
STL-OAK
PIA-OAK
MLI-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
MDW-OAK
ORD-OAK
STL-OAK
PIA-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 21, 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 $334 and $415 in December.The cheapest round-trip price found within the last 5 days was $197 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
Find flights from Illinois to Oakland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 21, 2026.
Illinois and Oakland flights
Browse other Illinois and Oakland flight options. Last updated on September 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 21, 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% |