$129+ Cheap flights from Oakland, CA (OAK) to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Jun 20 — Jun 271
Round-trip
1 adult, Economy
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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 May 21, 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 May 21, 2026.
This Southwest deal was found by Cheapflights users on 5/18. 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 10/25:05 am
OAK
- MDW
1 stop6h 00m
Southwest
Mon 10/59:30 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 5/18![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 5/16. 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 8/1311:20 am
OAK
- MDW
1 stop6h 55m
Southwest
Mon 8/1710:05 am
MDW
- OAK
1 stop6h 55m
Southwest
Deal found 5/16![Southwest logo]()
$331
This Alaska Airlines deal was found by Cheapflights users on 5/16. 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.
Sat 8/15:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Thu 8/66:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/16![Alaska Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sun 8/1611:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 8/198:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/17![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 5/19. 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.
Mon 7/611:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 7/149:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/19![Southwest logo]()
$335
This CheapOair deal was found by Cheapflights users on 5/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Wed 7/157:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$336
This Alaska Airlines deal was found by Cheapflights users on 5/18. 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.
Tue 10/137:00 am
OAK
- ORD
1 stop9h 53m
Alaska Airlines
Mon 10/197:20 am
ORD
- OAK
1 stop8h 44m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 5/17. 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 6/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 6/169:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/17![Southwest logo]()
$338
This Alaska Airlines deal was found by Cheapflights users on 5/17. 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.
Mon 6/82:58 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Tue 7/76:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$338
This Alaska Airlines deal was found by Cheapflights users on 5/17. 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 9/113:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Sat 9/127:20 am
ORD
- OAK
1 stop9h 13m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$340
This Alaska Airlines deal was found by Cheapflights users on 5/18. 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.
Fri 7/32:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Wed 7/156:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 5/18. 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.
Wed 9/911:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Sun 9/135:40 am
MDW
- OAK
1 stop6h 30m
Southwest
Deal found 5/18![Southwest logo]()
$342
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 May 21, 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 May 21, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/18. 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 10/122:44 pm
OAK
- ORD
1 stop7h 15m
Alaska Airlines
Fri 10/232:17 pm
ORD
- OAK
1 stop9h 31m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 5/20. 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.
Fri 7/102:55 pm
OAK
- MDW
1 stop7h 15m
Southwest
Thu 7/169:40 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/20![Southwest logo]()
$354
This Delta deal was found by Cheapflights users on 5/17. 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.
Tue 9/85:55 am
OAK
- MDW
2 stops10h 10m
Delta
Tue 9/159:30 am
MDW
- OAK
2 stops9h 01m
Delta
Deal found 5/17![Delta logo]()
$366
This Alaska Airlines deal was found by Cheapflights users on 5/17. 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 8/72:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Mon 8/107:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 5/16. 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.
Sat 6/67:55 pm
OAK
- MDW
1 stop7h 25m
Southwest
Mon 6/85:45 am
MDW
- OAK
1 stop7h 40m
Southwest
Deal found 5/16![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 5/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/25:05 pm
OAK
- ORD
2 stops12h 51m
Delta
Thu 8/67:45 am
ORD
- OAK
1 stop6h 07m
Delta
Deal found 5/20![Delta logo]()
$382
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:44 pm
OAK
- ORD
1 stop7h 15m
Alaska Airlines
Sun 11/17:00 am
ORD
- OAK
1 stop7h 52m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 5/18. 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.
Wed 6/245:15 am
OAK
- MDW
2 stops7h 20m
Southwest
Tue 6/301:10 pm
MDW
- OAK
1 stop7h 40m
Southwest
Deal found 5/18![Southwest logo]()
$366
This Alaska Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:55 am
OAK
- ORD
2 stops10h 04m
Alaska Airlines
Wed 9/167:20 am
ORD
- OAK
1 stop9h 13m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 5/16. 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 9/65:55 am
OAK
- MDW
2 stops10h 36m
Delta
Sat 9/129:20 am
MDW
- OAK
2 stops9h 11m
Delta
Deal found 5/16![Delta logo]()
$401
This Southwest deal was found by Cheapflights users on 5/19. 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.
Tue 7/285:15 am
OAK
- MDW
2 stops7h 20m
Southwest
Tue 8/43:10 pm
MDW
- OAK
2 stops8h 05m
Southwest
Deal found 5/19![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:30 pm
OAK
- ORD
1 stop7h 18m
Delta
Tue 8/43:48 pm
ORD
- OAK
2 stops10h 03m
Delta
Deal found 5/19![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 5/18. 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 10/26:10 am
OAK
- MDW
2 stops7h 05m
Southwest
Mon 10/55:30 pm
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 5/18![Southwest logo]()
$382
This Alaska Airlines deal was found by Cheapflights users on 5/16. 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 7/22:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Tue 7/76:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/16![Alaska Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 5/19. 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 7/2311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 7/278:15 pm
MDW
- OAK
1 stop6h 00m
Southwest
Deal found 5/19![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 5/18. 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.
Thu 8/134:57 pm
OAK
- STL
1 stop5h 44m
Delta
Tue 8/187:35 pm
STL
- OAK
1 stop6h 16m
Delta
Deal found 5/18![Delta logo]()
$432
This Alaska Airlines deal was found by Cheapflights users on 5/18. 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.
Sun 10/1112:20 pm
OAK
- ORD
1 stop9h 39m
Alaska Airlines
Fri 10/232:17 pm
ORD
- OAK
1 stop9h 31m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 5/18. 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.
Sun 8/211:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 8/105:55 pm
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 5/18![Southwest logo]()
$390
This Delta deal was found by Cheapflights users on 5/16. 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.
Sat 9/125:55 am
OAK
- STL
1 stop5h 26m
Delta
Wed 9/162:18 pm
STL
- OAK
2 stops11h 31m
Delta
Deal found 5/16![Delta logo]()
$437
This Alaska Airlines deal was found by Cheapflights users on 5/16. 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.
Sun 8/303:00 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Sun 9/67:00 am
ORD
- OAK
1 stop7h 49m
Alaska Airlines
Deal found 5/16![Alaska Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 5/16. 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 7/225:15 am
OAK
- MDW
2 stops7h 20m
Southwest
Sun 7/268:20 pm
MDW
- OAK
1 stop6h 25m
Southwest
Deal found 5/16![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 5/18. 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 6/3012:33 pm
OAK
- ORD
1 stop7h 24m
Delta
Tue 7/145:18 pm
ORD
- OAK
2 stops8h 32m
Delta
Deal found 5/18![Delta logo]()
$442
This Alaska Airlines deal was found by Cheapflights users on 5/20. 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.
Mon 8/318:04 am
OAK
- STL
1 stop7h 06m
Alaska Airlines
Tue 9/16:08 pm
STL
- OAK
1 stop20h 41m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 5/20. 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 6/2511:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 6/303:50 pm
MDW
- OAK
1 stop7h 10m
Southwest
Deal found 5/20![Southwest logo]()
$404
This Delta deal was found by Cheapflights users on 5/17. 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.
Sun 8/234:57 pm
OAK
- STL
1 stop5h 44m
Delta
Sat 8/295:00 pm
STL
- OAK
1 stop7h 04m
Delta
Deal found 5/17![Delta logo]()
$466
This Alaska Airlines deal was found by Cheapflights users on 5/20. 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.
Thu 6/182:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Mon 6/226:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 5/17. 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.
Fri 8/214:57 pm
OAK
- MLI
2 stops21h 25m
Delta
Fri 8/286:00 am
MLI
- OAK
2 stops12h 14m
Delta
Deal found 5/17![Delta logo]()
$528
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/274:45 pm
OAK
- STL
1 stop5h 25m
Southwest
Sat 8/11:30 pm
STL
- OAK
1 stop8h 00m
Southwest
Deal found 5/20![Southwest logo]()
$484
This Alaska Airlines deal was found by Cheapflights users on 5/16. 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 9/28:04 am
OAK
- STL
1 stop6h 59m
Alaska Airlines
Mon 9/75:59 pm
STL
- OAK
1 stop29h 27m
Alaska Airlines
Deal found 5/16![Alaska Airlines logo]()
$504
This Delta deal was found by Cheapflights users on 5/17. 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.
Fri 8/214:57 pm
OAK
- MLI
2 stops21h 25m
Delta
Sat 8/296:00 am
MLI
- OAK
2 stops12h 14m
Delta
Deal found 5/17![Delta logo]()
$528
Last-minute flights from Oakland to IllinoisDiscover last-minute flight deals from Oakland to Illinois. Data last updated May 21, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Illinois. Data last updated May 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
OAK
- ORD
2 stops12h 14m
Delta
Tue 6/97:37 pm
ORD
- OAK
1 stop6h 17m
Delta
Deal found 5/19![Delta logo]()
$346
This CheapOair deal was found by Cheapflights users on 5/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:13 pm
OAK
- ORD
1 stop15h 01m
Alaska Airlines
Tue 7/287:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$352
This Alaska Airlines deal was found by Cheapflights users on 5/17. 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.
Mon 6/82:58 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Wed 7/16:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$338
This Southwest deal was found by Cheapflights users on 5/17. 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 6/811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 6/169:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/17![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 5/17. 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 6/811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 6/1312:15 pm
MDW
- OAK
1 stop6h 55m
Southwest
Deal found 5/17![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 5/17. 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 6/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 6/169:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/17![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 5/16. 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.
Tue 6/98:35 pm
OAK
- MDW
1 stop6h 45m
Southwest
Mon 6/1511:45 am
MDW
- OAK
1 stop7h 30m
Southwest
Deal found 5/16![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:03 pm
OAK
- ORD
2 stops13h 02m
Delta
Tue 6/167:37 pm
ORD
- OAK
1 stop6h 17m
Delta
Deal found 5/19![Delta logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 5/17. 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.
Wed 6/102:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Thu 7/26:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/17![Alaska Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 5/21. 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 6/167:30 pm
OAK
- MDW
1 stop7h 10m
Southwest
Wed 6/179:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/21![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2211:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Wed 7/15:35 am
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 5/20![Southwest logo]()
$348
This CheapOair deal was found by Cheapflights users on 5/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/242:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Sat 6/275:59 pm
ORD
- OAK
1 stop6h 42m
Alaska Airlines
Deal found 5/18![Alaska Airlines logo]()
$345
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 May 21, 2026.
Search for one-way flight options from Oakland to Illinois. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
This Southwest deal was found by Cheapflights users on 5/17. 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.
Wed 8/1211:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 5/17![Southwest logo]()
$129
This Southwest deal was found by Cheapflights users on 5/20. 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.
Wed 7/152:50 pm
OAK
- MDW
1 stop7h 00m
Southwest
Deal found 5/20![Southwest logo]()
$139
This Delta deal was found by Cheapflights users on 5/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:33 pm
OAK
- ORD
1 stop7h 25m
Delta
Deal found 5/20![Delta logo]()
$139
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 7/145:15 am
OAK
- MDW
2 stops7h 20m
Southwest
Deal found 5/18![Southwest logo]()
$144
This CheapOair deal was found by Cheapflights users on 5/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:15 pm
OAK
- ORD
1 stop15h 06m
Alaska Airlines
Deal found 5/19![Alaska Airlines logo]()
$144
This Southwest deal was found by Cheapflights users on 5/17. 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 8/177:50 am
OAK
- MDW
2 stops7h 10m
Southwest
Deal found 5/17![Southwest logo]()
$154
This CheapOair deal was found by Cheapflights users on 5/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/102:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$154
This CheapOair deal was found by Cheapflights users on 5/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/62:58 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Deal found 5/16![Alaska Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 5/18. 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 8/105:20 am
OAK
- MDW
2 stops7h 15m
Southwest
Deal found 5/18![Southwest logo]()
$159
This CheapOair deal was found by Cheapflights users on 5/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/152:50 pm
OAK
- ORD
1 stop20h 31m
Alaska Airlines
Deal found 5/20![Alaska Airlines logo]()
$159
This Southwest deal was found by Cheapflights users on 5/18. 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 7/1311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/18![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 5/17. 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.
Wed 7/811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/17![Southwest logo]()
$171
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 May 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $330 (Southwest) |
One-way from | $129 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $453 |
Good round-trip deal | $444 or less |
Good one-way deal | $238 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 2,558,603 searches. Data last updated May 21, 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 - ORD
OAKORD
Oakland
Mon 10/12
2:44 pm-11:59 pm
1 stop7h 15m
Chicago O'Hare Intl
Fri 10/23
2:17 pm-9:48 pm
1 stop9h 31m
$340
OaklandChicago
OAK - ORD
OAKORD
Oakland
Fri 8/7
2:50 pm-11:36 pm
1 stop6h 46m
Chicago O'Hare Intl
Mon 8/10
7:59 pm-9:57 am
1 stop15h 58m
$340
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Fri 7/10
2:55 pm-12:10 am
1 stop7h 15m
Chicago Midway
Thu 7/16
9:40 pm-12:10 am
Nonstop4h 30m
$354
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 6/6
7:55 pm-5:20 am
1 stop7h 25m
Chicago Midway
Mon 6/8
5:45 am-11:25 am
1 stop7h 40m
$355
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 10/27
2:44 pm-11:59 pm
1 stop7h 15m
Chicago O'Hare Intl
Sun 11/1
7:00 am-12:52 pm
1 stop7h 52m
$362
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 9/15
11:55 am-11:59 pm
2 stops10h 04m
Chicago O'Hare Intl
Wed 9/16
7:20 am-2:33 pm
1 stop9h 13m
$364
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 9/8
5:55 am-6:05 pm
2 stops10h 10m
Chicago Midway
Tue 9/15
9:30 am-4:31 pm
2 stops9h 01m
$366
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Wed 6/24
5:15 am-2:35 pm
2 stops7h 20m
Chicago Midway
Tue 6/30
1:10 pm-6:50 pm
1 stop7h 40m
$366
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sun 8/2
5:05 pm-7:56 am
2 stops12h 51m
Chicago O'Hare Intl
Thu 8/6
7:45 am-11:52 am
1 stop6h 07m
$382
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 7/28
5:15 am-2:35 pm
2 stops7h 20m
Chicago Midway
Tue 8/4
3:10 pm-9:15 pm
2 stops8h 05m
$382
Showing 1-10 of 60 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-MDW
OAK-ORD
OAK-STL
OAK-MLI
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-MDW
OAK-ORD
OAK-STL
OAK-MLI
What is the cheapest month to book a flight from Oakland, California to Illinois?
Currently, April is the cheapest month in which you can book a flight from Oakland, California to Illinois (average of $93). Flying from Oakland, California to Illinois in December is currently the most expensive (average of $274). 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 May 21, 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 afternoon, which can drop the price by up to 57% versus a flight at noon.
How much does it cost to fly round-trip from Oakland, California to Illinois?
How far ahead should I book a flight from Oakland, California to Illinois?
Booking 20 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 May 21, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andUnited Airlines 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.
Crew
8.5
Food
7.0
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Food
7.0
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Food
7.0
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Food
7.0
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Food
7.0
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from Oakland to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Oakland to Illinois
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Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oakland to Illinois by cabin class
Find flights from Oakland to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oakland and Illinois flights
Browse other Oakland and Illinois flight options. Last updated on May 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oakland to Illinois flights
Consider these flights traveling from Oakland to Illinois.
Top 4 airlines flying from Oakland to Illinois
Discover the top 4 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 2,558,603 searches. Data last updated May 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$222 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$207 | Average$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$237 | Average$522 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$252 | Average$433 | FlexibilityNo cancel fee | On-time63% |