$63+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Mar 21 — Mar 281
1 adult, Economy
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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 February 19, 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 February 19, 2026.
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 4/2511:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 5/47:40 pm
MDW
- OAK
1 stop6h 25m
Southwest
Deal found 2/15![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/128:30 pm
OAK
- MDW
1 stop6h 05m
Southwest
Sat 3/149:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/15![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 2/16. 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 3/115:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 3/149:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/16![Southwest logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 2/17. 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 4/273:18 pm
OAK
- ORD
1 stop6h 25m
Alaska Airlines
Tue 5/58:50 am
ORD
- OAK
1 stop7h 48m
Alaska Airlines
Deal found 2/17![Alaska Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 2/17. 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 4/2510:45 am
OAK
- MDW
1 stop6h 35m
Southwest
Thu 4/309:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/17![Southwest logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 2/17. 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 4/292:09 pm
OAK
- ORD
1 stop7h 50m
Alaska Airlines
Sat 5/98:50 am
ORD
- OAK
1 stop7h 48m
Alaska Airlines
Deal found 2/17![Alaska Airlines logo]()
$230
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/178:05 am
OAK
- MDW
1 stop7h 00m
Southwest
Tue 3/245:10 pm
MDW
- OAK
1 stop6h 55m
Southwest
Deal found 2/15![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 2/19. 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 4/2112:34 pm
OAK
- ORD
1 stop6h 44m
Delta
Sat 4/252:09 pm
ORD
- OAK
1 stop9h 32m
Delta
Deal found 2/19![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/17. 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 4/11:45 pm
OAK
- MDW
1 stop5h 30m
Southwest
Fri 4/36:35 pm
MDW
- OAK
2 stops7h 35m
Southwest
Deal found 2/17![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 2/17. 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.
Sat 4/255:55 am
OAK
- ORD
2 stops10h 16m
Delta
Tue 4/287:10 pm
ORD
- OAK
1 stop6h 44m
Delta
Deal found 2/17![Delta logo]()
$242
This CheapOair deal was found by Cheapflights users on 2/19. 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 4/216:40 pm
OAK
- ORD
1 stop10h 00m
Alaska Airlines
Wed 4/223:52 pm
ORD
- OAK
1 stop8h 31m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$248
This Southwest deal was found by Cheapflights users on 2/17. 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 4/2111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 4/255:55 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/17![Southwest logo]()
$252
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 February 19, 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 February 19, 2026.
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/175:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Tue 3/249:00 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/15![Southwest logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:02 am
OAK
- ORD
1 stop10h 48m
Alaska Airlines
Tue 5/192:10 pm
ORD
- OAK
1 stop11h 40m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 2/16. 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.
Thu 4/912:35 pm
OAK
- ORD
1 stop6h 59m
Delta
Tue 4/147:10 pm
ORD
- OAK
1 stop6h 44m
Delta
Deal found 2/16![Delta logo]()
$278
This Southwest deal was found by Cheapflights users on 2/16. 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 4/283:00 pm
OAK
- MDW
1 stop6h 20m
Southwest
Thu 4/309:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/16![Southwest logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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.
Sat 5/22:09 pm
OAK
- ORD
1 stop7h 50m
Alaska Airlines
Mon 5/48:50 am
ORD
- OAK
1 stop7h 48m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$230
This Southwest deal was found by Cheapflights users on 2/16. 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 4/1811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 4/205:25 pm
MDW
- OAK
1 stop7h 05m
Southwest
Deal found 2/16![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 2/16. 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 4/81:30 pm
OAK
- MDW
1 stop6h 00m
Southwest
Mon 4/139:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/16![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 2/16. 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.
Thu 4/912:35 pm
OAK
- ORD
1 stop6h 59m
Delta
Wed 4/157:10 pm
ORD
- OAK
1 stop6h 44m
Delta
Deal found 2/16![Delta logo]()
$278
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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.
Thu 4/302:09 pm
OAK
- ORD
1 stop7h 50m
Alaska Airlines
Sat 5/28:50 am
ORD
- OAK
1 stop7h 48m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 2/18. 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 4/225:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 4/255:10 am
MDW
- OAK
1 stop6h 50m
Southwest
Deal found 2/18![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 2/17. 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 4/1312:10 pm
OAK
- MDW
1 stop7h 25m
Southwest
Fri 4/179:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/17![Southwest logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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 4/208:10 pm
OAK
- ORD
1 stop15h 03m
Alaska Airlines
Thu 4/238:50 am
ORD
- OAK
1 stop7h 48m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 2/17. 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 4/11:45 pm
OAK
- MDW
1 stop5h 30m
Southwest
Fri 4/33:30 pm
MDW
- OAK
1 stop7h 50m
Southwest
Deal found 2/17![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 2/18. 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.
Wed 3/185:55 am
OAK
- STL
1 stop5h 36m
Delta
Wed 3/256:12 pm
STL
- OAK
1 stop7h 34m
Delta
Deal found 2/18![Delta logo]()
$369
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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 3/317:00 am
OAK
- STL
1 stop29h 51m
Alaska Airlines
Tue 4/147:00 am
STL
- OAK
1 stop18h 43m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/172:00 pm
OAK
- ORD
1 stop6h 55m
Southwest
Tue 3/247:00 am
ORD
- OAK
1 stop8h 15m
Southwest
Deal found 2/15![Southwest logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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 3/317:00 am
OAK
- STL
1 stop29h 51m
Alaska Airlines
Wed 4/157:00 am
STL
- OAK
1 stop18h 43m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 2/17. 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 3/249:00 am
OAK
- ORD
1 stop7h 50m
Southwest
Wed 3/254:15 pm
ORD
- OAK
1 stop7h 30m
Southwest
Deal found 2/17![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 2/18. 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.
Wed 4/14:49 pm
OAK
- STL
1 stop5h 32m
Delta
Mon 4/136:45 pm
STL
- OAK
1 stop7h 09m
Delta
Deal found 2/18![Delta logo]()
$382
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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.
Wed 4/17:00 am
OAK
- STL
1 stop14h 59m
Alaska Airlines
Wed 4/157:00 am
STL
- OAK
1 stop18h 43m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 2/17. 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 4/2111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 4/255:55 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 2/17![Southwest logo]()
$252
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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 3/247:00 am
OAK
- STL
1 stop14h 59m
Alaska Airlines
Wed 3/257:00 am
STL
- OAK
1 stop18h 43m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/186:50 am
OAK
- MDW
1 stop7h 50m
Southwest
Mon 3/236:25 pm
MDW
- OAK
1 stop6h 20m
Southwest
Deal found 2/19![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 2/18. 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 5/111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 5/46:25 pm
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 2/18![Southwest logo]()
$268
This CheapOair deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 5/131:01 pm
OAK
- STL
1 stop8h 53m
Alaska Airlines
Fri 5/157:41 pm
STL
- OAK
1 stop16h 14m
Alaska Airlines
Deal found 2/15![Alaska Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 4/156:35 am
OAK
- ORD
1 stop6h 25m
Southwest
Fri 4/176:15 pm
ORD
- OAK
1 stop6h 20m
Southwest
Deal found 2/15![Southwest logo]()
$272
This CheapOair deal was found by Cheapflights users on 2/18. 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 3/1110:04 am
OAK
- STL
2 stops25h 47m
Alaska Airlines
Wed 3/183:50 pm
STL
- OAK
1 stop9h 53m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 2/17. 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 4/203:45 pm
OAK
- ORD
1 stop6h 10m
Southwest
Thu 4/237:20 pm
ORD
- OAK
1 stop6h 45m
Southwest
Deal found 2/17![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 2/17. 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 4/2112:34 pm
OAK
- EVV
2 stops26h 44m
Delta
Mon 4/275:58 pm
EVV
- OAK
2 stops19h 55m
Delta
Deal found 2/17![Delta logo]()
$665
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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 4/138:10 pm
OAK
- STL
2 stops25h 49m
Alaska Airlines
Wed 4/157:00 am
STL
- OAK
1 stop18h 43m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$380
Last-minute flights from Oakland to IllinoisDiscover last-minute flight deals from Oakland to Illinois. Data last updated February 19, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Illinois. Data last updated February 19, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/16. 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 3/1012:35 pm
OAK
- ORD
1 stop6h 59m
Delta
Tue 3/177:10 pm
ORD
- OAK
1 stop6h 36m
Delta
Deal found 2/16![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/16. 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 3/105:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Thu 3/126:05 am
MDW
- OAK
1 stop7h 40m
Southwest
Deal found 2/16![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 2/16. 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 3/115:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 3/149:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/16![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/115:55 am
OAK
- ORD
2 stops10h 39m
Delta
Tue 3/177:10 pm
ORD
- OAK
1 stop6h 36m
Delta
Deal found 2/19![Delta logo]()
$242
This CheapOair deal was found by Cheapflights users on 2/19. 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.
Wed 3/115:31 pm
OAK
- ORD
1 stop16h 30m
Alaska Airlines
Tue 3/177:00 am
ORD
- OAK
1 stop11h 37m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/128:30 pm
OAK
- MDW
1 stop6h 05m
Southwest
Sat 3/149:40 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/15![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/178:05 am
OAK
- MDW
1 stop7h 00m
Southwest
Tue 3/249:00 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/15![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/176:35 am
OAK
- ORD
2 stops10h 15m
Southwest
Tue 3/247:00 am
ORD
- OAK
1 stop8h 15m
Southwest
Deal found 2/15![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 2/18. 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 3/1712:35 pm
OAK
- ORD
1 stop6h 59m
Delta
Tue 3/247:20 am
ORD
- OAK
1 stop6h 31m
Delta
Deal found 2/18![Delta logo]()
$278
This CheapOair deal was found by Cheapflights users on 2/18. 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.
Tue 3/175:31 pm
OAK
- ORD
1 stop11h 08m
Alaska Airlines
Tue 3/243:22 pm
ORD
- OAK
1 stop10h 21m
Alaska Airlines
Deal found 2/18![Alaska Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/186:50 am
OAK
- MDW
1 stop7h 50m
Southwest
Mon 3/236:25 pm
MDW
- OAK
1 stop6h 20m
Southwest
Deal found 2/19![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 2/17. 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 3/2511:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Mon 3/309:30 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 2/17![Southwest logo]()
$282
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 February 19, 2026.
Search for one-way flight options from Oakland to Illinois. Find affordable one-way fares based on user searches. Data last updated February 19, 2026.
This Southwest deal was found by Cheapflights users on 2/16. 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 4/1811:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 2/16![Southwest logo]()
$63
This Southwest deal was found by Cheapflights users on 2/16. 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 4/2512:55 pm
OAK
- ORD
1 stop7h 25m
Southwest
Deal found 2/16![Southwest logo]()
$73
This Southwest deal was found by Cheapflights users on 2/16. 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 4/255:50 pm
OAK
- MDW
1 stop9h 50m
Southwest
Deal found 2/16![Southwest logo]()
$78
This Southwest deal was found by Cheapflights users on 2/18. 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 4/145:50 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 2/18![Southwest logo]()
$109
This CheapOair deal was found by Cheapflights users on 2/19. 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.
Mon 4/273:18 pm
OAK
- ORD
1 stop6h 25m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$112
This Expedia deal was found by Cheapflights users on 2/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:46 am
OAK
- ORD
1 stop10h 17m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$117
This Southwest deal was found by Cheapflights users on 2/17. 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 4/11:45 pm
OAK
- MDW
1 stop5h 30m
Southwest
Deal found 2/17![Southwest logo]()
$119
This Southwest deal was found by Cheapflights users on 2/19. 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 3/249:00 am
OAK
- ORD
1 stop7h 50m
Southwest
Deal found 2/19![Southwest logo]()
$119
This Delta deal was found by Cheapflights users on 2/18. 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.
Fri 4/105:55 am
OAK
- MDW
2 stops14h 36m
Delta
Deal found 2/18![Delta logo]()
$124
This Delta deal was found by Cheapflights users on 2/17. 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.
Wed 3/115:55 am
OAK
- ORD
2 stops8h 48m
Delta
Deal found 2/17![Delta logo]()
$124
This Expedia deal was found by Cheapflights users on 2/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:02 am
OAK
- ORD
1 stop15h 53m
Alaska Airlines
Deal found 2/16![Alaska Airlines logo]()
$134
This CheapOair deal was found by Cheapflights users on 2/19. 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 4/216:40 pm
OAK
- ORD
1 stop10h 00m
Alaska Airlines
Deal found 2/19![Alaska Airlines logo]()
$137
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 February 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $181 (Southwest) |
One-way from | $63 (Southwest) |
Popular in | November |
Cheapest in | September |
Average price | $357 |
Good round-trip deal | $334 or less |
Good one-way deal | $178 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 February 19, 2026.
Use the filters below to find and compare flights from Oakland to Illinois that are best for you.
Fly from
Oakland
Fly to
Illinois
Route
Depart
Return
Price
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 3/17
5:50 am-11:55 am
Nonstop4h 05m
Chicago Midway
Tue 3/24
9:00 pm-11:40 pm
Nonstop4h 40m
$217
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 5/16
6:02 am-6:50 pm
1 stop10h 48m
Chicago O'Hare Intl
Tue 5/19
2:10 pm-11:50 pm
1 stop11h 40m
$223
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 4/28
3:00 pm-11:20 pm
1 stop6h 20m
Chicago Midway
Thu 4/30
9:50 pm-12:25 am
Nonstop4h 35m
$227
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 4/18
11:55 pm-6:00 am
Nonstop4h 05m
Chicago Midway
Mon 4/20
5:25 pm-10:30 pm
1 stop7h 05m
$227
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Wed 4/8
1:30 pm-9:30 pm
1 stop6h 00m
Chicago Midway
Mon 4/13
9:50 pm-12:25 am
Nonstop4h 35m
$227
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Wed 4/22
5:50 am-11:55 am
Nonstop4h 05m
Chicago Midway
Sat 4/25
5:10 am-10:00 am
1 stop6h 50m
$227
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Mon 4/13
12:10 pm-9:35 pm
1 stop7h 25m
Chicago Midway
Fri 4/17
9:50 pm-12:25 am
Nonstop4h 35m
$227
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 5/2
2:09 pm-11:59 pm
1 stop7h 50m
Chicago O'Hare Intl
Mon 5/4
8:50 am-2:38 pm
1 stop7h 48m
$230
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Wed 4/1
1:45 pm-9:15 pm
1 stop5h 30m
Chicago Midway
Fri 4/3
3:30 pm-9:20 pm
1 stop7h 50m
$237
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 3/17
2:00 pm-10:55 pm
1 stop6h 55m
Chicago O'Hare Intl
Tue 3/24
7:00 am-1:15 pm
1 stop8h 15m
$237
Showing 1-10 of 57 results
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-EVV
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-EVV
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 $123). Flying from Oakland, California to Illinois in December is currently the most expensive (average of $233). 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 February 19, 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 54% versus a flight at noon.
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 February 19, 2026.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta 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.
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Comfort
7.8
Crew
8.5
Entertainment
7.0
Boarding
8.1
Food
7.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
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 February 19, 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 February 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$222 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$163 | Average$356 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$532 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$246 | Average$423 | FlexibilityNo cancel fee | On-time63% |