$119+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Aug 5 — Aug 121
Round-trip
1 adult, Economy
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Find cheap flights from Oakland to Illinois with Cheapflights
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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 July 6, 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 July 6, 2026.
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/811:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Sat 8/221:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/1![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/158:30 am
OAK
- MDW
1 stop7h 05m
Southwest
Sat 8/221:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/1![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/156:00 pm
OAK
- MDW
1 stop8h 30m
Southwest
Wed 8/195:20 pm
MDW
- OAK
1 stop8h 20m
Southwest
Deal found 7/1![Southwest logo]()
$257
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/112:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Tue 8/186:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/125:30 am
OAK
- MDW
1 stop6h 00m
Southwest
Tue 8/182:15 pm
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 7/1![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/165:30 am
OAK
- MDW
1 stop6h 00m
Southwest
Thu 9/178:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 7/1![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/1711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Thu 8/2010:15 am
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/3![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/56:55 pm
OAK
- MDW
1 stop7h 35m
Southwest
Mon 8/107:35 pm
MDW
- OAK
1 stop6h 30m
Southwest
Deal found 7/1![Southwest logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/102:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Wed 8/196:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/1711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 8/194:45 pm
MDW
- OAK
1 stop6h 35m
Southwest
Deal found 7/3![Southwest logo]()
$279
This Booking.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:13 pm
OAK
- ORD
1 stop28h 49m
Multiple Airlines
Wed 9/92:18 pm
ORD
- OAK
1 stop9h 10m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/58:55 am
OAK
- MDW
1 stop8h 15m
Southwest
Wed 8/128:20 am
MDW
- OAK
1 stop7h 45m
Southwest
Deal found 7/3![Southwest logo]()
$289
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 July 6, 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 July 6, 2026.
This Southwest deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 8/188:55 am
OAK
- MDW
1 stop8h 15m
Southwest
Tue 8/258:35 am
MDW
- OAK
1 stop6h 35m
Southwest
Deal found 7/4![Southwest logo]()
$289
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/241:29 pm
OAK
- ORD
1 stop8h 30m
Alaska Airlines
Mon 8/316:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 10/312:39 pm
OAK
- ORD
1 stop7h 13m
Delta
Sun 10/47:40 pm
ORD
- OAK
1 stop6h 19m
Delta
Deal found 7/5![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/209:15 am
OAK
- MDW
1 stop7h 10m
Southwest
Mon 8/242:05 pm
MDW
- OAK
2 stops7h 40m
Southwest
Deal found 7/1![Southwest logo]()
$294
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 7/2![Alaska Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/215:20 am
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 8/2410:15 am
MDW
- OAK
1 stop6h 35m
Southwest
Deal found 7/3![Southwest logo]()
$321
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/73:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Tue 9/87:20 am
ORD
- OAK
1 stop9h 13m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 10/55:00 pm
OAK
- ORD
2 stops14h 24m
Delta
Wed 10/711:19 am
ORD
- OAK
2 stops14h 37m
Delta
Deal found 7/5![Delta logo]()
$401
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 8/1511:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 8/1910:15 am
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/6![Southwest logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/255:10 pm
OAK
- ORD
1 stop18h 12m
Alaska Airlines
Mon 8/316:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/2210:15 am
OAK
- MDW
1 stop8h 00m
Southwest
Sun 8/308:25 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 7/3![Southwest logo]()
$348
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 9/66:00 am
OAK
- STL
1 stop5h 38m
Delta
Sat 9/125:00 pm
STL
- OAK
1 stop7h 01m
Delta
Deal found 7/3![Delta logo]()
$454
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/233:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Mon 8/316:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 7/2711:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Fri 7/319:40 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 7/1![Southwest logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/172:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Sat 8/226:00 am
ORD
- OAK
2 stops12h 30m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/118:55 am
OAK
- STL
2 stops7h 20m
Southwest
Sat 8/157:10 am
STL
- OAK
1 stop5h 55m
Southwest
Deal found 7/2![Southwest logo]()
$366
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/233:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Sat 8/296:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 10/411:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 10/78:35 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 7/1![Southwest logo]()
$367
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/63:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Wed 9/97:20 am
ORD
- OAK
1 stop9h 13m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/139:15 am
OAK
- MDW
1 stop6h 05m
Southwest
Sun 8/168:25 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 7/5![Southwest logo]()
$381
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/266:52 pm
OAK
- STL
1 stop20h 18m
Alaska Airlines
Mon 8/316:08 pm
STL
- OAK
1 stop20h 41m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/203:45 pm
OAK
- STL
1 stop7h 00m
Southwest
Wed 8/265:35 am
STL
- OAK
1 stop7h 30m
Southwest
Deal found 7/1![Southwest logo]()
$390
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 10/25:10 pm
OAK
- ORD
1 stop18h 15m
Alaska Airlines
Mon 10/127:49 pm
ORD
- OAK
1 stop17h 36m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$393
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 11/213:30 pm
OAK
- ORD
1 stop6h 29m
Alaska Airlines
Tue 12/19:20 am
ORD
- OAK
1 stop7h 24m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 11/177:55 am
OAK
- STL
1 stop5h 25m
Southwest
Sun 11/225:10 am
STL
- OAK
1 stop6h 55m
Southwest
Deal found 7/1![Southwest logo]()
$425
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/258:04 am
OAK
- STL
1 stop7h 06m
Alaska Airlines
Wed 8/266:35 am
STL
- OAK
1 stop8h 38m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 10/83:55 pm
OAK
- STL
Nonstop5h 30m
Southwest
Mon 10/125:50 pm
STL
- OAK
1 stop6h 45m
Southwest
Deal found 7/2![Southwest logo]()
$449
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:45 am
OAK
- STL
1 stop6h 35m
Southwest
Mon 11/239:35 am
STL
- OAK
1 stop8h 45m
Southwest
Deal found 7/2![Southwest logo]()
$489
Last-minute flights from Oakland to IllinoisDiscover last-minute flight deals from Oakland to Illinois. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Illinois. Data last updated July 6, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/56:55 pm
OAK
- MDW
1 stop7h 35m
Southwest
Mon 8/107:35 pm
MDW
- OAK
1 stop6h 30m
Southwest
Deal found 7/1![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/58:55 am
OAK
- MDW
1 stop8h 15m
Southwest
Wed 8/128:20 am
MDW
- OAK
1 stop7h 45m
Southwest
Deal found 7/3![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/811:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Sat 8/221:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/1![Southwest logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/102:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Wed 8/196:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/112:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Tue 8/186:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/125:30 am
OAK
- MDW
1 stop6h 00m
Southwest
Tue 8/182:15 pm
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 7/1![Southwest logo]()
$262
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/132:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Thu 8/206:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/158:30 am
OAK
- MDW
1 stop7h 05m
Southwest
Sat 8/221:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/1![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/156:00 pm
OAK
- MDW
1 stop8h 30m
Southwest
Wed 8/195:20 pm
MDW
- OAK
1 stop8h 20m
Southwest
Deal found 7/2![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/1711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Thu 8/2010:15 am
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/3![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/1711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 8/194:45 pm
MDW
- OAK
1 stop6h 35m
Southwest
Deal found 7/3![Southwest logo]()
$279
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/209:15 am
OAK
- MDW
1 stop7h 10m
Southwest
Mon 8/242:05 pm
MDW
- OAK
2 stops7h 40m
Southwest
Deal found 7/3![Southwest logo]()
$294
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 July 6, 2026.
Search for one-way flight options from Oakland to Illinois. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 7/3![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:39 pm
OAK
- STL
1 stop26h 38m
Frontier
Deal found 7/1![Frontier logo]()
$126
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/127:15 pm
OAK
- MDW
1 stop8h 40m
Southwest
Deal found 7/1![Southwest logo]()
$129
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/52:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$129
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/256:50 am
OAK
- MDW
2 stops7h 10m
Southwest
Deal found 7/1![Southwest logo]()
$134
This CheapOair deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/18:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$134
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/245:20 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 7/1![Southwest logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 9/912:13 pm
OAK
- ORD
1 stop15h 29m
Frontier
Deal found 7/4![Frontier logo]()
$139
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/56:55 pm
OAK
- MDW
1 stop7h 35m
Southwest
Deal found 7/3![Southwest logo]()
$145
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/132:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/212:13 pm
OAK
- ORD
1 stop28h 49m
Frontier
Deal found 7/1![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/2612:13 pm
OAK
- ORD
1 stop28h 49m
Frontier
Deal found 7/1![Frontier logo]()
$149
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 July 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | June |
Cheapest in | September |
Average price | $432 |
Good round-trip deal | $435 or less |
Good one-way deal | $217 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 July 6, 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 - MDW
OAKMDW
Oakland
Tue 8/18
8:55 am-7:10 pm
1 stop8h 15m
Chicago Midway
Tue 8/25
8:35 am-1:10 pm
1 stop6h 35m
$289
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Thu 8/20
9:15 am-6:25 pm
1 stop7h 10m
Chicago Midway
Mon 8/24
2:05 pm-7:45 pm
2 stops7h 40m
$294
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Fri 8/21
5:20 am-11:25 am
Nonstop4h 05m
Chicago Midway
Mon 8/24
10:15 am-2:50 pm
1 stop6h 35m
$321
OaklandChicago
OAK - ORD
OAKORD
Oakland
Mon 8/24
1:29 pm-11:59 pm
1 stop8h 30m
Chicago O'Hare Intl
Mon 8/31
6:01 am-11:06 am
1 stop7h 05m
$322
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
$331
Quickest round-trip
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 8/15
11:55 pm-5:55 am
Nonstop4h 00m
Chicago Midway
Wed 8/19
10:15 am-12:40 pm
Nonstop4h 25m
$335
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 8/22
10:15 am-8:15 pm
1 stop8h 00m
Chicago Midway
Sun 8/30
8:25 pm-10:55 pm
Nonstop4h 30m
$348
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Mon 7/27
11:55 pm-6:00 am
Nonstop4h 05m
Chicago Midway
Fri 7/31
9:40 pm-12:15 am
Nonstop4h 35m
$353
OaklandChicago
OAK - ORD
OAKORD
Oakland
Mon 9/7
3:13 pm-11:59 pm
1 stop6h 46m
Chicago O'Hare Intl
Tue 9/8
7:20 am-2:33 pm
1 stop9h 13m
$355
OaklandSt. Louis
OAK - STL
OAKSTL
Oakland
Tue 8/11
8:55 am-6:15 pm
2 stops7h 20m
Lambert-St Louis
Sat 8/15
7:10 am-11:05 am
1 stop5h 55m
$366
Showing 1-10 of 58 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-BMI
OAK-BRL
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-BMI
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 July 6, 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 19 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 July 6, 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.
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
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 July 6, 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 3 airlines flying from Oakland to Illinois
Discover the top 3 airlines that operate flights from Oakland to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$207 | Average$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$431 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$272 | Average$522 | FlexibilityNo cancel fee | On-time75% |