$119+ Cheap flights from Illinois to Oakland, CA (OAK)
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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Jun 5 — Jun 121
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Oakland with Cheapflights
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Cheapest flights from Illinois to OaklandExplore the most affordable flight options available from Illinois to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
Explore the most affordable flight options available from Illinois to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
This Southwest deal was found by Cheapflights users on 5/3. 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.
Tue 6/28:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Tue 6/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/3![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 5/3. 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 5/289:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Tue 6/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/3![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 5/3. 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 6/175:35 am
MDW
- OAK
1 stop6h 15m
Southwest
Wed 6/249:00 pm
OAK
- MDW
1 stop6h 25m
Southwest
Deal found 5/3![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 5/3. 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.
Tue 6/27:45 pm
ORD
- OAK
1 stop6h 12m
Delta
Tue 6/912:33 pm
OAK
- ORD
1 stop7h 24m
Delta
Deal found 5/3![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 5/4. 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 6/28:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Mon 6/88:30 pm
OAK
- MDW
1 stop6h 10m
Southwest
Deal found 5/4![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 5/3. 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 5/289:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sat 6/611:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/3![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 5/5. 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.
Wed 7/19:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Wed 7/83:55 pm
OAK
- MDW
1 stop6h 10m
Southwest
Deal found 5/5![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 5/2. 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 5/236:15 am
MDW
- OAK
1 stop8h 05m
Southwest
Wed 5/278:15 am
OAK
- MDW
1 stop6h 45m
Southwest
Deal found 5/2![Southwest logo]()
$271
This CheapOair deal was found by Cheapflights users on 5/1. 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 5/237:59 pm
ORD
- OAK
1 stop15h 46m
Alaska Airlines
Tue 5/268:15 pm
OAK
- ORD
1 stop14h 59m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$271
This CheapOair deal was found by Cheapflights users on 5/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:42 pm
ORD
- OAK
1 stop15h 01m
Alaska Airlines
Wed 9/233:00 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$277
This CheapOair deal was found by Cheapflights users on 5/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:10 pm
ORD
- OAK
1 stop11h 40m
Alaska Airlines
Mon 6/12:58 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$281
This CheapOair deal was found by Cheapflights users on 5/1. 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.
Thu 6/42:10 pm
ORD
- OAK
1 stop11h 40m
Alaska Airlines
Sat 6/62:58 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$285
Best flights from Illinois to OaklandDiscover carefully curated flight deals from Illinois to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
Discover carefully curated flight deals from Illinois to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
This Southwest deal was found by Cheapflights users on 5/4. 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 6/25:30 pm
MDW
- OAK
1 stop6h 35m
Southwest
Mon 6/89:05 pm
OAK
- MDW
1 stop6h 20m
Southwest
Deal found 5/4![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:45 pm
ORD
- OAK
1 stop6h 12m
Delta
Mon 6/86:00 am
OAK
- ORD
2 stops11h 31m
Delta
Deal found 5/2![Delta logo]()
$311
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/102:20 pm
ORD
- OAK
1 stop10h 21m
Alaska Airlines
Tue 7/710:37 am
OAK
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 5/2. 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 5/236:15 am
MDW
- OAK
1 stop8h 05m
Southwest
Fri 5/2911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/2![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/77:37 pm
ORD
- OAK
1 stop6h 17m
Delta
Tue 6/912:33 pm
OAK
- ORD
1 stop7h 24m
Delta
Deal found 5/2![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 5/2. 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 5/268:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sat 5/3012:55 pm
OAK
- MDW
1 stop8h 30m
Southwest
Deal found 5/2![Southwest logo]()
$319
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 9/242:18 pm
ORD
- OAK
1 stop10h 21m
Alaska Airlines
Sat 10/37:00 am
OAK
- ORD
1 stop8h 01m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 5/2. 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 6/235:50 pm
MDW
- OAK
2 stops7h 30m
Southwest
Tue 6/303:55 pm
OAK
- MDW
1 stop6h 10m
Southwest
Deal found 5/2![Southwest logo]()
$320
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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.
Sat 5/237:59 pm
ORD
- OAK
1 stop15h 46m
Alaska Airlines
Wed 5/272:58 pm
OAK
- ORD
2 stops13h 22m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 5/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:36 pm
STL
- OAK
2 stops8h 18m
Delta
Tue 6/235:03 pm
OAK
- STL
1 stop5h 40m
Delta
Deal found 5/4![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:00 pm
ORD
- OAK
1 stop8h 49m
Delta
Wed 9/91:15 pm
OAK
- ORD
1 stop6h 43m
Delta
Deal found 5/2![Delta logo]()
$368
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 5/227:59 pm
ORD
- OAK
1 stop29h 51m
Alaska Airlines
Sat 5/302:58 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 5/1. 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 9/136:00 am
MDW
- OAK
1 stop7h 10m
Southwest
Wed 9/307:50 am
OAK
- MDW
1 stop7h 10m
Southwest
Deal found 5/1![Southwest logo]()
$342
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 7/36:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Wed 7/152:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 5/2. 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 6/205:05 pm
MDW
- OAK
2 stops7h 30m
Southwest
Tue 6/2311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/2![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 5/3. 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.
Tue 6/165:36 pm
STL
- OAK
2 stops8h 18m
Delta
Tue 6/305:03 pm
OAK
- STL
1 stop5h 40m
Delta
Deal found 5/3![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 5/2. 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.
Mon 7/209:40 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Thu 7/2311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/2![Southwest logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:00 am
ORD
- OAK
1 stop7h 49m
Alaska Airlines
Wed 9/92:14 pm
OAK
- ORD
1 stop7h 45m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 5/6. 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.
Wed 5/274:30 pm
MDW
- OAK
1 stop6h 15m
Southwest
Fri 5/298:55 pm
OAK
- MDW
1 stop6h 55m
Southwest
Deal found 5/6![Southwest logo]()
$364
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Tue 6/25:33 pm
STL
- OAK
1 stop17h 22m
Alaska Airlines
Wed 6/31:01 pm
OAK
- STL
1 stop8h 53m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 5/5. 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.
Thu 5/287:59 pm
STL
- OAK
1 stop5h 58m
Delta
Wed 6/36:00 am
OAK
- STL
1 stop5h 32m
Delta
Deal found 5/5![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 5/2. 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 8/208:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Sun 8/234:35 pm
OAK
- MDW
1 stop6h 15m
Southwest
Deal found 5/2![Southwest logo]()
$381
This Alaska Airlines deal was found by Cheapflights users on 5/2. 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.
Sat 9/56:00 am
STL
- OAK
1 stop9h 13m
Alaska Airlines
Mon 9/78:04 am
OAK
- STL
1 stop6h 59m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$489
This Southwest deal was found by Cheapflights users on 5/2. 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 6/46:30 pm
STL
- OAK
1 stop7h 40m
Southwest
Fri 6/124:45 pm
OAK
- STL
1 stop5h 25m
Southwest
Deal found 5/2![Southwest logo]()
$428
This Southwest deal was found by Cheapflights users on 5/1. 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 5/286:20 am
STL
- OAK
1 stop5h 50m
Southwest
Sun 5/3111:55 pm
OAK
- STL
1 stop7h 10m
Southwest
Deal found 5/1![Southwest logo]()
$464
This Southwest deal was found by Cheapflights users on 5/5. 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 8/275:45 am
STL
- OAK
2 stops8h 50m
Southwest
Sun 8/301:45 pm
OAK
- STL
1 stop7h 15m
Southwest
Deal found 5/5![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 5/4. 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 6/165:25 am
STL
- OAK
2 stops8h 10m
Southwest
Tue 6/239:55 am
OAK
- STL
2 stops7h 10m
Southwest
Deal found 5/4![Southwest logo]()
$488
This Delta deal was found by Cheapflights users on 5/5. 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.
Sun 6/75:56 am
MLI
- OAK
2 stops12h 27m
Delta
Sun 6/145:03 pm
OAK
- MLI
2 stops15h 13m
Delta
Deal found 5/5![Delta logo]()
$943
This Southwest deal was found by Cheapflights users on 5/5. 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.
Fri 7/247:45 pm
STL
- OAK
1 stop6h 30m
Southwest
Sun 7/2611:55 pm
OAK
- STL
1 stop7h 15m
Southwest
Deal found 5/5![Southwest logo]()
$489
Last-minute flights from Illinois to OaklandDiscover last-minute flight deals from Illinois to Oakland. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Oakland. Data last updated May 6, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/2. 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 5/236:15 am
MDW
- OAK
1 stop8h 05m
Southwest
Wed 5/278:15 am
OAK
- MDW
1 stop6h 45m
Southwest
Deal found 5/2![Southwest logo]()
$271
This CheapOair deal was found by Cheapflights users on 5/1. 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 5/237:59 pm
ORD
- OAK
1 stop15h 46m
Alaska Airlines
Tue 5/268:15 pm
OAK
- ORD
1 stop14h 59m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$271
This CheapOair deal was found by Cheapflights users on 5/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:10 pm
ORD
- OAK
1 stop11h 40m
Alaska Airlines
Mon 6/12:58 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 5/3. 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 5/289:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Tue 6/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/3![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 5/6. 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.
Thu 5/288:00 am
ORD
- OAK
2 stops8h 55m
Southwest
Wed 6/310:15 am
OAK
- ORD
1 stop6h 35m
Southwest
Deal found 5/6![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 5/4. 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.
Mon 6/16:55 am
MDW
- OAK
1 stop7h 15m
Southwest
Mon 6/88:30 pm
OAK
- MDW
1 stop6h 10m
Southwest
Deal found 5/4![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 5/3. 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.
Tue 6/28:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Tue 6/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/3![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 5/3. 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.
Tue 6/27:45 pm
ORD
- OAK
1 stop6h 12m
Delta
Tue 6/912:33 pm
OAK
- ORD
1 stop7h 24m
Delta
Deal found 5/3![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 5/4. 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 6/28:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Mon 6/88:30 pm
OAK
- MDW
1 stop6h 10m
Southwest
Deal found 5/4![Southwest logo]()
$261
This Southwest deal was found by Cheapflights users on 5/1. 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 6/49:40 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Sat 6/611:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/1![Southwest logo]()
$265
This CheapOair deal was found by Cheapflights users on 5/1. 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.
Thu 6/42:10 pm
ORD
- OAK
1 stop11h 40m
Alaska Airlines
Sat 6/62:58 pm
OAK
- ORD
1 stop6h 57m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$285
This Southwest deal was found by Cheapflights users on 5/3. 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 6/175:35 am
MDW
- OAK
1 stop6h 15m
Southwest
Wed 6/249:00 pm
OAK
- MDW
1 stop6h 25m
Southwest
Deal found 5/3![Southwest logo]()
$252
One-way flights from Illinois to OaklandSearch for one-way flight options from Illinois to Oakland. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
Search for one-way flight options from Illinois to Oakland. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Southwest deal was found by Cheapflights users on 5/3. 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 6/179:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/3![Southwest logo]()
$119
This Delta deal was found by Cheapflights users on 5/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:45 am
ORD
- OAK
1 stop6h 03m
Delta
Deal found 5/4![Delta logo]()
$129
This Southwest deal was found by Cheapflights users on 5/1. 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 5/2711:00 am
MDW
- OAK
1 stop7h 50m
Southwest
Deal found 5/1![Southwest logo]()
$129
This Southwest deal was found by Cheapflights users on 5/2. 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 5/289:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 5/2![Southwest logo]()
$133
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:22 pm
MDW
- OAK
2 stops12h 35m
Delta
Deal found 5/1![Delta logo]()
$134
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 5/279:00 am
ORD
- OAK
1 stop7h 14m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$139
This Southwest deal was found by Cheapflights users on 5/6. 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.
Tue 6/211:00 am
MDW
- OAK
1 stop7h 50m
Southwest
Deal found 5/6![Southwest logo]()
$139
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 6/49:00 am
ORD
- OAK
1 stop7h 14m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$143
This CheapOair deal was found by Cheapflights users on 5/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:10 pm
ORD
- OAK
1 stop11h 40m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$144
This CheapOair deal was found by Cheapflights users on 5/1. 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.
Thu 5/282:10 pm
ORD
- OAK
1 stop11h 40m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$148
This Southwest deal was found by Cheapflights users on 5/4. 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 7/289:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/4![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 5/4. 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.
Fri 5/299:50 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 5/4![Southwest logo]()
$177
Find flight deals from Illinois to Oakland
Keep the following information in mind while searching for Illinois to Oakland flight deals. Data was last updated May 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 | February |
Cheapest in | September |
Average price | $319 |
Good round-trip deal | $373 or less |
Good one-way deal | $221 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Oakland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
Use the filters below to find and compare flights from Illinois to Oakland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 6/2
5:30 pm-10:05 pm
1 stop6h 35m
Oakland
Mon 6/8
9:05 pm-5:25 am
1 stop6h 20m
$271
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Tue 6/2
7:45 pm-11:57 pm
1 stop6h 12m
Oakland
Mon 6/8
6:00 am-7:31 pm
2 stops11h 31m
$311
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sat 5/23
6:15 am-12:20 pm
1 stop8h 05m
Oakland
Fri 5/29
11:55 pm-6:00 am
Nonstop4h 05m
$319
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 5/26
8:50 pm-11:25 pm
Nonstop4h 35m
Oakland
Sat 5/30
12:55 pm-11:25 pm
1 stop8h 30m
$319
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 6/23
5:50 pm-11:20 pm
2 stops7h 30m
Oakland
Tue 6/30
3:55 pm-12:05 am
1 stop6h 10m
$320
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Sun 6/7
7:37 pm-11:54 pm
1 stop6h 17m
Oakland
Tue 6/9
12:33 pm-9:57 pm
1 stop7h 24m
$342
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sun 9/13
6:00 am-11:10 am
1 stop7h 10m
Oakland
Wed 9/30
7:50 am-5:00 pm
1 stop7h 10m
$342
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sat 6/20
5:05 pm-10:35 pm
2 stops7h 30m
Oakland
Tue 6/23
11:55 pm-6:00 am
Nonstop4h 05m
$346
Quickest round-trip
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Mon 7/20
9:40 pm-12:10 am
Nonstop4h 30m
Oakland
Thu 7/23
11:55 pm-6:00 am
Nonstop4h 05m
$353
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 6/10
2:20 pm-10:41 pm
1 stop10h 21m
Oakland
Tue 7/7
10:37 am-11:36 pm
1 stop10h 59m
$355
Showing 1-10 of 59 resultsSorted by cheapest first
Best time to book a flight from Illinois to Oakland
Have a flexible travel schedule? Discover the best time to fly to Oakland from Illinois with our price prediction graph.
MDW-OAK
ORD-OAK
STL-OAK
BMI-OAK
MLI-OAK
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Illinois to Oakland
USIL-OAK
MDW-OAK
ORD-OAK
STL-OAK
BMI-OAK
What is the cheapest month to book a flight from Illinois to Oakland, California?
Currently, August is the cheapest month in which you can book a flight from Illinois to Oakland, California (average of $83). Flying from Illinois to Oakland, California in December is currently the most expensive (average of $288). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from IL to OAK?
Find hourly flight availability from Illinois to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2026.
One of the essential ways to save on airfare from Illinois to Oakland, California is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 46% on airfare.
How much does it cost to fly round-trip from Illinois to Oakland, California?
Related info for your journey
Find useful and relevant information for your journey from Illinois to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Complete your trip
Flights by cabin class
Oakland flight routes
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Popular flights
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Alternative routes for Illinois to Oakland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Oakland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Oakland by cabin class
Find flights from Illinois to Oakland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Oakland
Explore flights to Oakland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 6, 2026.
Illinois and Oakland flights
Browse other Illinois and Oakland flight options. Last updated on May 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Illinois to Oakland flights
Consider these flights traveling from Illinois to Oakland.
Top 2 airlines flying from Illinois to Oakland
Discover the top 2 airlines that operate flights from Illinois to Oakland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$236 | Average$434 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$264 | Average$355 | FlexibilityNo cancel fee | On-timeN/A |