$107+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Jun 30 — Jul 71
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 31, 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 31, 2026.
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/113:50 pm
MDW
- OAK
1 stop6h 00m
Southwest
Tue 8/188:30 pm
OAK
- MDW
1 stop7h 15m
Southwest
Deal found 5/29![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/115:20 pm
MDW
- OAK
1 stop8h 20m
Southwest
Thu 8/208:10 pm
OAK
- MDW
1 stop7h 15m
Southwest
Deal found 5/29![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 7/88:35 pm
OAK
- MDW
1 stop6h 45m
Southwest
Deal found 5/25![Southwest logo]()
$263
This Alaska Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 7/146:00 am
ORD
- OAK
1 stop9h 59m
Alaska Airlines
Tue 7/145:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 9/38:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Mon 9/75:20 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/29![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 7/142:40 pm
MDW
- OAK
1 stop7h 00m
Southwest
Tue 7/217:30 pm
OAK
- MDW
1 stop7h 10m
Southwest
Deal found 5/29![Southwest logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/246:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Wed 7/295:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/47:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Mon 8/1010:37 am
OAK
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$281
This Orbitz deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Mon 9/73:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$284
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/276:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Mon 8/311:29 pm
OAK
- ORD
1 stop8h 30m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:40 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Tue 7/2111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/28![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:12 pm
ORD
- OAK
2 stops11h 39m
Delta
Mon 8/3112:33 pm
OAK
- ORD
1 stop7h 25m
Delta
Deal found 5/28![Delta logo]()
$294
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 31, 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 31, 2026.
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/115:20 pm
MDW
- OAK
1 stop8h 20m
Southwest
Thu 8/208:10 pm
OAK
- MDW
1 stop7h 15m
Southwest
Deal found 5/29![Southwest logo]()
$256
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 8/47:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Mon 8/108:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 5/27![Alaska Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 9/47:44 pm
ORD
- OAK
1 stop6h 07m
Delta
Tue 9/81:15 pm
OAK
- ORD
1 stop6h 43m
Delta
Deal found 5/26![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” 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 7/88:35 pm
OAK
- MDW
1 stop6h 45m
Southwest
Deal found 5/25![Southwest logo]()
$263
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:25 am
ORD
- OAK
1 stop8h 59m
Alaska Airlines
Mon 11/910:16 am
OAK
- ORD
1 stop6h 44m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:45 am
ORD
- OAK
1 stop6h 04m
Delta
Thu 9/246:00 am
OAK
- ORD
2 stops10h 26m
Delta
Deal found 5/27![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 7/146:20 am
MDW
- OAK
1 stop6h 05m
Southwest
Tue 7/147:30 pm
OAK
- MDW
1 stop7h 10m
Southwest
Deal found 5/28![Southwest logo]()
$314
This Alaska Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/16:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Wed 7/810:37 am
OAK
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/26![Alaska Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/307:55 pm
STL
- OAK
1 stop5h 59m
Delta
Tue 7/75:05 pm
OAK
- STL
1 stop5h 36m
Delta
Deal found 5/26![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/269:40 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Tue 7/79:00 pm
OAK
- MDW
1 stop6h 25m
Southwest
Deal found 5/27![Southwest logo]()
$350
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/216:00 am
ORD
- OAK
1 stop9h 59m
Alaska Airlines
Sat 8/15:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/75:50 pm
MDW
- OAK
2 stops7h 35m
Southwest
Wed 7/153:55 pm
OAK
- MDW
1 stop6h 15m
Southwest
Deal found 5/30![Southwest logo]()
$354
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 9/286:55 pm
STL
- OAK
1 stop7h 04m
Delta
Tue 10/65:05 pm
OAK
- STL
1 stop5h 31m
Delta
Deal found 5/30![Delta logo]()
$392
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/286:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Thu 9/31:29 pm
OAK
- ORD
1 stop8h 30m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/249:40 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sun 7/265:05 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/26![Southwest logo]()
$380
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/64:40 pm
STL
- OAK
1 stop8h 15m
Alaska Airlines
Wed 10/712:20 pm
OAK
- STL
1 stop9h 39m
Alaska Airlines
Deal found 5/27![Alaska Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 9/236:55 pm
STL
- OAK
1 stop7h 04m
Delta
Sun 9/275:03 pm
OAK
- STL
1 stop5h 31m
Delta
Deal found 5/30![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/16:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Tue 7/72:50 pm
OAK
- ORD
2 stops13h 30m
Alaska Airlines
Deal found 5/27![Alaska Airlines logo]()
$382
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:45 pm
STL
- OAK
1 stop6h 06m
Delta
Mon 8/2412:33 pm
OAK
- STL
2 stops8h 53m
Delta
Deal found 5/28![Delta logo]()
$448
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 7/38:15 pm
MDW
- OAK
1 stop6h 00m
Southwest
Sat 7/1112:30 pm
OAK
- MDW
2 stops8h 45m
Southwest
Deal found 5/29![Southwest logo]()
$410
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:42 pm
ORD
- OAK
1 stop16h 44m
Alaska Airlines
Sun 7/197:52 am
OAK
- ORD
1 stop19h 08m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 7/109:40 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Mon 7/205:10 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 5/27![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/258:35 pm
MDW
- OAK
1 stop6h 15m
Southwest
Sun 6/285:10 am
OAK
- MDW
2 stops7h 30m
Southwest
Deal found 5/30![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/36:40 pm
STL
- OAK
1 stop7h 05m
Southwest
Mon 7/64:45 pm
OAK
- STL
1 stop5h 30m
Southwest
Deal found 5/26![Southwest logo]()
$450
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/295:25 am
STL
- OAK
2 stops8h 10m
Southwest
Thu 8/66:00 am
OAK
- STL
2 stops7h 15m
Southwest
Deal found 5/30![Southwest logo]()
$455
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:45 am
STL
- OAK
1 stop6h 00m
Southwest
Mon 7/134:45 pm
OAK
- STL
1 stop5h 30m
Southwest
Deal found 5/30![Southwest logo]()
$484
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/2712:09 pm
BMI
- OAK
2 stops11h 32m
Delta
Sat 7/46:00 am
OAK
- BMI
2 stops13h 37m
Delta
Deal found 5/29![Delta logo]()
$888
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/115:56 am
MLI
- OAK
2 stops12h 25m
Delta
Sat 7/185:30 pm
OAK
- MLI
2 stops14h 42m
Delta
Deal found 5/30![Delta logo]()
$1,419
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/1411:08 am
MLI
- OAK
2 stops14h 46m
Delta
Thu 6/185:03 pm
OAK
- MLI
2 stops15h 13m
Delta
Deal found 5/30![Delta logo]()
$3,113
Last-minute flights from Illinois to OaklandDiscover last-minute flight deals from Illinois to Oakland. Data last updated May 31, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Oakland. Data last updated May 31, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
Fri 6/197:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Sat 8/88:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$331
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/196:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Tue 7/282:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$343
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/206:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Wed 7/295:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$336
This Alaska Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” 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 6/206:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Tue 6/232:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 5/27![Alaska Airlines logo]()
$339
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/236:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Sun 7/265:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$350
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/246:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Wed 7/295:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/246:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Thu 7/235:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 5/28![Alaska Airlines logo]()
$314
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/265:45 am
MDW
- OAK
1 stop7h 40m
Southwest
Tue 7/77:30 pm
OAK
- MDW
1 stop7h 10m
Southwest
Deal found 5/30![Southwest logo]()
$323
This CheapOair deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
Fri 6/267:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Tue 6/307:52 am
OAK
- ORD
1 stop19h 08m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$323
This SmartFares deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Tue 7/72:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 5/27![Alaska Airlines logo]()
$338
This CheapOair deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Tue 7/1410:37 am
OAK
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 5/27![Alaska Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/309:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Tue 7/79:00 pm
OAK
- MDW
1 stop6h 25m
Southwest
Deal found 5/29![Southwest logo]()
$345
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 31, 2026.
Search for one-way flight options from Illinois to Oakland. Find affordable one-way fares based on user searches. Data last updated May 31, 2026.
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/258:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/29![Southwest logo]()
$107
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 6/309:00 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 5/28![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:30 am
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 5/28![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 10/19:30 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 5/29![Southwest logo]()
$135
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/246:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$137
This Alaska Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/136:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 5/29![Alaska Airlines logo]()
$140
This CheapOair deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/218:20 pm
ORD
- OAK
1 stop15h 06m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/262:15 pm
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 5/30![Southwest logo]()
$142
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 8/177:44 pm
ORD
- OAK
1 stop6h 07m
Delta
Deal found 5/28![Delta logo]()
$145
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/65:40 am
MDW
- OAK
1 stop6h 20m
Southwest
Deal found 5/29![Southwest logo]()
$145
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 9/235:10 pm
ORD
- OAK
2 stops8h 49m
Delta
Deal found 5/28![Delta logo]()
$150
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 9/231:14 pm
MDW
- OAK
2 stops12h 45m
Delta
Deal found 5/28![Delta logo]()
$150
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 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $233 (Southwest) |
One-way from | $107 (Southwest) |
Popular in | February |
Cheapest in | September |
Average price | $386 |
Good round-trip deal | $410 or less |
Good one-way deal | $209 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 31, 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 8/11
5:20 pm-11:40 pm
1 stop8h 20m
Oakland
Thu 8/20
8:10 pm-5:25 am
1 stop7h 15m
$256
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Wed 7/1
9:00 pm-11:30 pm
Nonstop4h 30m
Oakland
Wed 7/8
8:35 pm-5:20 am
1 stop6h 45m
$263
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Tue 8/4
7:59 pm-9:57 am
1 stop15h 58m
Oakland
Mon 8/10
8:10 pm-1:21 pm
1 stop15h 11m
$281
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Thu 11/5
7:25 am-2:24 pm
1 stop8h 59m
Oakland
Mon 11/9
10:16 am-7:00 pm
1 stop6h 44m
$289
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 7/14
6:20 am-10:25 am
1 stop6h 05m
Oakland
Tue 7/14
7:30 pm-4:40 am
1 stop7h 10m
$314
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Fri 9/4
7:44 pm-11:51 pm
1 stop6h 07m
Oakland
Tue 9/8
1:15 pm-9:58 pm
1 stop6h 43m
$331
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Tue 9/22
7:45 am-11:49 am
1 stop6h 04m
Oakland
Thu 9/24
6:00 am-6:26 pm
2 stops10h 26m
$340
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Fri 6/26
9:40 pm-12:10 am
Nonstop4h 30m
Oakland
Tue 7/7
9:00 pm-5:25 am
1 stop6h 25m
$350
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 7/7
5:50 pm-11:25 pm
2 stops7h 35m
Oakland
Wed 7/15
3:55 pm-12:10 am
1 stop6h 15m
$354
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 7/1
6:20 am-2:10 pm
1 stop9h 50m
Oakland
Wed 7/8
10:37 am-11:36 pm
1 stop10h 59m
$355
Showing 1-10 of 58 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 31, 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 42% 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.
Alternative routes
Complete your trip
Flights by cabin class
Oakland flight routes
Other flight options
Popular flights
Top destinations
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 31, 2026.
Illinois and Oakland flights
Browse other Illinois and Oakland flight options. Last updated on May 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Illinois to Oakland flights
Consider these flights traveling from Illinois to Oakland.
Top 3 airlines flying from Illinois to Oakland
Discover the top 3 airlines that operate flights from Illinois to Oakland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$165 | Average$354 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$236 | Average$441 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$264 | Average$377 | FlexibilityNo cancel fee | On-timeN/A |