$113+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OAK
Aug 29 — Sep 51
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Oakland with Cheapflights
1. Tell us where you want to go
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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 July 30, 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 July 30, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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 9/226:29 am
STL
- OAK
2 stops16h 59m
Alaska Airlines
Tue 9/295:10 pm
OAK
- STL
2 stops22h 00m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$233
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sat 9/121:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Sat 9/1911:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/29![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 7/26. 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.
Tue 10/278:35 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Fri 10/305:50 am
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/26![Southwest logo]()
$242
This Expedia deal was found by Cheapflights users on 7/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:55 pm
ORD
- OAK
1 stop16h 56m
Frontier
Mon 10/510:17 am
OAK
- ORD
1 stop17h 21m
Frontier
Deal found 7/29![Frontier logo]()
$244
This Trip.com deal was found by Cheapflights users on 7/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:20 am
ORD
- OAK
1 stop9h 13m
Alaska Airlines
Thu 9/171:29 pm
OAK
- ORD
1 stop8h 30m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$245
This Priceline deal was found by Cheapflights users on 7/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:20 am
ORD
- OAK
1 stop9h 13m
Multiple Airlines
Mon 9/286:51 pm
OAK
- ORD
1 stop8h 47m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 7/29. 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 8/278:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Mon 8/317:50 am
OAK
- MDW
2 stops7h 10m
Southwest
Deal found 7/29![Southwest logo]()
$248
This Priceline deal was found by Cheapflights users on 7/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:20 am
ORD
- OAK
1 stop9h 13m
Multiple Airlines
Mon 9/216:51 pm
OAK
- ORD
1 stop8h 47m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$251
This Southwest deal was found by Cheapflights users on 7/29. 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 9/248:35 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Mon 9/285:20 am
OAK
- MDW
2 stops7h 15m
Southwest
Deal found 7/29![Southwest logo]()
$252
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Mon 8/248:11 pm
ORD
- OAK
1 stop17h 07m
Frontier
Thu 8/2712:13 pm
OAK
- ORD
1 stop28h 49m
Frontier
Deal found 7/29![Frontier logo]()
$254
This CheapOair deal was found by Cheapflights users on 7/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:21 pm
ORD
- OAK
1 stop22h 01m
Frontier
Tue 9/2912:47 pm
OAK
- ORD
1 stop14h 51m
Frontier
Deal found 7/25![Frontier logo]()
$255
This Trip.com deal was found by Cheapflights users on 7/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:17 pm
STL
- OAK
1 stop7h 39m
Frontier
Thu 9/176:51 pm
OAK
- STL
1 stop14h 36m
Frontier
Deal found 7/27![Frontier logo]()
$256
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 July 30, 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 July 30, 2026.
This Southwest deal was found by Cheapflights users on 7/27. 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.
Thu 8/278:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Mon 8/3111:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/27![Southwest logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 9/122:18 pm
ORD
- OAK
1 stop7h 34m
Alaska Airlines
Sat 9/195:10 pm
OAK
- ORD
1 stop18h 12m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:44 pm
ORD
- OAK
1 stop6h 12m
Delta
Tue 9/112:33 pm
OAK
- ORD
1 stop7h 00m
Delta
Deal found 7/25![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 7/29. 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 8/208:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Tue 8/2511:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/29![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 7/26. 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.
Thu 9/245:55 pm
MDW
- OAK
1 stop6h 20m
Southwest
Mon 9/2811:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/26![Southwest logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 10/282:21 pm
ORD
- OAK
1 stop11h 20m
Alaska Airlines
Wed 11/45:13 pm
OAK
- ORD
1 stop18h 10m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sat 9/121:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Mon 9/215:20 am
OAK
- MDW
2 stops7h 15m
Southwest
Deal found 7/29![Southwest logo]()
$252
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 9/296:29 am
STL
- OAK
2 stops16h 59m
Alaska Airlines
Tue 10/67:04 am
OAK
- STL
2 stops14h 55m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 7/25. 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.
Tue 9/86:00 pm
MDW
- OAK
1 stop6h 30m
Southwest
Tue 9/1511:10 am
OAK
- MDW
1 stop6h 40m
Southwest
Deal found 7/25![Southwest logo]()
$257
This Alaska Airlines deal was found by Cheapflights users on 7/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:29 am
STL
- OAK
2 stops16h 59m
Alaska Airlines
Tue 9/293:13 pm
OAK
- STL
2 stops23h 57m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$284
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 10/277:20 am
ORD
- OAK
1 stop9h 14m
Alaska Airlines
Wed 10/287:04 am
OAK
- ORD
1 stop9h 49m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 7/26. 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.
Wed 9/98:35 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Wed 9/1611:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/26![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 12/128:00 am
ORD
- OAK
1 stop9h 44m
Alaska Airlines
Tue 1/53:30 pm
OAK
- ORD
1 stop6h 29m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$297
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 10/67:20 am
ORD
- OAK
1 stop9h 14m
Alaska Airlines
Mon 10/263:14 pm
OAK
- ORD
1 stop6h 45m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 7/25. 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.
Tue 9/88:35 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Tue 9/2911:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/25![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 7/28. 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.
Fri 9/114:55 pm
MDW
- OAK
1 stop7h 55m
Southwest
Fri 9/1811:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/28![Southwest logo]()
$302
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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.
Sun 9/66:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Wed 9/91:29 pm
OAK
- ORD
1 stop21h 53m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$302
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 8/207:36 pm
STL
- OAK
1 stop15h 47m
Alaska Airlines
Mon 8/245:10 pm
OAK
- STL
2 stops22h 00m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$322
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Mon 9/286:29 am
STL
- OAK
1 stop8h 50m
Alaska Airlines
Tue 10/67:04 am
OAK
- STL
2 stops14h 55m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:09 pm
MLI
- OAK
2 stops32h 50m
Delta
Wed 9/1612:39 pm
OAK
- MLI
2 stops19h 34m
Delta
Deal found 7/25![Delta logo]()
$704
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:09 pm
MLI
- OAK
2 stops32h 50m
Delta
Sun 9/1312:39 pm
OAK
- MLI
2 stops31h 51m
Delta
Deal found 7/25![Delta logo]()
$731
This Alaska Airlines deal was found by Cheapflights users on 7/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:20 am
ORD
- OAK
1 stop9h 13m
Alaska Airlines
Tue 9/155:10 pm
OAK
- ORD
1 stop18h 12m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$355
This Alaska Airlines deal was found by Cheapflights users on 7/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:52 pm
ORD
- OAK
1 stop9h 02m
Alaska Airlines
Wed 9/307:51 pm
OAK
- ORD
1 stop8h 29m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$355
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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 9/97:20 am
ORD
- OAK
1 stop9h 13m
Alaska Airlines
Wed 9/165:10 pm
OAK
- ORD
1 stop18h 12m
Alaska Airlines
Deal found 7/26![Alaska Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 7/29. 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.
Thu 11/511:08 am
MLI
- OAK
2 stops12h 50m
Delta
Sun 11/85:02 pm
OAK
- MLI
2 stops15h 18m
Delta
Deal found 7/29![Delta logo]()
$932
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 9/293:19 pm
STL
- OAK
1 stop9h 35m
Alaska Airlines
Wed 9/308:04 am
OAK
- STL
1 stop7h 06m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$361
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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.
Thu 8/277:36 pm
STL
- OAK
1 stop15h 47m
Alaska Airlines
Mon 8/316:52 pm
OAK
- STL
1 stop20h 18m
Alaska Airlines
Deal found 7/26![Alaska Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 7/28. 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.
Fri 9/411:08 am
MLI
- OAK
2 stops14h 48m
Delta
Wed 9/95:00 pm
OAK
- MLI
2 stops15h 13m
Delta
Deal found 7/28![Delta logo]()
$1,089
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:19 am
MLI
- OAK
2 stops14h 40m
Delta
Fri 9/115:00 pm
OAK
- MLI
2 stops15h 13m
Delta
Deal found 7/25![Delta logo]()
$1,095
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/611:08 am
MLI
- OAK
2 stops13h 30m
Delta
Sat 9/125:00 pm
OAK
- MLI
2 stops15h 13m
Delta
Deal found 7/25![Delta logo]()
$1,292
Last-minute flights from Illinois to OaklandDiscover last-minute flight deals from Illinois to Oakland. Data last updated July 30, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Oakland. Data last updated July 30, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/28. 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 8/186:40 am
MDW
- OAK
1 stop5h 50m
Southwest
Sat 8/2210:15 am
OAK
- MDW
1 stop8h 00m
Southwest
Deal found 7/28![Southwest logo]()
$257
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 8/186:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Mon 8/243:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 7/29. 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 8/208:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Tue 8/2511:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/29![Southwest logo]()
$237
This CheapOair deal was found by Cheapflights users on 7/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:11 pm
ORD
- OAK
1 stop17h 07m
Frontier
Sun 8/2312:13 pm
OAK
- ORD
1 stop28h 49m
Frontier
Deal found 7/26![Frontier logo]()
$272
This Southwest deal was found by Cheapflights users on 7/29. 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 8/218:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Mon 8/2411:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/29![Southwest logo]()
$287
This Booking.com deal was found by Cheapflights users on 7/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Mon 8/241:29 pm
OAK
- ORD
1 stop8h 30m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$307
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Mon 8/248:11 pm
ORD
- OAK
1 stop17h 07m
Frontier
Thu 8/2712:13 pm
OAK
- ORD
1 stop28h 49m
Frontier
Deal found 7/29![Frontier logo]()
$254
This Southwest deal was found by Cheapflights users on 7/28. 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 8/2510:30 am
MDW
- OAK
2 stops7h 30m
Southwest
Tue 9/111:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 7/28![Southwest logo]()
$252
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 8/262:18 pm
ORD
- OAK
1 stop9h 10m
Alaska Airlines
Wed 9/26:48 am
OAK
- ORD
1 stop10h 33m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:41 pm
ORD
- OAK
2 stops22h 37m
Frontier
Wed 9/212:13 pm
OAK
- ORD
1 stop28h 24m
Frontier
Deal found 7/29![Frontier logo]()
$296
This Southwest deal was found by Cheapflights users on 7/29. 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 8/278:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Mon 8/318:25 pm
OAK
- MDW
1 stop7h 15m
Southwest
Deal found 7/29![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:45 pm
STL
- OAK
1 stop18h 33m
Frontier
Tue 9/812:13 pm
OAK
- STL
2 stops29h 04m
Frontier
Deal found 7/26![Frontier logo]()
$300
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 July 30, 2026.
Search for one-way flight options from Illinois to Oakland. Find affordable one-way fares based on user searches. Data last updated July 30, 2026.
This Priceline deal was found by Cheapflights users on 7/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:50 am
ORD
- OAK
1 stop6h 28m
Frontier
Deal found 7/29![Frontier logo]()
$113
This Southwest deal was found by Cheapflights users on 7/29. 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 40m
Southwest
Deal found 7/29![Southwest logo]()
$119
This Frontier deal was found by Cheapflights users on 7/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2812:17 pm
STL
- OAK
1 stop7h 39m
Frontier
Deal found 7/26![Frontier logo]()
$121
This Southwest deal was found by Cheapflights users on 7/28. 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.
Fri 9/118:35 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 7/28![Southwest logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:06 am
ORD
- OAK
2 stops34h 38m
Frontier
Deal found 7/29![Frontier logo]()
$125
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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 8/206:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:58 pm
STL
- OAK
2 stops17h 20m
Frontier
Deal found 7/29![Frontier logo]()
$132
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:02 pm
ORD
- OAK
1 stop8h 42m
Frontier
Deal found 7/29![Frontier logo]()
$132
This CheapOair deal was found by Cheapflights users on 7/27. 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.
Mon 9/218:55 pm
ORD
- OAK
1 stop16h 56m
Frontier
Deal found 7/27![Frontier logo]()
$133
This Southwest deal was found by Cheapflights users on 7/25. 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.
Tue 8/252:15 pm
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 7/25![Southwest logo]()
$134
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 9/117:20 am
ORD
- OAK
1 stop9h 13m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$134
This Frontier deal was found by Cheapflights users on 7/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:50 am
ORD
- OAK
1 stop6h 28m
Frontier
Deal found 7/26![Frontier logo]()
$139
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 July 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $233 (Alaska Airlines) |
One-way from | $113 (Priceline) |
Popular in | June |
Cheapest in | September |
Average price | $407 |
Good round-trip deal | $581 or less |
Good one-way deal | $271 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 July 30, 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
Quickest round-trip
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Thu 8/27
8:35 pm-11:05 pm
Nonstop4h 30m
Oakland
Mon 8/31
11:55 pm-5:55 am
Nonstop4h 00m
$237
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Thu 8/20
8:35 pm-11:05 pm
Nonstop4h 30m
Oakland
Tue 8/25
11:55 pm-5:55 am
Nonstop4h 00m
$237
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Thu 9/24
5:55 pm-10:15 pm
1 stop6h 20m
Oakland
Mon 9/28
11:55 pm-5:55 am
Nonstop4h 00m
$247
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sat 9/12
1:55 pm-4:20 pm
Nonstop4h 25m
Oakland
Mon 9/21
5:20 am-2:35 pm
2 stops7h 15m
$252
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 9/8
6:00 pm-10:30 pm
1 stop6h 30m
Oakland
Tue 9/15
11:10 am-7:50 pm
1 stop6h 40m
$257
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Sat 9/12
2:18 pm-7:52 pm
1 stop7h 34m
Oakland
Sat 9/19
5:10 pm-1:22 pm
1 stop18h 12m
$277
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 10/28
2:21 pm-11:41 pm
1 stop11h 20m
Oakland
Wed 11/4
5:13 pm-1:23 pm
1 stop18h 10m
$277
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Wed 9/9
8:35 pm-11:10 pm
Nonstop4h 35m
Oakland
Wed 9/16
11:55 pm-5:55 am
Nonstop4h 00m
$277
St. LouisOakland
STL - OAK
STLOAK
Lambert-St Louis
Tue 9/29
6:29 am-9:28 pm
2 stops16h 59m
Oakland
Tue 10/6
7:04 am-11:59 pm
2 stops14h 55m
$284
St. LouisOakland
STL - OAK
STLOAK
Lambert-St Louis
Tue 9/22
6:29 am-9:28 pm
2 stops16h 59m
Oakland
Tue 9/29
3:13 pm-5:10 pm
2 stops23h 57m
$284
Showing 1-10 of 60 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, September is the cheapest month in which you can book a flight from Illinois to Oakland, California (average of $252). Flying from Illinois to Oakland, California in November is currently the most expensive (average of $549). 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 July 30, 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?
Airfare is below average for this route at the moment.
Illinois to Oakland, California flights typically cost between $278 and $520 in October.The cheapest round-trip price found within the last 5 days was $244 on Frontier (Oct 2-Oct 5).
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
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Alternative routes for Illinois to Oakland
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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 July 30, 2026.
Illinois and Oakland flights
Browse other Illinois and Oakland flight options. Last updated on July 30, 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 July 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$264 | Average$377 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$265 | Average$456 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$270 | Average$344 | FlexibilityNo cancel fee | On-time75% |