$126+ Cheap flights from Oakland, CA (OAK) to Illinois
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Nov 13 — Nov 201
Round-trip
1 adult, Economy
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Find cheap flights from Oakland to Illinois with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Oakland to IllinoisExplore the most affordable flight options available from Oakland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2026.
Explore the most affordable flight options available from Oakland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2026.
This Trip.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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.
Sun 11/222:29 pm -
1 stop12h 41m
Tue 12/16:21 am -
1 stop7h 12m
Deal found 10/11![Frontier logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:28 pm -
1 stop14h 33m
Tue 12/86:21 am -
1 stop7h 12m
Deal found 10/13![Frontier logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:55 pm -
1 stop9h 18m
Mon 11/165:15 pm -
1 stop20h 38m
Deal found 10/14![Frontier logo]()
$254
This Cheapflightsfares deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:28 pm -
1 stop14h 31m
Mon 12/76:21 am -
1 stop7h 12m
Deal found 10/14![Frontier logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:28 pm -
1 stop14h 33m
Sat 12/126:21 am -
1 stop7h 12m
Deal found 10/9![Frontier logo]()
$274
This Cheapflightsfares deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:18 am -
1 stop16h 55m
Mon 11/235:15 am -
1 stop7h 14m
Deal found 10/10![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 12/1612:28 pm -
1 stop14h 33m
Mon 1/46:11 am -
1 stop29h 26m
Deal found 10/9![Frontier logo]()
$281
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/222:29 pm -
1 stop12h 41m
Wed 12/26:21 am -
1 stop7h 12m
Deal found 10/12![Frontier logo]()
$284
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Tue 11/242:34 pm -
1 stop12h 36m
Tue 12/16:21 am -
1 stop7h 12m
Deal found 10/12![Frontier logo]()
$292
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:55 pm -
1 stop9h 18m
Sun 11/85:15 pm -
1 stop25h 45m
Deal found 10/9![Frontier logo]()
$295
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:50 pm -
Nonstop4h 05m
Tue 11/178:45 pm -
Nonstop4h 50m
Deal found 10/12![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 10/3110:55 pm -
Nonstop4h 10m
Wed 11/48:45 pm -
Nonstop4h 50m
Deal found 10/9![Southwest logo]()
$356
Best flights from Oakland to IllinoisDiscover carefully curated flight deals from Oakland to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 14, 2026.
Discover carefully curated flight deals from Oakland to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 12/1612:28 pm -
1 stop14h 33m
Mon 1/46:11 am -
1 stop29h 26m
Deal found 10/9![Frontier logo]()
$281
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:30 am -
Nonstop4h 00m
Tue 11/178:45 pm -
Nonstop4h 50m
Deal found 10/12![Southwest logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/1610:00 am -
1 stop6h 59m
Tue 11/177:20 am -
1 stop8h 44m
Deal found 10/9![Alaska Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 1/161:15 pm -
1 stop6h 38m
Wed 1/207:30 am -
1 stop6h 55m
Deal found 10/14![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 11/911:50 pm -
Nonstop4h 05m
Thu 11/129:55 am -
1 stop7h 05m
Deal found 10/10![Southwest logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 1/161:18 pm -
1 stop8h 41m
Thu 1/217:40 am -
1 stop8h 16m
Deal found 10/14![Alaska Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates ” 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 11/712:41 pm -
1 stop7h 24m
Sat 11/145:30 am -
2 stops12h 47m
Deal found 10/11![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:50 pm -
Nonstop4h 05m
Mon 11/910:15 am -
1 stop8h 10m
Deal found 10/13![Southwest logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 11/52:44 pm -
1 stop7h 05m
Mon 11/97:20 am -
1 stop8h 44m
Deal found 10/10![Alaska Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/38:30 am -
1 stop6h 50m
Fri 11/69:55 pm -
Nonstop4h 45m
Deal found 10/14![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 12/55:03 pm -
2 stops13h 46m
Sat 12/123:47 pm -
2 stops8h 22m
Deal found 10/9![Delta logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 1/161:18 pm -
1 stop8h 41m
Fri 1/228:00 am -
2 stops10h 17m
Deal found 10/14![Alaska Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:50 pm -
Nonstop4h 05m
Fri 11/135:55 am -
1 stop6h 30m
Deal found 10/10![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 12/312:34 pm -
1 stop7h 22m
Sun 12/67:18 pm -
1 stop6h 45m
Deal found 10/13![Delta logo]()
$401
This Alaska Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 1/2511:51 am -
1 stop23h 22m
Sun 1/312:11 pm -
1 stop7h 14m
Deal found 10/11![Alaska Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/412:41 pm -
1 stop7h 24m
Sun 11/87:35 am -
1 stop6h 26m
Deal found 10/11![Delta logo]()
$401
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/111:50 pm -
Nonstop4h 05m
Thu 11/59:55 pm -
Nonstop4h 45m
Deal found 10/11![Southwest logo]()
$385
This Alaska Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 10/317:02 am -
1 stop9h 18m
Wed 11/47:20 am -
1 stop29h 22m
Deal found 10/9![Alaska Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/142:00 pm -
1 stop6h 20m
Sun 11/159:55 pm -
Nonstop4h 45m
Deal found 10/11![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/128:20 pm -
1 stop7h 20m
Sun 11/159:55 pm -
Nonstop4h 45m
Deal found 10/9![Southwest logo]()
$395
Last-minute flights from Oakland to IllinoisDiscover last-minute flight deals from Oakland to Illinois. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Illinois. Data last updated October 14, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 10/3110:55 pm -
Nonstop4h 10m
Wed 11/48:45 pm -
Nonstop4h 50m
Deal found 10/9![Southwest logo]()
$356
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:55 pm -
1 stop9h 18m
Sun 11/85:15 pm -
1 stop25h 45m
Deal found 10/9![Frontier logo]()
$295
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:50 pm -
Nonstop4h 05m
Tue 11/178:45 pm -
Nonstop4h 50m
Deal found 10/12![Southwest logo]()
$349
This Cheapflightsfares deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:55 pm -
1 stop9h 18m
Mon 11/165:15 pm -
1 stop20h 38m
Deal found 10/14![Frontier logo]()
$254
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/128:30 pm -
1 stop5h 55m
Mon 11/168:45 pm -
Nonstop4h 50m
Deal found 10/13![Southwest logo]()
$359
This Cheapflightsfares deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:18 am -
1 stop16h 55m
Mon 11/235:15 am -
1 stop7h 14m
Deal found 10/10![Frontier logo]()
$280
This Frontier deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 11/195:55 pm -
1 stop9h 18m
Mon 11/235:15 am -
1 stop7h 14m
Deal found 10/10![Frontier logo]()
$305
This Cheapflightsfares deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:55 pm -
1 stop9h 18m
Sun 11/225:15 am -
1 stop7h 14m
Deal found 10/13![Frontier logo]()
$307
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Sat 11/213:52 pm -
1 stop11h 18m
Tue 12/16:21 am -
1 stop7h 12m
Deal found 10/12![Frontier logo]()
$303
This Trip.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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.
Sun 11/222:29 pm -
1 stop12h 41m
Tue 12/16:21 am -
1 stop7h 12m
Deal found 10/11![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/222:29 pm -
1 stop12h 41m
Wed 12/26:21 am -
1 stop7h 12m
Deal found 10/12![Frontier logo]()
$284
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Tue 11/242:34 pm -
1 stop12h 36m
Tue 12/16:21 am -
1 stop7h 12m
Deal found 10/12![Frontier logo]()
$292
One-way flights from Oakland to IllinoisSearch for one-way flight options from Oakland to Illinois. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
Search for one-way flight options from Oakland to Illinois. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Trip.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/125:55 pm -
1 stop9h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$126
This Cheapflightsfares deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:28 pm -
1 stop14h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1412:28 pm -
1 stop14h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$134
This Priceline deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/195:55 pm -
1 stop9h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/1112:48 pm -
2 stops20h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Frontier logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1410:30 am -
1 stop17h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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.
Tue 11/1012:48 pm -
2 stops20h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$141
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/95:55 pm -
1 stop9h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Frontier logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:28 pm -
1 stop14h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 12/912:28 pm -
2 stops24h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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.
Tue 11/1712:48 pm -
2 stops26h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$148
This Frontier deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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.
Sat 11/213:52 pm -
1 stop11h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Frontier logo]()
$148
Find flight deals from Oakland to Illinois
Keep the following information in mind while searching for Oakland to Illinois flight deals. Data was last updated October 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $230 (Trip.com) |
One-way from | $118 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $417 |
Good round-trip deal | $452 or less |
Good one-way deal | $269 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 14, 2026.
Use the filters below to find and compare flights from Oakland to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Fri 12/11
11:50 pm-5:55 am
Nonstop4h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$175
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Mon 11/9
11:50 pm-5:55 am
Nonstop4h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$175
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sat 12/12
11:50 pm-5:55 am
Nonstop4h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$175
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Wed 11/4
11:50 pm-5:55 am
Nonstop4h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$175
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Fri 11/6
11:50 pm-5:55 am
Nonstop4h 05m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$175
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Fri 11/13
12:41 pm-9:47 pm
1 stop7h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$180
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 11/12
12:41 pm-9:47 pm
1 stop7h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$180
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Tue 11/10
12:41 pm-9:47 pm
1 stop7h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$180
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sat 12/12
5:55 am-4:50 pm
2 stops8h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$185
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sat 11/7
6:00 am-6:00 pm
2 stops10h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$185
Showing 1-10 of 43 resultsSorted by cheapest first
Best time to book a flight from Oakland to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Oakland with our price prediction graph.
OAK-ORD
OAK-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Oakland to Illinois
OAK-USIL
OAK-ORD
OAK-MDW
What is the cheapest month to book a flight from Oakland, California to Illinois?
Currently, February is the cheapest month in which you can book a flight from Oakland, California to Illinois (average of $364). Flying from Oakland, California to Illinois in November is currently the most expensive (average of $566). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from OAK to IL?
Find hourly flight availability from Oakland to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2026.
When flying from Oakland, California to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 60% versus a flight in the afternoon.
How much does it cost to fly round-trip from Oakland, California to Illinois?
Airfare is below average for this route at the moment.
Oakland, California to Illinois flights typically cost between $468 and $653 in November.The cheapest round-trip price found within the last 5 days was $230 on Frontier (Nov 22-Dec 1).
How far ahead should I book a flight from Oakland, California to Illinois?
Booking 63 days in advance of your planned departure date is, on average, the best time to get cheap flights from Oakland, California to Illinois. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated October 14, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andDelta from Oakland to Illinois by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Entertainment
7.0
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from Oakland to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Oakland to Illinois
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Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oakland to Illinois by cabin class
Find flights from Oakland to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oakland and Illinois flights
Browse other Oakland and Illinois flight options. Last updated on October 14, 2026.
Popular flight searches
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Oakland to Illinois flights
Consider these flights traveling from Oakland to Illinois.
Top 3 airlines flying from Oakland to Illinois
Discover the top 3 airlines that operate flights from Oakland to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$408 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$272 | Average$516 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$275 | Average$443 | FlexibilityNo cancel fee | On-time63% |