$99+ Cheap flights from Oakland, CA (OAK) to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — ORD
Sep 25 — Oct 21
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 August 26, 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 August 26, 2026.
This Expedia deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Thu 10/2210:17 am -
1 stop16h 59m
Mon 10/263:30 pm -
1 stop22h 23m
Deal found 8/24![Frontier logo]()
$198
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:17 am -
1 stop17h 21m
Tue 9/291:21 pm -
1 stop24h 30m
Deal found 8/24![Frontier logo]()
$208
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/256:51 pm -
1 stop8h 47m
Mon 9/288:55 pm -
1 stop16h 56m
Deal found 8/21![Frontier logo]()
$218
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:17 am -
1 stop17h 21m
Fri 9/258:55 pm -
1 stop16h 56m
Deal found 8/25![Frontier logo]()
$228
This Orbitz deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/810:17 am -
1 stop16h 59m
Mon 10/123:30 pm -
1 stop22h 22m
Deal found 8/20![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 8/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:51 pm -
1 stop8h 47m
Tue 9/291:21 pm -
1 stop24h 30m
Deal found 8/25![Frontier logo]()
$233
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/2711:55 pm -
Nonstop4h 00m
Mon 11/29:55 pm -
Nonstop4h 40m
Deal found 8/21![Southwest logo]()
$237
This CheapOair deal was found by Cheapflights users on 8/25. 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.
Tue 9/2212:47 pm -
1 stop14h 51m
Fri 9/258:55 pm -
1 stop16h 56m
Deal found 8/25![Frontier logo]()
$238
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/216:51 pm -
1 stop8h 47m
Tue 9/221:21 pm -
1 stop24h 30m
Deal found 8/24![Frontier logo]()
$242
This Expedia deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Tue 9/2212:47 pm -
1 stop14h 51m
Thu 9/247:20 am -
1 stop9h 13m
Deal found 8/23![Multiple Airlines logo]()
$243
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/242:30 pm -
1 stop7h 20m
Tue 9/298:35 pm -
Nonstop4h 35m
Deal found 8/24![Southwest logo]()
$247
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/186:51 pm -
1 stop8h 47m
Mon 9/218:55 pm -
1 stop16h 56m
Deal found 8/21![Frontier logo]()
$248
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 August 26, 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 August 26, 2026.
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/242:30 pm -
1 stop7h 20m
Tue 9/298:35 pm -
Nonstop4h 35m
Deal found 8/24![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:47 pm -
1 stop29h 52m
Sun 9/279:29 pm -
1 stop13h 53m
Deal found 8/24![Multiple Airlines logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:13 pm -
1 stop6h 46m
Sat 9/262:18 pm -
1 stop7h 34m
Deal found 8/20![Alaska Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 12/146:00 am -
1 stop5h 30m
Mon 12/217:38 pm -
1 stop6h 18m
Deal found 8/21![Delta logo]()
$387
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/253:13 pm -
1 stop6h 46m
Sat 9/267:20 am -
1 stop9h 13m
Deal found 8/20![Alaska Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/1512:47 pm -
2 stops22h 32m
Thu 9/179:29 pm -
1 stop22h 27m
Deal found 8/20![Multiple Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/228:10 pm -
2 stops7h 35m
Mon 10/267:15 pm -
1 stop7h 20m
Deal found 8/22![Southwest logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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.
Sun 9/1310:17 am -
1 stop8h 22m
Sun 9/209:29 pm -
1 stop13h 53m
Deal found 8/21![Multiple Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/67:40 pm -
1 stop7h 45m
Tue 10/131:05 pm -
2 stops7h 50m
Deal found 8/22![Southwest logo]()
$303
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/171:29 pm -
1 stop8h 30m
Mon 9/217:20 am -
1 stop9h 13m
Deal found 8/25![Alaska Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 12/210:23 pm -
1 stop11h 34m
Mon 12/71:01 pm -
2 stops34h 27m
Deal found 8/23![Multiple Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/146:00 am -
1 stop5h 32m
Wed 10/212:38 pm -
2 stops11h 18m
Deal found 8/21![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/175:20 am -
2 stops7h 15m
Thu 9/246:15 am -
1 stop7h 20m
Deal found 8/20![Southwest logo]()
$325
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/69:59 am -
1 stop6h 54m
Tue 10/132:21 pm -
1 stop11h 21m
Deal found 8/22![Alaska Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am -
2 stops9h 41m
Sat 9/127:45 am -
1 stop6h 14m
Deal found 8/20![Delta logo]()
$395
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2511:55 pm -
Nonstop4h 00m
Wed 10/288:35 pm -
Nonstop4h 40m
Deal found 8/20![Southwest logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/2112:47 pm -
1 stop28h 43m
Sun 10/258:53 pm -
1 stop21h 32m
Deal found 8/22![Multiple Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/178:35 am -
1 stop7h 20m
Thu 9/178:35 pm -
Nonstop4h 35m
Deal found 8/21![Southwest logo]()
$329
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 11/108:00 am -
2 stops19h 40m
Wed 11/112:15 pm -
1 stop9h 18m
Deal found 8/20![Alaska Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/1012:39 pm -
1 stop7h 16m
Sat 9/128:25 am -
2 stops9h 55m
Deal found 8/24![Delta logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 12/210:23 pm -
1 stop11h 34m
Sun 12/612:47 pm -
1 stop10h 41m
Deal found 8/23![Multiple Airlines logo]()
$369
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/69:59 am -
1 stop6h 54m
Tue 10/207:00 am -
2 stops11h 24m
Deal found 8/22![Alaska Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 8/25. 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.
Thu 9/178:10 pm -
1 stop7h 15m
Mon 9/218:35 pm -
Nonstop4h 35m
Deal found 8/25![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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.
Thu 10/85:20 pm -
2 stops16h 07m
Sun 10/119:33 pm -
1 stop13h 32m
Deal found 8/21![Multiple Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/136:48 am -
1 stop15h 11m
Mon 9/147:20 am -
1 stop9h 13m
Deal found 8/21![Alaska Airlines logo]()
$381
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/1011:55 pm -
Nonstop4h 00m
Sat 9/121:55 pm -
Nonstop4h 25m
Deal found 8/20![Southwest logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 11/192:50 pm -
1 stop6h 59m
Sun 11/222:16 pm -
1 stop11h 04m
Deal found 8/22![Alaska Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Thu 9/1710:17 am -
1 stop8h 22m
Thu 9/249:29 pm -
1 stop13h 53m
Deal found 8/20![Multiple Airlines logo]()
$395
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/1311:55 pm -
1 stop7h 20m
Tue 10/208:35 am -
1 stop8h 30m
Deal found 8/24![Southwest logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Sun 10/2510:17 am -
1 stop7h 46m
Wed 10/282:07 pm -
2 stops28h 53m
Deal found 8/20![Multiple Airlines logo]()
$416
Last-minute flights from Oakland to IllinoisDiscover last-minute flight deals from Oakland to Illinois. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Illinois. Data last updated August 26, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Tue 9/1512:47 pm -
1 stop14h 51m
Thu 9/172:18 pm -
1 stop10h 52m
Deal found 8/20![Multiple Airlines logo]()
$249
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/186:51 pm -
1 stop8h 47m
Mon 9/218:55 pm -
1 stop16h 56m
Deal found 8/21![Frontier logo]()
$248
This Frontier deal was found by Cheapflights users on 8/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:51 pm -
1 stop8h 47m
Tue 9/291:21 pm -
1 stop24h 30m
Deal found 8/25![Frontier logo]()
$233
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/216:51 pm -
1 stop8h 47m
Tue 9/221:21 pm -
1 stop24h 30m
Deal found 8/24![Frontier logo]()
$242
This Expedia deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Tue 9/2212:47 pm -
1 stop14h 51m
Mon 9/288:55 pm -
1 stop16h 56m
Deal found 8/24![Frontier logo]()
$198
This CheapOair deal was found by Cheapflights users on 8/25. 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.
Tue 9/2212:47 pm -
1 stop14h 51m
Fri 9/258:55 pm -
1 stop16h 56m
Deal found 8/25![Frontier logo]()
$238
This Expedia deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Tue 9/2212:47 pm -
1 stop14h 51m
Thu 9/247:20 am -
1 stop9h 13m
Deal found 8/23![Multiple Airlines logo]()
$243
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:17 am -
1 stop17h 21m
Tue 9/291:21 pm -
1 stop24h 30m
Deal found 8/24![Frontier logo]()
$208
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:17 am -
1 stop17h 21m
Fri 9/258:55 pm -
1 stop16h 56m
Deal found 8/25![Frontier logo]()
$228
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/242:30 pm -
1 stop7h 20m
Tue 9/298:35 pm -
Nonstop4h 35m
Deal found 8/24![Southwest logo]()
$247
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/256:51 pm -
1 stop8h 47m
Mon 9/288:55 pm -
1 stop16h 56m
Deal found 8/21![Frontier logo]()
$218
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/2611:55 pm -
Nonstop4h 00m
Tue 9/298:35 pm -
Nonstop4h 35m
Deal found 8/24![Southwest logo]()
$237
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 August 26, 2026.
Search for one-way flight options from Oakland to Illinois. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This Frontier deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/176:51 pm -
1 stop8h 47m
Deal found 8/21![Frontier logo]()
$99
This Expedia deal was found by Cheapflights users on 8/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:47 pm -
1 stop14h 51m
Deal found 8/25![Frontier logo]()
$105
This Priceline deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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.
Fri 9/256:51 pm -
1 stop8h 47m
Deal found 8/21![Frontier logo]()
$109
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:47 pm -
1 stop14h 51m
Deal found 8/21![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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.
Fri 10/95:20 pm -
1 stop9h 56m
Deal found 8/21![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:20 pm -
2 stops35h 14m
Deal found 8/23![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 8/25. 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.
Mon 9/2111:55 pm -
Nonstop4h 00m
Deal found 8/25![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:20 pm -
2 stops35h 14m
Deal found 8/25![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/2712:48 pm -
2 stops22h 29m
Deal found 8/21![Multiple Airlines logo]()
$129
This Frontier deal was found by Cheapflights users on 8/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:51 pm -
1 stop8h 47m
Deal found 8/25![Frontier logo]()
$133
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/277:15 am -
2 stops7h 30m
Deal found 8/21![Southwest logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/2812:48 pm -
2 stops44h 39m
Deal found 8/23![Multiple Airlines logo]()
$134
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 August 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $198 (Expedia) |
One-way from | $99 (Frontier) |
Popular in | July |
Cheapest in | February |
Average price | $428 |
Good round-trip deal | $389 or less |
Good one-way deal | $221 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 August 26, 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
Thu 9/24
2:30 pm-11:50 pm
1 stop7h 20m
Chicago Midway
Tue 9/29
8:35 pm-11:10 pm
Nonstop4h 35m
$247
OaklandChicago
OAK Oakland - RFD Chicago Greater Rockford
OAKRFD
Oakland
Wed 9/23
12:47 pm-8:39 pm
1 stop29h 52m
Chicago Greater Rockford
Sun 9/27
9:29 pm-9:22 am
1 stop13h 53m
$277
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 9/24
3:13 pm-11:59 pm
1 stop6h 46m
Chicago O'Hare Intl
Sat 9/26
2:18 pm-7:52 pm
1 stop7h 34m
$277
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Fri 9/25
3:13 pm-11:59 pm
1 stop6h 46m
Chicago O'Hare Intl
Sat 9/26
7:20 am-2:33 pm
1 stop9h 13m
$277
OaklandChicago
OAK Oakland - RFD Chicago Greater Rockford
OAKRFD
Oakland
Tue 9/15
12:47 pm-1:19 pm
2 stops22h 32m
Chicago Greater Rockford
Thu 9/17
9:29 pm-5:56 pm
1 stop22h 27m
$297
OaklandChicago
OAK Oakland - RFD Chicago Greater Rockford
OAKRFD
Oakland
Sun 9/13
10:17 am-8:39 pm
1 stop8h 22m
Chicago Greater Rockford
Sun 9/20
9:29 pm-9:22 am
1 stop13h 53m
$300
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Thu 10/22
8:10 pm-5:45 am
2 stops7h 35m
Chicago Midway
Mon 10/26
7:15 pm-12:35 am
1 stop7h 20m
$303
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Tue 10/6
7:40 pm-5:25 am
1 stop7h 45m
Chicago Midway
Tue 10/13
1:05 pm-6:55 pm
2 stops7h 50m
$303
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 9/17
1:29 pm-11:59 pm
1 stop8h 30m
Chicago O'Hare Intl
Mon 9/21
7:20 am-2:33 pm
1 stop9h 13m
$308
OaklandChicago
OAK Oakland - RFD Chicago Greater Rockford
OAKRFD
Oakland
Wed 12/2
10:23 pm-11:57 am
1 stop11h 34m
Chicago Greater Rockford
Mon 12/7
1:01 pm-9:28 pm
2 stops34h 27m
$311
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Oakland to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Oakland with our price prediction graph.
OAK-MDW
OAK-RFD
OAK-ORD
OAK-STL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Oakland to Illinois
OAK-USIL
OAK-MDW
OAK-RFD
OAK-ORD
OAK-STL
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 July is currently the most expensive (average of $544). 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 August 26, 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 61% 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 $324 and $562 in October.The cheapest round-trip price found within the last 5 days was $198 on Frontier (Oct 22-Oct 26).
How far ahead should I book a flight from Oakland, California to Illinois?
Booking 61 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 August 26, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, 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
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
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Alternative routes for Oakland to Illinois
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Complete your trip
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Oakland and Illinois flights
Browse other Oakland and Illinois flight options. Last updated on August 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oakland to Illinois flights
Consider these flights traveling from Oakland to Illinois.
Top 4 airlines flying from Oakland to Illinois
Discover the top 4 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 August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$271 | Average$407 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$272 | Average$522 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$275 | Average$438 | FlexibilityNo cancel fee | On-time63% |