$88+ Cheap flights from Oakland, CA (OAK) to Chicago (CHI)
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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Sep 12 — Sep 191
Round-trip
1 adult, Economy
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Find cheap flights from Oakland to Chicago 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Oakland to Chicago are usually found in February or May, booked 72 days in advance, depart on a Tuesday or Monday and return on a Tuesday
Cheap flight deals from Oakland to Chicago
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Cheapest flights from Oakland to ChicagoExplore the most affordable flight options available from Oakland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2026.
Explore the most affordable flight options available from Oakland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:47 pm -
1 stop14h 51m
Tue 9/151:21 pm -
1 stop24h 30m
Deal found 8/12![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/3012:47 pm -
1 stop14h 51m
Tue 10/136:50 am -
1 stop31h 02m
Deal found 8/11![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:51 pm -
1 stop8h 47m
Tue 9/151:21 pm -
1 stop24h 30m
Deal found 8/12![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:47 pm -
1 stop14h 55m
Mon 10/266:50 am -
1 stop30h 28m
Deal found 8/12![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 10/1412:13 pm -
1 stop15h 29m
Mon 10/196:50 am -
1 stop30h 28m
Deal found 8/11![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:51 pm -
1 stop8h 47m
Mon 9/288:55 pm -
1 stop16h 56m
Deal found 8/12![Frontier logo]()
$191
This Frontier deal was found by Cheapflights users on 8/11. 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.
Thu 10/158:39 pm -
1 stop13h 18m
Tue 10/206:50 am -
1 stop6h 28m
Deal found 8/11![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Mon 10/510:17 am -
1 stop17h 21m
Tue 10/61:21 pm -
1 stop24h 30m
Deal found 8/11![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:47 pm -
1 stop14h 51m
Wed 9/166:30 am -
2 stops28h 52m
Deal found 8/12![Frontier logo]()
$203
This Southwest deal was found by Cheapflights users on 8/12. 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.
Mon 9/2811:55 pm -
Nonstop4h 00m
Thu 10/19:30 pm -
Nonstop4h 40m
Deal found 8/12![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 11/1411:50 pm -
Nonstop4h 05m
Mon 11/1610:00 am -
1 stop7h 00m
Deal found 8/12![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 8/11. 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.
Wed 10/77:15 am -
2 stops7h 30m
Thu 10/159:30 pm -
Nonstop4h 40m
Deal found 8/11![Southwest logo]()
$234
Best flights from Oakland to ChicagoDiscover carefully curated flight deals from Oakland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
Discover carefully curated flight deals from Oakland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 9/282:30 pm -
1 stop7h 20m
Thu 10/19:30 pm -
Nonstop4h 40m
Deal found 8/11![Southwest logo]()
$229
This Frontier deal was found by Cheapflights users on 8/12. 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.
Fri 10/98:39 pm -
1 stop7h 03m
Sun 10/116:50 am -
1 stop6h 28m
Deal found 8/12![Frontier logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/912:47 pm -
1 stop29h 52m
Thu 9/249:29 pm -
1 stop13h 53m
Deal found 8/8![Multiple Airlines logo]()
$269
This Booking.com deal was found by Cheapflights users on 8/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:10 pm -
1 stop18h 12m
Wed 9/91:03 pm -
1 stop7h 52m
Deal found 8/12![Alaska Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 8/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:41 pm -
1 stop7h 19m
Sat 10/174:30 pm -
1 stop7h 28m
Deal found 8/10![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 10/315:20 am -
2 stops7h 45m
Thu 11/55:55 am -
1 stop6h 30m
Deal found 8/12![Southwest logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/912:47 pm -
1 stop29h 52m
Sun 9/209:29 pm -
1 stop13h 53m
Deal found 8/8![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:17 am -
1 stop7h 56m
Sun 10/49:36 pm -
1 stop13h 46m
Deal found 8/10![Multiple Airlines logo]()
$281
This Alaska Airlines deal was found by Cheapflights users on 8/11. 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 9/141:29 pm -
1 stop8h 30m
Thu 9/177:20 am -
1 stop9h 13m
Deal found 8/11![Alaska Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 8/12. 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.
Wed 9/96:55 pm -
1 stop7h 35m
Wed 9/1610:30 am -
2 stops7h 30m
Deal found 8/12![Southwest logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/1010:17 am -
1 stop8h 22m
Thu 9/249:29 pm -
1 stop13h 53m
Deal found 8/8![Multiple Airlines logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:13 pm -
1 stop20h 09m
Sat 9/197:20 am -
1 stop9h 13m
Deal found 8/12![Alaska Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 10/168:10 pm -
2 stops7h 35m
Fri 10/239:30 pm -
Nonstop4h 40m
Deal found 8/12![Southwest logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/1010:17 am -
1 stop8h 22m
Sun 9/209:29 pm -
1 stop13h 53m
Deal found 8/8![Multiple Airlines logo]()
$287
This Alaska Airlines deal was found by Cheapflights users on 8/11. 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.
Tue 10/67:53 pm -
1 stop7h 47m
Wed 10/142:21 pm -
1 stop23h 09m
Deal found 8/11![Alaska Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:47 pm -
1 stop29h 52m
Wed 9/162:09 pm -
2 stops21h 13m
Deal found 8/12![Multiple Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/711:55 pm -
Nonstop4h 00m
Mon 9/216:15 am -
1 stop7h 20m
Deal found 8/8![Southwest logo]()
$347
This Alaska Airlines deal was found by Cheapflights users on 8/11. 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.
Fri 9/251:29 pm -
1 stop8h 30m
Fri 10/28:17 pm -
1 stop24h 13m
Deal found 8/11![Alaska Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 8/296:45 pm -
1 stop8h 55m
Sat 9/56:05 pm -
1 stop7h 50m
Deal found 8/10![Southwest logo]()
$366
This Alaska Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/85:10 pm -
1 stop18h 12m
Thu 9/247:20 am -
1 stop9h 13m
Deal found 8/8![Alaska Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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
Sun 9/209:29 pm -
1 stop13h 53m
Deal found 8/8![Multiple Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/158:10 pm -
2 stops7h 35m
Mon 10/196:05 am -
2 stops7h 50m
Deal found 8/8![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 8/9. 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 11/512:15 pm -
2 stops7h 45m
Tue 11/106:05 am -
2 stops9h 05m
Deal found 8/9![Southwest logo]()
$367
This Alaska Airlines deal was found by Cheapflights users on 8/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:51 pm -
1 stop8h 29m
Sun 10/47:49 pm -
1 stop17h 41m
Deal found 8/12![Alaska Airlines logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Tue 9/812:13 pm -
2 stops23h 06m
Thu 9/109:29 pm -
1 stop13h 53m
Deal found 8/11![Multiple Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 8/318:30 pm -
1 stop6h 00m
Thu 9/38:35 pm -
Nonstop4h 35m
Deal found 8/11![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 8/2811:55 pm -
Nonstop4h 00m
Sat 9/51:50 pm -
1 stop6h 05m
Deal found 8/11![Southwest logo]()
$390
Last-minute flights from Oakland to ChicagoDiscover last-minute flight deals from Oakland to Chicago. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chicago. Data last updated August 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/9. 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 9/511:55 pm -
Nonstop4h 00m
Fri 9/1110:15 am -
Nonstop4h 25m
Deal found 8/9![Southwest logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:47 pm -
1 stop14h 51m
Tue 9/151:21 pm -
1 stop24h 30m
Deal found 8/12![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:47 pm -
1 stop14h 51m
Wed 9/166:30 am -
2 stops28h 52m
Deal found 8/12![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:51 pm -
1 stop8h 47m
Tue 9/151:21 pm -
1 stop24h 30m
Deal found 8/12![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 8/9. 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.
Fri 9/1111:55 pm -
Nonstop4h 00m
Tue 9/156:50 am -
1 stop6h 15m
Deal found 8/9![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 8/9. 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.
Mon 9/1411:55 pm -
Nonstop4h 00m
Wed 9/161:55 pm -
2 stops7h 35m
Deal found 8/9![Southwest logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:17 am -
1 stop17h 21m
Tue 9/226:30 am -
2 stops31h 21m
Deal found 8/12![Frontier logo]()
$220
This Expedia deal was found by Cheapflights users on 8/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:47 pm -
1 stop14h 51m
Mon 9/288:55 pm -
1 stop16h 56m
Deal found 8/11![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:51 pm -
1 stop8h 47m
Mon 9/288:55 pm -
1 stop16h 56m
Deal found 8/12![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:51 pm -
2 stops27h 32m
Mon 9/288:55 pm -
1 stop16h 56m
Deal found 8/12![Frontier logo]()
$219
This Southwest deal was found by Cheapflights users on 8/12. 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.
Mon 9/2811:55 pm -
Nonstop4h 00m
Thu 10/19:30 pm -
Nonstop4h 40m
Deal found 8/12![Southwest logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/3012:47 pm -
1 stop14h 51m
Tue 10/136:50 am -
1 stop31h 02m
Deal found 8/11![Frontier logo]()
$172
One-way flights from Oakland to ChicagoSearch for one-way flight options from Oakland to Chicago. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
Search for one-way flight options from Oakland to Chicago. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:47 pm -
1 stop14h 51m
Deal found 8/10![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com 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 8/12![Frontier logo]()
$89
This Trip.com deal was found by Cheapflights users on 8/11. 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.
Thu 9/1010:17 am -
1 stop17h 21m
Deal found 8/11![Frontier logo]()
$97
This Frontier deal was found by Cheapflights users on 8/11. 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.
Mon 10/56:51 pm -
1 stop8h 47m
Deal found 8/11![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Sun 10/188:39 pm -
1 stop30h 37m
Deal found 8/11![Frontier logo]()
$101
This Expedia deal was found by Cheapflights users on 8/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:47 pm -
1 stop14h 51m
Deal found 8/11![Frontier logo]()
$106
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 9/1411:55 pm -
Nonstop4h 00m
Deal found 8/11![Southwest logo]()
$110
This CheapOair deal was found by Cheapflights users on 8/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:13 pm -
1 stop28h 49m
Deal found 8/11![Frontier logo]()
$111
This Trip.com deal was found by Cheapflights users on 8/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/129:50 am -
1 stop17h 26m
Deal found 8/12![Frontier logo]()
$113
This Southwest deal was found by Cheapflights users on 8/11. 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.
Fri 9/1111:55 pm -
Nonstop4h 00m
Deal found 8/11![Southwest logo]()
$119
This Southwest deal was found by Cheapflights users on 8/10. 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.
Wed 9/97:45 pm -
1 stop7h 55m
Deal found 8/10![Southwest logo]()
$120
This Delta deal was found by Cheapflights users on 8/11. 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.
Tue 9/2212:39 pm -
1 stop7h 16m
Deal found 8/11![Delta logo]()
$120
Find flight deals from Oakland to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $170 (Kiwi.com) |
One-way from | $88 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $463 |
Good round-trip deal | $372 or less |
Good one-way deal | $208 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland to Chicago 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 August 13, 2026.
Use the filters below to find and compare flights from Oakland to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Mon 9/28
2:30 pm-11:50 pm
1 stop7h 20m
Chicago Midway
Thu 10/1
9:30 pm-12:10 am
Nonstop4h 40m
$229
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sat 10/31
5:20 am-3:05 pm
2 stops7h 45m
Chicago Midway
Thu 11/5
5:55 am-10:25 am
1 stop6h 30m
$244
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Fri 10/9
8:39 pm-5:42 am
1 stop7h 03m
Chicago O'Hare Intl
Sun 10/11
6:50 am-11:18 am
1 stop6h 28m
$261
OaklandChicago
OAK Oakland - RFD Chicago Greater Rockford
OAKRFD
Oakland
Wed 9/9
12:47 pm-8:39 pm
1 stop29h 52m
Chicago Greater Rockford
Thu 9/24
9:29 pm-9:22 am
1 stop13h 53m
$269
OaklandChicago
OAK Oakland - RFD Chicago Greater Rockford
OAKRFD
Oakland
Wed 9/9
12:47 pm-8:39 pm
1 stop29h 52m
Chicago Greater Rockford
Sun 9/20
9:29 pm-9:22 am
1 stop13h 53m
$269
OaklandChicago
OAK Oakland - RFD Chicago Greater Rockford
OAKRFD
Oakland
Thu 10/1
10:17 am-8:13 pm
1 stop7h 56m
Chicago Greater Rockford
Sun 10/4
9:36 pm-9:22 am
1 stop13h 46m
$281
OaklandChicago
OAK Oakland - RFD Chicago Greater Rockford
OAKRFD
Oakland
Thu 9/10
10:17 am-8:39 pm
1 stop8h 22m
Chicago Greater Rockford
Thu 9/24
9:29 pm-9:22 am
1 stop13h 53m
$287
OaklandChicago
OAK Oakland - RFD Chicago Greater Rockford
OAKRFD
Oakland
Thu 9/10
10:17 am-8:39 pm
1 stop8h 22m
Chicago Greater Rockford
Sun 9/20
9:29 pm-9:22 am
1 stop13h 53m
$287
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Sat 9/5
5:10 pm-1:22 pm
1 stop18h 12m
Chicago O'Hare Intl
Wed 9/9
1:03 pm-6:55 pm
1 stop7h 52m
$303
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Wed 9/9
6:55 pm-4:30 am
1 stop7h 35m
Chicago Midway
Wed 9/16
10:30 am-4:00 pm
2 stops7h 30m
$307
Showing 1-10 of 57 resultsSorted by cheapest first
Compare providers for flights from Oakland to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oakland to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Oakland, California-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Oakland, California-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Oakland to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Oakland with our price prediction graph.
OAK-CHI
OAK-ORD
OAK-MDW
OAK-RFD
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 Chicago
OAK-CHI
OAK-ORD
OAK-MDW
OAK-RFD
What is the cheapest month to book a flight from Oakland, California to Chicago?
Currently, February is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $364). Flying from Oakland, California to Chicago 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 CHI?
Find hourly flight availability from Oakland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 13, 2026.
One of the essential ways to save on airfare from Oakland, California to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 61% on airfare.
Weekly flight availability from Oakland, California to Chicago
Explore weekly flight availability from Oakland to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 13, 2026.
The most flights from OAK to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Oakland, California to Chicago?
Airfare is below average for this route at the moment.
Oakland, California to Chicago flights typically cost between $364 and $587 in September.The cheapest round-trip price found within the last 5 days was $170 on Frontier (Sep 9-Sep 15).
How far ahead should I book a flight from Oakland, California to Chicago?
The best time to book flights from Oakland, California to Chicago is 60 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
The best insider tips for Oakland to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Oakland to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 13, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andUnited Airlines from Oakland to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Oakland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Oakland and Chicago flights
Browse other Oakland and Chicago flight options. Last updated on August 13, 2026.
Other flights from Oakland
Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on August 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Oakland to Chicago
Discover the top 4 airlines that operate flights from Oakland to Chicago. 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 August 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$407 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$269 | Average$439 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$272 | Average$522 | FlexibilityNo cancel fee | On-time75% |