$79+ Cheap flights from Oakland, CA (OAK) to Chicago (CHI)
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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Nov 10 — Nov 171
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 Thursday
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 October 11, 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 October 11, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:28 pm -
1 stop14h 31m
Wed 12/96:21 am -
1 stop7h 12m
Deal found 10/8![Frontier logo]()
$145
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 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
Mon 11/95:15 pm -
1 stop20h 38m
Deal found 10/8![Frontier logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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.
Wed 12/212:28 pm -
1 stop14h 31m
Sat 12/56:21 am -
1 stop7h 12m
Deal found 10/7![Frontier logo]()
$168
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:18 am -
1 stop16h 55m
Mon 11/165:15 pm -
1 stop20h 38m
Deal found 10/8![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Mon 11/165:55 pm -
1 stop9h 18m
Tue 11/174:36 pm -
2 stops21h 17m
Deal found 10/8![Frontier logo]()
$198
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:55 pm -
1 stop9h 18m
Thu 11/127:57 pm -
1 stop16h 45m
Deal found 10/9![Multiple Airlines logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/2210:17 am -
1 stop16h 59m
Mon 10/263:30 pm -
1 stop22h 23m
Deal found 10/7![Frontier logo]()
$226
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 Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/2811:55 pm -
Nonstop4h 00m
Wed 11/118:45 pm -
Nonstop4h 50m
Deal found 10/7![Southwest logo]()
$231
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 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 10/8![Frontier logo]()
$232
This Southwest deal was found by Cheapflights users on 10/8. 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 11/1611:50 pm -
Nonstop4h 05m
Tue 11/1710:00 am -
1 stop7h 00m
Deal found 10/8![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 10/8. 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 10/266:55 pm -
1 stop7h 35m
Thu 10/299:30 pm -
Nonstop4h 45m
Deal found 10/8![Southwest logo]()
$241
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 October 11, 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 October 11, 2026.
This Delta deal was found by Cheapflights users on 10/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:41 pm -
1 stop7h 06m
Mon 11/167:17 pm -
1 stop6h 38m
Deal found 10/8![Delta logo]()
$291
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 11/58:20 pm -
1 stop7h 20m
Thu 11/129:55 pm -
Nonstop4h 45m
Deal found 10/9![Southwest logo]()
$300
This KAYAK deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:00 am -
1 stop7h 31m
Wed 12/93:19 pm -
1 stop9h 31m
Deal found 10/7![Alaska Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 10/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:55 am -
2 stops10h 31m
Thu 12/107:18 pm -
1 stop6h 45m
Deal found 10/8![Delta logo]()
$296
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 10/9. 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.
Tue 11/1010:00 am -
1 stop6h 59m
Wed 11/112:15 pm -
1 stop8h 45m
Deal found 10/9![Alaska Airlines 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.
Wed 11/412:41 pm -
1 stop7h 24m
Sun 11/87:35 am -
1 stop6h 26m
Deal found 10/9![Delta logo]()
$347
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 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.
Sat 11/76:12 pm -
1 stop17h 05m
Sat 11/142:15 pm -
1 stop11h 04m
Deal found 10/11![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 10/7. Clicking the “Pick Dates” 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 12/46:55 am -
1 stop7h 45m
Sun 12/69:55 pm -
Nonstop4h 40m
Deal found 10/7![Southwest logo]()
$384
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.
Fri 4/910:45 am -
1 stop10h 55m
Sat 4/107:55 pm -
1 stop16h 10m
Deal found 10/9![Alaska Airlines logo]()
$421
This Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/1412:41 pm -
1 stop7h 06m
Tue 11/179:59 am -
2 stops8h 18m
Deal found 10/7![Delta logo]()
$386
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 Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/215:02 pm -
2 stops15h 01m
Tue 10/2710:12 am -
2 stops8h 10m
Deal found 10/7![Delta logo]()
$392
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 11/12:30 pm -
2 stops7h 15m
Thu 11/55:55 am -
1 stop6h 30m
Deal found 10/11![Southwest logo]()
$406
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 12/55:55 am -
2 stops10h 06m
Sat 12/1212:39 pm -
2 stops11h 30m
Deal found 10/9![Delta logo]()
$399
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 Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:41 pm -
1 stop7h 06m
Tue 11/177:17 pm -
1 stop6h 38m
Deal found 10/7![Delta logo]()
$421
Last-minute flights from Oakland to ChicagoDiscover last-minute flight deals from Oakland to Chicago. Data last updated October 11, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chicago. Data last updated October 11, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/2210:17 am -
1 stop16h 59m
Mon 10/263:30 pm -
1 stop22h 23m
Deal found 10/7![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 10/8. 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 10/266:55 pm -
1 stop7h 35m
Thu 10/299:30 pm -
Nonstop4h 45m
Deal found 10/8![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/2811:55 pm -
Nonstop4h 00m
Wed 11/118:45 pm -
Nonstop4h 50m
Deal found 10/7![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 10/8. 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.
Tue 11/311:50 pm -
Nonstop4h 05m
Thu 11/55:20 am -
2 stops8h 15m
Deal found 10/8![Southwest logo]()
$242
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 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
Mon 11/95:15 pm -
1 stop20h 38m
Deal found 10/8![Frontier logo]()
$152
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:55 pm -
1 stop9h 18m
Thu 11/127:57 pm -
1 stop16h 45m
Deal found 10/9![Multiple Airlines logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 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 10/8![Frontier logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:18 am -
1 stop16h 55m
Mon 11/165:15 pm -
1 stop20h 38m
Deal found 10/8![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Mon 11/165:55 pm -
1 stop9h 18m
Tue 11/174:36 pm -
2 stops21h 17m
Deal found 10/8![Frontier logo]()
$198
This Southwest deal was found by Cheapflights users on 10/8. 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 11/1611:50 pm -
Nonstop4h 05m
Tue 11/1710:00 am -
1 stop7h 00m
Deal found 10/8![Southwest logo]()
$237
This Travelocity deal was found by Cheapflights users on 10/8. 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 Travelocity 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 11/245:15 am -
1 stop7h 14m
Deal found 10/8![Frontier logo]()
$240
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
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 October 11, 2026.
Search for one-way flight options from Oakland to Chicago. Find affordable one-way fares based on user searches. Data last updated October 11, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:28 pm -
1 stop14h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$79
This Frontier deal was found by Cheapflights users on 10/8. 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 Frontier 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 10/8![Frontier logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 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 10/8![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/412:48 pm -
2 stops20h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/7![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/412:48 pm -
2 stops33h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Tue 12/812:28 pm -
2 stops21h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/135:55 pm -
1 stop9h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$116
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 1/1210:30 am -
2 stops23h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$118
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.
Mon 11/95:55 pm -
1 stop9h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/910:18 am -
2 stops23h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Mon 12/712:28 pm -
2 stops21h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$121
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 October 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $145 (Cheapflightsfares) |
One-way from | $79 (Cheapflightsfares) |
Popular in | December |
Cheapest in | February |
Average price | $408 |
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 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 7,457,451 searches. Data last updated October 11, 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 11/23
8:30 pm-4:25 am
1 stop5h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$126
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sat 12/5
12:25 pm-9:15 pm
1 stop6h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$126
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Sat 12/5
5:55 am-4:50 pm
2 stops8h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$131
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Wed 1/6
5:55 am-4:50 pm
2 stops8h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$131
OaklandChicago
OAK Oakland - ORD Chicago O'Hare Intl
OAKORD
Oakland
Thu 12/3
5:55 am-7:45 pm
2 stops11h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$131
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Thu 12/3
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 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
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
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
Quickest round-trip
OaklandChicago
OAK Oakland - MDW Chicago Midway
OAKMDW
Oakland
Thu 1/7
11:50 pm-5:50 am
Nonstop4h 00m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$183
Showing 1-10 of 41 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 October.
| 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
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
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 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 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 October 11, 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 October 11, 2026.
The most flights from OAK to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, 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 $337 and $595 in December.The cheapest round-trip price found within the last 5 days was $145 on Frontier (Dec 2-Dec 9).
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 63 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 October 11, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Southwest, 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.
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.0
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 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Oakland and Chicago flights
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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 October 11, 2026.
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Top 3 airlines flying from Oakland to Chicago
Discover the top 3 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 7,457,451 searches. Data last updated October 11, 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% |