$145+ Cheap flights from Chicago (CHI) to Oakland, CA (OAK)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
Jul 24 — Jul 311
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Oakland 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Oakland
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Cheapest flights from Chicago to OaklandExplore the most affordable flight options available from Chicago to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 24, 2026.
Explore the most affordable flight options available from Chicago to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 24, 2026.
This CheapOair deal was found by Cheapflights users on 6/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Mon 8/32:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 6/24. 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.
Wed 8/261:59 pm
ORD
- OAK
2 stops11h 57m
Delta
Sat 8/2912:33 pm
OAK
- ORD
1 stop6h 57m
Delta
Deal found 6/24![Delta logo]()
$302
This CheapOair deal was found by Cheapflights users on 6/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Sun 8/98:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:59 pm
ORD
- OAK
1 stop6h 57m
Delta
Wed 1/65:55 am
OAK
- ORD
2 stops8h 54m
Delta
Deal found 6/22![Delta logo]()
$312
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:50 pm
ORD
- OAK
2 stops10h 06m
Delta
Wed 1/65:55 am
OAK
- ORD
2 stops8h 54m
Delta
Deal found 6/22![Delta logo]()
$317
This SmartFares deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:59 pm
ORD
- OAK
1 stop6h 42m
Alaska Airlines
Sat 7/255:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 6/19![Alaska Airlines logo]()
$318
This Frontier deal was found by Cheapflights users on 6/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:50 am
ORD
- OAK
1 stop6h 28m
Frontier
Sun 9/208:39 pm
OAK
- ORD
1 stop7h 03m
Frontier
Deal found 6/22![Frontier logo]()
$320
This CheapOair deal was found by Cheapflights users on 6/24. 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.
Sat 7/185:59 pm
ORD
- OAK
1 stop6h 42m
Alaska Airlines
Fri 7/248:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 6/24![Alaska Airlines logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 6/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Sat 7/258:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$326
This Alaska Airlines deal was found by Cheapflights users on 6/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Wed 9/95:10 pm
OAK
- ORD
1 stop18h 12m
Alaska Airlines
Deal found 6/24![Alaska Airlines logo]()
$327
This Alaska Airlines deal was found by Cheapflights users on 6/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Sat 7/255:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 6/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/151:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Sat 8/2211:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 6/23![Southwest logo]()
$329
Best flights from Chicago to OaklandDiscover carefully curated flight deals from Chicago to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 24, 2026.
Discover carefully curated flight deals from Chicago to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 24, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Wed 8/52:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 6/24. 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.
Wed 8/267:44 pm
ORD
- OAK
1 stop6h 12m
Delta
Sat 8/2912:33 pm
OAK
- ORD
1 stop6h 57m
Delta
Deal found 6/24![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 6/21. 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.
Sat 8/151:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Sat 8/2211:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 6/21![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:40 pm
ORD
- OAK
1 stop6h 19m
Delta
Sat 10/312:39 pm
OAK
- ORD
1 stop7h 13m
Delta
Deal found 6/23![Delta logo]()
$307
This Alaska Airlines deal was found by Cheapflights users on 6/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:18 pm
ORD
- OAK
1 stop10h 52m
Alaska Airlines
Sun 9/273:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 6/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Sat 8/811:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 6/23![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 6/20. 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.
Tue 7/215:30 am
MDW
- OAK
1 stop6h 15m
Southwest
Sat 7/251:40 pm
OAK
- MDW
1 stop8h 40m
Southwest
Deal found 6/20![Southwest logo]()
$344
This Alaska Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:20 am
ORD
- OAK
1 stop8h 44m
Alaska Airlines
Wed 10/282:44 pm
OAK
- ORD
1 stop7h 15m
Alaska Airlines
Deal found 6/19![Alaska Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/309:40 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sat 8/18:35 pm
OAK
- MDW
1 stop6h 50m
Southwest
Deal found 6/19![Southwest logo]()
$345
This Alaska Airlines deal was found by Cheapflights users on 6/21. 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.
Wed 8/266:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Sat 8/295:10 pm
OAK
- ORD
1 stop18h 12m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 6/21. 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.
Thu 9/247:20 am
ORD
- OAK
1 stop9h 13m
Alaska Airlines
Sat 10/37:00 am
OAK
- ORD
1 stop9h 53m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/141:50 pm
MDW
- OAK
1 stop7h 55m
Southwest
Sat 8/1511:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 6/19![Southwest logo]()
$354
This Alaska Airlines deal was found by Cheapflights users on 6/22. 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 7/146:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Tue 7/145:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 6/22. 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.
Wed 8/1210:15 am
MDW
- OAK
Nonstop4h 25m
Southwest
Sun 8/1611:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Deal found 6/22![Southwest logo]()
$368
This Alaska Airlines deal was found by Cheapflights users on 6/20. 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 12/112:03 pm
ORD
- OAK
1 stop7h 16m
Alaska Airlines
Tue 1/53:30 pm
OAK
- ORD
1 stop6h 29m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$364
Last-minute flights from Chicago to OaklandDiscover last-minute flight deals from Chicago to Oakland. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oakland. Data last updated June 24, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 6/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Sat 7/258:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:40 pm
ORD
- OAK
1 stop6h 10m
Delta
Fri 7/2412:30 pm
OAK
- ORD
1 stop6h 59m
Delta
Deal found 6/22![Delta logo]()
$337
This SmartFares deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:59 pm
ORD
- OAK
1 stop6h 42m
Alaska Airlines
Sat 7/255:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 6/19![Alaska Airlines logo]()
$318
This CheapOair deal was found by Cheapflights users on 6/24. 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.
Sat 7/185:59 pm
ORD
- OAK
1 stop6h 42m
Alaska Airlines
Fri 7/248:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 6/24![Alaska Airlines logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 6/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Sat 7/255:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:52 am
ORD
- OAK
2 stops9h 29m
Delta
Fri 7/2412:30 pm
OAK
- ORD
1 stop6h 59m
Delta
Deal found 6/23![Delta logo]()
$336
This Alaska Airlines deal was found by Cheapflights users on 6/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/236:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Sat 7/255:35 pm
OAK
- ORD
1 stop9h 25m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$331
This CheapOair deal was found by Cheapflights users on 6/24. 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.
Fri 7/247:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Sun 7/268:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 6/24![Alaska Airlines logo]()
$327
This CheapOair deal was found by Cheapflights users on 6/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Wed 8/510:37 am
OAK
- ORD
1 stop10h 59m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$297
This CheapOair deal was found by Cheapflights users on 6/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Tue 8/47:52 am
OAK
- ORD
1 stop19h 08m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 6/20. 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.
Wed 7/295:30 am
MDW
- OAK
1 stop6h 15m
Southwest
Mon 8/311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 6/20![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 6/22. 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 7/309:40 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Sat 8/111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 6/22![Southwest logo]()
$332
One-way flights from Chicago to OaklandSearch for one-way flight options from Chicago to Oakland. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
Search for one-way flight options from Chicago to Oakland. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
This Frontier deal was found by Cheapflights users on 6/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:50 am
ORD
- OAK
1 stop6h 28m
Frontier
Deal found 6/22![Frontier logo]()
$145
This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:45 am
ORD
- OAK
1 stop6h 14m
Delta
Deal found 6/23![Delta logo]()
$149
This Alaska Airlines deal was found by Cheapflights users on 6/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:18 pm
ORD
- OAK
1 stop9h 10m
Alaska Airlines
Deal found 6/23![Alaska Airlines logo]()
$154
This Delta deal was found by Cheapflights users on 6/24. 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.
Wed 8/191:25 pm
MDW
- OAK
2 stops12h 31m
Delta
Deal found 6/24![Delta logo]()
$154
This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:59 pm
ORD
- OAK
2 stops11h 57m
Delta
Deal found 6/23![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:51 pm
MDW
- OAK
2 stops12h 05m
Delta
Deal found 6/22![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 6/21. 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 7/2110:00 am
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 6/21![Southwest logo]()
$165
This Southwest deal was found by Cheapflights users on 6/22. 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 8/2010:15 am
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 6/22![Southwest logo]()
$168
This Frontier deal was found by Cheapflights users on 6/21. 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 9/246:50 am
ORD
- OAK
1 stop6h 28m
Frontier
Deal found 6/21![Frontier logo]()
$169
This Southwest deal was found by Cheapflights users on 6/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:30 am
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 6/23![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 6/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:15 pm
MDW
- OAK
1 stop6h 05m
Southwest
Deal found 6/23![Southwest logo]()
$173
This CheapOair deal was found by Cheapflights users on 6/24. 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.
Wed 7/156:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 6/24![Alaska Airlines logo]()
$175
Find flight deals from Chicago to Oakland
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Oakland (OAK). 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 June 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (Delta) |
One-way from | $145 (Frontier) |
Popular in | November |
Cheapest in | September |
Average price | $571 |
Good round-trip deal | $294 or less |
Good one-way deal | $226 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Oakland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 24, 2026.
Use the filters below to find and compare flights from Chicago to Oakland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 7/29
6:20 am-2:10 pm
1 stop9h 50m
Oakland
Wed 8/5
2:50 pm-11:36 pm
1 stop6h 46m
$297
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 8/26
7:44 pm-11:56 pm
1 stop6h 12m
Oakland
Sat 8/29
12:33 pm-9:30 pm
1 stop6h 57m
$297
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Thu 9/24
7:40 pm-11:59 pm
1 stop6h 19m
Oakland
Sat 10/3
12:39 pm-9:52 pm
1 stop7h 13m
$307
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Thu 9/24
2:18 pm-11:10 pm
1 stop10h 52m
Oakland
Sun 9/27
3:13 pm-11:59 pm
1 stop6h 46m
$307
Quickest round-trip
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sat 8/15
1:55 pm-4:20 pm
Nonstop4h 25m
Oakland
Sat 8/22
11:55 pm-5:55 am
Nonstop4h 00m
$329
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Thu 8/6
8:35 pm-11:05 pm
Nonstop4h 30m
Oakland
Sat 8/8
11:55 pm-5:55 am
Nonstop4h 00m
$341
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Tue 7/21
5:30 am-9:45 am
1 stop6h 15m
Oakland
Sat 7/25
1:40 pm-12:20 am
1 stop8h 40m
$344
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Thu 7/30
9:40 pm-12:15 am
Nonstop4h 35m
Oakland
Sat 8/1
8:35 pm-5:25 am
1 stop6h 50m
$345
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Tue 10/27
7:20 am-2:04 pm
1 stop8h 44m
Oakland
Wed 10/28
2:44 pm-11:59 pm
1 stop7h 15m
$349
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Wed 8/26
6:01 am-11:06 am
1 stop7h 05m
Oakland
Sat 8/29
5:10 pm-1:22 pm
1 stop18h 12m
$349
Showing 1-10 of 35 resultsSorted by cheapest first
Compare providers for flights from Chicago to Oakland
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 Chicago to Oakland in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Oakland, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Oakland, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Oakland, California flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Oakland, California 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 Chicago-Oakland, California 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 Chicago to Oakland
Have a flexible travel schedule? Discover the best time to fly to Oakland from Chicago with our price prediction graph.
CHI-OAK
ORD-OAK
MDW-OAK
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Oakland
CHI-OAK
ORD-OAK
MDW-OAK
What is the cheapest month to book a flight from Chicago to Oakland, California?
Currently, August is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $83). Flying from Chicago to Oakland, California in December is currently the most expensive (average of $288). 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 CHI to OAK?
Find hourly flight availability from Chicago to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 24, 2026.
It’s typically best to fly out from Chicago to Oakland, California in the evening. Doing so could potentially save you 45% on the flight price compared to flying in the morning, which is usually more expensive.
How much does it cost to fly round-trip from Chicago to Oakland, California?
How often are flights from Chicago to Oakland delayed?
About 25% of weekly flights between Chicago and Oakland have experienced delays in the past year, with the average delay time being 102 minutes.
What is the most punctual flight time for Chicago to Oakland flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Oakland flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 30% of flights being delayed.
The best insider tips for Chicago to Oakland 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 Chicago to Oakland trip
Our travel experts
Reviews of airlines servicing Oakland
Get insights into the airlines that provide service to Oakland. 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 Oakland. Reviews last updated June 24, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andUnited Airlines from Chicago to Oakland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Entertainment
7.0
Overall
7.9
Crew
8.5
Food
7.0
Comfort
7.8
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Search flights from Chicago to Oakland by cabin class
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Other flights to Oakland
Explore flights to Oakland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 24, 2026.
Chicago and Oakland flights
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Other flights from Chicago
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Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Chicago to Oakland
Discover the top 3 airlines that operate flights from Chicago to Oakland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$165 | Average$344 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$245 | Average$429 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$264 | Average$377 | FlexibilityNo cancel fee | On-timeN/A |