$119+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Aug 5 — Aug 121
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 20 days in advance, depart on a Sunday or Saturday and return on a Wednesday
Cheap flight deals from Oakland to Chicago
Cheapest
Best
Last-minute
One-way
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 July 6, 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 July 6, 2026.
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/811:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Sat 8/221:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/1![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/158:30 am
OAK
- MDW
1 stop7h 05m
Southwest
Sat 8/221:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/1![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/156:00 pm
OAK
- MDW
1 stop8h 30m
Southwest
Wed 8/195:20 pm
MDW
- OAK
1 stop8h 20m
Southwest
Deal found 7/1![Southwest logo]()
$257
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/112:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Tue 8/186:20 am
ORD
- OAK
1 stop9h 50m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/125:30 am
OAK
- MDW
1 stop6h 00m
Southwest
Tue 8/182:15 pm
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 7/1![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/165:30 am
OAK
- MDW
1 stop6h 00m
Southwest
Thu 9/178:35 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 7/1![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/1711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Thu 8/2010:15 am
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/3![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/56:55 pm
OAK
- MDW
1 stop7h 35m
Southwest
Mon 8/107:35 pm
MDW
- OAK
1 stop6h 30m
Southwest
Deal found 7/1![Southwest logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/102:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Wed 8/196:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/1711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 8/194:45 pm
MDW
- OAK
1 stop6h 35m
Southwest
Deal found 7/3![Southwest logo]()
$279
This Booking.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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.
Wed 9/212:13 pm
OAK
- ORD
1 stop28h 49m
Multiple Airlines
Wed 9/92:18 pm
ORD
- OAK
1 stop9h 10m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/58:55 am
OAK
- MDW
1 stop8h 15m
Southwest
Wed 8/128:20 am
MDW
- OAK
1 stop7h 45m
Southwest
Deal found 7/3![Southwest logo]()
$289
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 July 6, 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 July 6, 2026.
This Southwest deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 8/188:55 am
OAK
- MDW
1 stop8h 15m
Southwest
Tue 8/258:35 am
MDW
- OAK
1 stop6h 35m
Southwest
Deal found 7/4![Southwest logo]()
$289
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 9/246:48 am
OAK
- ORD
1 stop10h 33m
Alaska Airlines
Mon 9/288:17 pm
ORD
- OAK
1 stop16h 49m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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
OAK
- ORD
1 stop7h 13m
Delta
Fri 9/255:10 pm
ORD
- OAK
2 stops8h 49m
Delta
Deal found 7/1![Delta logo]()
$360
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/209:15 am
OAK
- MDW
1 stop7h 10m
Southwest
Mon 8/242:05 pm
MDW
- OAK
2 stops7h 40m
Southwest
Deal found 7/1![Southwest logo]()
$294
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/241:29 pm
OAK
- ORD
1 stop8h 30m
Alaska Airlines
Mon 8/316:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/215:20 am
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 8/2410:15 am
MDW
- OAK
1 stop6h 35m
Southwest
Deal found 7/3![Southwest logo]()
$321
This Alaska Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/72:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Mon 8/107:59 pm
ORD
- OAK
1 stop15h 58m
Alaska Airlines
Deal found 7/2![Alaska Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 10/112:39 pm
OAK
- ORD
1 stop7h 13m
Delta
Sun 10/47:40 pm
ORD
- OAK
1 stop6h 19m
Delta
Deal found 7/4![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 8/1511:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 8/1910:15 am
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/6![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 10/312:39 pm
OAK
- ORD
1 stop7h 13m
Delta
Sun 10/47:40 pm
ORD
- OAK
1 stop6h 19m
Delta
Deal found 7/5![Delta logo]()
$391
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/2210:15 am
OAK
- MDW
1 stop8h 00m
Southwest
Sun 8/308:25 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 7/3![Southwest logo]()
$348
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/233:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Sat 8/296:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$387
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/172:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Sat 8/226:00 am
ORD
- OAK
2 stops12h 30m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 7/2711:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Fri 7/319:40 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 7/1![Southwest logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/196:48 am
OAK
- ORD
1 stop10h 33m
Alaska Airlines
Sun 8/306:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/3![Alaska Airlines logo]()
$401
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/411:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 10/78:35 pm
MDW
- OAK
Nonstop4h 40m
Southwest
Deal found 7/1![Southwest logo]()
$367
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/303:13 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Sun 9/66:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$419
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/139:15 am
OAK
- MDW
1 stop6h 05m
Southwest
Sun 8/168:25 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 7/5![Southwest logo]()
$381
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:04 pm
OAK
- ORD
2 stops11h 16m
Alaska Airlines
Thu 10/87:20 am
ORD
- OAK
1 stop8h 44m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$435
Last-minute flights from Oakland to ChicagoDiscover last-minute flight deals from Oakland to Chicago. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chicago. Data last updated July 6, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/2711:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Wed 7/295:30 am
MDW
- OAK
1 stop6h 15m
Southwest
Deal found 6/30![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/56:55 pm
OAK
- MDW
1 stop7h 35m
Southwest
Mon 8/107:35 pm
MDW
- OAK
1 stop6h 30m
Southwest
Deal found 7/1![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/58:55 am
OAK
- MDW
1 stop8h 15m
Southwest
Wed 8/128:20 am
MDW
- OAK
1 stop7h 45m
Southwest
Deal found 7/3![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/811:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Sat 8/221:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/1![Southwest logo]()
$237
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/102:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Wed 8/196:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$273
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/112:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Wed 8/196:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/125:30 am
OAK
- MDW
1 stop6h 00m
Southwest
Tue 8/182:15 pm
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 7/1![Southwest logo]()
$262
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/132:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Thu 8/206:01 am
ORD
- OAK
1 stop7h 05m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/158:30 am
OAK
- MDW
1 stop7h 05m
Southwest
Sat 8/221:55 pm
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/1![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/1711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Thu 8/2010:15 am
MDW
- OAK
Nonstop4h 25m
Southwest
Deal found 7/3![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/1711:55 pm
OAK
- MDW
Nonstop4h 00m
Southwest
Wed 8/194:45 pm
MDW
- OAK
1 stop6h 35m
Southwest
Deal found 7/3![Southwest logo]()
$279
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/209:15 am
OAK
- MDW
1 stop7h 10m
Southwest
Mon 8/242:05 pm
MDW
- OAK
2 stops7h 40m
Southwest
Deal found 7/1![Southwest logo]()
$294
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 July 6, 2026.
Search for one-way flight options from Oakland to Chicago. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 7/3![Southwest logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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.
Sat 8/2912:13 pm
OAK
- RFD
1 stop30h 32m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$127
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/127:15 pm
OAK
- MDW
1 stop8h 40m
Southwest
Deal found 7/1![Southwest logo]()
$129
This CheapOair deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/42:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$129
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/256:50 am
OAK
- MDW
2 stops7h 10m
Southwest
Deal found 7/1![Southwest logo]()
$134
This CheapOair deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/18:10 pm
OAK
- ORD
1 stop15h 11m
Alaska Airlines
Deal found 6/30![Alaska Airlines logo]()
$134
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/245:20 am
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 7/1![Southwest logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” 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 9/912:13 pm
OAK
- ORD
1 stop15h 29m
Frontier
Deal found 7/4![Frontier logo]()
$139
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” 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 8/56:55 pm
OAK
- MDW
1 stop7h 35m
Southwest
Deal found 7/3![Southwest logo]()
$145
This Alaska Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/132:50 pm
OAK
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 7/1![Alaska Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/212:13 pm
OAK
- ORD
1 stop28h 49m
Frontier
Deal found 7/1![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/2612:13 pm
OAK
- ORD
1 stop28h 49m
Frontier
Deal found 7/1![Frontier logo]()
$149
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 July 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | December |
Cheapest in | February |
Average price | $469 |
Good round-trip deal | $435 or less |
Good one-way deal | $217 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 July 6, 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 - MDW
OAKMDW
Oakland
Tue 8/18
8:55 am-7:10 pm
1 stop8h 15m
Chicago Midway
Tue 8/25
8:35 am-1:10 pm
1 stop6h 35m
$289
OaklandChicago
OAK - ORD
OAKORD
Oakland
Thu 9/24
6:48 am-7:21 pm
1 stop10h 33m
Chicago O'Hare Intl
Mon 9/28
8:17 pm-11:06 am
1 stop16h 49m
$289
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Thu 8/20
9:15 am-6:25 pm
1 stop7h 10m
Chicago Midway
Mon 8/24
2:05 pm-7:45 pm
2 stops7h 40m
$294
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Fri 8/21
5:20 am-11:25 am
Nonstop4h 05m
Chicago Midway
Mon 8/24
10:15 am-2:50 pm
1 stop6h 35m
$321
OaklandChicago
OAK - ORD
OAKORD
Oakland
Mon 8/24
1:29 pm-11:59 pm
1 stop8h 30m
Chicago O'Hare Intl
Mon 8/31
6:01 am-11:06 am
1 stop7h 05m
$322
OaklandChicago
OAK - ORD
OAKORD
Oakland
Fri 8/7
2:50 pm-11:36 pm
1 stop6h 46m
Chicago O'Hare Intl
Mon 8/10
7:59 pm-9:57 am
1 stop15h 58m
$331
Quickest round-trip
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 8/15
11:55 pm-5:55 am
Nonstop4h 00m
Chicago Midway
Wed 8/19
10:15 am-12:40 pm
Nonstop4h 25m
$335
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 8/22
10:15 am-8:15 pm
1 stop8h 00m
Chicago Midway
Sun 8/30
8:25 pm-10:55 pm
Nonstop4h 30m
$348
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Mon 7/27
11:55 pm-6:00 am
Nonstop4h 05m
Chicago Midway
Fri 7/31
9:40 pm-12:15 am
Nonstop4h 35m
$353
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 9/22
12:39 pm-9:52 pm
1 stop7h 13m
Chicago O'Hare Intl
Fri 9/25
5:10 pm-11:59 pm
2 stops8h 49m
$360
Showing 1-10 of 49 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 July.
| 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-MDW
OAK-ORD
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-MDW
OAK-ORD
OAK-RFD
What is the cheapest month to book a flight from Oakland, California to Chicago?
Currently, April is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $93). Flying from Oakland, California to Chicago in December is currently the most expensive (average of $274). 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 July 6, 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 at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 57% 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 July 6, 2026.
The most flights from OAK to CHI are scheduled on a Monday (3 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?
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 19 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 July 6, 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.
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Overall
7.9
Food
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.0
Overall
7.9
Food
7.0
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
Hammond
Lansing
Merrillville
Valparaiso
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 July 6, 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 July 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated July 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$207 | Average$395 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$252 | Average$436 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$272 | Average$522 | FlexibilityNo cancel fee | On-time75% |