$104+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — CHI
Apr 28 — May 51
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 July or February, booked 20 days in advance, depart on a Monday or Wednesday and return on a Tuesday
Cheap flight deals from Oakland to Chicago
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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 March 29, 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 March 29, 2026.
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 6/111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Thu 6/49:40 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 3/26![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/911:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Wed 5/135:15 pm
MDW
- OAK
1 stop6h 40m
Southwest
Deal found 3/25![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/1411:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 4/186:00 am
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 3/26![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/2510:45 am
OAK
- MDW
1 stop6h 35m
Southwest
Sat 5/210:30 am
MDW
- OAK
1 stop6h 20m
Southwest
Deal found 3/26![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 5/912:28 pm
OAK
- ORD
1 stop7h 22m
Delta
Tue 5/127:45 pm
ORD
- OAK
1 stop6h 12m
Delta
Deal found 3/26![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 5/111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Wed 5/63:55 pm
MDW
- OAK
1 stop6h 25m
Southwest
Deal found 3/27![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/155:55 am
OAK
- ORD
2 stops8h 23m
Delta
Sat 4/182:09 pm
ORD
- OAK
1 stop9h 32m
Delta
Deal found 3/25![Delta logo]()
$232
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/255:00 am
OAK
- MDW
2 stops7h 45m
Southwest
Sat 5/96:00 am
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 3/26![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:10 am
OAK
- ORD
2 stops9h 45m
Southwest
Wed 5/67:45 am
ORD
- OAK
2 stops9h 15m
Southwest
Deal found 3/25![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:25 pm
OAK
- ORD
2 stops9h 30m
Southwest
Sat 5/27:00 am
ORD
- OAK
1 stop10h 50m
Southwest
Deal found 3/24![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 5/291:25 pm
OAK
- MDW
1 stop7h 15m
Southwest
Mon 6/16:25 pm
MDW
- OAK
1 stop7h 30m
Southwest
Deal found 3/26![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:34 pm
OAK
- ORD
1 stop6h 44m
Delta
Wed 4/297:35 am
ORD
- OAK
1 stop6h 18m
Delta
Deal found 3/25![Delta logo]()
$242
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 March 29, 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 March 29, 2026.
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:04 pm
OAK
- ORD
2 stops13h 36m
Delta
Fri 4/177:10 pm
ORD
- OAK
1 stop6h 44m
Delta
Deal found 3/25![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 4/2511:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 5/25:55 pm
MDW
- OAK
Nonstop4h 35m
Southwest
Deal found 3/28![Southwest logo]()
$265
This Alaska Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 4/286:20 am
OAK
- ORD
1 stop8h 36m
Alaska Airlines
Wed 4/296:00 am
ORD
- OAK
1 stop9h 15m
Alaska Airlines
Deal found 3/28![Alaska Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 3/24. 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 4/155:55 am
OAK
- ORD
2 stops10h 57m
Delta
Thu 4/167:35 am
ORD
- OAK
1 stop6h 18m
Delta
Deal found 3/24![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 5/2912:10 pm
OAK
- ORD
2 stops9h 45m
Southwest
Mon 6/17:20 pm
ORD
- OAK
1 stop6h 45m
Southwest
Deal found 3/26![Southwest logo]()
$305
This Alaska Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/222:09 pm
OAK
- ORD
1 stop7h 50m
Alaska Airlines
Tue 4/288:50 am
ORD
- OAK
1 stop7h 48m
Alaska Airlines
Deal found 3/27![Alaska Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 5/195:45 am
OAK
- MDW
2 stops7h 20m
Southwest
Fri 5/227:40 pm
MDW
- OAK
1 stop6h 25m
Southwest
Deal found 3/27![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
OAK
- ORD
2 stops8h 51m
Delta
Wed 6/107:37 pm
ORD
- OAK
1 stop6h 17m
Delta
Deal found 3/25![Delta logo]()
$368
This Alaska Airlines deal was found by Cheapflights users on 3/24. 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 6/78:13 pm
OAK
- ORD
1 stop25h 42m
Alaska Airlines
Thu 6/112:20 pm
ORD
- OAK
1 stop10h 17m
Alaska Airlines
Deal found 3/24![Alaska Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1511:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Mon 5/187:40 pm
MDW
- OAK
1 stop6h 25m
Southwest
Deal found 3/25![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/115:55 am
OAK
- ORD
2 stops9h 58m
Delta
Mon 4/131:36 pm
ORD
- OAK
2 stops12h 18m
Delta
Deal found 3/27![Delta logo]()
$369
This Alaska Airlines deal was found by Cheapflights users on 3/24. 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.
Fri 5/86:41 am
OAK
- ORD
1 stop28h 32m
Alaska Airlines
Sun 5/107:59 pm
ORD
- OAK
1 stop20h 39m
Alaska Airlines
Deal found 3/24![Alaska Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:40 am
OAK
- MDW
2 stops7h 10m
Southwest
Sat 4/186:00 am
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 3/24![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 3/24. 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 7/156:00 am
OAK
- MDW
2 stops10h 25m
Delta
Fri 7/171:49 pm
MDW
- OAK
2 stops12h 02m
Delta
Deal found 3/24![Delta logo]()
$410
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Fri 7/109:40 pm
MDW
- OAK
Nonstop4h 30m
Southwest
Deal found 3/25![Southwest logo]()
$390
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 4/812:35 pm
OAK
- ORD
1 stop6h 59m
Delta
Thu 4/97:10 pm
ORD
- OAK
1 stop6h 36m
Delta
Deal found 3/28![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 5/2111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 5/306:00 am
MDW
- OAK
2 stops8h 25m
Southwest
Deal found 3/27![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 3/24. 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.
Sun 5/176:00 am
OAK
- ORD
2 stops10h 05m
Delta
Sat 5/237:45 am
ORD
- OAK
1 stop6h 03m
Delta
Deal found 3/24![Delta logo]()
$436
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 5/1711:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sun 5/249:10 am
MDW
- OAK
1 stop8h 20m
Southwest
Deal found 3/26![Southwest logo]()
$409
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/225:55 am
OAK
- MDW
2 stops10h 03m
Delta
Tue 4/282:12 pm
MDW
- OAK
2 stops11h 42m
Delta
Deal found 3/27![Delta logo]()
$443
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/295:15 am
OAK
- MDW
2 stops7h 20m
Southwest
Mon 8/101:50 pm
MDW
- OAK
2 stops7h 40m
Southwest
Deal found 3/25![Southwest logo]()
$436
Last-minute flights from Oakland to ChicagoDiscover last-minute flight deals from Oakland to Chicago. Data last updated March 29, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chicago. Data last updated March 29, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/1411:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Sat 4/186:45 am
MDW
- OAK
1 stop7h 25m
Southwest
Deal found 3/26![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:34 pm
OAK
- ORD
1 stop6h 44m
Delta
Wed 5/67:10 pm
ORD
- OAK
1 stop6h 44m
Delta
Deal found 3/25![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/155:55 am
OAK
- ORD
2 stops8h 23m
Delta
Sat 4/182:09 pm
ORD
- OAK
1 stop9h 32m
Delta
Deal found 3/25![Delta logo]()
$232
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:10 am
OAK
- ORD
2 stops9h 45m
Southwest
Wed 5/67:45 am
ORD
- OAK
2 stops9h 15m
Southwest
Deal found 3/25![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:25 pm
OAK
- ORD
2 stops8h 30m
Southwest
Fri 4/177:20 pm
ORD
- OAK
1 stop6h 45m
Southwest
Deal found 3/24![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/178:30 pm
OAK
- MDW
1 stop6h 05m
Southwest
Mon 4/207:40 pm
MDW
- OAK
1 stop6h 25m
Southwest
Deal found 3/24![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:34 pm
OAK
- ORD
1 stop6h 44m
Delta
Wed 4/297:35 am
ORD
- OAK
1 stop6h 18m
Delta
Deal found 3/25![Delta logo]()
$242
This CheapOair deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/236:41 am
OAK
- ORD
1 stop10h 22m
Alaska Airlines
Thu 4/303:52 pm
ORD
- OAK
1 stop8h 31m
Alaska Airlines
Deal found 3/26![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/248:55 pm
OAK
- MDW
1 stop6h 55m
Southwest
Fri 5/15:25 am
MDW
- OAK
1 stop6h 55m
Southwest
Deal found 3/27![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/2510:45 am
OAK
- MDW
1 stop6h 35m
Southwest
Sat 5/210:30 am
MDW
- OAK
1 stop6h 20m
Southwest
Deal found 3/26![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/255:00 am
OAK
- MDW
2 stops7h 45m
Southwest
Sat 5/96:45 am
MDW
- OAK
1 stop7h 25m
Southwest
Deal found 3/26![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:25 pm
OAK
- ORD
2 stops9h 30m
Southwest
Sat 5/27:00 am
ORD
- OAK
1 stop10h 50m
Southwest
Deal found 3/24![Southwest logo]()
$238
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 March 29, 2026.
Search for one-way flight options from Oakland to Chicago. Find affordable one-way fares based on user searches. Data last updated March 29, 2026.
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/2111:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/26![Southwest logo]()
$104
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/213:00 pm
OAK
- ORD
1 stop6h 55m
Southwest
Deal found 3/26![Southwest logo]()
$114
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 6/96:00 am
OAK
- MDW
2 stops10h 18m
Delta
Deal found 3/26![Delta logo]()
$124
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:04 pm
OAK
- ORD
2 stops13h 36m
Delta
Deal found 3/26![Delta logo]()
$124
This CheapOair deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/43:18 pm
OAK
- ORD
1 stop6h 25m
Alaska Airlines
Deal found 3/25![Alaska Airlines logo]()
$129
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/2711:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/27![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:55 pm
OAK
- MDW
Nonstop4h 05m
Southwest
Deal found 3/25![Southwest logo]()
$134
This CheapOair deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:57 am
OAK
- ORD
1 stop24h 16m
Alaska Airlines
Deal found 3/25![Alaska Airlines logo]()
$134
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:00 am
OAK
- ORD
1 stop7h 30m
Southwest
Deal found 3/25![Southwest logo]()
$140
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/185:00 am
OAK
- ORD
1 stop7h 30m
Southwest
Deal found 3/27![Southwest logo]()
$143
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:50 pm
OAK
- MDW
1 stop6h 50m
Southwest
Deal found 3/24![Southwest logo]()
$144
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/2512:34 pm
OAK
- ORD
1 stop6h 44m
Delta
Deal found 3/27![Delta logo]()
$144
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 March 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (Southwest) |
One-way from | $104 (Southwest) |
Popular in | December |
Cheapest in | July |
Average price | $369 |
Good round-trip deal | $383 or less |
Good one-way deal | $199 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 March 29, 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 - ORD
OAKORD
Oakland
Mon 4/13
5:04 pm-8:40 am
2 stops13h 36m
Chicago O'Hare Intl
Fri 4/17
7:10 pm-11:54 pm
1 stop6h 44m
$247
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 4/25
11:55 pm-6:00 am
Nonstop4h 05m
Chicago Midway
Sat 5/2
5:55 pm-8:30 pm
Nonstop4h 35m
$265
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 4/28
6:20 am-4:56 pm
1 stop8h 36m
Chicago O'Hare Intl
Wed 4/29
6:00 am-1:15 pm
1 stop9h 15m
$285
OaklandChicago
OAK - ORD
OAKORD
Oakland
Wed 4/15
5:55 am-6:52 pm
2 stops10h 57m
Chicago O'Hare Intl
Thu 4/16
7:35 am-11:53 am
1 stop6h 18m
$304
OaklandChicago
OAK - ORD
OAKORD
Oakland
Fri 5/29
12:10 pm-11:55 pm
2 stops9h 45m
Chicago O'Hare Intl
Mon 6/1
7:20 pm-12:05 am
1 stop6h 45m
$305
OaklandChicago
OAK - ORD
OAKORD
Oakland
Wed 4/22
2:09 pm-11:59 pm
1 stop7h 50m
Chicago O'Hare Intl
Tue 4/28
8:50 am-2:38 pm
1 stop7h 48m
$312
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 5/19
5:45 am-3:05 pm
2 stops7h 20m
Chicago Midway
Fri 5/22
7:40 pm-12:05 am
1 stop6h 25m
$361
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Fri 5/15
11:55 pm-6:00 am
Nonstop4h 05m
Chicago Midway
Mon 5/18
7:40 pm-12:05 am
1 stop6h 25m
$361
OaklandChicago
OAK - ORD
OAKORD
Oakland
Wed 6/3
6:00 am-4:51 pm
2 stops8h 51m
Chicago O'Hare Intl
Wed 6/10
7:37 pm-11:54 pm
1 stop6h 17m
$368
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 4/11
5:55 am-5:53 pm
2 stops9h 58m
Chicago O'Hare Intl
Mon 4/13
1:36 pm-11:54 pm
2 stops12h 18m
$369
Showing 1-10 of 51 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 March.
| 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 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
How far ahead should I book a flight from Oakland, California to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Oakland to Chicago. Price data was last updated on March 13, 2026.
The best time to book flights from Oakland, California to Chicago is 20 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.
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 $115). Flying from Oakland, California to Chicago in December is currently the most expensive (average of $233). 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 March 29, 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 54% 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 March 29, 2026.
The most flights from OAK to CHI are scheduled on a Monday (4 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?
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 March 29, 2026.
Peruse reviews from past customers who have flown with Southwest,Alaska Airlines, andUnited Airlines from Oakland to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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 locationsLansing
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Hammond
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Benton Harbor
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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 March 29, 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 March 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Oakland to Chicago
Discover the top 4 airlines that operate flights from Oakland to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$222 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$163 | Average$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$237 | Average$522 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$246 | Average$424 | FlexibilityNo cancel fee | On-time63% |