$89+ 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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAK
Sep 5 — Sep 121
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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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 August 6, 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 August 6, 2026.
This Priceline deal was found by Cheapflights users on 8/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:50 am -
1 stop6h 28m
Thu 11/58:39 pm -
1 stop6h 56m
Deal found 8/4![Frontier logo]()
$178
This CheapOair deal was found by Cheapflights users on 8/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:11 pm -
1 stop17h 07m
Wed 9/912:47 pm -
1 stop14h 51m
Deal found 8/3![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:02 pm -
1 stop8h 42m
Mon 10/198:39 pm -
1 stop7h 03m
Deal found 8/1![Frontier logo]()
$208
This Orbitz deal was found by Cheapflights users on 8/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:55 pm -
1 stop16h 56m
Mon 9/286:51 pm -
1 stop8h 47m
Deal found 8/3![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Sat 9/121:21 pm -
1 stop22h 01m
Fri 9/186:51 pm -
1 stop8h 47m
Deal found 8/1![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 8/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:50 am -
1 stop6h 28m
Thu 10/298:39 pm -
1 stop6h 56m
Deal found 8/5![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 8/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:02 pm -
1 stop8h 42m
Thu 10/298:39 pm -
1 stop6h 56m
Deal found 8/5![Frontier logo]()
$226
This Expedia deal was found by Cheapflights users on 8/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:20 am -
1 stop9h 13m
Mon 9/286:51 pm -
1 stop8h 47m
Deal found 8/5![Multiple Airlines logo]()
$228
This CheapOair deal was found by Cheapflights users on 8/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:50 am -
1 stop6h 28m
Wed 11/412:13 pm -
1 stop21h 44m
Deal found 8/4![Frontier logo]()
$232
This Expedia deal was found by Cheapflights users on 8/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:18 pm -
1 stop7h 34m
Mon 9/712:13 pm -
1 stop28h 08m
Deal found 8/2![Multiple Airlines logo]()
$233
This CheapOair deal was found by Cheapflights users on 8/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:02 pm -
1 stop24h 16m
Sat 10/3112:13 pm -
1 stop22h 44m
Deal found 8/4![Frontier logo]()
$236
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 9/51:55 pm -
Nonstop4h 25m
Fri 9/1111:55 pm -
Nonstop4h 00m
Deal found 8/5![Southwest logo]()
$237
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 August 6, 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 August 6, 2026.
This Alaska Airlines deal was found by Cheapflights users on 8/2. 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.
Wed 9/167:20 am -
1 stop9h 13m
Wed 9/236:48 am -
1 stop10h 33m
Deal found 8/2![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 8/1. 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 10/201:05 pm -
2 stops7h 50m
Wed 11/48:30 am -
1 stop6h 50m
Deal found 8/1![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:59 pm -
2 stops11h 57m
Tue 9/112:33 pm -
1 stop7h 00m
Deal found 8/3![Delta logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 8/3. 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.
Tue 10/202:21 pm -
1 stop11h 20m
Wed 11/46:20 am -
1 stop10h 40m
Deal found 8/3![Alaska Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 8/3. 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.
Thu 9/244:55 pm -
1 stop7h 55m
Mon 9/285:20 am -
2 stops7h 15m
Deal found 8/3![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 8/4. 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.
Fri 10/239:30 pm -
Nonstop4h 40m
Sat 10/3110:55 pm -
Nonstop5h 00m
Deal found 8/4![Southwest logo]()
$297
This Alaska Airlines deal was found by Cheapflights users on 8/1. 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.
Sat 8/222:18 pm -
1 stop7h 34m
Mon 8/241:29 pm -
1 stop8h 30m
Deal found 8/1![Alaska Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 8/5. 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.
Thu 12/105:30 am -
2 stops12h 47m
Wed 1/65:55 am -
2 stops8h 54m
Deal found 8/5![Delta logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 8/5. 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.
Wed 12/92:03 pm -
1 stop7h 16m
Tue 1/53:30 pm -
1 stop6h 29m
Deal found 8/5![Alaska Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 8/1. 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 8/271:50 pm -
2 stops7h 40m
Tue 9/17:45 pm -
1 stop7h 55m
Deal found 8/1![Southwest logo]()
$318
This Alaska Airlines deal was found by Cheapflights users on 8/5. 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.
Mon 9/287:20 am -
1 stop9h 13m
Tue 10/67:04 am -
1 stop9h 49m
Deal found 8/5![Alaska Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 8/6. 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.
Thu 10/16:15 pm -
1 stop6h 20m
Thu 10/83:20 pm -
2 stops7h 35m
Deal found 8/6![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 8/5. 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.
Sun 12/137:35 am -
1 stop6h 21m
Tue 1/55:55 am -
2 stops8h 54m
Deal found 8/5![Delta logo]()
$406
This Southwest deal was found by Cheapflights users on 8/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:30 am -
2 stops7h 30m
Wed 9/237:15 pm -
1 stop8h 40m
Deal found 8/2![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 8/4. 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 12/107:17 pm -
1 stop6h 38m
Fri 1/11:15 pm -
1 stop6h 38m
Deal found 8/4![Delta logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 8/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:25 am -
1 stop18h 02m
Mon 11/163:04 pm -
1 stop6h 45m
Deal found 8/4![Alaska Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 8/1. 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.
Fri 12/410:15 am -
2 stops9h 00m
Mon 12/78:30 pm -
1 stop7h 10m
Deal found 8/1![Southwest logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 8/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:01 am -
1 stop7h 05m
Wed 9/96:48 am -
2 stops15h 11m
Deal found 8/4![Alaska Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 8/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:45 pm -
Nonstop4h 45m
Sun 12/68:30 pm -
1 stop5h 55m
Deal found 8/2![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 8/5. 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 10/155:25 am -
1 stop6h 45m
Sun 10/188:55 pm -
1 stop6h 45m
Deal found 8/5![Southwest logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 8/1. 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 9/156:00 am -
2 stops17h 28m
Tue 9/226:48 am -
2 stops15h 11m
Deal found 8/1![Alaska Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 8/3. 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.
Tue 8/252:15 pm -
2 stops8h 25m
Tue 9/19:00 am -
2 stops8h 15m
Deal found 8/3![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 8/6. 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.
Thu 9/36:15 pm -
1 stop6h 35m
Mon 9/75:20 am -
2 stops7h 15m
Deal found 8/6![Southwest logo]()
$372
Last-minute flights from Chicago to OaklandDiscover last-minute flight deals from Chicago to Oakland. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oakland. Data last updated August 6, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 8/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:18 pm -
1 stop7h 34m
Mon 9/712:13 pm -
1 stop28h 08m
Deal found 8/2![Multiple Airlines logo]()
$233
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 9/51:55 pm -
Nonstop4h 25m
Fri 9/1111:55 pm -
Nonstop4h 00m
Deal found 8/5![Southwest logo]()
$237
This Vliegwinkel deal was found by Cheapflights users on 8/2. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:18 pm -
1 stop7h 34m
Fri 9/113:13 pm -
1 stop6h 46m
Deal found 8/2![Alaska Airlines logo]()
$263
This CheapOair deal was found by Cheapflights users on 8/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:11 pm -
1 stop17h 07m
Wed 9/912:47 pm -
1 stop14h 51m
Deal found 8/3![Frontier logo]()
$188
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Sat 9/121:21 pm -
1 stop22h 01m
Fri 9/186:51 pm -
1 stop8h 47m
Deal found 8/1![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 8/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:55 pm -
1 stop14h 27m
Wed 9/1612:47 pm -
1 stop14h 51m
Deal found 8/3![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Tue 9/151:21 pm -
1 stop24h 30m
Tue 9/2212:47 pm -
1 stop14h 51m
Deal found 8/1![Frontier logo]()
$261
This Southwest deal was found by Cheapflights users on 8/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:35 pm -
Nonstop4h 35m
Wed 9/2311:55 pm -
Nonstop4h 00m
Deal found 8/2![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 9/196:05 pm -
1 stop7h 50m
Sat 9/2611:55 pm -
Nonstop4h 00m
Deal found 8/5![Southwest logo]()
$267
This Expedia deal was found by Cheapflights users on 8/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:55 pm -
1 stop23h 01m
Mon 9/2810:17 am -
1 stop17h 21m
Deal found 8/3![Frontier logo]()
$178
This Expedia deal was found by Cheapflights users on 8/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:20 am -
1 stop9h 13m
Mon 9/286:51 pm -
1 stop8h 47m
Deal found 8/5![Multiple Airlines logo]()
$228
This Orbitz deal was found by Cheapflights users on 8/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:55 pm -
1 stop16h 56m
Mon 9/286:51 pm -
1 stop8h 47m
Deal found 8/3![Frontier logo]()
$211
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 August 6, 2026.
Search for one-way flight options from Chicago to Oakland. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Frontier deal was found by Cheapflights users on 8/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:50 am -
1 stop6h 28m
Deal found 8/2![Frontier logo]()
$89
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Thu 9/178:55 pm -
1 stop14h 27m
Deal found 8/1![Frontier logo]()
$100
This Frontier deal was found by Cheapflights users on 8/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:02 pm -
1 stop8h 42m
Deal found 8/6![Frontier logo]()
$119
This Delta deal was found by Cheapflights users on 8/5. 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 9/54:45 pm -
1 stop7h 53m
Deal found 8/5![Delta logo]()
$129
This Southwest deal was found by Cheapflights users on 8/4. 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.
Thu 9/178:35 pm -
Nonstop4h 35m
Deal found 8/4![Southwest logo]()
$129
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Fri 10/28:55 pm -
1 stop16h 56m
Deal found 8/1![Frontier logo]()
$130
This Trip.com deal was found by Cheapflights users on 8/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:18 pm -
1 stop9h 10m
Deal found 8/5![Alaska Airlines logo]()
$131
This Priceline deal was found by Cheapflights users on 8/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:50 am -
1 stop6h 28m
Deal found 8/5![Frontier logo]()
$133
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:24 am -
2 stops8h 50m
Deal found 8/3![Delta logo]()
$134
This Alaska Airlines deal was found by Cheapflights users on 8/5. 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.
Wed 8/266:01 am -
1 stop7h 05m
Deal found 8/5![Alaska Airlines logo]()
$139
This Southwest deal was found by Cheapflights users on 8/4. 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 8/253:05 pm -
1 stop7h 30m
Deal found 8/4![Southwest logo]()
$139
This Alaska Airlines deal was found by Cheapflights users on 8/5. 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.
Thu 9/177:20 am -
1 stop9h 13m
Deal found 8/5![Alaska Airlines logo]()
$140
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 August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $178 (Priceline) |
One-way from | $89 (Frontier) |
Popular in | November |
Cheapest in | September |
Average price | $416 |
Good round-trip deal | $581 or less |
Good one-way deal | $271 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 August 6, 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 Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Wed 9/16
7:20 am-2:33 pm
1 stop9h 13m
Oakland
Wed 9/23
6:48 am-7:21 pm
1 stop10h 33m
$277
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Tue 10/20
2:21 pm-11:41 pm
1 stop11h 20m
Oakland
Wed 11/4
6:20 am-7:00 pm
1 stop10h 40m
$277
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Tue 10/20
1:05 pm-6:55 pm
2 stops7h 50m
Oakland
Wed 11/4
8:30 am-5:20 pm
1 stop6h 50m
$282
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Thu 9/24
4:55 pm-10:50 pm
1 stop7h 55m
Oakland
Mon 9/28
5:20 am-2:35 pm
2 stops7h 15m
$282
Quickest round-trip
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Fri 10/23
9:30 pm-12:10 am
Nonstop4h 40m
Oakland
Sat 10/31
10:55 pm-5:55 am
Nonstop5h 00m
$297
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Sat 8/22
2:18 pm-7:52 pm
1 stop7h 34m
Oakland
Mon 8/24
1:29 pm-11:59 pm
1 stop8h 30m
$317
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Wed 12/9
2:03 pm-7:19 pm
1 stop7h 16m
Oakland
Tue 1/5
3:30 pm-11:59 pm
1 stop6h 29m
$317
ChicagoOakland
ORD Chicago O'Hare Intl - OAK Oakland
ORDOAK
Chicago O'Hare Intl
Mon 9/28
7:20 am-2:33 pm
1 stop9h 13m
Oakland
Tue 10/6
7:04 am-6:53 pm
1 stop9h 49m
$317
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Thu 8/27
1:50 pm-7:30 pm
2 stops7h 40m
Oakland
Tue 9/1
7:45 pm-5:40 am
1 stop7h 55m
$318
ChicagoOakland
MDW Chicago Midway - OAK Oakland
MDWOAK
Chicago Midway
Thu 10/1
6:15 pm-10:35 pm
1 stop6h 20m
Oakland
Thu 10/8
3:20 pm-12:55 am
2 stops7h 35m
$318
Showing 1-10 of 44 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 August.
| 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, September is the cheapest month in which you can book a flight from Chicago to Oakland, California (average of $265). Flying from Chicago to Oakland, California in November is currently the most expensive (average of $549). 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 August 6, 2026.
It’s typically best to fly out from Chicago to Oakland, California in the evening. Doing so could potentially save you 44% 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?
Airfare is below average for this route at the moment.
Chicago to Oakland, California flights typically cost between $286 and $672 in October.The cheapest round-trip price found within the last 5 days was $178 on Frontier (Oct 20-Nov 5).
How often are flights from Chicago to Oakland delayed?
About 26% of weekly flights between Chicago and Oakland have experienced delays in the past year, with the average delay time being 101 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 at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday 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 31% 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 August 6, 2026.
Get a feel of what it's like to fly with Southwest and United 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.
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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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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 August 6, 2026.
Chicago and Oakland flights
Browse other Chicago and Oakland flight options. Last updated on August 6, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 6, 2026.
Popular flight searches
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Consider these flights traveling from Chicago to Oakland.
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 August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$264 | Average$377 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$344 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$275 | Average$456 | FlexibilityNo cancel fee | On-time63% |