Cheap flights from Chicago (CHI) to Oakland (SJC)

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Lowest round trip fares by airline from Chicago and Oakland

Cheapest prices ($84 One Way, $168 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Oakland

Econo Lodge Inn and Suites Oakland Airport

Econo Lodge Inn and Suites Oakland Airport

2 out of 5
10 Hegenberger Road, Oakland, CA, 94621
The price is $119 per night from Aug 17 to Aug 18
Stay at this business-friendly hotel in Oakland. Enjoy free WiFi, free parking, and a free airport shuttle. Our guests praise the restaurant and the helpful ...
3.3/5 (442 reviews)
"Staff were friendly and flexible! I arrived early, and they gave me some options that I was happy with!"

Reviewed on Aug 7, 2022

Econo Lodge Inn and Suites Oakland Airport
Imperial Inn

Imperial Inn

2.5 out of 5
490 West MacArthur Blvd, Oakland, CA, 94609
The price is $110 per night from Aug 21 to Aug 22
Stay at this business-friendly motel in Oakland. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the comfy beds and the overall value ...
3.3/5 (912 reviews)
"Everything is fine. It is very clean that is very important to me. The only issue I have is the wifi. Most of the time it is not working."

Reviewed on Jul 15, 2022

Imperial Inn
Super 8 by Wyndham Berkeley

Super 8 by Wyndham Berkeley

2 out of 5
1619 University Avenue, Berkeley, CA, 94703
The price is $129 per night from Aug 21 to Aug 22
Stay at this business-friendly motel in Berkeley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the WiFi and the helpful staff in our ...
3.5/5 Good! (1,000 reviews)
"good place"

Reviewed on Aug 12, 2022

Super 8 by Wyndham Berkeley
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Oakland

Origin Chicago
Destination Oakland
Number of Daily Flights 71
Earliest Flight Departure Date Aug 23
Latest Flight Departure Date Aug 24
Popular Airlines United Airlines

Cheap flights from Chicago to Oakland

Chicago’s famous “L” Train has a stop at Chicago O’Hare International Airport (ORD), so consider taking it to this bustling airport. T

Typical flight times to Oakland International Airport (OAK) are just over four hours. For rapid access to Oakland city center, climb aboard the BART at the station located across from Terminal 1 at OAK.

Attractions and Tips

During your trip, spend time at Chabot Space and Science Center, appreciating the beauty of Oakland and looking skyward. If you’ve brought a child along on this adventure, don’t miss Children’s Fairyland, a 10-acre outdoor park featuring castles and other whimsical scenes sure to delight your tyke.

To get away from the hustle and bustle of Oakland proper, head to Redwood Regional Park and hike among the towering trees for which the region is famous.

For easy access to delectable eateries and hopping late-night bars, pick accommodations in downtown. For a more off-the-beaten-path experience, make Chinatown your destination of choice and spend your time exploring exotic shops and downing some dim sum.

Oakland’s climate is relatively static, fluctuating from the mid-40s in the winter to the mid-70s in the summer. If you plan to visit during the winter months, pack a coat. Otherwise, you should be able to enjoy the beautiful outdoor sites for which Oakland is so famous in just a light jacket.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.