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

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Lowest round trip fares by airline from Chicago and Oakland

Cheapest prices ($49 One Way, $108 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Oakland

Imperial Inn

Imperial Inn

2.5 out of 5
490 West MacArthur Blvd, Oakland, CA
The price is $87 per night from May 5 to May 6
$87
per night
May 5 - May 6
Stay at this motel in Oakland. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.8/10 (956 reviews)
"Great hospitality when I go there !"

Reviewed on Nov 25, 2023

Imperial Inn
Jack London Inn

Jack London Inn

2 out of 5
444 Embarcadero W, Oakland, CA
The price is $69 per night from Apr 23 to Apr 24
$69
per night
Apr 23 - Apr 24
Stay at this business-friendly hotel in Oakland. Enjoy free breakfast, free WiFi, and onsite parking. Our guests praise the helpful staff and the clean rooms ...
5.4/10 (1,001 reviews)
"I liked the employee's, they were really respectful and I didn't like that it was time to check out, wish I could've stayed longer."

Reviewed on Apr 17, 2024

Jack London Inn
Marina Inn

Marina Inn

2 out of 5
975 University Ave, Berkeley, CA
The price is $121 per night from Apr 24 to Apr 25
$121
per night
Apr 24 - Apr 25
Stay at this motel in Berkeley. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (743 reviews)
"Super clean. Recently renovated, no carpet so no foul smell"

Reviewed on Apr 12, 2024

Marina Inn
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
76
Earliest Flight Departure Date
Apr 25
Latest Flight Departure Date
Apr 26
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.