Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

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Lowest round trip fares by airline from Chicago and Oakland

Cheapest prices ($60 One Way, $119 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
The price is $119 per night from Jul 25 to Jul 25
Situated near the airport, this hotel is 1.8 mi (3 km) from Oracle Arena and 1.9 mi (3 km) from RingCentral Coliseum. Oakland Zoo and Jack London Square are ...
3/5 (2 reviews)
"Absolutely horrible. Disgustingly dirty and outdated Drafty and cold and in a bad area of town."

Reviewed on Jan 16, 2020

Econo Lodge Inn and Suites Oakland Airport
Imperial Inn

Imperial Inn

2.5 out of 5
490 West MacArthur Blvd, Oakland, CA
The price is $96 per night from Jul 25 to Jul 25
Located in Mosswood, this motel is within 1 mi (2 km) of Telegraph Avenue and Kaiser Permanente Oakland Medical Center. Fox Theater and Paramount Theatre are ...
3.5/5Good! (2 reviews)
"Cute hotel with nice updated rooms that we’ve stayed in before, but this time our room was not cleaned well, especially the bathroom. There was pubic hair on the toilet and in the shower, a wet towel hanging on the shower rod, no toilet paper was on the roll and there was pee on the toilet seat when ..."

Reviewed on Oct 9, 2018

Imperial Inn
Super 8 by Wyndham Berkeley

Super 8 by Wyndham Berkeley

2 out of 5
1619 University Avenue, Berkeley, CA
The price is $109 per night from Jul 25 to Jul 25
Located in Central Berkeley, this motel is within 3 mi (5 km) of University of California, Berkeley, Greek Theater, and Berkeley Marina. Telegraph Avenue and ...
3.5/5Good! (2 reviews)
clean, comfortable, noisey
"I've stayed here before and was hoping it was a problem with just my room. The main problem with this hotel is noise. The walls must have no insulation so you hear anything in the room next door. Talking, laughing, showering, sex. And don't expect to sleep if the people next door to you leave early. ..."

Reviewed on Mar 14, 2016

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 59
Earliest Flight Departure Date Jul 31
Latest Flight Departure Date Aug 1
Popular Airlines Alaska 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.