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.

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

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Lowest round trip fares by airline from Oakland and Chicago

Cheapest prices ($56 One Way, $93 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL
The price is $106 per night from Aug 10 to Aug 10
Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...
4.3/5Excellent! (15 reviews)
"I like the bunk beds- so interesting. I love the location. It is close to everything. You are in the heart of the city with lots of activities to do! The staff from day one have been so rude, so cold in attitude just unpleasant but I have tried to beasrespectful and polite as I can possibly be - ..."

Reviewed on Sep 21, 2020

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $129 per night from Aug 5 to Aug 5
Located in The Loop, this hotel is steps from Columbia College Chicago, Grant Park, and State Street. Art Institute of Chicago and Buckingham Fountain are also ...
3/5 (10 reviews)
"I liked the close proximity to downtown, Chicago. The two restaurants on the property as well as close parking in which you would need to pay."

Reviewed on Sep 25, 2020

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $45 per night from Aug 16 to Aug 16
Situated in Elk Grove Village, this motel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Apache Park is 2.9 mi (4.7 km) away.
3.8/5Good! (13 reviews)
"Really nice and clean place. The parking lot was clear."

Reviewed on Feb 23, 2021

Motel 6 Elk Grove Village, IL - O'Hare
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.

Flights Review

Mar 20, 2018

What free bag I was charged for both long time united card Ember too

A verified traveler
San Jose to Chicago · United

Fly From Oakland to Chicago

Origin Oakland
Destination Chicago
Number of Daily Flights 58
Earliest Flight Departure Date Aug 11
Latest Flight Departure Date Aug 12
Popular Airlines Alaska Airlines

Cheap flights from Oakland to Chicago

Oakland Metropolitan Oak International (OAK) is a modestly sized international airport offering frequent flights to Chicago Ohare International (ORD). Public transit offers simple and easy access to OAK, with BART running from downtown Oakland, San Francisco and Berkeley directly to the airport. Flights to ORD average 7 to 9 hours.

Upon arrival, grab a cab by heading to the lower-level curb front area next to the baggage claim. Free shuttles to all rental car companies are located outside baggage claim as well. Regional buses also offer rides to further destinations outside of the greater Chicago area.

Attractions and Tips

The Art Institute of Chicago is an internationally celebrated must for art lovers. The Briar Street Theatre, home of the popular performers of the Blue Man Group, is just a half hour drive from ORD and offers exciting live entertainment.

Baseball fans can see the Cubs at the legendary Wrigley Field during baseball season.

Chicago’s weather varies from frigid extremes in the winter months (often accompanied by snow and rain), and warm, but not blistering, in the summer. Visitors who travel during winter should check the status of flights that may be hindered due to snow, rain or ice.

When choosing a hotel, explore the whole city, as many neighborhoods highlight boutique and large chain establishments alike.

*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.