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

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Lowest round trip fares by airline from Oakland and Chicago

Cheapest prices ($54 One Way, $137 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, May 29 - Sat, Jun 15
SFO
San Francisco
MDW
Chicago
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 29 from San Francisco to Chicago, returning Sat, Jun 15, priced at $137 found 5 days ago
Wed, May 29 - Wed, Jun 12
SFO
San Francisco
MDW
Chicago
$150 Roundtrip, found 5 days ago
$150
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 29 from San Francisco to Chicago, returning Wed, Jun 12, priced at $150 found 5 days ago
Sat, Aug 17 - Sat, Aug 24
SFO
San Francisco
ORD
Chicago
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, Aug 17 from San Francisco to Chicago, returning Sat, Aug 24, priced at $174 found 2 days ago
Tue, May 28 - Tue, Jun 4
SFO
San Francisco
ORD
Chicago
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, May 28 from San Francisco to Chicago, returning Tue, Jun 4, priced at $189 found 2 days ago
Tue, Sep 10 - Thu, Sep 12
SFO
San Francisco
ORD
Chicago
$194 Roundtrip, found 2 days ago
$194
Roundtrip
found 2 days ago
Select United flight, departing Tue, Sep 10 from San Francisco to Chicago, returning Thu, Sep 12, priced at $194 found 2 days ago

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
The price is $96 per night from May 27 to May 28
$96
per night
May 27 - May 28
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.6/10 Good! (1,003 reviews)
"nice location and pretty bar inside the hotel"

Reviewed on May 6, 2024

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 $112 per night from May 12 to May 13
$112
per night
May 12 - May 13
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.2/10 (1,635 reviews)
Amazing stay while in Chicago
"I had an amazing time staying here. Highly recommend. I felt safe and the staff was so accommodating. Clean room and literally under 20 minutes from the airport."

Reviewed on May 7, 2024

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 $55 per night from May 12 to May 13
$55
per night
May 12 - May 13
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,171 reviews)
Convenient, clean, efficient
"This place has always been convenient, clean, friendly. The staff are really great. Estela at the front desk is an absolute gem. She will bend over backwards to accommodate you and can multitask like no other."

Reviewed on May 7, 2024

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.

Fly From Oakland to Chicago

Origin
Oakland
Destination
Chicago
Number of Daily Flights
76
Earliest Flight Departure Date
May 17
Latest Flight Departure Date
May 18
Popular Airlines
United 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.

Flights from Cities near Oakland

Flights to Cities near Chicago

Other Flights to Chicago

Other Flights from Oakland

*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.