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, $168 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Aug 3 - Sat, Aug 17
SFO
San Francisco
MDW
Chicago
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Aug 3 from San Francisco to Chicago, returning Sat, Aug 17, priced at $168 found 2 days ago
Tue, Jul 23 - Tue, Jul 30
SFO
San Francisco
ORD
Chicago
$179 Roundtrip, found 4 hours ago
$179
Roundtrip
found 4 hours ago
Select Alaska Airlines flight, departing Tue, Jul 23 from San Francisco to Chicago, returning Tue, Jul 30, priced at $179 found 4 hours ago
Tue, Jun 11 - Mon, Jun 17
SJC
San Jose
ORD
Chicago
$188 Roundtrip, found 9 hours ago
$188
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Tue, Jun 11 from San Jose to Chicago, returning Mon, Jun 17, priced at $188 found 9 hours ago
Sat, Jul 20 - Tue, Jul 30
SFO
San Francisco
ORD
Chicago
$204 Roundtrip, found 4 hours ago
$204
Roundtrip
found 4 hours ago
Select United flight, departing Sat, Jul 20 from San Francisco to Chicago, returning Tue, Jul 30, priced at $204 found 4 hours ago
Wed, Jan 1 - Tue, Jan 7
SFO
San Francisco
ORD
Chicago
$209 Roundtrip, found 8 hours ago
$209
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Wed, Jan 1 from San Francisco to Chicago, returning Tue, Jan 7, priced at $209 found 8 hours 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 $89 per night from May 28 to May 29
$89
per night
May 28 - May 29
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! (1,004 reviews)
Always
"Everything was as expected."

Reviewed on May 21, 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 $117 per night from May 27 to May 28
$117
per night
May 27 - May 28
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 ...
6.4/10 (1,655 reviews)
"The shower was incredibly dirty. The entire bathroom was dirty. The sheets were paper thin. The TV was from the 1900s. However the staff was pleasant."

Reviewed on May 20, 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 $63 per night from Jun 9 to Jun 10
$63
per night
Jun 9 - Jun 10
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 ...
7.8/10 Good! (1,173 reviews)
"Good"

Reviewed on May 22, 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
77
Earliest Flight Departure Date
May 31
Latest Flight Departure Date
Jun 1
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.