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

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Lowest round trip fares by airline from Oakland and Chicago

Cheapest prices ($50 One Way, $138 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Feb 24 - Wed, Feb 26
SJC
San Jose
ORD
Chicago
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Feb 24 from San Jose to Chicago, returning Wed, Feb 26, priced at $138 found 6 days ago
Mon, Jan 27 - Mon, Feb 10
SJC
San Jose
MDW
Chicago
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Jan 27 from San Jose to Chicago, returning Mon, Feb 10, priced at $138 found 5 days ago
Sat, Jan 11 - Thu, Jan 16
SFO
San Francisco
MDW
Chicago
$138 Roundtrip, found 14 hours ago
$138
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Jan 11 from San Francisco to Chicago, returning Thu, Jan 16, priced at $138 found 14 hours ago
Mon, Jan 13 - Mon, Jan 13
SFO
San Francisco
ORD
Chicago
$138 Roundtrip, found 14 hours ago
$138
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Mon, Jan 13 from San Francisco to Chicago, returning Mon, Jan 13, priced at $138 found 14 hours ago
Tue, Feb 4 - Wed, Feb 12
SFO
San Francisco
ORD
Chicago
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Feb 4 from San Francisco to Chicago, returning Wed, Feb 12, priced at $197 found 6 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 $75 per night from Dec 24 to Dec 25
$75
includes taxes & fees
$63 per night
Dec 24 - Dec 25
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. ...
7.8/10 Good! (1,519 reviews)
"Great location and amenities!"

Reviewed on Nov 24, 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 $94 per night from Dec 8 to Dec 9
$94
includes taxes & fees
$80 per night
Dec 8 - Dec 9
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (2,017 reviews)
"Old facility but they did OK by keeping the quality up--except the bathroom sink was very slow to drain. Housekeeping should check sinks and bathtubs/showers between guests."

Reviewed on Nov 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 $61 per night from Dec 1 to Dec 2
$61
includes taxes & fees
$54 per night
Dec 1 - Dec 2
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! (1,335 reviews)
"This is the best place to stay in Illinois!!!! Very very clean rooms and great prices to stay everyday!!!!!"

Reviewed on Nov 25, 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
60
Earliest Flight Departure Date
Dec 4
Latest Flight Departure Date
Dec 5
Popular Airlines
American 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.