Cheap flights from San Diego (SAN) to Chicago (CHI)

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Lowest round trip fares by airline from San Diego and Chicago

Cheapest prices ($57 One Way, $113 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, 60611
The price is $71 per night from Feb 8 to Feb 9
$71
per night
Feb 8 - Feb 9
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
3.9/5 Very Good! (1,023 reviews)
"Nice place. Clean. Enjoyed it!"

Reviewed on Jan 16, 2023

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL, 60605
The price is $87 per night from Feb 5 to Feb 6
$87
per night
Feb 5 - Feb 6
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
3/5 (1,068 reviews)
"Nice and clean"

Reviewed on Feb 1, 2023

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, 60007
The price is $50 per night from Feb 8 to Feb 9
$50
per night
Feb 8 - Feb 9
Stay at this business-friendly motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
4/5 Very Good! (1,032 reviews)
"Close to the airport. Clean. Working air conditioning"

Reviewed on Jan 27, 2023

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 San Diego to Chicago

Origin
San Diego
Destination
Chicago
Number of Daily Flights
24
Earliest Flight Departure Date
Feb 9
Latest Flight Departure Date
Feb 10
Popular Airlines
American Airlines

Cheap flights from San Diego to Chicago

Leave coastal California and explore the Windy City for business or leisure, by flying from San Diego to Chicago O'Hare International Airport (ORD). Begin your tour through this Midwest cultural mecca by visiting the Museum Campus, where you can discover marine life at the Shedd Aquarium, or study dinosaur fossils at the Field Museum. This museum complex is part of the waterfront Grant Park, which boasts an array of other attractions like the Buckingham Fountain and the Petrillo Music Shell.

Key Facts

You can explore downtown Chicago by riding CTA trains, or driving along Interstate-90 in a rental car. This highway will also lead you to Chicago's suburbs such as Elgin and Park Ridge. Head to the U.S. Cellular Field to cheer on the Chicago White Sox, or visit Wrigley Field to root for the Chicago Cubs.

Book a room along Magnificent Mile to enjoy great views of Chicago's iconic skyline, and then do some shopping in upscale designer stores. Visit the Chicago History Museum and discover the heritage of Chi-Town. Take an elevator to the top of the Willis Tower and enjoy sweeping views of downtown Chicago and Lake Michigan.

Hints and Tips

The flight from San Diego International Airport (SAN) to Chicago takes about four hours to complete. Once you land at ORD, check out the historic military airplanes on display in Terminal 2.

*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.