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 ($47 One Way, $128 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

4 out of 5
19 East Ohio Street, Chicago, IL
The price is $58 per night from Mar 31 to Apr 1
$58
per night
Mar 31 - Apr 1
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! (1,007 reviews)
"Good choice for the price. The location is surrounded by lots of other hotels, and is close to downtown attractions."

Reviewed on Mar 16, 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 $80 per night from Mar 20 to Mar 21
$80
per night
Mar 20 - Mar 21
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.2/10 (1,565 reviews)
"OK"

Reviewed on Mar 15, 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 $60 per night from Mar 24 to Mar 25
$60
per night
Mar 24 - Mar 25
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! (1,143 reviews)
"Nice and excellent area for airport travelers"

Reviewed on Mar 15, 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 San Diego to Chicago

Origin
San Diego
Destination
Chicago
Number of Daily Flights
27
Earliest Flight Departure Date
Mar 26
Latest Flight Departure Date
Mar 27
Popular Airlines
United 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.