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 ($43 One Way, $86 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
The price is $79 per night from Jan 23 to Jan 24
Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Water Tower Place ...
4.1/5 Very Good! (14 reviews)
"I really appreciated the staff there. Thanks"

Reviewed on Oct 16, 2021

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 $79 per night from Jan 23 to Jan 24
Located in The Loop, this hotel is steps from Lakefront Trail, Grant Park, and Columbia College Chicago. Art Institute of Chicago and State Street are also within ...
3.4/5 Good! (9 reviews)
"Friendly staff, conveniently located, great value!"

Reviewed on Oct 5, 2021

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 $40 per night from Feb 6 to Feb 7
Situated in Elk Grove Village, this motel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Rivers Casino and Donald E. Stephens Convention ...
3.9/5 Very Good! (13 reviews)
"This was a very great bang for your buck! Clean and Quiet"

Reviewed on Sep 11, 2021

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.

Flights Review

Fly From San Diego to Chicago

Origin San Diego
Destination Chicago
Number of Daily Flights 23
Earliest Flight Departure Date Jan 27
Latest Flight Departure Date Jan 28
Popular Airlines Alaska 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.