We use marketing and analytics cookies.
Click "Accept" if thata's okay with you.

Find Cheap Flights from San Diego to Chicago (SAN to CHI)

From where?
Show more
Show more
  • Please enter origin city or airport.
  • Please enter destination city or airport.
  • Please enter valid from city or airport code.
  • Please enter valid to city or airport code.
  • Please enter depart date.
  • Please enter depart date.
  • Please enter return date.
  • Please select number of passengers.
San Diego
- Chicago
×
Traveler / Coach Class
  • originquery:
  • destquery:
  • originCityCode:
  • originLocation:
  • originCity:
  • destCity:
  • totalPax:
  • roomCount:
  • adultCount:
  • seniorCount:
  • childrenCount:
  • roomOneAd:
  • roomOneSr:
  • roomOneCh:
  • roomTwoAd:
  • roomTwoSr:
  • roomTwoCh:
  • roomThreeAd:
  • roomThreeSr:
  • roomThreeCh:
  • showOrDropdown:
  • cabinClass:
  • Please enter origin city or airport.
  • Please enter destination city or airport.
  • Please enter valid from city or airport code.
  • Please enter valid to city or airport code.
  • Select check-in date.
  • Select check-out date.
  Enter airport or city
  Enter airport or city
×
1 Room, Travelers
From where?
Show more
Show more
  • originquery:
  • originCityCode:
  • originLocation:
  • originCity:
  • destquery:
  • destCityCode:
  • destLocation:
  • destCity:
  • dropoffLocation:
  • adultCount:
  • childrenCount:
  • roomCount:
  • roomOneAd:
  • roomOneCh:
  • roomTwoAd:
  • roomTwoCh:
  • roomThreeAd:
  • roomThreeCh:
Where are you going?
Show more
  • Please enter City/Airport/Landmark.
  • Please enter a valid City/Airport/Landmark.
  • Pick-Up Location can not be left blank!
  • Please enter a valid Pick-Up Location.
  • Select check-in date.
  • Select check-out date.
  • Select pick-up & drop-off date.
  Enter Destination
×
1 Room, Traveler
Choose your drop-off location
Show more
  Pick-up Location
×
Where do you want to stay?
Show more
  • Please enter City/Airport/Landmark.
  • Please enter a valid City/Airport/Landmark.
  • Select check-in date.
  • Select check-out date.
  City, Airport or Landmark
×
1 Room, Traveler
Choose your pick-up location
Show more
Choose your drop-off location
Show more
  • Please enter origin city or airport.
  • Please enter destination city or airport.
  • Please enter valid from city or airport code.
  • Please enter valid to city or airport code.
  • Please enter depart date.
  • Please enter return date.
  Pick-up City / Airport / Zip
×
Need help booking? Our agents are ready!Choose from over 500 airlines.Call us 24/7 at 1-845-848-0154
Hawaiian AirlinesHawaiian Airlines
JetBlue AirwaysJetBlue Airways
Turkish AirlinesTurkish Airlines
Call us
Here’s why travelers choose CheapOair

Get Great Deals!

Choose from 500+ airlines for low airfares!

Price Match Promise

Find low prices to destinations worldwide.

Easy Cancellations with CheapOair

Convenient self-service options available online.

Expert Guidance

Get personalized assistance from our travel experts.

San Diego to Chicago Flight Deals

 

* All fares above were last found on:  .Fares are round trip. Fares incl. all fuel surcharges, taxes & fees and our service fees. Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions

Cheap Flights from San Diego to Chicago

Looking for flights from San Diego (SAN) to Chicago (CHI)? Find affordable air travel deals on CheapOair and save big on air tickets online. Known for its history, culture and an excellent art scene, Chicago is an absolute paradise for Shopaholics. Museum lovers should head to the Museum Campus, animal lovers to the Lincoln Park Zoo and photography enthusiasts to the Museum of Photography when in Chicago. Also, you can opt for the Chicago CityPASS an avail discount admission to some of the top museums and attractions. To reach Chicago from San Diego, you may choose amongst the top airlines such as Frontier Airlines, Spirit Airlines, and Virgin America. Your flight from San Diego to Chicago takes about four hours thirty minutes to cover a distance of about 1,729 miles excluding layover time, make sure to carry an IPod or an mp3 player to keep yourself entertained.

CheapOair Customer Reviews

Excellent prices

I have used CheapOair twice and love this site!!! Excellent prices and great airlines . I would highly recommend CheapOair to book your trips through. - Susan  Dec 18, 2024

Prague Christmas Markets

My wife, Jessica, and our 19-year-old daughter traveled to Prague from Dec 4–11 and had an incredible experience! They stayed at the Dominican Hotel, a charming and conveniently located spot in the heart of Prague. We booked the trip through CheapOair, bundling the hotel and airfare, and found it to be a great value overall. The booking process was seamless, and all confirmation emails were timely and easy to follow. I was especially impressed with the convenience of using CheapOair—it made setting up the trip straightforward without needing a separate travel agent. Their flights were with TAP Air Portugal, and everything went smoothly. Flights were on time, and the airline provided excellent service. We decided to upgrade to Comfort Seating, which was well worth the extra cost for the added comfort, especially for a longer trip. However, I wish we didn’t have to pay extra to select seats so my wife and daughter could sit together—it would be great if that were included in the base price. CheapOair also provided options for early check-in and travel add-ons through their emails, making planning even easier. For excursions, we used Viator.com to arrange activities directly, which worked perfectly. The trip was well-organized, hassle-free, and a fantastic experience overall. We’ll definitely book through CheapOair again and recommend it to anyone looking for a simple and cost-effective way to plan their travel. Thank you for helping make this trip memorable! - Raleigh  Dec 13, 2024

x