US$35️ Cheap Flights from San Diego to Chicago (2024)

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San Diego to Chicago - Flights Starting at US$35

Book one-way or return flights from San Diego to Chicago from as little as US$35. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

We've found these cheap flights for you. You may book a one-way or round trip as per your needs.

We monitor flight fares to help you seize the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Cheapest airlines flights from San Diego to Chicago

View airlines operating flights from San Diego to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines

From US$35

Spirit Airlines

From US$41

Alaska Airlines

From US$88

Southwest Airlines

From US$98

Delta Air Lines

From US$110

United Airlines

From US$119

Sun Country Airlines

From US$150

Jetblue Airways

From US$202

American Airlines

From US$317

ANA airlines

Find more flights and airlines

Alternative Routes from San Diego to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from San Diego to Chicago.

Cheapest
SAN
16:07
6h 49m
1 transfer
ORD
00:56
San Diego International Airport - O'Hare International Airport
Wed, May 8Frontier Airlines
US$35
SAN
19:09
12h 13m
1 transfer
MDW
09:22
San Diego International Airport - Midway International Airport
Tue, May 7Frontier Airlines
US$43
SAN
08:44
10h 24m
1 transfer
RFD
21:08
San Diego International Airport - Chicago Rockford International Airport
Thu, May 9Frontier Airlines
US$169
SAN
08:44
10h 24m
1 transfer
RFD
21:08
San Diego International Airport - Chicago Rockford International Airport
Thu, May 9Frontier Airlines
US$169
Find More Flights

Frequently Asked Questions

When are flight tickets from San Diego (SAN) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from San Diego to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from San Diego (SAN) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around $282.
How long does it take to fly from San Diego (SAN) to Chicago (CHI) and what is the distance?
It takes around 4 hours 18 minutes to fly from San Diego (SAN) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.
What are the most popular airlines that fly from San Diego (SAN) to Chicago (CHI)?
Airlines with flights from San Diego (SAN) to Chicago (CHI): United Airlines, Emirates, Qatar Airways, Southwest Airlines, Aer Lingus and American Airlines.

How to find a cheap flight from San Diego to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from San Diego to Chicago. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

San Diego to Chicago Flight Information

Cheapest nonstop flight price	$35
Cheapest round-trip ticket price	$157
Off-season for travel	April
Peak season for travel	October
Flight distance	2,786.63km
Average flight time	4 hours 18 minutes
Popular airline	American Airlines