Cheap Flight Deals from San Diego to Chicago

We've found these cheap flights for you. You can book one-way or return flight tickets.

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One way

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

Best Time to Book Flights from San Diego to Chicago

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

Cheapest flights

From price

May

27 4
4 11
11 18
18 25
Jun

25 1
1 8
8 15
15 22
22 29
Jul

29 6
6 13
13 20

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

FAQ

When are flight from San Diego (SAN) to Chicago (CHI) the cheapest?

Airlines adjust prices for flights from San Diego to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from San Diego (SAN) to Chicago (CHI) cost?

According to Trip.com's data, the lowest price is around AU$ 512.
How long is the flights from San Diego (SAN) to Chicago (CHI)?

It takes about 5 hours 13 minutes to fly from San Diego (SAN) to Chicago (CHI).
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): Alaska Airlines, United Airlines, Southwest Airlines, Aer Lingus, Gulf Air, Iberia, Cathay Pacific, Lufthansa and American Airlines.
How many airports in Chicago (CHI)?

There are 3 airport(s) in Chicago (CHI): Midway International Airport, O'Hare International Airport and Chicago Rockford International Airport.

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

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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

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Flight Information from San Diego to Chicago

Cheapest one-way flight price	AU$ 94
Cheapest return ticket price	AU$ 225
Off-season for travel	March
Peak season for travel	January
Flight distance	2,786.63km
Average flight time	5 hours 13 minutes
Popular airline	American Airlines