S$ 53 Cheap Flights from San Diego to Chicago (SAN-CHI)

Cheap Flights from San Diego to Chicago

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Cheap Flights from San Diego to Chicago starting at S$ 53

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

One way
Round-trip

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

Cheapest time to fly from San Diego to Chicago

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

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

Cheapest Airlines flying 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 S$ 58

Spirit Airlines

From S$ 67

American Airlines

From S$ 118

Alaska Airlines

From S$ 120

Southwest Airlines

From S$ 133

United Airlines

From S$ 162

Sun Country Airlines

From S$ 186

Jetblue Airways

From S$ 260

Delta Air Lines

From S$ 426

ANA airlines

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Alternative Routes from San Diego to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from San Diego to Chicago.

Cheapest
SAN
19:09
12h 13m
1 transfer
MDW
09:22
San Diego International Airport - Midway International Airport
Tue, May 7Frontier Airlines
S$ 58
SAN
16:07
6h 49m
1 transfer
ORD
00:56
San Diego International Airport - O'Hare International Airport
Wed, May 8Frontier Airlines
S$ 58
SAN
08:44
10h 24m
1 transfer
RFD
21:08
San Diego International Airport - Chicago Rockford International Airport
Thu, May 9Frontier Airlines
S$ 226
SAN
08:44
10h 24m
1 transfer
RFD
21:08
San Diego International Airport - Chicago Rockford International Airport
Thu, May 9Frontier Airlines
S$ 226
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Frequently Asked Questions

When to buy flight tickets 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 cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much is a flight from San Diego (SAN) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around S$ 383.
How long is a flight from San Diego (SAN) to Chicago (CHI)?
It takes about 4 hours 16 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, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What time does the earliest flight from San Diego to Chicago depart?
The earliest flight departs from San Diego (SAN) at 06:15 and arrives in Chicago (ORD) at 12:25.
What time does the latest flight from San Diego to Chicago depart?
The latest flight departs from San Diego (SAN) at 18:10 and arrives in Chicago (MDW) at 00:05.
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, American Airlines, Southwest Airlines and Aer Lingus.
What's the most popular airline for direct flights from San Diego (SAN) to Chicago (CHI)?
United Airlines operates 1 direct flights from San Diego (SAN) to Chicago (CHI).
How many airports in Chicago?
There are 5 airports near Chicago: O'Hare International Airport, Chicago Du Page County Airport, Midway International Airport, Chicago Palwaukee 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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Find cheapest flight ticket from San Diego to Chicago

Cheapest direct flight price	S$ 53
Cheapest return ticket price	S$ 213
Cheapest month	April
Peak season for travel	July
Flight distance	2,786.63km
Average flight time	4 hours 16 minutes
Popular airline	American Airlines