$52 Cheap Flights from San Diego (SAN) to Chicago (MDW)

View $52 flight on Tue, Oct 14, 2025Opens in a new window

Popular airlines from San Diego Intl. Airport (SAN) to Chicago Midway Airport (MDW)

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Cheap Flights from San Diego to Chicago (SAN-MDW)

Prices were available within the past 7 days and start at $52 for one-way flights and $104 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Oct 25 - Wed, Oct 29
SAN
San Diego
MDW
Chicago
$104 Roundtrip, found 1 day ago
$104
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Oct 25 from San Diego to Chicago, returning Wed, Oct 29, priced at $104 found 1 day ago
Southwest Airlines
Tue, Sep 23 - Sat, Sep 27
SAN
San Diego
MDW
Chicago
$114 Roundtrip, found 1 day ago
$114
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 23 from San Diego to Chicago, returning Sat, Sep 27, priced at $114 found 1 day ago
Southwest Airlines
Mon, Aug 25 - Sat, Sep 6
SAN
San Diego
MDW
Chicago
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Aug 25 from San Diego to Chicago, returning Sat, Sep 6, priced at $119 found 1 day ago
Southwest Airlines
Sat, Sep 6 - Sat, Sep 13
SAN
San Diego
MDW
Chicago
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 6 from San Diego to Chicago, returning Sat, Sep 13, priced at $119 found 1 day ago
Southwest Airlines
Tue, Sep 23 - Sat, Sep 27
SAN
San Diego
MDW
Chicago
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 23 from San Diego to Chicago, returning Sat, Sep 27, priced at $124 found 1 day ago
Southwest Airlines
Wed, Sep 10 - Thu, Sep 11
SAN
San Diego
MDW
Chicago
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 10 from San Diego to Chicago, returning Thu, Sep 11, priced at $124 found 1 day ago
Southwest Airlines
Fri, Oct 10 - Tue, Oct 14
SAN
San Diego
MDW
Chicago
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Oct 10 from San Diego to Chicago, returning Tue, Oct 14, priced at $126 found 1 day ago
Southwest Airlines
Wed, Oct 15 - Mon, Oct 20
SAN
San Diego
MDW
Chicago
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 15 from San Diego to Chicago, returning Mon, Oct 20, priced at $129 found 2 days ago
Frontier Airlines
Mon, Sep 22 - Thu, Sep 25
SAN
San Diego
MDW
Chicago
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Sep 22 from San Diego to Chicago, returning Thu, Sep 25, priced at $172 found 1 day ago
Delta
Sun, Aug 24 - Mon, Aug 25
SAN
San Diego
MDW
Chicago
$251 Roundtrip, found 7 hours ago
$251
Roundtrip
found 7 hours ago
Select Delta flight, departing Sun, Aug 24 from San Diego to Chicago, returning Mon, Aug 25, priced at $251 found 7 hours ago

Find the cheapest month to fly from San Diego (SAN) to Chicago (MDW)

February is typically the cheapest month to fly

From $118 - $379 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $247
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $247
Flights from San Diego (SAN) to Chicago (MDW)
Origin airport
San Diego Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$104
Distance
1725 mi
Average flight time
7 hours 1 min

San Diego to Chicago Flights

The cheapest times to fly from San Diego to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Diego to Chicago are during the month of October. You can find some of the cheapest flights from San Diego to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San Diego to Chicago

Sunday is one of the best days to book for cheap flights from San Diego to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San Diego to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Diego to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $52 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Diego to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San Diego to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW) cost?
You can pick up cheap return tickets starting at $104 from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving SAN on July 29 2025 and touching down at MDW. The price was last updated on July 10 2025 and has not changed since.
What is the cheapest month to fly from SAN to MDW?
The cheapest flights from SAN to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW)?
Hop on a nonstop flight with Southwest Airlines and go straight from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from SAN to MDW?
At the moment, the cheapest airline offering one-way flights from SAN to MDW is Southwest Airlines. You can jet off on this route from $52. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SAN on September 30 2025. Prices were last updated on July 10 2025 and have not changed since.
How many flights per day from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW)?
When departing from San Diego Intl. Airport (SAN), you can choose from an average of 2 daily nonstop flights to Midway Intl. Airport (MDW).
What are the most popular departure times for flights from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW)?
More travelers fly between SAN and MDW at 11 AM than at any other time. Prefer a quieter experience? Travel outside of rush hours and you're likely to save on your ticket as well.
What day of the week has the most flights from SAN to MDW?
Fly on a Sunday if you're searching for the largest selection of flights from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW).
What is the earliest flight from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW)?
San Diego Intl. Airport (SAN)'s earliest flight to Midway Intl. Airport (MDW) is at approximately 6:55AM UTC-8. With a total travel time of 3h 50m, you'll touch down at around 12:45PM UTC-6.
How long does it take to fly from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW)?
Flights from SAN to MDW have an average travel time of 3 hours and 51 minutes. The total distance between these two airports is 1,750 mi.
What airline has the least delays from SAN to MDW?
United Airlines has the strongest track record for on-time direct flights from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW), with an on-time score of 100%. Use the Expedia App to check your flight schedule before you head off and get real-time updates about any trip changes.
What is the best time to fly from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW)?
To avoid potential delays on the San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW) route, fly before 3 PM. Flights after this time have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from San Diego Intl. Airport (SAN)?
Board a direct flight from San Diego Intl. Airport (SAN) to Chicago and touch down at O'Hare Intl. Airport (ORD). An alternative point of entry into the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW) last-minute?
Holding off until right before your break to book a flight from SAN to MDW often results in higher prices. While it's possible to find some last-minute offers, they aren't always guaranteed. Be flexible with your travel plans to maximize your chances of scoring a bargain.
Is it cheaper to book a SAN to MDW flight and hotel package?
You can save money by booking a SAN to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. After selecting your preferred flights and accommodations, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from San Diego Intl. Airport (SAN) to Midway Intl. Airport (MDW)?
If you reserved your SAN to MDW flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

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