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Cheap flights from San Diego to Chicago from $77

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Diego to Chicago departing on 9/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from San Diego to Chicago

Cheap round-trip flights

Southwest Logo
11:00 am - 5:10 pmSAN-MDW
4h 10mnonstop
Southwest Logo
8:25 pm - 10:45 pmMDW-SAN
4h 20mnonstop
$153Southwest
Find Deal
Tue, Oct 14 - Tue, Oct 21
Frontier Logo
10:52 am - 12:36 amSAN-MDW
11h 44m1 stop
Frontier Logo
6:24 pm - 11:50 pmMDW-SAN
7h 26m1 stop
$154Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Frontier Logo
9:14 am - 5:22 pmSAN-MDW
6h 08m1 stop
Frontier Logo
2:57 pm - 8:24 pmMDW-SAN
7h 27m1 stop
$155Frontier
Find Deal
Thu, Nov 13 - Sat, Nov 15
Frontier Logo
1:18 pm - 9:58 pmSAN-MDW
6h 40m1 stop
Frontier Logo
6:24 pm - 11:50 pmMDW-SAN
7h 26m1 stop
$169Frontier
Find Deal
Thu, Oct 2 - Fri, Oct 10
Frontier Logo
1:18 pm - 9:58 pmSAN-MDW
6h 40m1 stop
Frontier Logo
10:18 am - 4:42 pmMDW-SAN
8h 24m1 stop
$170Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5
Southwest Logo
6:30 am - 12:35 pmSAN-MDW
4h 05mnonstop
Southwest Logo
11:15 am - 1:35 pmMDW-SAN
4h 20mnonstop
$175Southwest
Find Deal
Tue, Oct 14 - Fri, Nov 7
Southwest Logo
11:00 am - 5:10 pmSAN-MDW
4h 10mnonstop
Southwest Logo
11:55 am - 2:10 pmMDW-SAN
4h 15mnonstop
$177Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
11:10 am - 6:30 pmSAN-MDW
5h 20m1 stop
Southwest Logo
7:30 pm - 9:50 pmMDW-SAN
4h 20mnonstop
$180Southwest
Find Deal
Fri, Nov 7 - Sat, Nov 8
Southwest Logo
6:25 pm - 12:25 amSAN-MDW
4h 00mnonstop
Southwest Logo
6:05 pm - 10:10 pmMDW-SAN
6h 05m1 stop
$185Southwest
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Tue, Oct 14 - Fri, Nov 7
Delta Logo
10:20 pm - 8:40 amSAN-MDW
8h 20m1 stop
Delta Logo
5:09 pm - 11:14 pmMDW-SAN
8h 05m1 stop
$257Delta
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Thu, Oct 30 - Tue, Nov 4

Southwest flights from San Diego to Chicago Midway Airport

Our best Southwest deals on San Diego to Chicago Midway Airport flight tickets
Southwest
Oct 14
SAN11:00 amSan Diego
4h 10m
MDW5:10 pmChicago Midway
Oct 21
MDW8:25 pmChicago Midway
4h 20m
SAN10:45 pmSan Diego
$153
Find similar
Southwest
Oct 14
SAN6:30 amSan Diego
4h 05m
MDW12:35 pmChicago Midway
Nov 7
MDW11:15 amChicago Midway
4h 20m
SAN1:35 pmSan Diego
$175
Find similar
Southwest
Oct 15
SAN11:00 amSan Diego
4h 10m
MDW5:10 pmChicago Midway
Oct 22
MDW11:55 amChicago Midway
4h 15m
SAN2:10 pmSan Diego
$177
Find similar

Frontier flights from San Diego to Chicago Midway Airport

Our best Frontier deals on San Diego to Chicago Midway Airport flight tickets
Frontier
Oct 16
SAN10:52 amSan Diego
11h 44m
1 stop
MDW12:36 amChicago Midway
Oct 20
MDW6:24 pmChicago Midway
7h 26m
1 stop
SAN11:50 pmSan Diego
$154
Find similar
Frontier
Nov 13
SAN9:14 amSan Diego
6h 08m
1 stop
MDW5:22 pmChicago Midway
Nov 15
MDW2:57 pmChicago Midway
7h 27m
1 stop
SAN8:24 pmSan Diego
$155
Find similar
Frontier
Oct 2
SAN1:18 pmSan Diego
6h 40m
1 stop
MDW9:58 pmChicago Midway
Oct 10
MDW6:24 pmChicago Midway
7h 26m
1 stop
SAN11:50 pmSan Diego
$169
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momondo Fare Finder

 
Customize your flight search to find flights from San Diego to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from San Diego to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 10/14

11:00 am-5:10 pm

Nonstop4h 10m

Chicago Midway

Tue 10/21

8:25 pm-10:45 pm

Nonstop4h 20m

$153

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 10/16

10:52 am-12:36 am

1 stop11h 44m

Chicago Midway

Mon 10/20

6:24 pm-11:50 pm

1 stop7h 26m

$154

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 11/13

9:14 am-5:22 pm

1 stop6h 08m

Chicago Midway

Sat 11/15

2:57 pm-8:24 pm

1 stop7h 27m

$155

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 10/2

1:18 pm-9:58 pm

1 stop6h 40m

Chicago Midway

Fri 10/10

6:24 pm-11:50 pm

1 stop7h 26m

$169

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 10/2

1:18 pm-9:58 pm

1 stop6h 40m

Chicago Midway

Sun 10/5

10:18 am-4:42 pm

1 stop8h 24m

$170

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 10/14

6:30 am-12:35 pm

Nonstop4h 05m

Chicago Midway

Fri 11/7

11:15 am-1:35 pm

Nonstop4h 20m

$175

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 10/15

11:00 am-5:10 pm

Nonstop4h 10m

Chicago Midway

Wed 10/22

11:55 am-2:10 pm

Nonstop4h 15m

$177

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 11/7

11:10 am-6:30 pm

1 stop5h 20m

Chicago Midway

Sat 11/8

7:30 pm-9:50 pm

Nonstop4h 20m

$180

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 10/14

6:25 pm-12:25 am

Nonstop4h 00m

Chicago Midway

Fri 11/7

6:05 pm-10:10 pm

1 stop6h 05m

$185

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 10/30

10:20 pm-8:40 am

1 stop8h 20m

Chicago Midway

Tue 11/4

5:09 pm-11:14 pm

1 stop8h 05m

$257

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from San Diego to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from San Diego, with most prices found around $254. If you are unable to visit Chicago Midway Airport during the month of September, then departing from San Diego during the month December is also very affordable. Most momondo users find prices during this month for around $288.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from San Diego. The lowest ticket price found for a Tuesday departure recently was $393. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from San Diego because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $556.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from San Diego in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $394 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $545. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest San Diego to Chicago Midway flight route?

Fly from San Diego to Chicago Midway for the best San Diego - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from San Diego when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $342 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from San Diego for as low as $225 on momondo.

What cabin class options are available on San Diego to Chicago Midway flights?

There is only 1 cabin class available to choose from on San Diego to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San Diego to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between San Diego to Chicago Midway Airport.

How have San Diego to Chicago Midway Airport flight prices changed over time?

As of September 2025, prices for San Diego to Chicago Midway Airport flights are approximately 16% cheaper when compared to flights at the same time last year.

When to book flights from San Diego to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San Diego to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San Diego to Chicago Midway Airport (SAN to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Diego to Chicago Midway Airport

Best Price Found

$179

Fastest flight time

3h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Diego in the past 72 hours is $179. The best round-trip flight deal from San Diego to Chicago Midway Airport found on momondo in the last 72 hours is $215.
The fastest flight from San Diego to Chicago Midway Airport takes 3h 50m
Direct flights go from San Diego to Chicago Midway Airport every day.
Search flight deals

  • How far is San Diego to Chicago Midway by plane?

    A flight from San Diego to Chicago Midway will travel around 1723.1 mi. Flights usually cover this in 3h 55m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from San Diego Airport to Chicago Midway Airport?

    Prices for flights from San Diego Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from San Diego Airport to Chicago Midway Airport?

  • How old do you have to be to fly from San Diego Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Diego Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from San Diego to Chicago Midway Airport?

  • What is the most popular airline from San Diego to Chicago Midway Airport?

Best airlines flying from San Diego to Chicago Midway Airport

Compare and see reviews for airlines that fly from San Diego to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $123Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
SouthwestPriceFrom $229Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From San Diego to Chicago Midway Airport

    The lowest priced Southwest flight from San Diego to Chicago Midway Airport from the last 72 hours was $229. Generally, Southwest has 28 flights on this route every week with an average price of $420. Southwest is rated 8.0/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from San Diego to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Diego to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from San Diego to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from San Diego on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from San Diego to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from San Diego. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from San Diego to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from San Diego are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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