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Cheap flights from San Diego to Chicago from $85

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 1/10. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:25 am - 7:54 pm
SAN
-
MDW
11h 29m1 stop
Frontier Logo
9:09 pm - 11:31 pm
MDW
-
SAN
28h 22m1 stop
$161Frontier
Fri, Jan 16 - Mon, Jan 19
Frontier Logo
6:25 am - 7:54 pm
SAN
-
MDW
11h 29m1 stop
Frontier Logo
9:09 pm - 11:31 pm
MDW
-
SAN
28h 22m1 stop
$163Frontier
Fri, Jan 16 - Mon, Jan 19
Southwest Logo
7:25 am - 1:20 pm
SAN
-
MDW
3h 55mnonstop
Southwest Logo
7:40 pm - 10:10 pm
MDW
-
SAN
4h 30mnonstop
$167Southwest
Sat, Jan 10 - Sat, Jan 17
Frontier Logo
6:30 am - 3:49 pm
SAN
-
MDW
31h 19m2 stops
Frontier Logo
7:30 am - 3:11 pm
MDW
-
SAN
9h 41m1 stop
$168Frontier
Sun, Feb 1 - Sun, Feb 8
Frontier Logo
6:54 am - 5:20 pm
SAN
-
MDW
8h 26m1 stop
Frontier Logo
9:09 pm - 11:31 pm
MDW
-
SAN
28h 22m1 stop
$169Frontier
Thu, Jan 15 - Mon, Jan 19
Southwest Logo
6:25 am - 12:25 pm
SAN
-
MDW
4h 00mnonstop
Southwest Logo
7:50 pm - 10:20 pm
MDW
-
SAN
4h 30mnonstop
$177Southwest
Wed, Jan 7 - Wed, Jan 7
Frontier Logo
6:25 am - 3:33 pm
SAN
-
MDW
7h 08m1 stop
Frontier Logo
11:05 am - 12:24 am
MDW
-
SAN
15h 19m1 stop
$179Frontier
Mon, Jan 12 - Thu, Jan 15
Frontier Logo
3:29 pm - 11:45 am
SAN
-
MDW
18h 16m2 stops
Frontier Logo
3:00 pm - 11:59 pm
MDW
-
SAN
10h 59m1 stop
$182Frontier
Sat, Jan 10 - Mon, Jan 12
Frontier Logo
2:56 pm - 3:49 pm
SAN
-
MDW
22h 53m2 stops
Frontier Logo
7:30 am - 3:11 pm
MDW
-
SAN
9h 41m1 stop
$183Frontier
Thu, Jan 29 - Sun, Feb 1
Southwest Logo
11:40 am - 7:05 pm
SAN
-
MDW
5h 25m1 stop
Southwest Logo
8:10 am - 1:35 pm
MDW
-
SAN
7h 25m1 stop
$186Southwest
Wed, Jan 14 - Wed, Jan 21

Frontier flights from San Diego to Chicago Midway Airport

Our best Frontier deals on San Diego to Chicago Midway Airport flight tickets
Frontier
Jan 18
SAN6:54 amSan Diego
8h 26m
1 stop
MDW5:20 pmChicago Midway
Jan 19
MDW9:09 pmChicago Midway
28h 22m
1 stop
SAN11:31 pmSan Diego
$153
Find similar
Frontier
Jan 16
SAN6:25 amSan Diego
11h 29m
1 stop
MDW7:54 pmChicago Midway
Jan 19
MDW9:09 pmChicago Midway
28h 22m
1 stop
SAN11:31 pmSan Diego
$161
Find similar
Frontier
Jan 16
SAN6:25 amSan Diego
11h 29m
1 stop
MDW7:54 pmChicago Midway
Jan 19
MDW9:09 pmChicago Midway
28h 22m
1 stop
SAN11:31 pmSan Diego
$163
Find similar

Southwest flights from San Diego to Chicago Midway Airport

Our best Southwest deals on San Diego to Chicago Midway Airport flight tickets
Southwest
Jan 10
SAN7:25 amSan Diego
3h 55m
MDW1:20 pmChicago Midway
Jan 17
MDW7:40 pmChicago Midway
4h 30m
SAN10:10 pmSan Diego
$167
Find similar
Southwest
Jan 28
SAN7:30 amSan Diego
7h 15m
1 stop
MDW4:45 pmChicago Midway
Feb 3
MDW2:10 pmChicago Midway
7h 30m
1 stop
SAN7:40 pmSan Diego
$176
Find similar
Southwest
Jan 13
SAN11:40 amSan Diego
5h 25m
1 stop
MDW7:05 pmChicago Midway
Jan 17
MDW7:40 pmChicago Midway
4h 30m
SAN10:10 pmSan Diego
$177
Find similar

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 December 18, 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

Fri 1/16

6:25 am-7:54 pm

1 stop11h 29m

Chicago Midway

Mon 1/19

9:09 pm-11:31 pm

1 stop28h 22m

$161

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 1/16

6:25 am-7:54 pm

1 stop11h 29m

Chicago Midway

Mon 1/19

9:09 pm-11:31 pm

1 stop28h 22m

$163

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sat 1/10

7:25 am-1:20 pm

Nonstop3h 55m

Chicago Midway

Sat 1/17

7:40 pm-10:10 pm

Nonstop4h 30m

$167

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sun 2/1

6:30 am-3:49 pm

2 stops31h 19m

Chicago Midway

Sun 2/8

7:30 am-3:11 pm

1 stop9h 41m

$168

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 1/15

6:54 am-5:20 pm

1 stop8h 26m

Chicago Midway

Mon 1/19

9:09 pm-11:31 pm

1 stop28h 22m

$169

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 1/7

6:25 am-12:25 pm

Nonstop4h 00m

Chicago Midway

Wed 1/7

7:50 pm-10:20 pm

Nonstop4h 30m

$177

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Mon 1/12

6:25 am-3:33 pm

1 stop7h 08m

Chicago Midway

Thu 1/15

11:05 am-12:24 am

1 stop15h 19m

$179

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sat 1/10

3:29 pm-11:45 am

2 stops18h 16m

Chicago Midway

Mon 1/12

3:00 pm-11:59 pm

1 stop10h 59m

$182

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 1/29

2:56 pm-3:49 pm

2 stops22h 53m

Chicago Midway

Sun 2/1

7:30 am-3:11 pm

1 stop9h 41m

$183

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 1/14

11:40 am-7:05 pm

1 stop5h 25m

Chicago Midway

Wed 1/21

8:10 am-1:35 pm

1 stop7h 25m

$186

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 November is, on average, the cheapest month to fly to Chicago Midway Airport from San Diego, with most prices found around $272. If you are unable to visit Chicago Midway Airport during the month of November, then departing from San Diego during the month December is also very affordable. Most momondo users find prices during this month for around $273.

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 $381. 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 $547.

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 $376 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $508. 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 $340 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 $226 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 December 2025, prices for San Diego to Chicago Midway Airport flights are approximately 45% more expensive 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

$189

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 $189. The best round-trip flight deal from San Diego to Chicago Midway Airport found on momondo in the last 72 hours is $307.
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 50m, 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 $110Free CancellationRating
5.8
3,080 reviews
Search Frontier flights
SouthwestPriceFrom $205Free CancellationRating
7.9
4,252 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 $205. Generally, Southwest has 7 flights on this route every week with an average price of $390. Southwest is rated 7.9/10 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
Portage
Lansing
Valparaiso
Schererville
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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