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Cheap flights from Chicago Midway Airport to San Diego from $76

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San Diego departing on 10/28. 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 Chicago Midway Airport to San Diego

Cheap round-trip flights

Southwest Logo
8:20 am - 10:50 amMDW-SAN
4h 30mnonstop
Southwest Logo
7:35 pm - 1:30 amSAN-MDW
3h 55mnonstop
$133Southwest
Find Deal
Wed, Nov 12 - Sun, Nov 16
Southwest Logo
6:15 pm - 11:25 pmMDW-SAN
7h 10m1 stop
Southwest Logo
7:35 pm - 1:30 amSAN-MDW
3h 55mnonstop
$143Southwest
Find Deal
Wed, Nov 12 - Sun, Nov 16
Southwest Logo
6:35 pm - 10:55 pmMDW-SAN
6h 20m1 stop
Southwest Logo
8:05 pm - 5:05 amSAN-MDW
7h 00m1 stop
$152Southwest
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Thu, Nov 13 - Mon, Nov 17
Southwest Logo
8:35 pm - 11:00 pmMDW-SAN
4h 25mnonstop
Southwest Logo
5:00 pm - 10:55 pmSAN-MDW
3h 55mnonstop
$153Southwest
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Wed, Nov 5 - Wed, Nov 12
Frontier Logo
1:53 pm - 7:06 pmMDW-SAN
7h 13m1 stop
Frontier Logo
6:35 am - 3:53 pmSAN-MDW
7h 18m1 stop
$154Frontier
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Thu, Oct 2 - Mon, Oct 6
Frontier Logo
12:30 pm - 11:17 amMDW-SAN
24h 47m1 stop
Frontier Logo
9:14 am - 5:22 pmSAN-MDW
6h 08m1 stop
$155Frontier
Find Deal
Thu, Oct 30 - Thu, Nov 6
Frontier Logo
6:24 pm - 8:08 pmMDW-SAN
27h 44m1 stop
Frontier Logo
6:41 am - 12:36 amSAN-MDW
15h 55m1 stop
$156Frontier
Find Deal
Thu, Oct 16 - Thu, Oct 23
Frontier Logo
12:30 pm - 11:17 amMDW-SAN
24h 47m1 stop
Frontier Logo
9:14 am - 5:22 pmSAN-MDW
6h 08m1 stop
$161Frontier
Find Deal
Thu, Oct 30 - Thu, Nov 6
Southwest Logo
8:25 pm - 10:45 pmMDW-SAN
4h 20mnonstop
Southwest Logo
4:50 pm - 10:50 pmSAN-MDW
4h 00mnonstop
$163Southwest
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Wed, Oct 8 - Sat, Oct 18
Multiple Airlines Logo
4:48 pm - 12:31 pmMDW-SAN
21h 43m2 stops
Multiple Airlines Logo
1:18 pm - 9:58 pmSAN-MDW
6h 40m1 stop
$198Multiple Airlines
Find Deal
Mon, Sep 29 - Thu, Oct 2

Southwest flights from Chicago Midway Airport to San Diego

Our best Southwest deals on Chicago Midway Airport to San Diego flight tickets
Southwest
Nov 12
MDW8:20 amChicago Midway
4h 30m
SAN10:50 amSan Diego
Nov 16
SAN7:35 pmSan Diego
3h 55m
MDW1:30 amChicago Midway
$133
Find similar
Southwest
Nov 12
MDW6:15 pmChicago Midway
7h 10m
1 stop
SAN11:25 pmSan Diego
Nov 16
SAN7:35 pmSan Diego
3h 55m
MDW1:30 amChicago Midway
$143
Find similar
Southwest
Nov 13
MDW6:35 pmChicago Midway
6h 20m
1 stop
SAN10:55 pmSan Diego
Nov 17
SAN8:05 pmSan Diego
7h 00m
1 stop
MDW5:05 amChicago Midway
$152
Find similar

Delta flights from Chicago Midway Airport to San Diego

Our best Delta deals on Chicago Midway Airport to San Diego flight tickets
Delta
Oct 1
MDW10:35 amChicago Midway
9h 35m
1 stop
SAN6:10 pmSan Diego
Oct 6
SAN10:30 pmSan Diego
9h 10m
1 stop
MDW9:40 amChicago Midway
$257
Find similar
Delta
Oct 1
MDW9:35 amChicago Midway
6h 15m
1 stop
SAN1:50 pmSan Diego
Oct 3
SAN6:15 amSan Diego
9h 20m
1 stop
MDW5:35 pmChicago Midway
$285
Find similar
Delta
Sep 23
MDW1:43 pmChicago Midway
9h 04m
1 stop
SAN8:47 pmSan Diego
Sep 30
SAN7:45 amSan Diego
7h 50m
1 stop
MDW5:35 pmChicago Midway
$300
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momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San Diego 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 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Diego that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 11/12

8:20 am-10:50 am

Nonstop4h 30m

San Diego

Sun 11/16

7:35 pm-1:30 am

Nonstop3h 55m

$133

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 11/12

6:15 pm-11:25 pm

1 stop7h 10m

San Diego

Sun 11/16

7:35 pm-1:30 am

Nonstop3h 55m

$143

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 11/13

6:35 pm-10:55 pm

1 stop6h 20m

San Diego

Mon 11/17

8:05 pm-5:05 am

1 stop7h 00m

$152

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 11/5

8:35 pm-11:00 pm

Nonstop4h 25m

San Diego

Wed 11/12

5:00 pm-10:55 pm

Nonstop3h 55m

$153

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 10/2

1:53 pm-7:06 pm

1 stop7h 13m

San Diego

Mon 10/6

6:35 am-3:53 pm

1 stop7h 18m

$154

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 10/30

12:30 pm-11:17 am

1 stop24h 47m

San Diego

Thu 11/6

9:14 am-5:22 pm

1 stop6h 08m

$155

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 10/16

6:24 pm-8:08 pm

1 stop27h 44m

San Diego

Thu 10/23

6:41 am-12:36 am

1 stop15h 55m

$156

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Thu 10/30

12:30 pm-11:17 am

1 stop24h 47m

San Diego

Thu 11/6

9:14 am-5:22 pm

1 stop6h 08m

$161

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Wed 10/8

8:25 pm-10:45 pm

Nonstop4h 20m

San Diego

Sat 10/18

4:50 pm-10:50 pm

Nonstop4h 00m

$163

ChicagoSan Diego

MDW - SAN

MDWSAN

Chicago Midway

Mon 9/29

4:48 pm-12:31 pm

2 stops21h 43m

San Diego

Thu 10/2

1:18 pm-9:58 pm

1 stop6h 40m

$198

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 San Diego from

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

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 San Diego?

If you are unable to visit San Diego during the month of January, then departing from Chicago Midway Airport during the month October is also very affordable. Most momondo users find prices during this month for around $272.

What is the cheapest day to depart on your flight to San Diego?

The cheapest day to depart from Chicago Midway Airport to San Diego is on a Thursday. Travelers who choose to depart for San Diego on a Thursday will often find tickets for as low as $361. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $460. These prices are subject to change though, so be sure to set up a Price Alert for flights to San Diego.

What is the cheapest time of day to depart on your flight to San Diego?

The cheapest time of day to fly to San Diego is at noon when flights can be purchased for as low as $288. Flights in the afternoon are often more expensive with an average ticket price of $449.

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

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

How far in advance should I book a flight to San Diego?

You are more likely to see cheaper flights to San Diego from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Diego for around $368 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Diego from Chicago Midway Airport for as low as $181 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway to San Diego 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 Chicago Midway Airport to San Diego flights?

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

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

As of September 2025, prices for Chicago Midway Airport to San Diego flights are approximately 154% more expensive when compared to flights at the same time last year.

When to book flights from Chicago Midway Airport to San Diego

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

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

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

Best Price Found

$114

Fastest flight time

4h 10m

Direct flights

Every day

Airports in San Diego

1 airport
The best one-way flight to San Diego from Chicago Midway Airport in the past 72 hours is $114. The best round-trip flight deal from Chicago Midway Airport to San Diego found on momondo in the last 72 hours is $168.
The fastest flight from Chicago Midway Airport to San Diego takes 4h 10m
Direct flights go from Chicago Midway Airport to San Diego every day.
There is 1 airport near San Diego: San Diego (SAN)
Search flight deals

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

    San Diego is 1723.1 mi away from Chicago Midway. Flights usually cover this in 4h 15m, depending on flying conditions and air traffic around both airports.

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

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

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San Diego Airport.

  • What documentation or ID do you need to fly to San Diego Airport?

    The necessary travel and health documents for your San Diego Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Chicago Midway Airport to San Diego

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Diego with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $108Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
SouthwestPriceFrom $202Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Diego

    Southwest operates around 18 flights from Chicago Midway Airport to San Diego every week. The average price of these flights found in the last 72 hours has been $416, but momondo users have found Southwest deals from Chicago Midway Airport to San Diego from as low as $202 round-trip. Southwest has been scored 8.0/10 in 4,242 reviews.

Traveling to a place near San Diego?

Book flights to San Diego if you plan to visit one of these locations
Coronado
Chula Vista
El Cajon
Julian
La Mesa
National City
Poway
Imperial Beach
San Ysidro
Borrego Springs
Lemon Grove
Alpine
Santee

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San Diego from Chicago.

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

Yes. momondo enables you to select and highlight flights to San Diego from Chicago with this policy.

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

Once you have performed a search for Chicago to San Diego flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to San Diego, momondo offers a useful price alert feature which will track prices for flights to San Diego from Chicago and alert you when they change.

An easier way to manage your San Diego trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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