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Cheap flights from Chicago Midway Airport to San Diego from $53

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 1/14. 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

These are some of the best round-trip flight deals from Chicago Midway Airport to San Diego that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to San Diego.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to San Diego? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to San Diego, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to San Diego

Find recent round-trip train or bus tickets from Chicago Midway Airport to San Diego.

All round-trip flight deals to San Diego

The cheapest plane tickets to San Diego found on KAYAK recently.
12:43 pm - 7:06 pmMDW-SAN
8h 23m1 stop
8:45 am - 8:14 pmSAN-MDW
9h 29m1 stop
$108Frontier
Find Deal
Thu, Jan 9 - Mon, Jan 13
10:04 pm - 11:49 pmMDW-SAN
27h 45m1 stop
10:35 am - 11:48 amSAN-MDW
23h 13m1 stop
$113Frontier
Find Deal
Mon, Jan 6 - Thu, Jan 9
8:15 am - 1:32 pmMDW-SAN
7h 17m1 stop
8:45 am - 8:12 pmSAN-MDW
9h 27m1 stop
$115Frontier
Find Deal
Wed, Feb 5 - Mon, Feb 10
8:41 pm - 11:54 amMDW-SAN
17h 13m1 stop
10:35 am - 11:48 amSAN-MDW
23h 13m1 stop
$116Frontier
Find Deal
Mon, Jan 6 - Thu, Jan 9
12:43 pm - 7:10 pmMDW-SAN
8h 27m1 stop
10:35 am - 11:48 amSAN-MDW
23h 13m1 stop
$117Frontier
Find Deal
Mon, Dec 16 - Thu, Jan 9
4:50 pm - 9:06 pmMDW-SAN
6h 16m1 stop
7:20 am - 4:10 pmSAN-MDW
6h 50m1 stop
$300Delta
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Tue, Dec 24 - Tue, Dec 31
7:15 am - 10:27 pmMDW-SAN
17h 12m2 stops
8:55 pm - 9:32 pmSAN-MDW
22h 37m2 stops
Sun, Dec 15 - Tue, Dec 24
4:50 pm - 9:06 pmMDW-SAN
6h 16m1 stop
6:15 am - 5:11 pmSAN-MDW
8h 56m1 stop
$362Delta
Find Deal
Tue, Dec 24 - Wed, Jan 1
8:45 pm - 8:20 amMDW-SAN
13h 35m1 stop
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
$381Southwest
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Tue, Dec 31 - Fri, Jan 10
9:25 am - 10:30 pmMDW-SAN
15h 05m2 stops
11:10 am - 5:05 pmSAN-MDW
3h 55mnonstop
$386Southwest
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Tue, Dec 31 - Fri, Jan 10
8:15 am - 1:29 pmMDW-SAN
7h 14m1 stop
$53Frontier
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Tue, Jan 14
12:43 pm - 6:58 pmMDW-SAN
8h 15m1 stop
$54Frontier
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Mon, Feb 3
9:30 am - 2:27 pmMDW-SAN
6h 57m1 stop
$150Delta
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Sat, Dec 14
3:19 pm - 9:15 pmMDW-SAN
7h 56m1 stop
$185Delta
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Thu, Nov 28
7:40 pm - 10:00 pmMDW-SAN
4h 20mnonstop
$196Southwest
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Tue, Dec 24
4:15 pm - 6:45 pmMDW-SAN
4h 30mnonstop
$199Southwest
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Tue, Jan 14
6:31 pm - 10:12 pmMDW-SAN
29h 41m3 stops
Sun, Jan 5
6:31 pm - 10:12 pmMDW-SAN
29h 41m3 stops
Thu, Jan 2
9:20 am - 11:46 amMDW-SAN
28h 26m3 stops
$468WestJet
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Sat, Mar 15
10:19 am - 11:45 amMDW-SAN
27h 26m3 stops
$476WestJet
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Tue, Jan 21
7:25 am - 11:56 pmMDW-SAN
18h 31m1 stop
6:25 am - 11:20 amSAN-MDW
26h 55m1 stop
$291Frontier
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Mon, Nov 25 - Fri, Nov 29
7:00 am - 6:18 pmMDW-SAN
13h 18m1 stop
6:25 am - 11:20 amSAN-MDW
26h 55m1 stop
$317Frontier
Find Deal
Tue, Nov 26 - Fri, Nov 29
7:00 am - 11:56 pmMDW-SAN
18h 56m1 stop
9:06 pm - 11:44 amSAN-MDW
12h 38m1 stop
$324Frontier
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Fri, Nov 22 - Wed, Nov 27
9:00 am - 5:08 pmMDW-SAN
10h 08m1 stop
1:48 pm - 12:13 amSAN-MDW
8h 25m1 stop
$328Frontier
Find Deal
Tue, Nov 26 - Tue, Dec 3
2:20 pm - 6:10 pmMDW-SAN
5h 50m1 stop
1:45 pm - 7:40 pmSAN-MDW
3h 55mnonstop
$644Southwest
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Tue, Nov 26 - Sun, Dec 1
5:35 am - 8:05 amMDW-SAN
4h 30mnonstop
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
$655Southwest
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Fri, Nov 22 - Tue, Nov 26
5:35 pm - 10:25 pmMDW-SAN
6h 50m1 stop
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
$660Southwest
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Fri, Nov 22 - Tue, Nov 26
10:41 am - 6:15 pmMDW-SAN
9h 34m1 stop
10:10 pm - 8:50 amSAN-MDW
8h 40m1 stop
$896Delta
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Sat, Nov 23 - Sun, Dec 1
9:30 am - 6:05 pmMDW-SAN
10h 35m2 stops
10:10 pm - 8:50 amSAN-MDW
8h 40m1 stop
$1,164Delta
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Fri, Nov 22 - Sun, Dec 1
2:17 pm - 11:28 pmMDW-SAN
11h 11m2 stops
12:50 pm - 9:46 pmSAN-MDW
6h 56m1 stop
$1,270Delta
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Sat, Nov 23 - Thu, Nov 28
4:15 pm - 6:45 pmMDW-SAN
4h 30mnonstop
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
$398Southwest
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Wed, Feb 26 - Tue, Mar 4
8:40 am - 11:20 amMDW-SAN
4h 40mnonstop
6:55 am - 12:45 pmSAN-MDW
3h 50mnonstop
$402Southwest
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Tue, Jan 14 - Thu, Jan 16
8:25 pm - 10:50 pmMDW-SAN
4h 25mnonstop
3:45 pm - 9:35 pmSAN-MDW
3h 50mnonstop
$406Southwest
Find Deal
Fri, Dec 13 - Sun, Dec 15
6:50 pm - 9:25 pmMDW-SAN
4h 35mnonstop
6:55 am - 12:45 pmSAN-MDW
3h 50mnonstop
$427Southwest
Find Deal
Fri, Jan 17 - Mon, Jan 20
7:40 pm - 10:00 pmMDW-SAN
4h 20mnonstop
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
$435Southwest
Find Deal
Tue, Dec 17 - Sun, Dec 22
5:35 am - 8:05 amMDW-SAN
4h 30mnonstop
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
$439Southwest
Find Deal
Thu, Dec 19 - Sun, Dec 22
6:10 am - 8:40 amMDW-SAN
4h 30mnonstop
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
$443Southwest
Find Deal
Fri, Dec 20 - Wed, Dec 25
6:10 am - 8:40 amMDW-SAN
4h 30mnonstop
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
$450Southwest
Find Deal
Fri, Dec 20 - Mon, Dec 30
4:15 pm - 6:45 pmMDW-SAN
4h 30mnonstop
6:35 am - 12:30 pmSAN-MDW
3h 55mnonstop
$455Southwest
Find Deal
Wed, Feb 12 - Sat, Mar 22
4:40 pm - 7:10 pmMDW-SAN
4h 30mnonstop
12:15 pm - 6:10 pmSAN-MDW
3h 55mnonstop
$459Southwest
Find Deal
Fri, Feb 28 - Sat, Mar 8

Frontier flights from Chicago Midway Airport to San Diego

Our best Frontier deals on Chicago Midway Airport to San Diego flight tickets
Frontier
Jan 9
MDW12:43 pmChicago Midway
8h 23m
1 stop
SAN7:06 pmSan Diego
Jan 13
SAN8:45 amSan Diego
9h 29m
1 stop
MDW8:14 pmChicago Midway
Frontier
Jan 6
MDW10:04 pmChicago Midway
27h 45m
1 stop
SAN11:49 pmSan Diego
Jan 9
SAN10:35 amSan Diego
23h 13m
1 stop
MDW11:48 amChicago Midway
Frontier
Feb 5
MDW8:15 amChicago Midway
7h 17m
1 stop
SAN1:32 pmSan Diego
Feb 10
SAN8:45 amSan Diego
9h 27m
1 stop
MDW8:12 pmChicago Midway

Delta flights from Chicago Midway Airport to San Diego

Our best Delta deals on Chicago Midway Airport to San Diego flight tickets
Delta
Dec 24
MDW4:50 pmChicago Midway
6h 16m
1 stop
SAN9:06 pmSan Diego
Dec 31
SAN7:20 amSan Diego
6h 50m
1 stop
MDW4:10 pmChicago Midway
Delta
Dec 24
MDW4:50 pmChicago Midway
6h 16m
1 stop
SAN9:06 pmSan Diego
Jan 1
SAN6:15 amSan Diego
8h 56m
1 stop
MDW5:11 pmChicago Midway
Delta
Jan 18
MDW10:57 amChicago Midway
9h 54m
1 stop
SAN6:51 pmSan Diego
Jan 25
SAN6:15 amSan Diego
6h 38m
1 stop
MDW2:53 pmChicago Midway

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 April, then departing from Chicago Midway Airport during the month May is also very affordable. Most momondo users find prices during this month for around $373.

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 Tuesday. Travelers who choose to depart for San Diego on a Tuesday will often find tickets for as low as $370. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $466. 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 in the evening when flights can be purchased for as low as $388. Flights at noon are often more expensive with an average ticket price of $451.

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?

Most flyers found that booking tickets 55 days in advance of their planned departure date is the best time to get cheap flights to San Diego. During this timeframe, flight prices are around $405. However, in the past 72 hours, people saw flights from Chicago Midway Airport for as low as $303.

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

There are 1 cabin classes 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?

You could potentially save up to 72% on your flight if you consider stops on a Chicago Midway Airport to San Diego flight.

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

As of November 2024, prices for Chicago Midway Airport to San Diego flights are approximately 13% cheaper 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

$53

Fastest flight time

4h 20m

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 $53. The best round-trip flight deal from Chicago Midway Airport to San Diego found on momondo in the last 72 hours is $108.
The fastest flight from Chicago Midway Airport to San Diego takes 4h 20m
Direct flights go from Chicago Midway Airport to San Diego every day.
There is 1 airport near San Diego: San Diego (SAN)

  • 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 40m, 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 $110Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
SouthwestPriceFrom $201Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
DeltaPriceFrom $237Free CancellationRating
8.0
8,755 reviews
Search Delta flights
  • Southwest Flights From Chicago Midway Airport to San Diego

    Southwest operates around 16 flights from Chicago Midway Airport to San Diego every week. The average price of these flights found in the last 72 hours has been $427, but momondo users have found Southwest deals from Chicago Midway Airport to San Diego from as low as $201 round-trip. Southwest has been scored 8.1/10 in 5,005 reviews.


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.


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