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Cheap flights from San Diego to Chicago Midway Airport 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 San Diego to Chicago Midway Airport departing on 2/27. 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

These are some of the best round-trip flight deals from San Diego to Chicago 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 San Diego to Chicago.

Cheap last minute flights

Planning a quick getaway from San Diego to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from San Diego to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
2:32 pm - 12:13 amSAN-MDW
7h 41m1 stop
8:15 am - 1:32 pmMDW-SAN
7h 17m1 stop
$107Frontier
Find Deal
Wed, Jan 15 - Tue, Jan 21
2:32 pm - 12:13 amSAN-MDW
7h 41m1 stop
12:43 pm - 7:13 pmMDW-SAN
8h 30m1 stop
$108Frontier
Find Deal
Wed, Jan 8 - Mon, Jan 13
6:25 am - 12:13 amSAN-MDW
15h 48m1 stop
8:15 am - 11:49 pmMDW-SAN
17h 34m1 stop
$118Frontier
Find Deal
Wed, Jan 8 - Wed, Jan 15
10:35 am - 11:48 amSAN-MDW
23h 13m1 stop
12:43 pm - 7:10 pmMDW-SAN
8h 27m1 stop
$120Frontier
Find Deal
Thu, Dec 12 - Mon, Dec 16
10:35 am - 11:48 amSAN-MDW
23h 13m1 stop
12:43 pm - 6:58 pmMDW-SAN
8h 15m1 stop
$121Frontier
Find Deal
Thu, Jan 9 - Thu, Jan 30
6:25 am - 5:47 pmSAN-MDW
9h 22m1 stop
6:00 am - 1:16 pmMDW-SAN
9h 16m1 stop
$320Delta
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Wed, Jan 8 - Sat, Jan 11
7:25 am - 4:12 pmSAN-MDW
6h 47m1 stop
10:57 am - 6:51 pmMDW-SAN
9h 54m1 stop
$373Delta
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Sat, Jan 18 - Sat, Jan 25
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
6:10 am - 8:40 amMDW-SAN
4h 30mnonstop
$412Southwest
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Wed, Dec 25 - Thu, Jan 2
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
3:40 pm - 8:15 pmMDW-SAN
6h 35m1 stop
$421Southwest
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Wed, Dec 25 - Thu, Jan 2
10:15 am - 11:48 amSAN-MDW
23h 33m2 stops
12:57 pm - 7:36 amMDW-SAN
20h 39m2 stops
Sat, Dec 7 - Tue, Dec 10
4:06 pm - 12:17 amSAN-MDW
6h 11m1 stop
$53Frontier
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Thu, Feb 27
2:32 pm - 12:17 amSAN-MDW
7h 45m1 stop
$54Frontier
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Wed, Jan 29
10:10 pm - 8:51 amSAN-MDW
8h 41m1 stop
$150Delta
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Tue, Mar 11
7:10 am - 4:24 pmSAN-MDW
7h 14m1 stop
$170Delta
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Thu, Dec 19
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
$176Southwest
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Tue, Dec 24
7:16 pm - 12:27 amSAN-MDW
27h 11m3 stops
Fri, Dec 27
7:10 am - 5:05 pmSAN-MDW
7h 55m2 stops
$186Southwest
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Tue, Jan 21
1:59 pm - 11:48 amSAN-MDW
19h 49m2 stops
Thu, Dec 5
12:35 pm - 5:47 pmSAN-MDW
27h 12m3 stops
$289WestJet
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Fri, Jan 31
12:35 pm - 5:43 pmSAN-MDW
27h 08m3 stops
$290WestJet
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Mon, Feb 3
6:25 am - 8:42 pmSAN-MDW
12h 17m1 stop
8:15 am - 11:49 pmMDW-SAN
17h 34m1 stop
$223Frontier
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Mon, Dec 2 - Wed, Dec 4
8:38 am - 8:46 pmSAN-MDW
10h 08m1 stop
8:41 pm - 9:16 amMDW-SAN
14h 35m1 stop
$270Frontier
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Fri, Nov 29 - Thu, Dec 19
6:25 am - 8:42 pmSAN-MDW
12h 17m1 stop
12:43 pm - 6:58 pmMDW-SAN
8h 15m1 stop
$278Frontier
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Mon, Dec 2 - Thu, Jan 30
10:53 am - 7:50 pmSAN-MDW
6h 57m1 stop
7:15 am - 6:01 pmMDW-SAN
12h 46m1 stop
$294Frontier
Find Deal
Mon, Dec 2 - Sun, Feb 2
6:15 am - 5:54 pmSAN-MDW
9h 39m1 stop
12:44 pm - 6:10 pmMDW-SAN
7h 26m1 stop
$896Delta
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Sat, Nov 30 - Sat, Dec 7
1:10 pm - 7:10 pmSAN-MDW
4h 00mnonstop
8:05 am - 10:35 amMDW-SAN
4h 30mnonstop
$898Southwest
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Sat, Nov 30 - Sat, Dec 7
8:15 am - 4:35 pmSAN-MDW
6h 20m1 stop
8:05 am - 10:35 amMDW-SAN
4h 30mnonstop
$903Southwest
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Sat, Nov 30 - Sat, Dec 7
6:30 am - 12:30 pmSAN-MDW
4h 00mnonstop
8:10 pm - 10:35 pmMDW-SAN
4h 25mnonstop
$918Southwest
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Thu, Nov 28 - Mon, Dec 2
11:26 am - 9:46 pmSAN-MDW
8h 20m1 stop
7:17 pm - 11:50 pmMDW-SAN
6h 33m1 stop
$1,017Delta
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Thu, Nov 28 - Sun, Dec 1
6:30 am - 6:32 pmSAN-MDW
10h 02m2 stops
9:30 am - 2:27 pmMDW-SAN
6h 57m1 stop
$1,166Delta
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Fri, Nov 29 - Thu, Dec 19
4:50 pm - 10:40 pmSAN-MDW
3h 50mnonstop
5:35 am - 8:05 amMDW-SAN
4h 30mnonstop
$412Southwest
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Wed, Dec 25 - Fri, Jan 3
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
7:40 pm - 10:00 pmMDW-SAN
4h 20mnonstop
$467Southwest
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Sun, Dec 22 - Wed, Jan 1
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
8:40 am - 11:20 amMDW-SAN
4h 40mnonstop
$468Southwest
Find Deal
Sun, Dec 15 - Sun, Jan 19
6:20 am - 12:20 pmSAN-MDW
4h 00mnonstop
4:15 pm - 6:45 pmMDW-SAN
4h 30mnonstop
$472Southwest
Find Deal
Mon, Dec 30 - Tue, Jan 7
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
7:40 pm - 10:00 pmMDW-SAN
4h 20mnonstop
$477Southwest
Find Deal
Sun, Dec 29 - Tue, Dec 31
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
6:10 am - 8:40 amMDW-SAN
4h 30mnonstop
$483Southwest
Find Deal
Sun, Dec 22 - Thu, Jan 2
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
8:10 pm - 10:35 pmMDW-SAN
4h 25mnonstop
$492Southwest
Find Deal
Thu, Dec 26 - Thu, Jan 2
6:55 pm - 12:50 amSAN-MDW
3h 55mnonstop
8:10 pm - 10:35 pmMDW-SAN
4h 25mnonstop
$494Southwest
Find Deal
Thu, Dec 19 - Sun, Dec 22
6:25 am - 12:25 pmSAN-MDW
4h 00mnonstop
8:40 am - 11:20 amMDW-SAN
4h 40mnonstop
$496Southwest
Find Deal
Wed, Dec 18 - Fri, Jan 10
6:25 am - 12:25 pmSAN-MDW
4h 00mnonstop
8:15 pm - 10:40 pmMDW-SAN
4h 25mnonstop
$508Southwest
Find Deal
Mon, Dec 16 - Sat, Jan 4

Frontier flights from San Diego to Chicago Midway Airport

Our best Frontier deals on San Diego to Chicago Midway Airport flight tickets
Frontier
Jan 15
SAN2:32 pmSan Diego
7h 41m
1 stop
MDW12:13 amChicago Midway
Jan 21
MDW8:15 amChicago Midway
7h 17m
1 stop
SAN1:32 pmSan Diego
Frontier
Jan 8
SAN2:32 pmSan Diego
7h 41m
1 stop
MDW12:13 amChicago Midway
Jan 13
MDW12:43 pmChicago Midway
8h 30m
1 stop
SAN7:13 pmSan Diego
Frontier
Jan 8
SAN6:25 amSan Diego
15h 48m
1 stop
MDW12:13 amChicago Midway
Jan 15
MDW8:15 amChicago Midway
17h 34m
1 stop
SAN11:49 pmSan Diego

Southwest flights from San Diego to Chicago Midway Airport

Our best Southwest deals on San Diego to Chicago Midway Airport flight tickets
Southwest
Dec 25
SAN4:50 pmSan Diego
3h 50m
MDW10:40 pmChicago Midway
Jan 2
MDW6:10 amChicago Midway
4h 30m
SAN8:40 amSan Diego
Southwest
Dec 25
SAN4:50 pmSan Diego
3h 50m
MDW10:40 pmChicago Midway
Jan 2
MDW3:40 pmChicago Midway
6h 35m
1 stop
SAN8:15 pmSan Diego
Southwest
Dec 23
SAN6:55 pmSan Diego
3h 55m
MDW12:50 amChicago Midway
Jan 1
MDW9:50 amChicago Midway
6h 55m
1 stop
SAN2:45 pmSan Diego

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from San Diego, with most prices found around $159. If you are unable to visit Chicago Midway Airport during the month of February, then departing from San Diego during the month July is also very affordable. Most momondo users find prices during this month for around $210.

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 $244. 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, Sunday 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 $387.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $231 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $377. 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?

We recommend purchasing flights from San Diego to Chicago Midway Airport 41 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago Midway Airport for $274. In the past 72 hours, momondo users found flights from San Diego to Chicago Midway Airport for as low as $118.

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

There are 1 cabin classes 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?

You could potentially save up to 69% on your flight if you consider stops on a San Diego to Chicago Midway Airport flight.

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

As of November 2024, prices for San Diego to Chicago Midway Airport flights are approximately 16% 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

$53

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 $53. The best round-trip flight deal from San Diego to Chicago Midway Airport found on momondo in the last 72 hours is $107.
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.

  • 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 $128Free CancellationRating
6.1
3,523 reviews
Search Frontier flights
SouthwestPriceFrom $252Free CancellationRating
8.1
4,979 reviews
Search Southwest flights
DeltaPriceFrom $258Free CancellationRating
8.0
8,730 reviews
Search Delta 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 $252. Generally, Southwest has 6 flights on this route every week with an average price of $477. Southwest is rated 8.1/10 by our users.


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.


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