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Cheap flights from San Juan Luis Munoz Marin Intl Airport to Chicago from $143

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 Juan Luis Munoz Marin Intl Airport to Chicago departing on 7/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from San Juan Luis Munoz Marin Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$246Southwest
Thu, Aug 27 - Mon, Aug 31
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:11 am - 4:38 pm
MDW
-
SJU
9h 27m
1 stop
$256Delta
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
$266Southwest
Wed, Aug 26 - Sat, Aug 29
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:05 am - 1:42 pm
MDW
-
SJU
6h 37m
1 stop
$281Delta
Fri, Aug 28 - Tue, Sep 1
Southwest Logo
10:20 pm - 9:25 am
SJU
-
MDW
12h 05m
1 stop
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$301Southwest
Mon, Aug 3 - Thu, Aug 13
Southwest Logo
5:30 am - 2:55 pm
SJU
-
MDW
10h 25m
2 stops
Southwest Logo
8:05 pm - 9:10 am
MDW
-
SJU
12h 05m
1 stop
$306Southwest
Thu, Aug 6 - Sun, Aug 9
Southwest Logo
5:30 am - 2:55 pm
SJU
-
MDW
10h 25m
2 stops
Southwest Logo
12:20 pm - 10:00 pm
MDW
-
SJU
8h 40m
1 stop
$311Southwest
Thu, Sep 3 - Wed, Sep 9
Southwest Logo
1:45 pm - 10:20 pm
SJU
-
MDW
9h 35m
2 stops
Southwest Logo
7:50 am - 4:40 pm
MDW
-
SJU
7h 50m
2 stops
$316Southwest
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
5:05 am - 12:35 pm
SJU
-
MDW
8h 30m
1 stop
Southwest Logo
1:00 pm - 10:50 pm
MDW
-
SJU
8h 50m
1 stop
$321Southwest
Sat, Sep 5 - Fri, Sep 11
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
7:50 pm - 9:25 am
MDW
-
SJU
12h 35m
1 stop
$323Southwest
Fri, Aug 14 - Fri, Aug 21

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Frontier flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Our best Frontier deals on San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flight tickets
Frontier
Aug 27
SJU3:48 pmSan Juan Luis Munoz Marin Intl
7h 59m
1 stop
MDW10:47 pmChicago Midway
Sep 8
MDW11:50 amChicago Midway
12h 06m
2 stops
SJU12:56 amSan Juan Luis Munoz Marin Intl
$379
Frontier
Aug 27
SJU3:48 pmSan Juan Luis Munoz Marin Intl
7h 59m
1 stop
MDW10:47 pmChicago Midway
Sep 9
MDW7:25 amChicago Midway
15h 32m
2 stops
SJU11:57 pmSan Juan Luis Munoz Marin Intl
$380
Frontier
Jul 14
SJU6:32 amSan Juan Luis Munoz Marin Intl
13h 05m
1 stop
MDW6:37 pmChicago Midway
Jul 21
MDW6:05 amChicago Midway
7h 11m
1 stop
SJU2:16 pmSan Juan Luis Munoz Marin Intl
$396

Southwest flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Our best Southwest deals on San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flight tickets
Southwest
Aug 27
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 30m
2 stops
MDW2:30 pmChicago Midway
Aug 31
MDW3:15 pmChicago Midway
6h 50m
1 stop
SJU11:05 pmSan Juan Luis Munoz Marin Intl
$246
Southwest
Aug 26
SJU5:15 amSan Juan Luis Munoz Marin Intl
7h 50m
2 stops
MDW12:05 pmChicago Midway
Aug 29
MDW7:50 amChicago Midway
9h 15m
2 stops
SJU6:05 pmSan Juan Luis Munoz Marin Intl
$266
Southwest
Aug 3
SJU10:20 pmSan Juan Luis Munoz Marin Intl
12h 05m
1 stop
MDW9:25 amChicago Midway
Aug 13
MDW3:15 pmChicago Midway
6h 50m
1 stop
SJU11:05 pmSan Juan Luis Munoz Marin Intl
$301

momondo Fare Finder

 
Customize your flight search to find flights from San Juan Luis Munoz Marin Intl Airport 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 July 4, 2026.
Use the filters below to find and compare flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/27

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Mon 8/31

3:15 pm-11:05 pm

1 stop6h 50m

$246

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/26

12:56 pm-10:36 pm

1 stop10h 40m

Chicago Midway

Sat 8/29

6:11 am-4:38 pm

1 stop9h 27m

$256

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/26

5:15 am-12:05 pm

2 stops7h 50m

Chicago Midway

Sat 8/29

7:50 am-6:05 pm

2 stops9h 15m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/28

12:56 pm-10:36 pm

1 stop10h 40m

Chicago Midway

Tue 9/1

6:05 am-1:42 pm

1 stop6h 37m

$281

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 8/3

10:20 pm-9:25 am

1 stop12h 05m

Chicago Midway

Thu 8/13

3:15 pm-11:05 pm

1 stop6h 50m

$301

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/6

5:30 am-2:55 pm

2 stops10h 25m

Chicago Midway

Sun 8/9

8:05 pm-9:10 am

1 stop12h 05m

$306

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/3

5:30 am-2:55 pm

2 stops10h 25m

Chicago Midway

Wed 9/9

12:20 pm-10:00 pm

1 stop8h 40m

$311

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/19

1:45 pm-10:20 pm

2 stops9h 35m

Chicago Midway

Sat 8/22

7:50 am-4:40 pm

2 stops7h 50m

$316

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/5

5:05 am-12:35 pm

1 stop8h 30m

Chicago Midway

Fri 9/11

1:00 pm-10:50 pm

1 stop8h 50m

$321

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/14

6:30 am-1:45 pm

2 stops8h 15m

Chicago Midway

Fri 8/21

7:50 pm-9:25 am

1 stop12h 35m

$323

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 Juan Luis Munoz Marin Intl Airport 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 typical price of a round-trip flight between San Juan Luis Munoz Marin Intl Airport and Chicago Midway Airport?

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

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from San Juan Luis Munoz Marin Intl Airport, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from San Juan Luis Munoz Marin Intl Airport during the month August is also very affordable. Most momondo users find prices during this month for around $302.

What is the cheapest San Juan Luis Munoz Marin Intl to Chicago Midway flight route?

Fly from San Juan Luis Munoz Marin Intl to Chicago Midway for the best San Juan Luis Munoz Marin Intl - Chicago Midway flight prices

What cabin class options are available on San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flights?

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

How have San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flight prices changed over time?

As of July 2026, prices for San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flights are approximately 19% cheaper when compared to flights at the same time last year.

When to book flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San Juan Luis Munoz Marin Intl Airport 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 Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport (SJU to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Fastest flight time

4h 50m

Direct flights

Mon and Sun
The fastest flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport takes 4h 50m
Direct flights go from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

  • How far is San Juan Luis Munoz Marin Intl to Chicago Midway by plane?

    Chicago Midway is 2057.4 mi away from San Juan Luis Munoz Marin Intl. 4h 50m is a normal flight duration for this route.

  • When did momondo last update prices for flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

    Prices for flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from San Juan Luis Munoz Marin Intl Airport to Chicago Midway 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 San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport.

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

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

  • What is the most popular airline from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

Best airlines flying from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $266Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

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Why use momondo?

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

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

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

momondo does allow users to show only those flights to Chicago from San Juan which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Juan to Chicago.

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Of course. momondo tracks the price of San Juan to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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