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Cheap flights from San Juan Luis Munoz Marin Intl Airport to Chicago from $109

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 4/21. 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 Juan Luis Munoz Marin Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
9:01 am - 9:21 pm
SJU
-
MDW
13h 20m
1 stop
Frontier Logo
5:30 am - 8:00 pm
MDW
-
SJU
13h 30m
1 stop
$202Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
3:19 pm - 4:13 pm
SJU
-
MDW
25h 54m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$213Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$214Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
8:41 am - 2:01 am
MDW
-
SJU
16h 20m
1 stop
$217Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:13 pm
MDW
-
SJU
7h 13m
1 stop
$223Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
6:07 pm - 2:01 pm
SJU
-
MDW
20h 54m
1 stop
Frontier Logo
6:30 am - 11:53 pm
MDW
-
SJU
16h 23m
1 stop
$229Frontier
Thu, Apr 9 - Mon, Apr 13
Multiple Airlines Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Multiple Airlines Logo
6:00 am - 5:31 pm
MDW
-
SJU
10h 31m
1 stop
$233Multiple Airlines
Thu, May 7 - Mon, May 11
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$235Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$237Frontier
Fri, May 8 - Mon, May 11
Multiple Airlines Logo
6:30 am - 10:19 pm
SJU
-
MDW
16h 49m
2 stops
Multiple Airlines Logo
6:00 am - 5:31 pm
MDW
-
SJU
10h 31m
1 stop
$241Multiple Airlines
Tue, May 5 - Fri, May 8

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
Apr 9
SJU9:01 amSan Juan Luis Munoz Marin Intl
13h 20m
1 stop
MDW9:21 pmChicago Midway
Apr 13
MDW5:30 amChicago Midway
13h 30m
1 stop
SJU8:00 pmSan Juan Luis Munoz Marin Intl
$202
Frontier
May 8
SJU3:19 pmSan Juan Luis Munoz Marin Intl
25h 54m
1 stop
MDW4:13 pmChicago Midway
May 11
MDW9:14 amChicago Midway
15h 47m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$213
Frontier
May 7
SJU3:18 pmSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
MDW10:19 pmChicago Midway
May 10
MDW9:14 amChicago Midway
15h 47m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$214

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
Apr 21
SJU5:35 amSan Juan Luis Munoz Marin Intl
9h 10m
1 stop
MDW1:45 pmChicago Midway
Apr 24
MDW4:35 pmChicago Midway
6h 20m
1 stop
SJU11:55 pmSan Juan Luis Munoz Marin Intl
$281
Southwest
May 7
SJU2:00 pmSan Juan Luis Munoz Marin Intl
11h 05m
1 stop
MDW12:05 amChicago Midway
May 10
MDW1:45 pmChicago Midway
9h 20m
2 stops
SJU12:05 amSan Juan Luis Munoz Marin Intl
$286
Southwest
Mar 7
SJU3:35 pmSan Juan Luis Munoz Marin Intl
5h 20m
MDW6:55 pmChicago Midway
Mar 10
MDW3:45 pmChicago Midway
7h 30m
1 stop
SJU12:15 amSan Juan Luis Munoz Marin Intl
$297

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 March 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

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/9

9:01 am-9:21 pm

1 stop13h 20m

Chicago Midway

Mon 4/13

5:30 am-8:00 pm

1 stop13h 30m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/8

3:19 pm-4:13 pm

1 stop25h 54m

Chicago Midway

Mon 5/11

9:14 am-2:01 am

1 stop15h 47m

$213

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/10

9:14 am-2:01 am

1 stop15h 47m

$214

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 5/4

8:41 am-2:01 am

1 stop16h 20m

$217

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 5/4

6:00 am-2:13 pm

1 stop7h 13m

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/9

6:07 pm-2:01 pm

1 stop20h 54m

Chicago Midway

Mon 4/13

6:30 am-11:53 pm

1 stop16h 23m

$229

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Mon 5/11

6:00 am-5:31 pm

1 stop10h 31m

$233

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/10

9:14 am-2:01 am

1 stop15h 47m

$235

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/8

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Mon 5/11

9:14 am-2:01 am

1 stop15h 47m

$237

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 5/5

6:30 am-10:19 pm

2 stops16h 49m

Chicago Midway

Fri 5/8

6:00 am-5:31 pm

1 stop10h 31m

$241

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 cheapest month to fly to Chicago Midway Airport?

The month of December 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 $302. If you are unable to visit Chicago Midway Airport during the month of December, then departing from San Juan Luis Munoz Marin Intl Airport during the month November is also very affordable. Most momondo users find prices during this month for around $336.

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 to Chicago Midway flights?

There is only 1 cabin class available to choose from on San Juan Luis Munoz Marin Intl to Chicago Midway 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 March 2026, prices for San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flights are approximately 33% more expensive 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

  • 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 $419Free CancellationRating
8.0
4,304 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.

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

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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