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Cheap flights from San Juan Luis Munoz Marin Intl Airport to Chicago from $114

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.
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Atlanta Hartsfield-Jackson
$220Frontier
Fri, Oct 23 - Mon, Oct 26
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:21 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 45m1 stop Atlanta Hartsfield-Jackson
$222Frontier
Thu, Oct 8 - Tue, Oct 13
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Atlanta Hartsfield-Jackson
$222Frontier
Fri, Oct 16 - Mon, Oct 19
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Atlanta Hartsfield-Jackson
$222Frontier
Fri, Oct 16 - Mon, Oct 19
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Atlanta Hartsfield-Jackson
$222Frontier
Fri, Oct 23 - Mon, Oct 26
Frontier Logo
3:55 am - 7:47 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
17h 52m1 stop Orlando
Frontier Logo
8:42 pm - 2:24 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
27h 42m1 stop Orlando
$230Frontier
Thu, Nov 19 - Sun, Nov 22
Frontier Logo
5:01 am - 2:55 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
11h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:50 pm - 1:07 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
7h 17m1 stop Atlanta Hartsfield-Jackson
$240Frontier
Fri, Dec 4 - Mon, Dec 14
Frontier Logo
5:01 am - 2:55 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
11h 54m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
9:37 pm - 10:40 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
11h 03m1 stop Orlando
$240Frontier
Fri, Dec 4 - Sun, Dec 6
Southwest Logo
12:40 pm - 9:25 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 45m2 stops Orlando Baltimore/Washington
Southwest Logo
2:40 pm - 10:15 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
6h 35m1 stop Baltimore/Washington
$266Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
8:15 am - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 30m1 stop Fort Lauderdale
Southwest Logo
2:50 pm - 12:10 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 20m2 stops Detroit Metropolitan Wayne County Baltimore/Washington
$286Southwest
Tue, Oct 6 - Fri, Oct 30

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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
Oct 23
SJU5:11 pmSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
MDW11:43 pmChicago Midway
Oct 26
MDW6:15 amChicago Midway
8h 51m
1 stop
SJU4:06 pmSan Juan Luis Munoz Marin Intl
$220
Frontier
Oct 8
SJU5:11 pmSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
MDW11:43 pmChicago Midway
Oct 13
MDW6:21 amChicago Midway
8h 45m
1 stop
SJU4:06 pmSan Juan Luis Munoz Marin Intl
$222
Frontier
Nov 19
SJU3:55 amSan Juan Luis Munoz Marin Intl
17h 52m
1 stop
MDW7:47 pmChicago Midway
Nov 22
MDW8:42 pmChicago Midway
27h 42m
1 stop
SJU2:24 amSan Juan Luis Munoz Marin Intl
$230

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
Oct 21
SJU12:40 pmSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW9:25 pmChicago Midway
Oct 24
MDW2:40 pmChicago Midway
6h 35m
1 stop
SJU10:15 pmSan Juan Luis Munoz Marin Intl
$266
Southwest
Oct 6
SJU5:05 amSan Juan Luis Munoz Marin Intl
8h 20m
2 stops
MDW12:25 pmChicago Midway
Oct 30
MDW2:50 pmChicago Midway
8h 20m
2 stops
SJU12:10 amSan Juan Luis Munoz Marin Intl
$286
Southwest
Sep 22
SJU5:15 amSan Juan Luis Munoz Marin Intl
7h 50m
2 stops
MDW12:05 pmChicago Midway
Sep 29
MDW12:45 pmChicago Midway
8h 20m
2 stops
SJU10:05 pmSan Juan Luis Munoz Marin Intl
$289

momondo Fare Finder

 
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

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/23

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Mon 10/26

6:15 am-4:06 pm

1 stop8h 51m

$220

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/8

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Tue 10/13

6:21 am-4:06 pm

1 stop8h 45m

$222

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/16

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Mon 10/19

6:15 am-4:06 pm

1 stop8h 51m

$222

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/16

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Mon 10/19

6:15 am-4:06 pm

1 stop8h 51m

$222

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/23

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Mon 10/26

6:15 am-4:06 pm

1 stop8h 51m

$222

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 11/19

3:55 am-7:47 pm

1 stop17h 52m

Chicago Midway

Sun 11/22

8:42 pm-2:24 am

1 stop27h 42m

$230

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/4

5:01 am-2:55 pm

1 stop11h 54m

Chicago Midway

Mon 12/14

3:50 pm-1:07 am

1 stop7h 17m

$240

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/4

5:01 am-2:55 pm

1 stop11h 54m

Chicago Midway

Sun 12/6

9:37 pm-10:40 am

1 stop11h 03m

$240

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/21

12:40 pm-9:25 pm

2 stops9h 45m

Chicago Midway

Sat 10/24

2:40 pm-10:15 pm

1 stop6h 35m

$266
Quickest round-trip

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 10/6

8:15 am-2:45 pm

1 stop7h 30m

Chicago Midway

Fri 10/30

2:50 pm-12:10 am

2 stops8h 20m

$286

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?

Prices are currently low for flights on this route.

Typical prices usually range from $255 to $412.
The lowest price recently found on this route was $222.

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 September is also very affordable. Most momondo users find prices during this month for around $276.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from San Juan Luis Munoz Marin Intl Airport. The lowest ticket price found for a Saturday departure recently was $552. 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 Juan Luis Munoz Marin Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $726.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from San Juan Luis Munoz Marin Intl Airport in the morning is the least expensive time of day to depart. momondo users have found prices as low as $552 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $726. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 September 2026, prices for San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flights are approximately 69% 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

Best Price Found

$114

Fastest flight time

7h 32m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from San Juan Luis Munoz Marin Intl Airport in the past 72 hours is $114. The best round-trip flight deal from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport found on momondo in the last 72 hours is $220.
The fastest flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport takes 7h 32m
Direct flights go from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport on 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. 7h 32m 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
8.0
4,192 reviews
Search Southwest flights

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

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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.

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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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