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Cheap flights from San Juan Luis Munoz Marin Intl Airport to Chicago from $110

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 11/22. 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
4:31 pm - 10:12 pmSJU-MDW
7h 41m1 stop
Frontier Logo
6:15 am - 3:11 pmMDW-SJU
6h 56m1 stop
$211Frontier
Find Deal
sex, dez 5 - seg, dez 8
Frontier Logo
2:11 am - 7:30 amSJU-MDW
7h 19m1 stop
Frontier Logo
9:30 am - 11:09 pmMDW-SJU
11h 39m1 stop
$226Frontier
Find Deal
sáb, nov 15 - qui, nov 20
Frontier Logo
10:39 pm - 8:32 amSJU-MDW
11h 53m1 stop
Frontier Logo
5:30 pm - 2:54 amMDW-SJU
7h 24m1 stop
$227Frontier
Find Deal
dom, nov 16 - qui, nov 20
Frontier Logo
10:40 am - 4:57 pmSJU-MDW
8h 17m1 stop
Frontier Logo
2:16 pm - 10:32 amMDW-SJU
18h 16m1 stop
$231Frontier
Find Deal
qua, nov 26 - qui, dez 4
Frontier Logo
3:59 am - 4:30 pmSJU-MDW
14h 31m1 stop
Frontier Logo
5:30 pm - 2:54 amMDW-SJU
7h 24m1 stop
$242Frontier
Find Deal
qua, nov 19 - qui, nov 27
Multiple Airlines Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Multiple Airlines Logo
12:35 pm - 12:35 amMDW-SJU
10h 00m1 stop
$245Multiple Airlines
Find Deal
qui, dez 11 - seg, dez 15
Southwest Logo
9:05 am - 2:45 pmSJU-MDW
7h 40m1 stop
Southwest Logo
9:50 am - 8:55 pmMDW-SJU
9h 05m2 stops
$252Southwest
Find Deal
qua, jan 28 - qua, fev 4
Multiple Airlines Logo
10:40 am - 4:57 pmSJU-MDW
8h 17m1 stop
Multiple Airlines Logo
3:52 pm - 12:16 amMDW-SJU
30h 24m1 stop
$254Multiple Airlines
Find Deal
qua, nov 26 - sex, dez 5
Southwest Logo
6:10 am - 11:35 amSJU-MDW
7h 25m1 stop
Southwest Logo
1:35 pm - 12:05 amMDW-SJU
8h 30m2 stops
$267Southwest
Find Deal
sex, jan 30 - dom, fev 1
Delta Logo
6:15 am - 12:01 pmSJU-MDW
7h 46m1 stop
Delta Logo
6:00 am - 2:30 pmMDW-SJU
6h 30m1 stop
$336Delta
Find Deal
sex, jan 23 - ter, fev 3

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
Jan 28
SJU9:05 amSan Juan Luis Munoz Marin Intl
7h 40m
1 stop
MDW2:45 pmChicago Midway
Feb 4
MDW9:50 amChicago Midway
9h 05m
2 stops
SJU8:55 pmSan Juan Luis Munoz Marin Intl
$252
Find similar
Southwest
Jan 30
SJU6:10 amSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW11:35 amChicago Midway
Feb 1
MDW1:35 pmChicago Midway
8h 30m
2 stops
SJU12:05 amSan Juan Luis Munoz Marin Intl
$267
Find similar
Southwest
Feb 18
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
Feb 24
MDW1:15 pmChicago Midway
7h 55m
1 stop
SJU11:10 pmSan Juan Luis Munoz Marin Intl
$277
Find similar

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
Dec 5
SJU4:31 pmSan Juan Luis Munoz Marin Intl
7h 41m
1 stop
MDW10:12 pmChicago Midway
Dec 8
MDW6:15 amChicago Midway
6h 56m
1 stop
SJU3:11 pmSan Juan Luis Munoz Marin Intl
$211
Find similar
Frontier
Nov 15
SJU2:11 amSan Juan Luis Munoz Marin Intl
7h 19m
1 stop
MDW7:30 amChicago Midway
Nov 20
MDW9:30 amChicago Midway
11h 39m
1 stop
SJU11:09 pmSan Juan Luis Munoz Marin Intl
$226
Find similar
Frontier
Nov 16
SJU10:39 pmSan Juan Luis Munoz Marin Intl
11h 53m
1 stop
MDW8:32 amChicago Midway
Nov 20
MDW5:30 pmChicago Midway
7h 24m
1 stop
SJU2:54 amSan Juan Luis Munoz Marin Intl
$227
Find similar

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 novembro 3, 2025.
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

sex 12/5

4:31 pm-10:12 pm

1 stop7h 41m

Chicago Midway

seg 12/8

6:15 am-3:11 pm

1 stop6h 56m

$211

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

sáb 11/15

2:11 am-7:30 am

1 stop7h 19m

Chicago Midway

qui 11/20

9:30 am-11:09 pm

1 stop11h 39m

$226

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

dom 11/16

10:39 pm-8:32 am

1 stop11h 53m

Chicago Midway

qui 11/20

5:30 pm-2:54 am

1 stop7h 24m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qua 11/26

10:40 am-4:57 pm

1 stop8h 17m

Chicago Midway

qui 12/4

2:16 pm-10:32 am

1 stop18h 16m

$231

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qua 11/19

3:59 am-4:30 pm

1 stop14h 31m

Chicago Midway

qui 11/27

5:30 pm-2:54 am

1 stop7h 24m

$242

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qui 12/11

10:42 am-9:53 pm

1 stop13h 11m

Chicago Midway

seg 12/15

12:35 pm-12:35 am

1 stop10h 00m

$245

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qua 1/28

9:05 am-2:45 pm

1 stop7h 40m

Chicago Midway

qua 2/4

9:50 am-8:55 pm

2 stops9h 05m

$252

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

qua 11/26

10:40 am-4:57 pm

1 stop8h 17m

Chicago Midway

sex 12/5

3:52 pm-12:16 am

1 stop30h 24m

$254

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

sex 1/30

6:10 am-11:35 am

1 stop7h 25m

Chicago Midway

dom 2/1

1:35 pm-12:05 am

2 stops8h 30m

$267

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

sex 1/23

6:15 am-12:01 pm

1 stop7h 46m

Chicago Midway

ter 2/3

6:00 am-2:30 pm

1 stop6h 30m

$336

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 $299. 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 $317.

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

According to our data, Friday 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 Friday departure recently was $154. 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, Saturday 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 $580.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $580. 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 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.

Can stopping save me money on San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport.

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

As of November 2025, prices for San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flights are approximately 67% 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

5h 10m

Direct flights

Mon and Sun
The fastest flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport takes 5h 10m
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. 7h 19m 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
FrontierPriceFrom $148Free CancellationRating
5.8
3,117 reviews
Search Frontier flights
SouthwestPriceFrom $394Free CancellationRating
8.0
4,238 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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