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Cheap flights from Chicago Midway Airport to San Juan 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 Chicago Midway Airport to San Juan departing on 1/19. 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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0 bags

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Find the cheapest flights from Chicago Midway Airport to San Juan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 10:17 amMDW-SJU
26h 17m1 stop
Frontier Logo
8:00 am - 2:47 pmSJU-MDW
8h 47m1 stop
$214Frontier
Find Deal
Fri, Jan 9 - Thu, Jan 15
Frontier Logo
10:18 am - 2:50 amMDW-SJU
14h 32m1 stop
Frontier Logo
8:00 am - 2:47 pmSJU-MDW
8h 47m1 stop
$215Frontier
Find Deal
Sun, Jan 11 - Thu, Jan 15
Frontier Logo
4:00 pm - 9:27 amMDW-SJU
39h 27m2 stops
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
$221Frontier
Find Deal
Thu, Nov 27 - Thu, Dec 4
Frontier Logo
6:15 pm - 9:27 amMDW-SJU
37h 12m2 stops
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
$222Frontier
Find Deal
Thu, Nov 27 - Thu, Dec 4
Delta Logo
6:00 am - 2:14 pmMDW-SJU
6h 14m1 stop
Delta Logo
1:57 pm - 11:47 pmSJU-MDW
11h 50m1 stop
$227Delta
Find Deal
Mon, Dec 8 - Wed, Dec 10
Southwest Logo
8:20 am - 2:55 pmMDW-SJU
4h 35mnonstop
Southwest Logo
5:40 am - 12:30 pmSJU-MDW
8h 50m2 stops
$248Southwest
Find Deal
Sat, Jan 31 - Wed, Feb 4
Southwest Logo
1:15 pm - 11:10 pmMDW-SJU
7h 55m1 stop
Southwest Logo
5:30 am - 2:45 pmSJU-MDW
11h 15m2 stops
$252Southwest
Find Deal
Wed, Jan 21 - Sat, Jan 31
Multiple Airlines Logo
12:35 pm - 12:35 amMDW-SJU
10h 00m1 stop
Multiple Airlines Logo
7:06 pm - 1:59 pmSJU-MDW
20h 53m1 stop
$258Multiple Airlines
Find Deal
Mon, Dec 15 - Mon, Dec 22
Delta Logo
10:49 am - 11:20 pmMDW-SJU
10h 31m1 stop
Delta Logo
6:38 pm - 11:47 pmSJU-MDW
7h 09m1 stop
$272Delta
Find Deal
Sun, Dec 7 - Thu, Dec 11
Multiple Airlines Logo
10:18 am - 11:49 pmMDW-SJU
11h 31m2 stops
Multiple Airlines Logo
8:00 am - 2:47 pmSJU-MDW
8h 47m1 stop
$274Multiple Airlines
Find Deal
Fri, Jan 9 - Thu, Jan 15

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

Our best Delta deals on Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flight tickets
Delta
Dec 8
MDW6:00 amChicago Midway
6h 14m
1 stop
SJU2:14 pmSan Juan Luis Munoz Marin Intl
Dec 10
SJU1:57 pmSan Juan Luis Munoz Marin Intl
11h 50m
1 stop
MDW11:47 pmChicago Midway
$227
Find similar
Delta
Dec 7
MDW10:49 amChicago Midway
10h 31m
1 stop
SJU11:20 pmSan Juan Luis Munoz Marin Intl
Dec 11
SJU6:38 pmSan Juan Luis Munoz Marin Intl
7h 09m
1 stop
MDW11:47 pmChicago Midway
$272
Find similar

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

Our best Southwest deals on Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flight tickets
Southwest
Jan 31
MDW8:20 amChicago Midway
4h 35m
SJU2:55 pmSan Juan Luis Munoz Marin Intl
Feb 4
SJU5:40 amSan Juan Luis Munoz Marin Intl
8h 50m
2 stops
MDW12:30 pmChicago Midway
$248
Find similar
Southwest
Jan 21
MDW1:15 pmChicago Midway
7h 55m
1 stop
SJU11:10 pmSan Juan Luis Munoz Marin Intl
Jan 31
SJU5:30 amSan Juan Luis Munoz Marin Intl
11h 15m
2 stops
MDW2:45 pmChicago Midway
$252
Find similar
Southwest
Jan 18
MDW1:50 pmChicago Midway
8h 45m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 22
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
$267
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl 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 October 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/9

6:00 am-10:17 am

1 stop26h 17m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:00 am-2:47 pm

1 stop8h 47m

$214

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/11

10:18 am-2:50 am

1 stop14h 32m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:00 am-2:47 pm

1 stop8h 47m

$215

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/27

4:00 pm-9:27 am

2 stops39h 27m

San Juan Luis Munoz Marin Intl

Thu 12/4

10:42 am-9:53 pm

1 stop13h 11m

$221

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/27

6:15 pm-9:27 am

2 stops37h 12m

San Juan Luis Munoz Marin Intl

Thu 12/4

10:42 am-9:53 pm

1 stop13h 11m

$222

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/8

6:00 am-2:14 pm

1 stop6h 14m

San Juan Luis Munoz Marin Intl

Wed 12/10

1:57 pm-11:47 pm

1 stop11h 50m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 1/31

8:20 am-2:55 pm

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

Wed 2/4

5:40 am-12:30 pm

2 stops8h 50m

$248

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/21

1:15 pm-11:10 pm

1 stop7h 55m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-2:45 pm

2 stops11h 15m

$252

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/15

12:35 pm-12:35 am

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Mon 12/22

7:06 pm-1:59 pm

1 stop20h 53m

$258

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 12/7

10:49 am-11:20 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Thu 12/11

6:38 pm-11:47 pm

1 stop7h 09m

$272

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/9

10:18 am-11:49 pm

2 stops11h 31m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:00 am-2:47 pm

1 stop8h 47m

$274

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 San Juan from

How to get the cheapest flight ticket from Chicago Midway Airport to San Juan Luis Munoz Marin Intl 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 Chicago Midway Airport and San Juan Luis Munoz Marin Intl Airport?

What is the cheapest month to fly to San Juan Luis Munoz Marin Intl Airport?

If you aren’t able to travel to San Juan Luis Munoz Marin Intl Airport during the month of May, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $342.

What is the cheapest day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?

On average, the least expensive day to fly to San Juan Luis Munoz Marin Intl Airport from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $392. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $444.

What is the cheapest time of day to depart on your flight to San Juan Luis Munoz Marin Intl Airport?

The cheapest time of day to fly to San Juan Luis Munoz Marin Intl Airport is in the evening when flights can be purchased for as low as $314. Flights in the morning are often more expensive with an average ticket price of $449.

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

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

How far in advance should I book a flight to San Juan Luis Munoz Marin Intl Airport?

You are more likely to see cheaper flights to San Juan Luis Munoz Marin Intl Airport from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan Luis Munoz Marin Intl Airport for around $422 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan Luis Munoz Marin Intl Airport from Chicago Midway Airport for as low as $355 on momondo.

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

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

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

As of October 2025, prices for Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flights are approximately 52% more expensive when compared to flights at the same time last year.

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

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport (MDW to SJU) flight deals and tips

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

Best Price Found

$686

Fastest flight time

4h 35m

Direct flights

Mon and Sun
The best flight deal from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport found on momondo in the last 72 hours is $686
The fastest flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport takes 4h 35m
Direct flights go from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

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

    Chicago Midway and San Juan Luis Munoz Marin Intl are 2057.4 mi apart from one another. In terms of flight time, this usually takes a little over 4h 35m.

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

    Prices for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport are updated daily.

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

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

  • What documentation or ID do you need to fly to San Juan Luis Munoz Marin Intl Airport?

    The travel and health documents you'll need for your trip to San Juan Luis Munoz Marin Intl 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 San Juan Luis Munoz Marin Intl 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 Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

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

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

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $144Free CancellationRating
5.8
3,124 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,114 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
9,001 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
7,994 reviews
Search Delta flights
SouthwestPriceFrom $380Free CancellationRating
8.0
4,240 reviews
Search Southwest flights

Traveling to a place near San Juan?

Book flights to San Juan if you plan to visit one of these locations
Carolina
Fajardo
Dorado
Luquillo
Caguas
Humacao
Rio Grande
Bayamón

Why use momondo?

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

Finding the right flight to San Juan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San Juan quick and easy, saving you time and money.

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

All flight searches from Chicago to San Juan on momondo can be filtered to show those which offer flexible booking policies.

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

Once all potential Chicago to San Juan flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Chicago to San Juan 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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