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Cheap flights from Chicago Midway Airport to San Juan from $114

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 11/17. 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

Frontier Logo
6:30 am - 12:57 amMDW-SJU
16h 27m1 stop
Frontier Logo
3:59 pm - 9:32 pmSJU-MDW
7h 33m1 stop
$208Frontier
Find Deal
vie., dic. 5 - mié., dic. 10
Frontier Logo
8:05 am - 12:29 amMDW-SJU
15h 24m2 stops
Frontier Logo
6:22 am - 11:20 pmSJU-MDW
17h 58m2 stops
$209Frontier
Find Deal
mar., oct. 7 - sáb., oct. 11
Frontier Logo
5:15 pm - 9:56 amMDW-SJU
15h 41m2 stops
Frontier Logo
1:26 pm - 9:47 amSJU-MDW
21h 21m2 stops
$224Frontier
Find Deal
vie., oct. 3 - mié., oct. 8
Southwest Logo
4:35 pm - 11:50 pmMDW-SJU
6h 15m1 stop
Southwest Logo
2:45 pm - 10:45 pmSJU-MDW
9h 00m1 stop
$227Southwest
Find Deal
vie., oct. 17 - mar., oct. 21
Frontier Logo
8:05 am - 12:29 amMDW-SJU
15h 24m2 stops
Frontier Logo
4:22 pm - 10:47 pmSJU-MDW
7h 25m1 stop
$228Frontier
Find Deal
mar., oct. 7 - sáb., oct. 11
Frontier Logo
1:37 pm - 2:19 pmMDW-SJU
23h 42m1 stop
Frontier Logo
4:24 pm - 11:38 amSJU-MDW
21h 14m1 stop
$233Frontier
Find Deal
jue., oct. 30 - lun., nov. 3
Frontier Logo
9:15 am - 12:29 amMDW-SJU
14h 14m1 stop
Frontier Logo
2:03 am - 2:33 pmSJU-MDW
14h 30m1 stop
$240Frontier
Find Deal
jue., oct. 30 - dom., nov. 2
Multiple Airlines Logo
8:25 am - 12:29 amMDW-SJU
15h 04m1 stop
Multiple Airlines Logo
4:04 pm - 12:37 pmSJU-MDW
21h 33m1 stop
$260Multiple Airlines
Find Deal
jue., oct. 23 - jue., oct. 30
Multiple Airlines Logo
1:37 pm - 4:23 pmMDW-SJU
24h 46m2 stops
Multiple Airlines Logo
4:24 pm - 11:38 amSJU-MDW
21h 14m1 stop
$264Multiple Airlines
Find Deal
vie., nov. 14 - lun., nov. 17
Delta Logo
10:35 am - 11:49 pmMDW-SJU
11h 14m1 stop
Delta Logo
7:30 am - 4:25 pmSJU-MDW
10h 55m1 stop
$267Delta
Find Deal
lun., ene. 26 - mié., feb. 4

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

Our best Frontier deals on Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flight tickets
Frontier
Dec 5
MDW6:30 amChicago Midway
16h 27m
1 stop
SJU12:57 amSan Juan Luis Munoz Marin Intl
Dec 10
SJU3:59 pmSan Juan Luis Munoz Marin Intl
7h 33m
1 stop
MDW9:32 pmChicago Midway
$208
Find similar
Frontier
Oct 7
MDW8:05 amChicago Midway
15h 24m
2 stops
SJU12:29 amSan Juan Luis Munoz Marin Intl
Oct 11
SJU6:22 amSan Juan Luis Munoz Marin Intl
17h 58m
2 stops
MDW11:20 pmChicago Midway
$209
Find similar
Frontier
Oct 3
MDW5:15 pmChicago Midway
15h 41m
2 stops
SJU9:56 amSan Juan Luis Munoz Marin Intl
Oct 8
SJU1:26 pmSan Juan Luis Munoz Marin Intl
21h 21m
2 stops
MDW9:47 amChicago Midway
$224
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
Oct 17
MDW4:35 pmChicago Midway
6h 15m
1 stop
SJU11:50 pmSan Juan Luis Munoz Marin Intl
Oct 21
SJU2:45 pmSan Juan Luis Munoz Marin Intl
9h 00m
1 stop
MDW10:45 pmChicago Midway
$227
Find similar
Southwest
Oct 1
MDW7:40 amChicago Midway
11h 05m
1 stop
SJU7:45 pmSan Juan Luis Munoz Marin Intl
Oct 8
SJU2:45 pmSan Juan Luis Munoz Marin Intl
9h 00m
1 stop
MDW10:45 pmChicago Midway
$356
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 septiembre 17, 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

vie. 12/5

6:30 am-12:57 am

1 stop16h 27m

San Juan Luis Munoz Marin Intl

mié. 12/10

3:59 pm-9:32 pm

1 stop7h 33m

$208

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 10/7

8:05 am-12:29 am

2 stops15h 24m

San Juan Luis Munoz Marin Intl

sáb. 10/11

6:22 am-11:20 pm

2 stops17h 58m

$209

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 10/3

5:15 pm-9:56 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

mié. 10/8

1:26 pm-9:47 am

2 stops21h 21m

$224

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 10/17

4:35 pm-11:50 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

mar. 10/21

2:45 pm-10:45 pm

1 stop9h 00m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 10/7

8:05 am-12:29 am

2 stops15h 24m

San Juan Luis Munoz Marin Intl

sáb. 10/11

4:22 pm-10:47 pm

1 stop7h 25m

$228

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

jue. 10/30

1:37 pm-2:19 pm

1 stop23h 42m

San Juan Luis Munoz Marin Intl

lun. 11/3

4:24 pm-11:38 am

1 stop21h 14m

$233

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

jue. 10/30

9:15 am-12:29 am

1 stop14h 14m

San Juan Luis Munoz Marin Intl

dom. 11/2

2:03 am-2:33 pm

1 stop14h 30m

$240

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

jue. 10/23

8:25 am-12:29 am

1 stop15h 04m

San Juan Luis Munoz Marin Intl

jue. 10/30

4:04 pm-12:37 pm

1 stop21h 33m

$260

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 11/14

1:37 pm-4:23 pm

2 stops24h 46m

San Juan Luis Munoz Marin Intl

lun. 11/17

4:24 pm-11:38 am

1 stop21h 14m

$264

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

lun. 1/26

10:35 am-11:49 pm

1 stop11h 14m

San Juan Luis Munoz Marin Intl

mié. 2/4

7:30 am-4:25 pm

1 stop10h 55m

$267

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 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 November, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $328.

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 Monday. momondo users have found tickets for Monday departures for as low as $396. 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 $447.

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 $305. Flights in the morning are often more expensive with an average ticket price of $447.

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 $326 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 September 2025, prices for Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flights are approximately 48% 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

Fastest flight time

4h 35m

Direct flights

Mon and Sun
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 6h 15m.

  • 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 $133Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
7,961 reviews
Search Delta flights
SouthwestPriceFrom $364Free CancellationRating
8.0
4,242 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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