Cheap flights from Chicago Midway Airport to San Juan from $124

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
8:37 pm - 2:13 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
27h 36m1 stop Orlando
Frontier Logo
5:01 am - 11:33 amSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
8h 32m1 stop Atlanta Hartsfield-Jackson
$245Frontier
Sun, Dec 6 - Wed, Dec 9
Frontier Logo
1:18 pm - 2:43 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
23h 25m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
3:48 pm - 11:46 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 58m1 stop Atlanta Hartsfield-Jackson
$246Frontier
Sat, Jan 23 - Tue, Jan 26
Frontier Logo
12:28 pm - 1:07 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 39m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
2:41 am - 11:46 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
23h 05m1 stop Atlanta Hartsfield-Jackson
$246Frontier
Tue, Dec 8 - Mon, Jan 11
Southwest Logo
1:55 pm - 11:15 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
7h 20m1 stop Orlando
Southwest Logo
6:10 am - 1:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 20m1 stop Baltimore/Washington
$266Southwest
Sat, Jan 30 - Fri, Feb 5
Southwest Logo
3:35 pm - 12:35 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
7h 00m1 stop Orlando
Southwest Logo
6:10 am - 1:00 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
8h 50m2 stops Baltimore/Washington Detroit Metropolitan Wayne County
$266Southwest
Mon, Feb 1 - Thu, Feb 4
Southwest Logo
1:25 pm - 10:55 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
7h 30m1 stop Baltimore/Washington
Southwest Logo
5:40 am - 2:50 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
11h 10m2 stops Orlando Miami
$266Southwest
Sat, Dec 5 - Wed, Dec 9
Delta Logo
6:00 am - 5:25 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
9h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:10 pm - 10:17 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
8h 07m1 stop Atlanta Hartsfield-Jackson
$290Delta
Mon, Jan 11 - Thu, Jan 14
Delta Logo
6:00 am - 5:25 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
9h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:35 pm - 11:55 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 20m1 stop Atlanta Hartsfield-Jackson
$290Delta
Mon, Jan 11 - Wed, Jan 20
Multiple Airlines Logo
8:42 pm - 11:18 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
24h 36m1 stop Orlando
Multiple Airlines Logo
10:21 pm - 2:37 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
18h 16m2 stops Orlando Knoxville McGhee Tyson
$730Multiple Airlines
Sun, Nov 22 - Sat, Nov 28
Multiple Airlines Logo
8:42 pm - 2:24 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
27h 42m1 stop Orlando
Multiple Airlines Logo
3:55 am - 2:37 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
12h 42m2 stops Orlando Knoxville McGhee Tyson
$732Multiple Airlines
Sat, Nov 21 - Sat, Nov 28

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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 6
MDW8:37 pmChicago Midway
27h 36m
1 stop
SJU2:13 amSan Juan Luis Munoz Marin Intl
Dec 9
SJU5:01 amSan Juan Luis Munoz Marin Intl
8h 32m
1 stop
MDW11:33 amChicago Midway
$245
Frontier
Jan 23
MDW1:18 pmChicago Midway
23h 25m
1 stop
SJU2:43 pmSan Juan Luis Munoz Marin Intl
Jan 26
SJU3:48 pmSan Juan Luis Munoz Marin Intl
9h 58m
1 stop
MDW11:46 pmChicago Midway
$246
Frontier
Jan 17
MDW1:18 pmChicago Midway
10h 18m
1 stop
SJU1:36 amSan Juan Luis Munoz Marin Intl
Jan 20
SJU3:48 pmSan Juan Luis Munoz Marin Intl
9h 58m
1 stop
MDW11:46 pmChicago Midway
$248

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 30
MDW1:55 pmChicago Midway
7h 20m
1 stop
SJU11:15 pmSan Juan Luis Munoz Marin Intl
Feb 3
SJU6:05 amSan Juan Luis Munoz Marin Intl
10h 45m
2 stops
MDW2:50 pmChicago Midway
$266
Southwest
Jan 17
MDW3:35 pmChicago Midway
7h 00m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 22
SJU5:35 amSan Juan Luis Munoz Marin Intl
9h 40m
2 stops
MDW1:15 pmChicago Midway
$286
Southwest
Nov 9
MDW8:40 pmChicago Midway
13h 00m
1 stop
SJU11:40 amSan Juan Luis Munoz Marin Intl
Nov 11
SJU6:10 amSan Juan Luis Munoz Marin Intl
10h 50m
1 stop
MDW3:00 pmChicago Midway
$306

momondo Fare Finder

 
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

Cheapest round-trip

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Sun 12/6

8:37 pm-2:13 am

1 stop27h 36m

San Juan Luis Munoz Marin Intl

Wed 12/9

5:01 am-11:33 am

1 stop8h 32m

$245

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Sat 1/23

1:18 pm-2:43 pm

1 stop23h 25m

San Juan Luis Munoz Marin Intl

Tue 1/26

3:48 pm-11:46 pm

1 stop9h 58m

$246

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Tue 12/8

12:28 pm-1:07 am

1 stop10h 39m

San Juan Luis Munoz Marin Intl

Mon 1/11

2:41 am-11:46 pm

1 stop23h 05m

$246

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Sat 1/30

1:55 pm-11:15 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Fri 2/5

6:10 am-1:30 pm

1 stop9h 20m

$266
Quickest round-trip

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Mon 2/1

3:35 pm-12:35 am

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Thu 2/4

6:10 am-1:00 pm

2 stops8h 50m

$266

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Sat 12/5

1:25 pm-10:55 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Wed 12/9

5:40 am-2:50 pm

2 stops11h 10m

$266

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Mon 1/11

6:00 am-5:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Thu 1/14

4:10 pm-10:17 pm

1 stop8h 07m

$290

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Mon 1/11

6:00 am-5:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Wed 1/20

6:35 pm-11:55 pm

1 stop7h 20m

$290

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Sun 11/22

8:42 pm-11:18 pm

1 stop24h 36m

San Juan Luis Munoz Marin Intl

Sat 11/28

10:21 pm-2:37 pm

2 stops18h 16m

$730

ChicagoSan Juan

MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl

MDWSJU

Chicago Midway

Sat 11/21

8:42 pm-2:24 am

1 stop27h 42m

San Juan Luis Munoz Marin Intl

Sat 11/28

3:55 am-2:37 pm

2 stops12h 42m

$732

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?

Prices are currently low for flights on this route.

Typical prices usually range from $401 to $789.
The lowest price recently found on this route was $245.

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 February, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $264.

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 $417. 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 $504.

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 $367. Flights in the morning are often more expensive with an average ticket price of $522.

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 from Chicago Midway Airport 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 $414 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 $319 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport 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 November 2026, prices for Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flights are approximately 38% 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

$124

Fastest flight time

4h 40m

Direct flights

Sun
The best one-way flight to San Juan Luis Munoz Marin Intl Airport from Chicago Midway Airport in the past 72 hours is $124. The best round-trip flight deal from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport found on momondo in the last 72 hours is $245.
The fastest flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport takes 4h 40m
Direct flights go from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport on Sunday. There are no airlines offering direct flights.

Frequently asked questions about flying from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

  • 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 40m.

  • 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 $91Free CancellationRating
5.5
2,512 reviews
Search Frontier flights
DeltaPriceFrom $132Free CancellationRating
7.8
8,697 reviews
Search Delta flights
SouthwestPriceFrom $276Free CancellationRating
8.0
4,215 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
Rio Grande
Luquillo
Humacao
Caguas
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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1 adult
Thu 12/3
Thu 12/10

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