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Cheap flights from Chicago Midway Airport to San Juan from $113

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 7/3. 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 Chicago Midway Airport to San Juan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:54 am - 10:29 pm
MDW
-
SJU
10h 35m
1 stop
Delta Logo
2:40 pm - 9:46 pm
SJU
-
MDW
8h 06m
1 stop
$226Delta
Wed, Aug 19 - Wed, Sep 2
Southwest Logo
11:00 am - 6:15 pm
MDW
-
SJU
6h 15m
1 stop
Southwest Logo
2:25 pm - 8:45 pm
SJU
-
MDW
7h 20m
1 stop
$236Southwest
Sat, Aug 22 - Wed, Aug 26
Southwest Logo
7:15 am - 4:55 pm
MDW
-
SJU
8h 40m
1 stop
Southwest Logo
10:00 am - 6:00 pm
SJU
-
MDW
9h 00m
1 stop
$246Southwest
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
12:20 pm - 9:05 pm
MDW
-
SJU
7h 45m
1 stop
Southwest Logo
10:25 am - 7:40 pm
SJU
-
MDW
10h 15m
1 stop
$256Southwest
Tue, Aug 18 - Sat, Aug 22
Frontier Logo
6:00 am - 2:16 pm
MDW
-
SJU
7h 16m
1 stop
Frontier Logo
6:32 am - 2:27 pm
SJU
-
MDW
8h 55m
1 stop
$258Frontier
Mon, Aug 10 - Mon, Aug 17
Delta Logo
1:05 pm - 10:23 pm
MDW
-
SJU
8h 18m
1 stop
Delta Logo
2:40 pm - 9:46 pm
SJU
-
MDW
8h 06m
1 stop
$266Delta
Fri, Sep 4 - Tue, Sep 8
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
$276Southwest
Tue, Sep 1 - Mon, Sep 7
Delta Logo
10:35 am - 10:23 pm
MDW
-
SJU
10h 48m
1 stop
Delta Logo
2:40 pm - 9:46 pm
SJU
-
MDW
8h 06m
1 stop
$286Delta
Thu, Sep 3 - Tue, Sep 8
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
Southwest Logo
6:00 am - 1:30 pm
SJU
-
MDW
8h 30m
2 stops
$296Southwest
Tue, Sep 1 - Wed, Sep 9
Frontier Logo
6:00 am - 2:16 pm
MDW
-
SJU
7h 16m
1 stop
Frontier Logo
6:32 am - 2:27 pm
SJU
-
MDW
8h 55m
1 stop
$303Frontier
Mon, Aug 10 - Sat, Aug 15

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
Aug 22
MDW7:50 amChicago Midway
7h 50m
2 stops
SJU4:40 pmSan Juan Luis Munoz Marin Intl
Aug 31
SJU6:30 amSan Juan Luis Munoz Marin Intl
8h 15m
2 stops
MDW1:45 pmChicago Midway
$236
Southwest
Aug 20
MDW1:00 pmChicago Midway
8h 50m
2 stops
SJU10:50 pmSan Juan Luis Munoz Marin Intl
Aug 24
SJU5:00 amSan Juan Luis Munoz Marin Intl
8h 20m
2 stops
MDW12:20 pmChicago Midway
$246
Southwest
Aug 17
MDW11:15 amChicago Midway
10h 00m
1 stop
SJU10:15 pmSan Juan Luis Munoz Marin Intl
Aug 22
SJU10:25 amSan Juan Luis Munoz Marin Intl
10h 15m
1 stop
MDW7:40 pmChicago Midway
$256

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
Aug 19
MDW10:54 amChicago Midway
10h 35m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Sep 2
SJU2:40 pmSan Juan Luis Munoz Marin Intl
8h 06m
1 stop
MDW9:46 pmChicago Midway
$226
Delta
Sep 4
MDW1:05 pmChicago Midway
8h 18m
1 stop
SJU10:23 pmSan Juan Luis Munoz Marin Intl
Sep 8
SJU2:40 pmSan Juan Luis Munoz Marin Intl
8h 06m
1 stop
MDW9:46 pmChicago Midway
$266
Delta
Sep 3
MDW10:35 amChicago Midway
10h 48m
1 stop
SJU10:23 pmSan Juan Luis Munoz Marin Intl
Sep 8
SJU2:40 pmSan Juan Luis Munoz Marin Intl
8h 06m
1 stop
MDW9:46 pmChicago Midway
$286

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 May 12, 2026.
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 - SJU

MDWSJU

Chicago Midway

Wed 8/19

10:54 am-10:29 pm

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Wed 9/2

2:40 pm-9:46 pm

1 stop8h 06m

$226
Quickest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/22

11:00 am-6:15 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Wed 8/26

2:25 pm-8:45 pm

1 stop7h 20m

$236

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/20

7:15 am-4:55 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Mon 8/24

10:00 am-6:00 pm

1 stop9h 00m

$246

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/18

12:20 pm-9:05 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Sat 8/22

10:25 am-7:40 pm

1 stop10h 15m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 8/10

6:00 am-2:16 pm

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Mon 8/17

6:32 am-2:27 pm

1 stop8h 55m

$258

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/4

1:05 pm-10:23 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

Tue 9/8

2:40 pm-9:46 pm

1 stop8h 06m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 9/1

12:45 pm-10:00 pm

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Mon 9/7

6:00 am-2:30 pm

2 stops9h 30m

$276

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 9/3

10:35 am-10:23 pm

1 stop10h 48m

San Juan Luis Munoz Marin Intl

Tue 9/8

2:40 pm-9:46 pm

1 stop8h 06m

$286

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 9/1

12:45 pm-10:00 pm

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Wed 9/9

6:00 am-1:30 pm

2 stops8h 30m

$296

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 8/10

6:00 am-2:16 pm

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Sat 8/15

6:32 am-2:27 pm

1 stop8h 55m

$303

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 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 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 $382. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday 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 $465.

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 $374. Flights at noon are often more expensive with an average ticket price of $484.

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 $386 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 $274 on momondo.

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

As of May 2026, prices for Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flights are approximately 6% 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 40m

Direct flights

Mon and Sun
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 Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

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
DeltaPriceFrom $132Free CancellationRating
7.9
8,445 reviews
Search Delta flights
FrontierPriceFrom $138Free CancellationRating
5.6
2,951 reviews
Search Frontier flights
SouthwestPriceFrom $352Free CancellationRating
8.0
4,295 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
Rio Grande
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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