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Cheap flights from Chicago Midway Airport to San Juan from $94

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 3/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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
6:10 am - 3:06 pm
MDW
-
SJU
6h 56m
1 stop
Frontier Logo
6:30 am - 6:13 pm
SJU
-
MDW
12h 43m
1 stop
$188Frontier
Tue, Feb 24 - Tue, Mar 10
Multiple Airlines Logo
6:00 am - 5:58 pm
MDW
-
SJU
10h 58m
1 stop
Multiple Airlines Logo
10:52 am - 1:41 pm
SJU
-
MDW
27h 49m
1 stop
$189Multiple Airlines
Mon, Mar 9 - Wed, Mar 11
Frontier Logo
6:00 am - 3:02 pm
MDW
-
SJU
7h 02m
1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m
1 stop
$192Frontier
Mon, Feb 23 - Wed, Mar 4
Frontier Logo
6:00 am - 3:02 pm
MDW
-
SJU
7h 02m
1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m
1 stop
$193Frontier
Mon, Feb 23 - Wed, Mar 4
Frontier Logo
6:10 am - 3:06 pm
MDW
-
SJU
6h 56m
1 stop
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
$197Frontier
Tue, Feb 24 - Thu, Mar 5
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m
1 stop
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
$202Frontier
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
6:10 am - 3:06 pm
MDW
-
SJU
6h 56m
1 stop
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m
1 stop
$209Frontier
Tue, Feb 24 - Fri, Feb 27
Frontier Logo
6:00 am - 3:02 pm
MDW
-
SJU
7h 02m
1 stop
Frontier Logo
4:11 pm - 10:29 pm
SJU
-
MDW
8h 18m
1 stop
$211Frontier
Mon, Feb 23 - Thu, Mar 5
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
Frontier Logo
3:08 am - 4:13 pm
SJU
-
MDW
14h 05m
1 stop
$213Frontier
Thu, Apr 23 - Fri, May 1
Multiple Airlines Logo
9:15 am - 11:37 am
MDW
-
SJU
24h 22m
1 stop
Multiple Airlines Logo
6:50 pm - 1:41 pm
SJU
-
MDW
20h 51m
1 stop
$215Multiple Airlines
Sat, Feb 28 - Fri, Mar 6

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
Feb 24
MDW6:10 amChicago Midway
6h 56m
1 stop
SJU3:06 pmSan Juan Luis Munoz Marin Intl
Mar 10
SJU6:30 amSan Juan Luis Munoz Marin Intl
12h 43m
1 stop
MDW6:13 pmChicago Midway
$188
Frontier
Feb 23
MDW6:00 amChicago Midway
7h 02m
1 stop
SJU3:02 pmSan Juan Luis Munoz Marin Intl
Mar 4
SJU5:25 pmSan Juan Luis Munoz Marin Intl
23h 01m
1 stop
MDW2:26 pmChicago Midway
$192
Frontier
Feb 23
MDW6:00 amChicago Midway
7h 02m
1 stop
SJU3:02 pmSan Juan Luis Munoz Marin Intl
Mar 4
SJU5:25 pmSan Juan Luis Munoz Marin Intl
23h 01m
1 stop
MDW2:26 pmChicago Midway
$193

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 February 2, 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

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/24

6:10 am-3:06 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Tue 3/10

6:30 am-6:13 pm

1 stop12h 43m

$188

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/9

6:00 am-5:58 pm

1 stop10h 58m

San Juan Luis Munoz Marin Intl

Wed 3/11

10:52 am-1:41 pm

1 stop27h 49m

$189

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/23

6:00 am-3:02 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:25 pm-2:26 pm

1 stop23h 01m

$192

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/23

6:00 am-3:02 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:25 pm-2:26 pm

1 stop23h 01m

$193

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/24

6:10 am-3:06 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

$197

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/23

9:22 pm-9:54 am

1 stop10h 32m

San Juan Luis Munoz Marin Intl

Thu 2/26

6:00 am-1:56 pm

1 stop9h 56m

$202

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 2/24

6:10 am-3:06 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Fri 2/27

3:53 am-2:55 pm

1 stop13h 02m

$209

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/23

6:00 am-3:02 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-10:29 pm

1 stop8h 18m

$211

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 4/23

9:14 am-2:01 am

1 stop15h 47m

San Juan Luis Munoz Marin Intl

Fri 5/1

3:08 am-4:13 pm

1 stop14h 05m

$213

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/28

9:15 am-11:37 am

1 stop24h 22m

San Juan Luis Munoz Marin Intl

Fri 3/6

6:50 pm-1:41 pm

1 stop20h 51m

$215

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 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 February is also cheap. Prices for this month can be found on momondo for an average of $331.

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 $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 $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 $329. Flights at noon are often more expensive with an average ticket price of $466.

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 $402 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 $286 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 February 2026, prices for Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport flights are approximately 63% 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 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
5.7
3,050 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,393 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
7.9
8,128 reviews
Search Delta flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,273 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

    Southwest is one of the most popular airlines flying from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport, operating 1 flight/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport starts from $379 round-trip, up to an average price of $492. Our users have rated Southwest at 8.0/10.

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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