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Cheap flights from Chicago Midway Airport to San Juan from $137

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 9/14. 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
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.
Southwest Logo
3:15 pm - 11:10 pm
MDW
-
SJU
6h 55m
1 stop
Southwest Logo
2:35 pm - 10:25 pm
SJU
-
MDW
8h 50m
2 stops
$274Southwest
Fri, Sep 11 - Fri, Sep 18
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
Southwest Logo
2:25 pm - 8:50 pm
SJU
-
MDW
7h 25m
1 stop
$274Southwest
Wed, Sep 2 - Wed, Sep 16
Southwest Logo
12:20 pm - 9:05 pm
MDW
-
SJU
7h 45m
1 stop
Southwest Logo
2:25 pm - 8:45 pm
SJU
-
MDW
7h 20m
1 stop
$274Southwest
Tue, Aug 25 - Tue, Sep 1
Delta Logo
12:46 pm - 10:29 pm
MDW
-
SJU
8h 43m
1 stop
Delta Logo
7:00 am - 3:44 pm
SJU
-
MDW
9h 44m
1 stop
$316Delta
Tue, Aug 25 - Tue, Sep 1
Delta Logo
12:46 pm - 10:29 pm
MDW
-
SJU
8h 43m
1 stop
Delta Logo
7:00 am - 3:44 pm
SJU
-
MDW
9h 44m
1 stop
$316Delta
Wed, Aug 26 - Tue, Sep 1
Delta Logo
11:35 am - 10:19 pm
MDW
-
SJU
9h 44m
1 stop
Delta Logo
2:59 pm - 10:45 pm
SJU
-
MDW
8h 46m
1 stop
$331Delta
Fri, Sep 11 - Thu, Sep 17
Frontier Logo
6:25 am - 3:19 pm
MDW
-
SJU
7h 54m
1 stop
Frontier Logo
6:30 am - 5:51 pm
SJU
-
MDW
12h 21m
1 stop
$356Frontier
Wed, Sep 23 - Wed, Sep 30
Frontier Logo
6:25 am - 3:19 pm
MDW
-
SJU
7h 54m
1 stop
Frontier Logo
6:30 am - 5:51 pm
SJU
-
MDW
12h 21m
1 stop
$366Frontier
Wed, Sep 23 - Wed, Sep 30
Multiple Airlines Logo
4:45 pm - 5:02 am
MDW
-
SJU
11h 17m
1 stop
Multiple Airlines Logo
6:00 am - 2:59 pm
SJU
-
MDW
33h 59m
2 stops
$427Multiple Airlines
Wed, Aug 12 - Sun, Aug 16
Multiple Airlines Logo
9:29 am - 2:33 am
MDW
-
SJU
15h 04m
2 stops
Multiple Airlines Logo
7:04 pm - 12:59 pm
SJU
-
MDW
19h 55m
1 stop
$755Multiple Airlines
Mon, Nov 23 - Mon, Nov 30

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Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Sep 9
MDW6:25 amChicago Midway
7h 54m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
Sep 16
SJU6:30 amSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
MDW5:51 pmChicago Midway
$368
Frontier
Aug 25
MDW6:05 amChicago Midway
7h 11m
1 stop
SJU2:16 pmSan Juan Luis Munoz Marin Intl
Aug 30
SJU3:48 pmSan Juan Luis Munoz Marin Intl
7h 59m
1 stop
MDW10:47 pmChicago Midway
$378
Frontier
Sep 18
MDW6:25 amChicago Midway
7h 54m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
Sep 23
SJU6:30 amSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
MDW5:51 pmChicago Midway
$402

Southwest flights from Chicago Midway Airport to San Juan

Our best Southwest deals on Chicago Midway Airport to San Juan flight tickets
Southwest
Aug 26
MDW12:45 pmChicago Midway
8h 15m
2 stops
SJU10:00 pmSan Juan Luis Munoz Marin Intl
Sep 2
SJU6:00 amSan Juan Luis Munoz Marin Intl
8h 30m
2 stops
MDW1:30 pmChicago Midway
$274
Southwest
Aug 27
MDW11:15 amChicago Midway
9h 55m
1 stop
SJU10:10 pmSan Juan Luis Munoz Marin Intl
Aug 29
SJU5:55 amSan Juan Luis Munoz Marin Intl
11h 45m
1 stop
MDW4:40 pmChicago Midway
$275
Southwest
Oct 23
MDW4:15 pmChicago Midway
8h 05m
2 stops
SJU1:20 amSan Juan Luis Munoz Marin Intl
Oct 30
SJU5:30 amSan Juan Luis Munoz Marin Intl
8h 55m
2 stops
MDW1:25 pmChicago Midway
$276

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San Juan 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 July 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Juan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/11

3:15 pm-11:10 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Fri 9/18

2:35 pm-10:25 pm

2 stops8h 50m

$274

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/2

12:45 pm-10:00 pm

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Wed 9/16

2:25 pm-8:50 pm

1 stop7h 25m

$274
Quickest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/25

12:20 pm-9:05 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 9/1

2:25 pm-8:45 pm

1 stop7h 20m

$274

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/25

12:46 pm-10:29 pm

1 stop8h 43m

San Juan Luis Munoz Marin Intl

Tue 9/1

7:00 am-3:44 pm

1 stop9h 44m

$316

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/26

12:46 pm-10:29 pm

1 stop8h 43m

San Juan Luis Munoz Marin Intl

Tue 9/1

7:00 am-3:44 pm

1 stop9h 44m

$316

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/11

11:35 am-10:19 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Thu 9/17

2:59 pm-10:45 pm

1 stop8h 46m

$331

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/23

6:25 am-3:19 pm

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Wed 9/30

6:30 am-5:51 pm

1 stop12h 21m

$356

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/23

6:25 am-3:19 pm

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Wed 9/30

6:30 am-5:51 pm

1 stop12h 21m

$366

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/12

4:45 pm-5:02 am

1 stop11h 17m

San Juan Luis Munoz Marin Intl

Sun 8/16

6:00 am-2:59 pm

2 stops33h 59m

$427

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 11/23

9:29 am-2:33 am

2 stops15h 04m

San Juan Luis Munoz Marin Intl

Mon 11/30

7:04 pm-12:59 pm

1 stop19h 55m

$755

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

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?

Prices are currently typical for flights on this route.

Typical prices usually range from $256 to $551.
The lowest price recently found on this route was $274.

What is the cheapest month to fly to San Juan?

If you’re not able to fly to San Juan in February, then January is your next best option. Flight prices from Chicago Midway Airport to San Juan during January average around $254.

What is the cheapest day to depart on your flight to San Juan?

The cheapest day to depart from Chicago Midway Airport to San Juan is on a Tuesday when prices can be found for as low as $429. The most expensive day to fly to San Juan is Friday, with ticket prices averaging around $516.

What is the cheapest time of day to depart on your flight to San Juan?

The cheapest time of day to fly to San Juan is in the evening when flights can be purchased for as low as $365. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $525 on average. Flights to San Juan from Chicago Midway Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago Midway to San Juan flight route?

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

How far in advance should I book a flight from Chicago Midway Airport to San Juan?

You are more likely to see cheaper flights to San Juan from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $399 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan from Chicago Midway Airport for as low as $326 on momondo.

What cabin class options are available on Chicago Midway Airport to San Juan flights?

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

Cheap Chicago Midway Airport to San Juan flight deals and tips

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

Fastest flight time

4h 40m

Direct flights

Mon and Sun

Airports in San Juan

2 airports
The fastest flight from Chicago Midway Airport to San Juan takes 4h 40m
Direct flights go from Chicago Midway Airport to San Juan on Monday and Sunday. There are no airlines offering direct flights.
There are 2 airports in San Juan. From Chicago Midway Airport there are direct flights to San Juan Luis Munoz Marin Intl (SJU).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to San Juan

  • How far is Chicago Midway to San Juan by plane?

    The straight-line distance from Chicago Midway to San Juan is 2052.0 mi. 4h 40m is a normal flight duration for this route.

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

    Prices for flights from Chicago Midway Airport to San Juan are refreshed on a daily basis.

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

  • How old do you have to be to fly from Chicago Midway Airport to San Juan?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to San Juan.

  • What documentation or ID do you need to fly to San Juan?

    The necessary travel and health documents for your San Juan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago Midway Airport to San Juan

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Juan with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $91Free CancellationRating
5.6
2,753 reviews
Search Frontier flights
DeltaPriceFrom $132Free CancellationRating
7.8
8,483 reviews
Search Delta flights
SouthwestPriceFrom $346Free CancellationRating
8.0
4,228 reviews
Search Southwest flights

Why use momondo?

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

It is quick and easy to find Chicago to San Juan flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to San Juan that suits you.

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

Yes. momondo enables you to select and highlight flights to San Juan from Chicago with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to San Juan.

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

Price alerts on flights to San Juan from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your San Juan trip

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Find better results for your trip to Puerto Rico

Fly into one of these airports located in San Juan

Airports listed have a maximum distance of 7.1 mi from San Juan
San Juan Isla Grande Airport
San Juan Luis Munoz Marin Intl Airport