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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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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.
Delta Logo
10:55 am - 8:45 pm
MDW
-
SJU
8h 50m
1 stop
Delta Logo
2:42 pm - 10:15 pm
SJU
-
MDW
8h 33m
1 stop
$256Delta
Sat, Jul 18 - Tue, Jul 21
Delta Logo
11:05 am - 8:45 pm
MDW
-
SJU
8h 40m
1 stop
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
$266Delta
Thu, Jul 30 - Wed, Aug 5
Southwest Logo
1:25 pm - 11:45 pm
MDW
-
SJU
9h 20m
1 stop
Southwest Logo
6:30 am - 3:35 pm
SJU
-
MDW
10h 05m
1 stop
$296Southwest
Tue, Jul 14 - Thu, Aug 20
Southwest Logo
6:05 am - 6:15 pm
MDW
-
SJU
11h 10m
1 stop
Southwest Logo
5:05 am - 11:00 am
SJU
-
MDW
6h 55m
1 stop
$306Southwest
Sat, Aug 8 - Sat, Aug 15
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
Southwest Logo
8:20 am - 2:45 pm
SJU
-
MDW
7h 25m
1 stop
$316Southwest
Tue, Aug 4 - Tue, Aug 11
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
$321Frontier
Thu, Jul 30 - Thu, Aug 6
Southwest Logo
6:05 am - 6:15 pm
MDW
-
SJU
11h 10m
1 stop
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$326Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
4:40 pm - 12:15 am
MDW
-
SJU
6h 35m
1 stop
Southwest Logo
5:00 am - 12:20 pm
SJU
-
MDW
8h 20m
2 stops
$331Southwest
Tue, Jul 21 - Mon, Aug 31
Delta Logo
12:41 pm - 10:29 pm
MDW
-
SJU
8h 48m
1 stop
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
$336Delta
Thu, Jul 30 - Wed, Aug 5
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
$341Frontier
Tue, Aug 4 - Sun, Aug 9

Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Aug 10
MDW6:00 amChicago Midway
7h 16m
1 stop
SJU2:16 pmSan Juan Luis Munoz Marin Intl
Aug 17
SJU6:32 amSan Juan Luis Munoz Marin Intl
8h 55m
1 stop
MDW2:27 pmChicago Midway
$258
Frontier
Aug 20
MDW6:00 amChicago Midway
7h 15m
1 stop
SJU2:15 pmSan Juan Luis Munoz Marin Intl
Aug 22
SJU6:25 amSan Juan Luis Munoz Marin Intl
8h 42m
1 stop
MDW2:07 pmChicago Midway
$303
Frontier
Aug 22
MDW6:00 amChicago Midway
7h 15m
1 stop
SJU2:15 pmSan Juan Luis Munoz Marin Intl
Aug 29
SJU6:25 amSan Juan Luis Munoz Marin Intl
8h 42m
1 stop
MDW2:07 pmChicago Midway
$321

Delta flights from Chicago Midway Airport to San Juan

Our best Delta deals on Chicago Midway Airport to San Juan 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
Aug 13
MDW10:54 amChicago Midway
10h 35m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Aug 20
SJU2:59 pmSan Juan Luis Munoz Marin Intl
8h 37m
1 stop
MDW10:36 pmChicago Midway
$236
Delta
Aug 20
MDW10:54 amChicago Midway
10h 35m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Aug 25
SJU2:59 pmSan Juan Luis Munoz Marin Intl
8h 37m
1 stop
MDW10:36 pmChicago Midway
$266

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 May 11, 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

Sat 7/18

10:55 am-8:45 pm

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Tue 7/21

2:42 pm-10:15 pm

1 stop8h 33m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 7/30

11:05 am-8:45 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Wed 8/5

2:59 pm-10:36 pm

1 stop8h 37m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 7/14

1:25 pm-11:45 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Thu 8/20

6:30 am-3:35 pm

1 stop10h 05m

$296

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/8

6:05 am-6:15 pm

1 stop11h 10m

San Juan Luis Munoz Marin Intl

Sat 8/15

5:05 am-11:00 am

1 stop6h 55m

$306

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/4

12:45 pm-10:00 pm

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Tue 8/11

8:20 am-2:45 pm

1 stop7h 25m

$316

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 7/30

6:00 am-2:16 pm

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Thu 8/6

6:32 am-2:27 pm

1 stop8h 55m

$321

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/8

6:05 am-6:15 pm

1 stop11h 10m

San Juan Luis Munoz Marin Intl

Tue 8/11

5:15 am-12:05 pm

2 stops7h 50m

$326
Quickest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 7/21

4:40 pm-12:15 am

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Mon 8/31

5:00 am-12:20 pm

2 stops8h 20m

$331

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 7/30

12:41 pm-10:29 pm

1 stop8h 48m

San Juan Luis Munoz Marin Intl

Wed 8/5

2:59 pm-10:36 pm

1 stop8h 37m

$336

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/4

6:00 am-2:16 pm

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Sun 8/9

6:32 am-2:27 pm

1 stop8h 55m

$341

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?

What is the cheapest month to fly to San Juan?

If you’re not able to fly to San Juan in April, then January is your next best option. Flight prices from Chicago Midway Airport to San Juan during January average around $133.

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 $382. The most expensive day to fly to San Juan is Friday, with ticket prices averaging around $465.

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 $376. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $486 on average. Flights to San Juan from Chicago Midway Airport at noon 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 $386 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 $274 on momondo.

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 35m

Direct flights

Mon and Sun

Airports in San Juan

2 airports
The fastest flight from Chicago Midway Airport to San Juan takes 4h 35m
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 35m 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
DeltaPriceFrom $132Free CancellationRating
7.9
8,456 reviews
Search Delta flights
FrontierPriceFrom $138Free CancellationRating
5.6
2,955 reviews
Search Frontier flights
SouthwestPriceFrom $352Free CancellationRating
7.9
4,301 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