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Cheap flights from Chicago Midway Airport to San Juan from $119

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 9/27. 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

Frontier Logo
2:15 pm - 2:50 amMDW-SJU
10h 35m1 stop
Frontier Logo
3:00 pm - 11:25 pmSJU-MDW
10h 25m1 stop
$229Frontier
Find Deal
Fri, Dec 12 - Tue, Dec 16
Frontier Logo
9:15 am - 12:41 amMDW-SJU
13h 26m1 stop
Frontier Logo
10:39 pm - 2:33 pmSJU-MDW
17h 54m2 stops
$241Frontier
Find Deal
Thu, Nov 13 - Sun, Nov 16
Frontier Logo
6:20 am - 3:19 pmMDW-SJU
6h 59m1 stop
Frontier Logo
10:39 pm - 10:26 amSJU-MDW
13h 47m1 stop
$245Frontier
Find Deal
Mon, Nov 10 - Fri, Nov 14
Frontier Logo
9:15 am - 12:41 amMDW-SJU
13h 26m1 stop
Frontier Logo
10:39 pm - 5:15 pmSJU-MDW
20h 36m2 stops
$247Frontier
Find Deal
Thu, Nov 6 - Sun, Nov 9
Frontier Logo
9:15 am - 12:41 amMDW-SJU
13h 26m1 stop
Frontier Logo
7:30 am - 12:30 amSJU-MDW
19h 00m1 stop
$248Frontier
Find Deal
Thu, Nov 13 - Sun, Nov 16
Frontier Logo
10:49 am - 2:30 amMDW-SJU
14h 41m1 stop
Frontier Logo
9:06 pm - 11:17 amSJU-MDW
15h 11m1 stop
$256Frontier
Find Deal
Thu, Oct 23 - Sun, Oct 26
Frontier Logo
8:35 am - 9:42 amMDW-SJU
24h 07m1 stop
Frontier Logo
3:40 am - 10:21 amSJU-MDW
7h 41m1 stop
$258Frontier
Find Deal
Sat, Oct 11 - Fri, Oct 17
Frontier Logo
5:15 pm - 9:56 amMDW-SJU
15h 41m2 stops
Frontier Logo
7:50 pm - 4:00 pmSJU-MDW
21h 10m2 stops
$263Frontier
Find Deal
Mon, Sep 15 - Sun, Sep 28
Logo
1:49 pm - 12:43 amMDW-SJU
9h 54m1 stop
Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
$308
Find Deal
Thu, Oct 2 - Sat, Oct 4
Logo
10:51 am - 8:56 pmMDW-SJU
9h 05m1 stop
Logo
9:26 pm - 3:58 pmSJU-MDW
19h 32m2 stops
$309
Find Deal
Sat, Sep 20 - Mon, Sep 22

Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Dec 12
MDW2:15 pmChicago Midway
10h 35m
1 stop
SJU2:50 amSan Juan Luis Munoz Marin Intl
Dec 16
SJU3:00 pmSan Juan Luis Munoz Marin Intl
10h 25m
1 stop
MDW11:25 pmChicago Midway
$229
Find similar
Frontier
Nov 13
MDW9:15 amChicago Midway
13h 26m
1 stop
SJU12:41 amSan Juan Luis Munoz Marin Intl
Nov 16
SJU10:39 pmSan Juan Luis Munoz Marin Intl
17h 54m
2 stops
MDW2:33 pmChicago Midway
$241
Find similar
Frontier
Nov 10
MDW6:20 amChicago Midway
6h 59m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
Nov 14
SJU10:39 pmSan Juan Luis Munoz Marin Intl
13h 47m
1 stop
MDW10:26 amChicago Midway
$245
Find similar

Southwest flights from Chicago Midway Airport to San Juan

Our best Southwest deals on Chicago Midway Airport to San Juan flight tickets
Southwest
Sep 6
MDW9:35 amChicago Midway
11h 15m
2 stops
SJU9:50 pmSan Juan Luis Munoz Marin Intl
Sep 13
SJU7:45 amSan Juan Luis Munoz Marin Intl
8h 50m
2 stops
MDW3:35 pmChicago Midway
$421
Find similar
Southwest
Sep 8
MDW1:45 pmChicago Midway
8h 45m
2 stops
SJU11:30 pmSan Juan Luis Munoz Marin Intl
Sep 19
SJU5:00 amSan Juan Luis Munoz Marin Intl
8h 50m
2 stops
MDW12:50 pmChicago Midway
$438
Find similar
Southwest
Sep 5
MDW1:00 pmChicago Midway
6h 45m
1 stop
SJU8:45 pmSan Juan Luis Munoz Marin Intl
Sep 13
SJU7:45 amSan Juan Luis Munoz Marin Intl
8h 50m
2 stops
MDW3:35 pmChicago Midway
$465
Find similar

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 August 25, 2025.
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

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 12/12

2:15 pm-2:50 am

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Tue 12/16

3:00 pm-11:25 pm

1 stop10h 25m

$229

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/13

9:15 am-12:41 am

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Sun 11/16

10:39 pm-2:33 pm

2 stops17h 54m

$241

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 11/10

6:20 am-3:19 pm

1 stop6h 59m

San Juan Luis Munoz Marin Intl

Fri 11/14

10:39 pm-10:26 am

1 stop13h 47m

$245

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/6

9:15 am-12:41 am

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Sun 11/9

10:39 pm-5:15 pm

2 stops20h 36m

$247

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/13

9:15 am-12:41 am

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Sun 11/16

7:30 am-12:30 am

1 stop19h 00m

$248

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/23

10:49 am-2:30 am

1 stop14h 41m

San Juan Luis Munoz Marin Intl

Sun 10/26

9:06 pm-11:17 am

1 stop15h 11m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/11

8:35 am-9:42 am

1 stop24h 07m

San Juan Luis Munoz Marin Intl

Fri 10/17

3:40 am-10:21 am

1 stop7h 41m

$258

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 9/15

5:15 pm-9:56 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

Sun 9/28

7:50 pm-4:00 pm

2 stops21h 10m

$263

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/2

1:49 pm-12:43 am

1 stop9h 54m

San Juan Luis Munoz Marin Intl

Sat 10/4

12:28 am-7:11 am

1 stop7h 43m

$308

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/20

10:51 am-8:56 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Mon 9/22

9:26 pm-3:58 pm

2 stops19h 32m

$309

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 cheapest month to fly to San Juan?

If you’re not able to fly to San Juan in November, then May is your next best option. Flight prices from Chicago Midway Airport to San Juan during May average around $328.

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 Monday when prices can be found for as low as $392. The most expensive day to fly to San Juan is Sunday, with ticket prices averaging around $446.

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 $306. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $445 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 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 $419 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 $306 on momondo.

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

There are 1 cabin classes available to choose from on Chicago Midway 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 35m

Direct flights

Sun

Airports in San Juan

1 airport
The fastest flight from Chicago Midway Airport to San Juan takes 4h 35m
Direct flights go from Chicago Midway Airport to San Juan on Sunday. There are no airlines offering direct flights.
There is 1 airport near San Juan: San Juan Luis Munoz Marin Intl (SJU)
Search flight deals

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

    The straight-line distance from Chicago Midway to San Juan is 2052.0 mi. 6h 39m 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 $133Free CancellationRating
5.8
3,201 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,029 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
8,940 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
7,981 reviews
Search Delta flights
SouthwestPriceFrom $352Free CancellationRating
8.0
4,243 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