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Cheap flights from Chicago Midway Airport to San Juan from $114

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 11/17. 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
6:30 am - 12:57 amMDW-SJU
16h 27m1 stop
Frontier Logo
3:59 pm - 9:32 pmSJU-MDW
7h 33m1 stop
$208Frontier
Find Deal
Fri, Dec 5 - Wed, Dec 10
Frontier Logo
8:05 am - 12:29 amMDW-SJU
15h 24m2 stops
Frontier Logo
6:22 am - 11:20 pmSJU-MDW
17h 58m2 stops
$209Frontier
Find Deal
Tue, Oct 7 - Sat, Oct 11
Frontier Logo
5:15 pm - 9:56 amMDW-SJU
15h 41m2 stops
Frontier Logo
1:26 pm - 9:47 amSJU-MDW
21h 21m2 stops
$224Frontier
Find Deal
Fri, Oct 3 - Wed, Oct 8
Southwest Logo
4:35 pm - 11:50 pmMDW-SJU
6h 15m1 stop
Southwest Logo
2:45 pm - 10:45 pmSJU-MDW
9h 00m1 stop
$227Southwest
Find Deal
Fri, Oct 17 - Tue, Oct 21
Frontier Logo
8:05 am - 12:29 amMDW-SJU
15h 24m2 stops
Frontier Logo
4:22 pm - 10:47 pmSJU-MDW
7h 25m1 stop
$228Frontier
Find Deal
Tue, Oct 7 - Sat, Oct 11
Frontier Logo
1:37 pm - 2:19 pmMDW-SJU
23h 42m1 stop
Frontier Logo
4:24 pm - 11:38 amSJU-MDW
21h 14m1 stop
$233Frontier
Find Deal
Thu, Oct 30 - Mon, Nov 3
Frontier Logo
9:15 am - 12:29 amMDW-SJU
14h 14m1 stop
Frontier Logo
2:03 am - 2:33 pmSJU-MDW
14h 30m1 stop
$240Frontier
Find Deal
Thu, Oct 30 - Sun, Nov 2
Multiple Airlines Logo
8:25 am - 12:29 amMDW-SJU
15h 04m1 stop
Multiple Airlines Logo
4:04 pm - 12:37 pmSJU-MDW
21h 33m1 stop
$260Multiple Airlines
Find Deal
Thu, Oct 23 - Thu, Oct 30
Multiple Airlines Logo
1:37 pm - 4:23 pmMDW-SJU
24h 46m2 stops
Multiple Airlines Logo
4:24 pm - 11:38 amSJU-MDW
21h 14m1 stop
$264Multiple Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
Delta Logo
10:35 am - 11:49 pmMDW-SJU
11h 14m1 stop
Delta Logo
7:30 am - 4:25 pmSJU-MDW
10h 55m1 stop
$267Delta
Find Deal
Mon, Jan 26 - Wed, Feb 4

Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Dec 5
MDW6:30 amChicago Midway
16h 27m
1 stop
SJU12:57 amSan Juan Luis Munoz Marin Intl
Dec 10
SJU3:59 pmSan Juan Luis Munoz Marin Intl
7h 33m
1 stop
MDW9:32 pmChicago Midway
$208
Find similar
Frontier
Oct 7
MDW8:05 amChicago Midway
15h 24m
2 stops
SJU12:29 amSan Juan Luis Munoz Marin Intl
Oct 11
SJU6:22 amSan Juan Luis Munoz Marin Intl
17h 58m
2 stops
MDW11:20 pmChicago Midway
$209
Find similar
Frontier
Oct 3
MDW5:15 pmChicago Midway
15h 41m
2 stops
SJU9:56 amSan Juan Luis Munoz Marin Intl
Oct 8
SJU1:26 pmSan Juan Luis Munoz Marin Intl
21h 21m
2 stops
MDW9:47 amChicago Midway
$224
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
Oct 17
MDW4:35 pmChicago Midway
6h 15m
1 stop
SJU11:50 pmSan Juan Luis Munoz Marin Intl
Oct 21
SJU2:45 pmSan Juan Luis Munoz Marin Intl
9h 00m
1 stop
MDW10:45 pmChicago Midway
$227
Find similar
Southwest
Oct 1
MDW7:40 amChicago Midway
11h 05m
1 stop
SJU7:45 pmSan Juan Luis Munoz Marin Intl
Oct 8
SJU2:45 pmSan Juan Luis Munoz Marin Intl
9h 00m
1 stop
MDW10:45 pmChicago Midway
$356
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 September 17, 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 12/5

6:30 am-12:57 am

1 stop16h 27m

San Juan Luis Munoz Marin Intl

Wed 12/10

3:59 pm-9:32 pm

1 stop7h 33m

$208

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 10/7

8:05 am-12:29 am

2 stops15h 24m

San Juan Luis Munoz Marin Intl

Sat 10/11

6:22 am-11:20 pm

2 stops17h 58m

$209

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 10/3

5:15 pm-9:56 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

Wed 10/8

1:26 pm-9:47 am

2 stops21h 21m

$224

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 10/17

4:35 pm-11:50 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Tue 10/21

2:45 pm-10:45 pm

1 stop9h 00m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 10/7

8:05 am-12:29 am

2 stops15h 24m

San Juan Luis Munoz Marin Intl

Sat 10/11

4:22 pm-10:47 pm

1 stop7h 25m

$228

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/30

1:37 pm-2:19 pm

1 stop23h 42m

San Juan Luis Munoz Marin Intl

Mon 11/3

4:24 pm-11:38 am

1 stop21h 14m

$233

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/30

9:15 am-12:29 am

1 stop14h 14m

San Juan Luis Munoz Marin Intl

Sun 11/2

2:03 am-2:33 pm

1 stop14h 30m

$240

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/23

8:25 am-12:29 am

1 stop15h 04m

San Juan Luis Munoz Marin Intl

Thu 10/30

4:04 pm-12:37 pm

1 stop21h 33m

$260

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 11/14

1:37 pm-4:23 pm

2 stops24h 46m

San Juan Luis Munoz Marin Intl

Mon 11/17

4:24 pm-11:38 am

1 stop21h 14m

$264

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/26

10:35 am-11:49 pm

1 stop11h 14m

San Juan Luis Munoz Marin Intl

Wed 2/4

7:30 am-4:25 pm

1 stop10h 55m

$267

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 $396. The most expensive day to fly to San Juan is Thursday, with ticket prices averaging around $447.

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 $305. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $447 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 $422 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 to San Juan flights?

There is only 1 cabin class 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

Mon and 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 Monday and 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 15m 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
3,173 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,023 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
7,961 reviews
Search Delta flights
SouthwestPriceFrom $364Free CancellationRating
8.0
4,242 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.

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Fri 10/17
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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