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Cheap flights from Chicago Midway Airport to San Juan from $117

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 2/1. 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
8:19 pm - 12:42 pm
MDW
-
SJU
14h 23m1 stop
Frontier Logo
8:31 pm - 3:49 pm
SJU
-
MDW
21h 18m2 stops
$200Frontier
Sun, Jan 18 - Thu, Jan 22
Frontier Logo
6:10 am - 3:06 pm
MDW
-
SJU
6h 56m1 stop
Frontier Logo
2:07 pm - 2:26 pm
SJU
-
MDW
26h 19m1 stop
$201Frontier
Wed, Feb 25 - Wed, Mar 4
Frontier Logo
8:00 am - 7:07 pm
MDW
-
SJU
9h 07m1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m1 stop
$202Frontier
Sat, Feb 14 - Sat, Feb 21
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
Frontier Logo
4:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
$203Frontier
Fri, Jan 30 - Thu, Feb 5
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m1 stop
$204Frontier
Fri, Feb 6 - Wed, Feb 11
Frontier Logo
4:31 pm - 2:50 am
MDW
-
SJU
8h 19m1 stop
Frontier Logo
5:45 am - 2:06 pm
SJU
-
MDW
10h 21m1 stop
$215Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
Frontier Logo
8:02 pm - 2:26 pm
SJU
-
MDW
20h 24m1 stop
$216Frontier
Fri, Feb 6 - Sat, Feb 14
Frontier Logo
8:15 am - 10:44 pm
MDW
-
SJU
12h 29m1 stop
Frontier Logo
5:45 am - 2:06 pm
SJU
-
MDW
10h 21m1 stop
$217Frontier
Fri, Jan 2 - Mon, Jan 12
Frontier Logo
6:00 am - 3:02 pm
MDW
-
SJU
7h 02m1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m1 stop
$220Frontier
Wed, Feb 18 - Wed, Feb 25
Multiple Airlines Logo
8:19 pm - 12:42 pm
MDW
-
SJU
14h 23m1 stop
Multiple Airlines Logo
8:05 pm - 7:52 pm
SJU
-
MDW
25h 47m1 stop
$221Multiple Airlines
Sun, Jan 18 - Thu, Jan 22

Southwest flights from Chicago Midway Airport to San Juan

Our best Southwest deals on Chicago Midway Airport to San Juan flight tickets
Southwest
Jan 12
MDW8:30 amChicago Midway
6h 35m
1 stop
SJU5:05 pmSan Juan Luis Munoz Marin Intl
Jan 14
SJU9:05 amSan Juan Luis Munoz Marin Intl
11h 30m
1 stop
MDW6:35 pmChicago Midway
$225
Find similar
Southwest
Jan 5
MDW2:20 pmChicago Midway
9h 05m
1 stop
SJU1:25 amSan Juan Luis Munoz Marin Intl
Jan 14
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
$245
Find similar
Southwest
Jan 26
MDW2:20 pmChicago Midway
8h 15m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 31
SJU5:30 amSan Juan Luis Munoz Marin Intl
11h 15m
2 stops
MDW2:45 pmChicago Midway
$265
Find similar

Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Jan 18
MDW8:19 pmChicago Midway
14h 23m
1 stop
SJU12:42 pmSan Juan Luis Munoz Marin Intl
Jan 22
SJU8:31 pmSan Juan Luis Munoz Marin Intl
21h 18m
2 stops
MDW3:49 pmChicago Midway
$200
Find similar
Frontier
Feb 25
MDW6:10 amChicago Midway
6h 56m
1 stop
SJU3:06 pmSan Juan Luis Munoz Marin Intl
Mar 5
SJU4:11 pmSan Juan Luis Munoz Marin Intl
8h 18m
1 stop
MDW10:29 pmChicago Midway
$201
Find similar
Frontier
Feb 14
MDW8:00 amChicago Midway
9h 07m
1 stop
SJU7:07 pmSan Juan Luis Munoz Marin Intl
Feb 21
SJU5:25 pmSan Juan Luis Munoz Marin Intl
23h 01m
1 stop
MDW2:26 pmChicago Midway
$202
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 December 15, 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

Sun 1/18

8:19 pm-12:42 pm

1 stop14h 23m

San Juan Luis Munoz Marin Intl

Thu 1/22

8:31 pm-3:49 pm

2 stops21h 18m

$200

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 2/25

6:10 am-3:06 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Wed 3/4

2:07 pm-2:26 pm

1 stop26h 19m

$201

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/14

8:00 am-7:07 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Sat 2/21

5:25 pm-2:26 pm

1 stop23h 01m

$202

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/30

1:00 pm-11:59 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Thu 2/5

4:22 pm-10:19 pm

1 stop7h 57m

$203

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 2/6

1:00 pm-11:59 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Wed 2/11

5:25 pm-2:26 pm

1 stop23h 01m

$204

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/9

4:31 pm-2:50 am

1 stop8h 19m

San Juan Luis Munoz Marin Intl

Mon 1/12

5:45 am-2:06 pm

1 stop10h 21m

$215

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 2/6

1:00 pm-11:59 pm

1 stop8h 59m

San Juan Luis Munoz Marin Intl

Sat 2/14

8:02 pm-2:26 pm

1 stop20h 24m

$216

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/2

8:15 am-10:44 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Mon 1/12

5:45 am-2:06 pm

1 stop10h 21m

$217

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 2/18

6:00 am-3:02 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Wed 2/25

5:25 pm-2:26 pm

1 stop23h 01m

$220

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/18

8:19 pm-12:42 pm

1 stop14h 23m

San Juan Luis Munoz Marin Intl

Thu 1/22

8:05 pm-7:52 pm

1 stop25h 47m

$221

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 May, then February is your next best option. Flight prices from Chicago Midway Airport to San Juan during February average around $344.

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 $391. The most expensive day to fly to San Juan is Friday, with ticket prices averaging around $444.

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 $318. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $446 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 $424 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 $336 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

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

  • 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
FrontierPriceFrom $144Free CancellationRating
5.8
3,082 reviews
Search Frontier flights
DeltaPriceFrom $325Free CancellationRating
7.9
8,010 reviews
Search Delta flights
SouthwestPriceFrom $381Free CancellationRating
7.9
4,250 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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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