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Cheap flights from Chicago Midway Airport to San Juan from $104

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 4/13. 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

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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
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
Frontier Logo
6:30 am - 7:59 am
SJU
-
MDW
26h 29m
1 stop
$222Frontier
Thu, Apr 9 - Thu, Apr 16
Frontier Logo
6:30 am - 1:01 am
MDW
-
SJU
17h 31m
1 stop
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
$224Frontier
Fri, Apr 10 - Fri, Apr 17
Frontier Logo
5:30 am - 11:40 pm
MDW
-
SJU
17h 10m
1 stop
Frontier Logo
10:54 am - 8:04 am
SJU
-
MDW
22h 10m
1 stop
$229Frontier
Fri, Apr 10 - Wed, Apr 15
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
Frontier Logo
3:08 am - 8:04 am
SJU
-
MDW
29h 56m
1 stop
$230Frontier
Wed, Apr 8 - Tue, Apr 14
Frontier Logo
5:01 am - 2:01 am
MDW
-
SJU
20h 00m
1 stop
Frontier Logo
3:19 pm - 7:59 am
SJU
-
MDW
17h 40m
1 stop
$231Frontier
Thu, Apr 2 - Thu, Apr 16
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
Frontier Logo
3:19 pm - 7:59 am
SJU
-
MDW
17h 40m
1 stop
$232Frontier
Thu, Apr 9 - Thu, Apr 16
Frontier Logo
6:00 am - 8:49 pm
MDW
-
SJU
13h 49m
1 stop
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
$233Frontier
Sat, Apr 11 - Fri, Apr 24
Frontier Logo
9:04 am - 2:01 am
MDW
-
SJU
15h 57m
1 stop
Frontier Logo
3:08 am - 7:21 am
SJU
-
MDW
29h 13m
1 stop
$234Frontier
Sun, Apr 19 - Tue, Apr 28
Multiple Airlines Logo
6:10 am - 7:50 pm
MDW
-
SJU
12h 40m
1 stop
Multiple Airlines Logo
3:08 am - 7:31 pm
SJU
-
MDW
17h 23m
2 stops
$235Multiple Airlines
Tue, Apr 14 - Tue, Apr 14
Frontier Logo
6:00 am - 2:08 am
MDW
-
SJU
19h 08m
2 stops
Frontier Logo
3:03 am - 8:04 am
SJU
-
MDW
30h 01m
1 stop
$236Frontier
Wed, May 6 - Tue, May 12

Frontier flights from Chicago Midway Airport to San Juan

Our best Frontier deals on Chicago Midway Airport to San Juan flight tickets
Frontier
Apr 9
MDW2:56 pmChicago Midway
8h 56m
1 stop
SJU12:52 amSan Juan Luis Munoz Marin Intl
Apr 16
SJU6:30 amSan Juan Luis Munoz Marin Intl
26h 29m
1 stop
MDW7:59 amChicago Midway
$222
Frontier
Apr 10
MDW6:30 amChicago Midway
17h 31m
1 stop
SJU1:01 amSan Juan Luis Munoz Marin Intl
Apr 17
SJU3:23 pmSan Juan Luis Munoz Marin Intl
8h 03m
1 stop
MDW10:26 pmChicago Midway
$224
Frontier
Apr 10
MDW5:30 amChicago Midway
17h 10m
1 stop
SJU11:40 pmSan Juan Luis Munoz Marin Intl
Apr 15
SJU10:54 amSan Juan Luis Munoz Marin Intl
22h 10m
1 stop
MDW8:04 amChicago Midway
$229

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 March 15, 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

Thu 4/9

2:56 pm-12:52 am

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Thu 4/16

6:30 am-7:59 am

1 stop26h 29m

$222

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 4/10

6:30 am-1:01 am

1 stop17h 31m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-10:26 pm

1 stop8h 03m

$224

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 4/10

5:30 am-11:40 pm

1 stop17h 10m

San Juan Luis Munoz Marin Intl

Wed 4/15

10:54 am-8:04 am

1 stop22h 10m

$229

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 4/8

2:56 pm-12:52 am

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Tue 4/14

3:08 am-8:04 am

1 stop29h 56m

$230

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 4/2

5:01 am-2:01 am

1 stop20h 00m

San Juan Luis Munoz Marin Intl

Thu 4/16

3:19 pm-7:59 am

1 stop17h 40m

$231

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 4/9

2:56 pm-12:52 am

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Thu 4/16

3:19 pm-7:59 am

1 stop17h 40m

$232
Quickest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 4/11

6:00 am-8:49 pm

1 stop13h 49m

San Juan Luis Munoz Marin Intl

Fri 4/24

3:23 pm-10:26 pm

1 stop8h 03m

$233

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 4/19

9:04 am-2:01 am

1 stop15h 57m

San Juan Luis Munoz Marin Intl

Tue 4/28

3:08 am-7:21 am

1 stop29h 13m

$234

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 4/14

6:10 am-7:50 pm

1 stop12h 40m

San Juan Luis Munoz Marin Intl

Tue 4/14

3:08 am-7:31 pm

2 stops17h 23m

$235

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 5/6

6:00 am-2:08 am

2 stops19h 08m

San Juan Luis Munoz Marin Intl

Tue 5/12

3:03 am-8:04 am

1 stop30h 01m

$236

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 February, then January is your next best option. Flight prices from Chicago Midway Airport to San Juan during January average around $304.

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 $381. The most expensive day to fly to San Juan is Friday, with ticket prices averaging around $454.

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 $361. 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 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 $384 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 $262 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
DeltaPriceFrom $132Free CancellationRating
7.9
8,292 reviews
Search Delta flights
FrontierPriceFrom $142Free CancellationRating
5.7
3,032 reviews
Search Frontier flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,318 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