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Cheap flights from Chicago Midway Airport to Puerto Rico from $109

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 Puerto Rico departing on 1/11. 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 Puerto Rico

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:52 pm - 1:42 amMDW-SJU
7h 50m1 stop
Frontier Logo
7:10 am - 1:02 pmSJU-MDW
31h 52m1 stop
$209Frontier
Find Deal
Wed, Jan 7 - Wed, Jan 14
Frontier Logo
6:00 am - 3:06 pmMDW-SJU
7h 06m1 stop
Frontier Logo
7:00 am - 5:11 pmSJU-MDW
12h 11m1 stop
$212Frontier
Find Deal
Sat, Feb 7 - Sat, Feb 14
Frontier Logo
6:00 am - 3:01 pmMDW-SJU
7h 01m1 stop
Frontier Logo
8:00 am - 2:47 pmSJU-MDW
8h 47m1 stop
$216Frontier
Find Deal
Thu, Jan 8 - Thu, Jan 15
Frontier Logo
3:52 pm - 1:42 amMDW-SJU
7h 50m1 stop
Frontier Logo
7:10 am - 11:26 pmSJU-MDW
18h 16m2 stops
$219Frontier
Find Deal
Mon, Jan 12 - Thu, Jan 15
Frontier Logo
8:56 pm - 9:55 amMDW-SJU
10h 59m1 stop
Frontier Logo
4:11 pm - 11:25 pmSJU-MDW
9h 14m1 stop
$224Frontier
Find Deal
Fri, Jan 23 - Sat, Jan 31
Frontier Logo
6:00 am - 3:01 pmMDW-SJU
7h 01m1 stop
Frontier Logo
8:00 am - 2:47 pmSJU-MDW
8h 47m1 stop
$225Frontier
Find Deal
Sun, Jan 11 - Thu, Jan 15
Frontier Logo
3:32 pm - 2:39 amMDW-SJU
9h 07m1 stop
Frontier Logo
4:06 pm - 11:25 pmSJU-MDW
9h 19m1 stop
$228Frontier
Find Deal
Wed, Dec 31 - Mon, Jan 12
Frontier Logo
2:05 pm - 8:45 amMDW-SJU
17h 40m1 stop
Frontier Logo
9:00 am - 12:41 pmSJU-MDW
29h 41m2 stops
$230Frontier
Find Deal
Sat, Nov 1 - Tue, Nov 4
Multiple Airlines Logo
6:15 pm - 11:55 pmMDW-SJU
27h 40m1 stop
Multiple Airlines Logo
9:15 am - 1:01 pmSJU-MDW
29h 46m1 stop
$259Multiple Airlines
Find Deal
Thu, Nov 27 - Wed, Dec 3
Delta Logo
10:36 am - 11:20 pmMDW-SJU
10h 44m1 stop
Delta Logo
1:55 pm - 11:47 pmSJU-MDW
11h 52m1 stop
$263Delta
Find Deal
Sun, Dec 7 - Fri, Dec 12

Frontier flights from Chicago Midway Airport to Puerto Rico

Our best Frontier deals on Chicago Midway Airport to Puerto Rico flight tickets
Frontier
Jan 7
MDW3:52 pmChicago Midway
7h 50m
1 stop
SJU1:42 amSan Juan Luis Munoz Marin Intl
Jan 14
SJU7:10 amSan Juan Luis Munoz Marin Intl
31h 52m
1 stop
MDW1:02 pmChicago Midway
$209
Find similar
Frontier
Feb 7
MDW6:00 amChicago Midway
7h 06m
1 stop
SJU3:06 pmSan Juan Luis Munoz Marin Intl
Feb 14
SJU7:00 amSan Juan Luis Munoz Marin Intl
12h 11m
1 stop
MDW5:11 pmChicago Midway
$212
Find similar
Frontier
Jan 8
MDW6:00 amChicago Midway
7h 01m
1 stop
SJU3:01 pmSan Juan Luis Munoz Marin Intl
Jan 15
SJU8:00 amSan Juan Luis Munoz Marin Intl
8h 47m
1 stop
MDW2:47 pmChicago Midway
$216
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Puerto Rico 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 October 22, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/7

3:52 pm-1:42 am

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Wed 1/14

7:10 am-1:02 pm

1 stop31h 52m

$209

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/7

6:00 am-3:06 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:00 am-5:11 pm

1 stop12h 11m

$212

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/8

6:00 am-3:01 pm

1 stop7h 01m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:00 am-2:47 pm

1 stop8h 47m

$216

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/12

3:52 pm-1:42 am

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Thu 1/15

7:10 am-11:26 pm

2 stops18h 16m

$219

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/23

8:56 pm-9:55 am

1 stop10h 59m

San Juan Luis Munoz Marin Intl

Sat 1/31

4:11 pm-11:25 pm

1 stop9h 14m

$224

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/11

6:00 am-3:01 pm

1 stop7h 01m

San Juan Luis Munoz Marin Intl

Thu 1/15

8:00 am-2:47 pm

1 stop8h 47m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 12/31

3:32 pm-2:39 am

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Mon 1/12

4:06 pm-11:25 pm

1 stop9h 19m

$228

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 11/1

2:05 pm-8:45 am

1 stop17h 40m

San Juan Luis Munoz Marin Intl

Tue 11/4

9:00 am-12:41 pm

2 stops29h 41m

$230

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/27

6:15 pm-11:55 pm

1 stop27h 40m

San Juan Luis Munoz Marin Intl

Wed 12/3

9:15 am-1:01 pm

1 stop29h 46m

$259

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 12/7

10:36 am-11:20 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Fri 12/12

1:55 pm-11:47 pm

1 stop11h 52m

$263

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 Puerto Rico from

How to get the cheapest flight ticket from Chicago Midway Airport to Puerto Rico

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 Puerto Rico?

If you don’t want to visit Puerto Rico in May, then you should wait until November to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $342.

What is the cheapest day to depart on your flight to Puerto Rico?

On average, the least expensive day to fly to Puerto Rico from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $59. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Saturday, with ticket prices averaging around $519.

What is the cheapest time of day to depart on your flight to Puerto Rico?

Our most recent data shows that the best time of day to fly to Puerto Rico is in the evening. Flights from Chicago Midway Airport to Puerto Rico during this time can be as low as $324. In contrast, the most expensive time of day to depart to Puerto Rico is in the morning when prices are around $526.

What is the cheapest Chicago Midway to Puerto Rico flight route?

Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago Midway - Puerto Rico flight prices

How far in advance should I book a flight to Puerto Rico?

You are more likely to see cheaper flights to Puerto Rico from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $422 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Chicago Midway Airport for as low as $355 on momondo.

What cabin class options are available on Chicago Midway to Puerto Rico flights?

There is only 1 cabin class available to choose from on Chicago Midway to Puerto Rico 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 Puerto Rico flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Puerto Rico

Fastest flight time

4h 35m

Direct flights

Sun

Airports in Puerto Rico

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

  • When did momondo last update prices for flights from Chicago Midway Airport to Puerto Rico?

    Prices for flights from Chicago Midway Airport to Puerto Rico are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Puerto Rico?

  • How old do you have to be to fly from Chicago Midway Airport to Puerto Rico?

    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 Puerto Rico.

  • What documentation or ID do you need to fly to Puerto Rico?

    The necessary travel and health documents for your Puerto Rico 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.

  • What is the most popular plane model from Chicago Midway Airport to Puerto Rico?

Best airlines flying from Chicago Midway Airport to Puerto Rico

Compare and see reviews for airlines that fly from Chicago Midway Airport to Puerto Rico with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $142Free CancellationRating
5.8
3,130 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,097 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
8,988 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
7,980 reviews
Search Delta flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,237 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Puerto Rico?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Puerto Rico from Chicago.

Can I find flights from Chicago to Puerto Rico with flexible booking policies on momondo?

Flights from Chicago to Puerto Rico with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Puerto Rico?

Once all potential Chicago to Puerto Rico flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Puerto Rico right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Puerto Rico, momondo offers a useful price alert feature which will track prices for flights to Puerto Rico from Chicago and alert you when they change.

An easier way to manage your Puerto Rico trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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