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Cheap flights from Chicago Midway Airport to Puerto Rico from $63

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 2/24. 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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Find the cheapest flights from Chicago Midway Airport to Puerto Rico

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Puerto Rico that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Puerto Rico.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Puerto Rico? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Puerto Rico, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Puerto Rico

Find recent round-trip train or bus tickets from Chicago Midway Airport to Puerto Rico.

All round-trip flight deals to Puerto Rico

The cheapest plane tickets to Puerto Rico found on KAYAK recently.
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
12:59 am - 1:09 pmSJU-MDW
14h 10m1 stop
$133Frontier
Find Deal
Mon, Dec 9 - Mon, Dec 16
11:33 am - 2:19 amMDW-SJU
12h 46m1 stop
6:00 am - 3:43 pmSJU-MDW
11h 43m1 stop
$138Frontier
Find Deal
Mon, Jan 20 - Mon, Jan 27
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
7:14 pm - 3:12 pmSJU-MDW
21h 58m1 stop
$139Frontier
Find Deal
Mon, Dec 9 - Sat, Dec 14
10:58 am - 2:19 amMDW-SJU
13h 21m1 stop
6:00 am - 3:43 pmSJU-MDW
11h 43m1 stop
$143Frontier
Find Deal
Sun, Jan 26 - Mon, Jan 27
1:20 pm - 12:50 amMDW-SJU
9h 30m2 stops
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$210Southwest
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Sun, Feb 2 - Wed, Feb 5
8:15 am - 5:43 pmMDW-SJU
31h 28m2 stops
3:20 am - 10:45 pmSJU-MDW
45h 25m2 stops
Mon, Dec 9 - Sat, Dec 14
8:15 am - 5:43 pmMDW-SJU
31h 28m2 stops
9:32 pm - 10:45 pmSJU-MDW
27h 13m3 stops
Mon, Dec 9 - Sun, Dec 15
1:20 pm - 12:40 amMDW-SJU
9h 20m1 stop
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$275Southwest
Find Deal
Wed, Jan 15 - Thu, Jan 23
6:00 am - 2:20 pmMDW-SJU
6h 20m1 stop
2:02 pm - 10:20 pmSJU-MDW
10h 18m1 stop
$334Delta
Find Deal
Tue, Jan 28 - Fri, Feb 7
6:00 am - 5:15 pmMDW-SJU
9h 15m1 stop
3:30 pm - 10:06 pmSJU-MDW
8h 36m1 stop
$354Delta
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Wed, Dec 11 - Wed, Dec 18
4:20 pm - 1:44 amMDW-SJU
7h 24m1 stop
$63Frontier
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Mon, Feb 24
9:59 pm - 10:50 amMDW-SJU
10h 51m1 stop
$64Frontier
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Mon, Jan 6
7:45 am - 1:59 amMDW-SJU
16h 14m1 stop
$66Frontier
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Mon, Feb 3
9:59 pm - 10:50 amMDW-SJU
10h 51m1 stop
$67Frontier
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Mon, Jan 6
10:05 am - 12:25 amMDW-SJU
12h 20m2 stops
$105Southwest
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Wed, Jan 22
6:30 am - 5:43 pmMDW-SJU
33h 13m2 stops
Sun, Dec 8
7:15 am - 1:22 pmMDW-SJU
28h 07m2 stops
Sat, Dec 14
6:00 am - 2:20 pmMDW-SJU
6h 20m1 stop
$162Delta
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Tue, Jan 14
12:44 pm - 11:45 pmMDW-SJU
9h 01m1 stop
$167Delta
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Tue, Jan 21
5:55 am - 3:10 pmMDW-SJU
7h 15m1 stop
$170Southwest
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Sat, Jan 11
8:50 am - 8:36 pmMDW-SJU
9h 46m1 stop
6:20 am - 11:42 amSJU-MDW
7h 22m1 stop
$258Frontier
Find Deal
Tue, Nov 26 - Wed, Dec 4
7:42 am - 7:17 pmMDW-SJU
9h 35m1 stop
6:20 am - 5:18 pmSJU-MDW
12h 58m1 stop
$278Frontier
Find Deal
Mon, Nov 25 - Thu, Dec 5
2:56 pm - 2:20 amMDW-SJU
9h 24m1 stop
6:20 am - 5:18 pmSJU-MDW
12h 58m1 stop
$318Frontier
Find Deal
Sat, Nov 23 - Thu, Dec 5
7:42 am - 7:17 pmMDW-SJU
9h 35m1 stop
6:20 am - 11:42 amSJU-MDW
7h 22m1 stop
$338Frontier
Find Deal
Mon, Nov 25 - Wed, Dec 4
3:19 pm - 11:22 pmMDW-SJU
6h 03m1 stop
1:50 pm - 9:46 pmSJU-MDW
9h 56m1 stop
$414Delta
Find Deal
Sun, Nov 24 - Wed, Dec 4
11:40 am - 12:40 amMDW-SJU
11h 00m2 stops
3:40 pm - 11:15 pmSJU-MDW
9h 35m1 stop
$444Southwest
Find Deal
Mon, Nov 25 - Wed, Nov 27
11:40 am - 12:40 amMDW-SJU
11h 00m2 stops
5:35 am - 1:15 pmSJU-MDW
9h 40m2 stops
$465Southwest
Find Deal
Mon, Nov 25 - Wed, Nov 27
3:19 pm - 11:22 pmMDW-SJU
6h 03m1 stop
1:50 pm - 9:46 pmSJU-MDW
9h 56m1 stop
$514Delta
Find Deal
Sun, Nov 24 - Mon, Dec 2
9:09 pm - 11:40 pmMDW-SJU
24h 31m3 stops
8:05 pm - 8:41 amSJU-MDW
14h 36m1 stop
Fri, Nov 22 - Mon, Nov 25
5:10 am - 7:49 pmMDW-SJU
60h 39m3 stops
11:12 am - 11:10 amSJU-MDW
25h 58m2 stops
Sat, Nov 23 - Sat, Nov 30
8:45 am - 3:20 pmMDW-SJU
4h 35mnonstop
5:00 pm - 8:15 pmSJU-MDW
5h 15mnonstop
$1,233Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22

Frontier flights from Chicago Midway Airport to Puerto Rico

Our best Frontier deals on Chicago Midway Airport to Puerto Rico flight tickets
Frontier
Dec 9
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 16
SJU12:59 amSan Juan Luis Munoz Marin Intl
14h 10m
1 stop
MDW1:09 pmChicago Midway
Frontier
Jan 20
MDW11:33 amChicago Midway
12h 46m
1 stop
SJU2:19 amSan Juan Luis Munoz Marin Intl
Jan 27
SJU6:00 amSan Juan Luis Munoz Marin Intl
11h 43m
1 stop
MDW3:43 pmChicago Midway
Frontier
Dec 9
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 14
SJU7:14 pmSan Juan Luis Munoz Marin Intl
21h 58m
1 stop
MDW3:12 pmChicago Midway

Southwest flights from Chicago Midway Airport to Puerto Rico

Our best Southwest deals on Chicago Midway Airport to Puerto Rico flight tickets
Southwest
Feb 2
MDW1:20 pmChicago Midway
9h 30m
2 stops
SJU12:50 amSan Juan Luis Munoz Marin Intl
Feb 5
SJU2:55 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
MDW7:45 pmChicago Midway
Southwest
Jan 15
MDW1:20 pmChicago Midway
9h 20m
1 stop
SJU12:40 amSan Juan Luis Munoz Marin Intl
Jan 23
SJU2:55 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
MDW7:45 pmChicago Midway
Southwest
Jan 28
MDW10:05 amChicago Midway
12h 20m
2 stops
SJU12:25 amSan Juan Luis Munoz Marin Intl
Feb 3
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 45m
1 stop
MDW11:45 amChicago Midway

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 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 Sunday. momondo users have found tickets for Sunday departures for as low as $230. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Friday, with ticket prices averaging around $330.

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

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

There are 1 cabin classes 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.

Can stopping save me money on Chicago Midway Airport to Puerto Rico flights?

You could potentially save up to 66% on your flight if you consider stops on a Chicago Midway Airport to Puerto Rico flight.

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

Best Price Found

$63

Fastest flight time

4h 35m

Direct flights

Mon and Sun

Airports in Puerto Rico

1 airport
The best one-way flight to Puerto Rico from Chicago Midway Airport in the past 72 hours is $63. The best round-trip flight deal from Chicago Midway Airport to Puerto Rico found on momondo in the last 72 hours is $133.
The fastest flight from Chicago Midway Airport to Puerto Rico takes 4h 35m
Direct flights go from Chicago Midway Airport to Puerto Rico on Monday and Sunday. The only airline offering direct flights is Southwest.
There is 1 airport near Puerto Rico: San Juan Luis Munoz Marin Intl (SJU)

  • 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 $119Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $199Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $275Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
DeltaPriceFrom $374Free CancellationRating
8.0
8,755 reviews
Search Delta 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.


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