HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Puerto Rico

$123+ Cheap flights from Midway (MDW) to Puerto Rico

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Puerto Rico with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to Puerto Rico

Keep the following information in mind while searching for Midway to Puerto Rico flight deals. Data was last updated November 26, 2025.

Round-trip from

$215
(CheapOair)

One-way from

$123
(Super.com)

Popular in

December

Cheapest in

April

Average price

$436

Good one-way deal

$292 or less
From Chicago Midway to Puerto Rico
Search Deals
One-way flight from Chicago Midway to Puerto Rico
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a one-way flight from Chicago Midway to Puerto Rico.
Search Deals

Find flight deals from Midway to Puerto Rico

Cheapest flights from Midway to Puerto Rico
Explore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 26, 2025.

This Frontier deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/142:59 pmMDW - SJU
1 stop6h 51mFrontier
Sun 12/213:54 amSJU - MDW
1 stop12h 11mFrontier
Deal found 11/25$215
This Priceline deal was found by Cheapflights users on 11/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Mon 12/1511:05 amSJU - MDW
1 stop12h 53mFrontier
Deal found 11/26$222
This Kiwi.com deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:15 amMDW - SJU
2 stops40h 19mFrontier
Tue 12/303:54 amSJU - MDW
1 stop12h 43mFrontier
Deal found 11/24$228
This Gotogate deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:15 amMDW - SJU
1 stop6h 56mFrontier
Mon 12/224:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 11/25$233
This Frontier deal was found by Cheapflights users on 11/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:10 pmMDW - SJU
1 stop9h 40mFrontier
Thu 12/184:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 11/26$238
This CheapOair deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:10 pmMDW - SJU
1 stop22h 49mFrontier
Sun 12/143:55 amSJU - MDW
1 stop20h 03mFrontier
Deal found 11/25$243
This Super.com deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/72:59 pmMDW - SJU
1 stop6h 51mFrontier
Fri 12/124:31 pmSJU - MDW
1 stop7h 41mFrontier
Deal found 11/25$244
This Frontier deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/142:59 pmMDW - SJU
1 stop6h 51mFrontier
Thu 12/184:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 11/25$252
This CheapOair deal was found by Cheapflights users on 11/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/123:52 pmMDW - SJU
1 stop8h 58mFrontier
Fri 12/194:16 pmSJU - MDW
1 stop7h 56mFrontier
Deal found 11/26$254

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated November 26, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico that are best for you.

Fly from

Midway

Fly to

Puerto Rico

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/19

6:00 am-2:31 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Fri 1/23

3:55 pm-10:22 pm

1 stop8h 27m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/13

6:45 am-5:17 pm

1 stop8h 32m

San Juan Luis Munoz Marin Intl

Fri 1/23

3:55 pm-10:22 pm

1 stop8h 27m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

11:50 am-10:25 pm

1 stop8h 35m

San Juan Luis Munoz Marin Intl

Fri 1/30

9:05 am-6:35 pm

1 stop11h 30m

$245

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/22

9:50 am-11:10 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Tue 1/27

9:05 am-6:35 pm

1 stop11h 30m

$245

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/21

9:50 am-11:10 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Wed 1/28

5:40 am-2:15 pm

2 stops10h 35m

$245

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/11

1:35 pm-12:05 am

2 stops8h 30m

San Juan Luis Munoz Marin Intl

Wed 1/14

6:10 am-1:55 pm

2 stops9h 45m

$245

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/5

6:10 am-9:50 pm

1 stop13h 40m

San Juan Luis Munoz Marin Intl

Mon 2/9

2:20 pm-11:50 pm

1 stop11h 30m

$252

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/25

6:00 am-5:17 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:30 am-11:59 am

1 stop6h 29m

$270

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/22

2:20 pm-12:35 am

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Wed 2/18

2:35 pm-10:05 pm

2 stops9h 30m

$286

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/2

9:50 am-8:55 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Sat 2/7

8:40 am-1:45 pm

1 stop7h 05m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/26

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from Midway to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Puerto Rico

What is the cheapest month to book a flight from Chicago Midway Airport to Puerto Rico?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $127). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $298). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to PR?

Find hourly flight availability from Midway to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 26, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 55% on flights from Chicago Midway Airport to Puerto Rico by exploring options for tickets in the evening.

What is the cheapest day to fly from Chicago Midway Airport to Puerto Rico?

Use this chart to determine the cheapest time to fly round-trip from Midway to Puerto Rico. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to Puerto Rico flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How often are flights from Chicago to Puerto Rico delayed?

About 22% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 96 minutes.

What is the most punctual flight time for Chicago to Puerto Rico flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Puerto Rico flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 22% of flights being delayed.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated November 26, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Spirit Airlines from Chicago Midway Airport to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,158 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,099 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Puerto Rico?

    Airlines like Delta and Southwest fly from Chicago Midway Airport to Puerto Rico in about 6h 31m. The time it takes to get you to your destination can typically vary by up to 2h 04m. Airlines will cover a distance of 2057 mi. This flight may include one or multiple stops.

  • What are the cheapest flights from Chicago Midway Airport to Puerto Rico?

    Looking for the cheapest flight from Chicago Midway Airport to Puerto Rico? While on average our users pay $443, our data indicates the cheapest price to be $292. The most popular route (Chicago Midway - San Juan Luis Munoz Marin Intl), is priced around $180.

  • Can I find deals for flights from Midway to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Midway to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Puerto Rico.

  • Can I find deals for business class flights from Midway to Puerto Rico?

    Yes. Cheapflights offers flight deals from Midway to Puerto Rico by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Puerto Rico?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $127). Flying from Chicago Midway Airport to Puerto Rico in June is currently the most expensive (average of $298). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
Midway to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Simpson Bay flights
Midway to Montego Bay flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
Midway to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
Midway to Providenciales flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Christiansted flights
Midway to George Town flights
Midway to Santo Domingo flights
Midway to Simpson Bay flights
O'Hare Intl to Ponce flights
O'Hare Intl to Road Town flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Kingston flights
O'Hare Intl to St. John's flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Fort-de-France flights
O'Hare Intl to St. George's flights
O'Hare Intl to Castries flights
Midway to Castries flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Havana flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Freeport flights
O'Hare Intl to Pointe-à-Pitre flights
Midway to Kingston flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Gustavia flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to The Valley flights

Top 4 airlines flying from Midway to Puerto Rico

Discover the top 4 airlines that operate flights from Midway to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$287FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$149Average$327FlexibilityNo cancel feeOn-time65%
DeltaCheapest$325Average$405FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$379Average$498FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.