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$83+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Oct 12 — Oct 191
From?
To?
Sat 10/12
Sat 10/19
1 adult, Economy
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Cheap Midway to Puerto Rico flights in October & November 2024

Find cheap flight options from Midway to Puerto Rico specifically for the months of October and November 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,544,716 searches. Prices were last updated on October 7, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Puerto Rico in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
This Frontier deal was found by Cheapflights users on 10/6. 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.
Mon 11/118:31 pmMDW - SJU
1 stop12h 52mFrontier
Thu 11/141:38 pmSJU - MDW
1 stop11h 42mFrontier
Deal found 10/6$128
This Southwest deal was found by Cheapflights users on 10/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/3011:05 amMDW - SJU
1 stop10h 15mSouthwest
Wed 11/66:10 amSJU - MDW
1 stop10h 05mSouthwest
Deal found 10/6$220
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/236:00 amMDW - SJU
1 stop9h 18mDelta
Fri 11/112:57 pmSJU - MDW
1 stop9h 41mDelta
Deal found 10/7$444
This Mytrip deal was found by Cheapflights users on 10/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/229:09 pmMDW - SJU
3 stops34h 58mMultiple Airlines
Mon 11/257:50 pmSJU - MDW
1 stop14h 51mMultiple Airlines
Deal found 10/6$451

Midway to Puerto Rico 2024 flight deals

Discover exclusive flight deals for travel between Midway and Puerto Rico in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,544,716 searches. Data last updated October 7, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Puerto Rico in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
This Frontier deal was found by Cheapflights users on 10/6. 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.
Mon 11/118:31 pmMDW - SJU
1 stop12h 52mFrontier
Thu 11/141:38 pmSJU - MDW
1 stop11h 42mFrontier
Deal found 10/6$128
This Southwest deal was found by Cheapflights users on 10/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/301:25 pmMDW - SJU
1 stop7h 55mSouthwest
Wed 11/66:10 amSJU - MDW
2 stops12h 55mSouthwest
Deal found 10/6$220
This eDestinos deal was found by Cheapflights users on 10/6. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/39:21 amMDW - SJU
1 stop28h 32mMultiple Airlines
Fri 12/1311:45 amSJU - MDW
3 stops49h 41mMultiple Airlines
Deal found 10/6$334
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2910:13 amMDW - SJU
1 stop11h 06mDelta
Wed 1/16:30 amSJU - MDW
1 stop10h 04mDelta
Deal found 10/7$389

Midway to Puerto Rico flights leaving soon

Find last-minute flight options from Midway to Puerto Rico for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,544,716 searches. Data last updated October 7, 2024.
Book one of these great deals on flights from Chicago to Puerto Rico. To prevent any unwanted surprises, users should verify their flight info before booking.
This Booking.com deal was found by Cheapflights users on 10/6. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/122:54 pmMDW - SJU
1 stop11h 54mFrontier
Thu 10/175:06 pmSJU - MDW
1 stop21h 38mFrontier
Deal found 10/6$330
This Southwest deal was found by Cheapflights users on 10/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/175:25 amMDW - SJU
1 stop8h 45mSouthwest
Tue 10/228:30 amSJU - MDW
1 stop10h 15mSouthwest
Deal found 10/7$384
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/122:10 pmMDW - SJU
1 stop7h 11mDelta
Sat 10/198:00 amSJU - MDW
1 stop10h 24mDelta
Deal found 10/7$663

One-way flights to Puerto Rico from Midway

Search for one-way flight options from Midway to Puerto Rico. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,544,716 searches. Data last updated October 7, 2024.
Some of the best available deals we've found on one-way flights from Chicago to Puerto Rico. Users in need of a round-trip flight from Chicago to Puerto Rico instead should update the search form at the top of page.
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/256:59 pmMDW - SJU
1 stop7h 49mFrontier
Deal found 10/7$83
This Southwest deal was found by Cheapflights users on 10/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/61:10 pmMDW - SJU
1 stop9h 20mSouthwest
Deal found 10/7$110
This Trip.com deal was found by Cheapflights users on 10/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/611:59 amMDW - SJU
1 stop11h 08mMultiple Airlines
Deal found 10/6$113
This Delta deal was found by Cheapflights users on 10/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/76:00 amMDW - SJU
1 stop6h 15mDelta
Deal found 10/6$162

Find flights from Midway to Puerto Rico within your budget

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 2,544,716 searches. Data last updated October 7, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$128 - $334

Route

Depart

Return

Price

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Mon 11/11

1 stop12h 52m

San Juan Luis Munoz Marin Intl

Thu 11/14

1 stop11h 42m

$128

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Wed 10/30

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Wed 11/6

1 stop10h 05m

$220

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/17

1 stop8h 39m

San Juan Luis Munoz Marin Intl

Mon 1/27

1 stop7h 59m

$324

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 12/3

1 stop28h 32m

San Juan Luis Munoz Marin Intl

Fri 12/13

3 stops49h 41m

$334

Flights are sorted by cheapest first

Deals found on 10/6

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.

Travel insights for flights from Midway to Puerto Rico

Get recent, data-driven insights about flights from Midway to Puerto Rico including ideal travel times, pricing trends, and more.

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

Currently, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $102). Flying from Chicago Midway Airport to Puerto Rico in July is currently the most expensive (average of $283). 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 October 7, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 53% on flights from Chicago Midway Airport to Puerto Rico by exploring options for tickets in the afternoon.

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 June 30, 2024.

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

Find deals

What are the most popular airlines that fly from Chicago Midway Airport to Puerto Rico?

Our users search for these airlines the most when looking for flights from Midway to Puerto Rico. Data last updated on October 7, 2024.

When booking a flight from Chicago Midway Airport to Puerto Rico, you may want to consider flying on Frontier, Spirit Airlines or Delta as they are the most popular for this route.

Frontier

Frontier

From $119

Spirit Airlines

Spirit Airlines

From $187

Delta

Delta

From $379

Southwest

Southwest

From $267

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 October 7, 2024.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Delta, Frontier and Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,228 reviews

Boarding

8.3

Crew

8.7

Overall

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.2
Very good
5,228 reviews
Southwest
8.2
Very good
5,228 reviews

Boarding

8.3

Crew

8.7

Overall

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,974 reviews
Southwest
8.2
Very good
5,228 reviews

Boarding

8.3

Crew

8.7

Overall

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,651 reviews
Southwest
8.2
Very good
5,228 reviews

Boarding

8.3

Crew

8.7

Overall

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • Can I find flights from Chicago Midway Airport to Puerto Rico for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Puerto Rico for under $200. The cheapest flight booked recently is on Frontier for just $128, but on average you can expect to pay $251.

  • Are there nonstop flights from Chicago Midway Airport to Puerto Rico for under $1,300 on Cheapflights?

    Cheapflights has at least 2 direct flights from Chicago Midway Airport to Puerto Rico under $1,300. A good price for a nonstop flight from Chicago Midway Airport to Puerto Rico is less than $1,279.

  • Are there last-minute flights available from Chicago Midway Airport to Puerto Rico for under $400?

    There are currently 3+ open flights from Chicago Midway Airport to Puerto Rico within the next 7 days for less than $400.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Puerto Rico one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Puerto Rico are Frontier ($83), Southwest ($110), and Delta ($162).

  • 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 $510, our data indicates the cheapest price to be $373. The most popular route (Chicago Midway - San Juan Luis Munoz Marin Intl), is priced around $129.

  • What does MDW to SJU mean?

    MDW stands for Chicago Midway Airport, while SJU stands for San Juan Luis Munoz Marin Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Aguadilla Borinquen Airport (BQN), Ponce Mercedita Airport (PSE), San Juan Isla Grande Airport (SIG), Vieques Airport (VQS), Culebra Airport (CPX).

  • Can I find deals for flights from Midway to Puerto Rico that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Puerto Rico flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Puerto Rico with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Puerto Rico flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Midway to Puerto Rico that allow pets onboard?

    Many airlines flying from Midway to Puerto Rico offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Puerto Rico?

    Yes, you can often find last-minute deals on Midway to Puerto Rico flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Puerto Rico flight deals updated?

    The Chicago Midway Airport to Puerto Rico flight deals you see on this page were last updated on 10/7.

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

    Currently, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $102). Flying from Chicago Midway Airport to Puerto Rico in July is currently the most expensive (average of $283). 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

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Alternative routes for Midway to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.

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Midway to Castries flights
O'Hare Intl to Pointe-à-Pitre flights
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O'Hare Intl to Kingstown flights
Midway to Georgetown 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 2,544,716 searches. Data last updated October 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$309FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$187Average$272FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$267Average$409FlexibilityNo cancel feeOn-time63%
DeltaCheapest$379Average$754FlexibilityNo cancel feeOn-timeN/A
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