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Cheap flights from Midway (MDW) to San Juan from $96

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 7/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — SJU
Jun 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
1 adult, Economy
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The best prices from Chicago Midway to San Juan are usually found in September or October, booked 40 days in advance, depart on a Sunday or Wednesday and return on a Friday

Cheap flight deals from Midway to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 6, 2024.

Popular in

March

Cheapest in

September

Round-trip from

$245

One-way from

$96
High demand for flights, 39% potential price rise
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Best time to find cheap flights, 30% potential price drop
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From Chicago Midway to San Juan
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One-way flight from Chicago Midway to San Juan
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What is the cheapest day to fly round-trip from Chicago Midway Airport to San Juan?

Flights from Chicago Midway Airport to San Juan are found to be more expensive on Wednesday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to San Juan.

How far in advance should I book a flight from Chicago Midway Airport to San Juan?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 57 days in advance, which can save you up to 25% on flights from Chicago Midway Airport to San Juan compared to booking the week you need them. Waiting 57 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $258. For sooner than that we have options available in the next 3 days from $283.

What is the cheapest month to fly from Chicago Midway Airport to San Juan?

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, October can be a great choice for travel to San Juan. Flights to San Juan from Chicago Midway Airport in October are about $319 on average during October, but can be found for as low as $90.

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

It’s typically best to fly out from Chicago Midway Airport to San Juan in the evening. Doing so could potentially save you 39% on the flight price compared to flying in the afternoon, which is usually more expensive.

Cheap Midway to San Juan flights in June & July 2024

Find cheap flight options from Midway to San Juan specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 6, 2024.
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Thu 7/1110:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$191
Tue 7/169:45 pmMDW - SJU
2 stops16h 08mFrontier
Thu 7/1810:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$201
Mon 7/85:14 pmMDW - SJU
1 stop7h 51mFrontier
Thu 7/115:27 amSJU - MDW
1 stop17h 19mFrontier
Deal found 6/6$212
Mon 7/85:14 pmMDW - SJU
1 stop7h 51mFrontier
Wed 7/103:03 amSJU - MDW
1 stop7h 17mFrontier
Deal found 6/6$213
Sat 6/297:49 amMDW - SJU
1 stop23h 51mFrontier
Tue 7/98:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 6/6$216
Mon 7/295:14 pmMDW - SJU
1 stop7h 51mFrontier
Tue 8/68:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 6/6$227
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Sat 7/1310:15 pmSJU - MDW
1 stop12h 30mFrontier
Deal found 6/6$230
Sat 6/2211:51 amMDW - SJU
1 stop13h 08mFrontier
Wed 6/2610:15 pmSJU - MDW
1 stop12h 16mFrontier
Deal found 6/5$231
Wed 7/109:31 amMDW - SJU
1 stop16h 41mFrontier
Wed 7/179:45 pmSJU - MDW
1 stop10h 00mFrontier
Deal found 6/5$236

Midway to San Juan 2024 flight deals

Discover exclusive flight deals for travel between Midway and San Juan in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Thu 7/1110:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$191
Thu 8/12:36 pmMDW - SJU
1 stop11h 36mFrontier
Wed 8/74:01 pmSJU - MDW
2 stops30h 59mFrontier
Deal found 6/6$196
Tue 7/169:45 pmMDW - SJU
2 stops16h 08mFrontier
Thu 7/1810:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$201
Mon 7/85:14 pmMDW - SJU
1 stop7h 51mFrontier
Thu 7/115:27 amSJU - MDW
1 stop17h 19mFrontier
Deal found 6/6$212
Mon 7/85:14 pmMDW - SJU
1 stop7h 51mFrontier
Wed 7/103:03 amSJU - MDW
1 stop7h 17mFrontier
Deal found 6/6$213
Sat 6/297:49 amMDW - SJU
1 stop23h 51mFrontier
Tue 7/98:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 6/6$216
Mon 7/295:14 pmMDW - SJU
1 stop7h 51mFrontier
Tue 8/68:41 pmSJU - MDW
1 stop12h 55mFrontier
Deal found 6/6$227
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Sat 7/1310:15 pmSJU - MDW
1 stop12h 30mFrontier
Deal found 6/6$230
Thu 8/83:45 pmMDW - SJU
1 stop13h 05mFrontier
Thu 8/157:00 amSJU - MDW
1 stop7h 59mFrontier
Deal found 6/6$231

Midway to San Juan flights leaving soon

Find last-minute flight options from Midway to San Juan 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 3,050,429 searches. Data last updated June 6, 2024.
Wed 6/128:27 amMDW - SJU
1 stop17h 41mFrontier
Tue 6/1811:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 6/4$247
Thu 6/132:36 pmMDW - SJU
1 stop11h 32mFrontier
Sun 6/168:41 pmSJU - MDW
1 stop11h 50mFrontier
Deal found 6/6$251
Tue 6/117:36 pmMDW - SJU
1 stop11h 33mFrontier
Sun 6/169:45 amSJU - MDW
1 stop15h 39mFrontier
Deal found 6/5$261
Wed 6/128:27 amMDW - SJU
1 stop17h 41mFrontier
Sat 6/225:57 pmSJU - MDW
1 stop16h 34mFrontier
Deal found 6/5$265
Wed 6/128:27 amMDW - SJU
1 stop17h 41mFrontier
Fri 6/218:41 pmSJU - MDW
1 stop12h 53mFrontier
Deal found 6/5$266
Wed 6/196:20 amMDW - SJU
1 stop18h 39mFrontier
Tue 6/258:41 pmSJU - MDW
1 stop11h 50mFrontier
Deal found 6/5$267
Tue 6/187:36 pmMDW - SJU
1 stop6h 32mFrontier
Sat 6/223:08 amSJU - MDW
1 stop7h 23mFrontier
Deal found 6/5$268
Sat 6/87:49 amMDW - SJU
1 stop16h 58mFrontier
Thu 6/138:41 pmSJU - MDW
1 stop11h 50mFrontier
Deal found 6/5$269
Wed 6/128:27 amMDW - SJU
1 stop17h 41mFrontier
Sat 6/153:08 amSJU - MDW
1 stop7h 23mFrontier
Deal found 6/5$271

One-way flights to San Juan from Midway

Search for one-way flight options from Midway to San Juan. 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 3,050,429 searches. Data last updated June 6, 2024.
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Deal found 6/6$96
Tue 7/169:45 pmMDW - SJU
2 stops16h 08mFrontier
Deal found 6/5$99
Wed 7/109:31 amMDW - SJU
1 stop16h 41mFrontier
Deal found 6/5$112
Tue 6/117:36 pmMDW - SJU
1 stop11h 33mFrontier
Deal found 6/5$126
Thu 8/1510:59 amMDW - SJU
1 stop12h 21mFrontier
Deal found 6/5$132
Wed 8/213:28 pmMDW - SJU
1 stop8h 57mFrontier
Deal found 6/5$135
Sat 6/2211:51 amMDW - SJU
1 stop13h 08mFrontier
Deal found 6/5$136
Fri 6/145:12 pmMDW - SJU
1 stop7h 47mFrontier
Deal found 6/5$139
Thu 6/132:36 pmMDW - SJU
1 stop11h 32mFrontier
Deal found 6/4$140

Find flights from Midway to San Juan within your budget

Customize your flight search to find flights from Midway 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, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$227 - $344

Route

Depart

Return

Price

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 7/9

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Tue 7/16

1 stop24h 26m

$227

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 7/9

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Sat 7/13

1 stop12h 30m

$230

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 6/22

1 stop13h 08m

San Juan Luis Munoz Marin Intl

Wed 6/26

1 stop12h 16m

$231

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Wed 7/10

1 stop16h 41m

San Juan Luis Munoz Marin Intl

Wed 7/17

1 stop10h 00m

$236

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Thu 7/4

1 stop11h 36m

San Juan Luis Munoz Marin Intl

Thu 7/11

1 stop17h 19m

$237

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 6/29

1 stop23h 51m

San Juan Luis Munoz Marin Intl

Wed 7/3

2 stops13h 18m

$239

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Thu 7/4

2 stops15h 26m

San Juan Luis Munoz Marin Intl

Wed 7/10

1 stop7h 17m

$244

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Wed 6/12

1 stop17h 41m

San Juan Luis Munoz Marin Intl

Tue 6/18

2 stops11h 20m

$247

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/20

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Sat 8/24

1 stop8h 27m

$344

Flights are sorted by cheapest first

Deals found on 6/6

How far ahead should I book a flight from Chicago Midway Airport to San Juan?

Use this chart to determine the optimal time to book a round-trip flight from Midway to San Juan. Price data was last updated on May 31, 2024.
The best time to book flights from Chicago Midway Airport to San Juan is 40 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Search Deals

What is the cheapest day to fly from Chicago Midway Airport to San Juan?

Use this chart to determine the cheapest time to fly round-trip from Midway to San Juan. Price data was last updated on June 2, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago Midway Airport to San Juan flight should consider departing on Saturday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from Midway to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan 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.

Temperature and rainfall in San Juan by month

Plan your trip to San Juan by taking into account the average temperature and rainfall totals by month.

SJU

Temperature

77 - 82.4 °F

If weather is an important factor for your trip to San Juan, 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 San Juan

Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated June 6, 2024.
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,368 reviews
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.2
Okay
3,985 reviews
Delta
8.0
Very good
10,368 reviews

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Midway to San Juan. 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 San Juan for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to San Juan for under $300. The cheapest flight booked recently is on Frontier for just $227, but on average you can expect to pay $252.

  • Are there last-minute flights available from Chicago Midway Airport to San Juan for under $300?

    There are currently 20+ open flights from Chicago Midway Airport to San Juan within the next 7 days for less than $300.

  • What is the cheapest airline to fly from Chicago Midway Airport to San Juan round-trip?

    Frontier, at $227, was found to be the cheapest airline from Chicago Midway Airport to San Juan.. You may be able to fly from Chicago Midway Airport to San Juan for 18% less than the average price by searching for this airline.

  • What are the cheapest flights from Chicago Midway Airport to San Juan?

    The cheapest flight price from Chicago Midway Airport to San Juan is $58. On average you can expect to pay $162. The most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), can usually be booked for $198.

  • What does MDW to SJU mean?

    This is defined as Chicago Midway Airport (MDW) and San Juan Luis Munoz Marin Intl Airport (SJU). Codes like San Juan Luis Munoz Marin Intl Airport are often used to just call airports uniquely. Ready for more IATA code knowledge? These are related airports for your current travel destination: Ponce Mercedita Airport (PSE), San Juan Isla Grande Airport (SIG), Culebra Airport (CPX), Vieques Airport (VQS), Ceiba J. Aponte de la Torre Airport (NRR).

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

    The amount of baggage you can bring on your Midway to San Juan 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 San Juan with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to San Juan 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 San Juan that include hotel bookings?

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

  • How can I find direct flights from Midway to San Juan?

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

  • Can I find deals for business class flights from Midway to San Juan?

    Yes. Cheapflights offers flight deals from Midway to San Juan 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 San Juan that allow pets onboard?

    Many airlines flying from Midway to San Juan 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 San Juan?

    Yes, you can often find last-minute deals on Midway to San Juan 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 San Juan flight deals updated?

    The Chicago Midway Airport to San Juan flight deals you see on this page were last updated on 6/6.

  • What are the most popular airlines that fly from Chicago Midway Airport to San Juan?

    The most popular airlines flying from Chicago Midway Airport to San Juan are Delta, Frontier and Spirit Airlines. Something to consider prior to booking your flight.

  • What is the cheapest month to book a flight from Chicago Midway Airport to San Juan?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $245). Flying from Chicago Midway Airport to San Juan in March is currently the most expensive (average of $338). 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

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

O'Hare Intl to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Ponce flights
O'Hare Intl to Mayagüez flights
O'Hare Intl to Culebra flights

Top 3 airlines flying from Midway to San Juan

Discover the top 3 airlines that operate flights from Midway to San Juan. 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 3,050,429 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$254FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$167Average$267FlexibilityNo cancel feeOn-time65%
DeltaCheapest$361Average$754FlexibilityNo cancel feeOn-timeN/A
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Search flights from Midway to San Juan by cabin class

Find flights from Midway to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Weekly flight availability from Midway to San Juan

Explore weekly flight availability from Midway to San Juan. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 6, 2024.
Sunday2daily flights
Monday1daily flight
Tuesday1daily flight
Wednesday1daily flight
Thursday1daily flight
Friday1daily flight
Saturday1daily flight

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