HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Edit search

MDW - SJU
Sep 10 - Sep 17
San Juan

$63+ Cheap flights from Midway (MDW) to San Juan

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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Sep 10 — Sep 171
Tue 9/10
Tue 9/17
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Edit search

MDW - SJU
Sep 10 - Sep 17

Find cheap flights from Midway to San Juan 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.

The best prices from Chicago Midway to San Juan are usually found in October or September, 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 September 5, 2024.

Popular in

March

Cheapest in

October

Round-trip from

$128
(Frontier)

One-way from

$63
(Cheapflightsfares)
High demand for flights, 37% potential price rise
Search Deals
Best time to find cheap flights, 40% potential price drop
Search Deals
From Chicago Midway to San Juan
Search Deals
One-way flight from Chicago Midway to San Juan
Search Deals

Cheap Midway to San Juan flights in September & October 2024

Find cheap flight options from Midway to San Juan specifically for the months of September and October 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,924,376 searches. Prices were last updated on September 5, 2024.
The lowest fares we've come across on flights traveling from Chicago to San Juan in September and October 2024. Check back soon for alternative fares.
This Mytrip deal was found by Cheapflights users on 9/5. 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.
Thu 10/38:56 amMDW - SJU
1 stop6h 51mFrontier
Thu 10/105:06 pmSJU - MDW
1 stop21h 38mFrontier
Deal found 9/5$170
This Gotogate deal was found by Cheapflights users on 9/4. 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.
Sun 9/298:41 amMDW - SJU
1 stop22h 21mFrontier
Fri 10/43:03 amSJU - MDW
1 stop29h 43mFrontier
Deal found 9/4$172
This Trip.com deal was found by Cheapflights users on 9/5. 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.
Thu 10/106:54 pmMDW - SJU
1 stop7h 54mFrontier
Sat 10/122:50 amSJU - MDW
1 stop12h 05mFrontier
Deal found 9/5$173
This Trip.com deal was found by Cheapflights users on 9/3. 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.
Sun 10/68:41 amMDW - SJU
1 stop22h 21mFrontier
Fri 10/119:21 amSJU - MDW
1 stop10h 47mFrontier
Deal found 9/3$179
This Trip.com deal was found by Cheapflights users on 9/4. 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.
Sun 9/295:30 amMDW - SJU
1 stop21h 45mFrontier
Sun 10/68:30 pmSJU - MDW
1 stop11h 10mFrontier
Deal found 9/4$180
This CheapOair deal was found by Cheapflights users on 9/5. 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.
Sun 9/298:41 amMDW - SJU
1 stop22h 21mFrontier
Sun 10/68:30 pmSJU - MDW
1 stop11h 10mFrontier
Deal found 9/5$185
This CheapOair deal was found by Cheapflights users on 9/4. 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.
Sun 9/228:41 amMDW - SJU
1 stop22h 21mFrontier
Mon 9/309:21 amSJU - MDW
1 stop10h 47mFrontier
Deal found 9/4$186
This CheapOair deal was found by Cheapflights users on 9/4. 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.
Sun 9/228:41 amMDW - SJU
1 stop22h 21mFrontier
Fri 9/273:03 amSJU - MDW
1 stop29h 43mFrontier
Deal found 9/4$192
This Mytrip deal was found by Cheapflights users on 9/5. 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.
Thu 10/179:04 amMDW - SJU
1 stop15h 51mFrontier
Sun 10/205:52 pmSJU - MDW
1 stop22h 01mFrontier
Deal found 9/5$193

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 2,924,376 searches. Data last updated September 5, 2024.
The lowest fares we've come across on flights traveling from Chicago to San Juan in September and October 2024. Check back soon for alternative fares.
This Mytrip deal was found by Cheapflights users on 9/5. 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.
Thu 10/38:56 amMDW - SJU
1 stop6h 51mFrontier
Thu 10/105:06 pmSJU - MDW
1 stop21h 38mFrontier
Deal found 9/5$170
This Gotogate deal was found by Cheapflights users on 9/4. 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.
Sun 9/298:41 amMDW - SJU
1 stop22h 21mFrontier
Fri 10/43:03 amSJU - MDW
1 stop29h 43mFrontier
Deal found 9/4$172
This Trip.com deal was found by Cheapflights users on 9/5. 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.
Thu 10/106:54 pmMDW - SJU
1 stop7h 54mFrontier
Sat 10/122:50 amSJU - MDW
1 stop12h 05mFrontier
Deal found 9/5$173
This CheapOair deal was found by Cheapflights users on 9/4. 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.
Wed 11/1310:59 amMDW - SJU
1 stop12h 21mFrontier
Sun 11/179:09 pmSJU - MDW
1 stop15h 39mFrontier
Deal found 9/4$178
This Trip.com deal was found by Cheapflights users on 9/3. 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.
Sun 10/68:41 amMDW - SJU
1 stop22h 21mFrontier
Fri 10/119:21 amSJU - MDW
1 stop10h 47mFrontier
Deal found 9/3$179
This Trip.com deal was found by Cheapflights users on 9/4. 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.
Sun 9/295:30 amMDW - SJU
1 stop21h 45mFrontier
Sun 10/68:30 pmSJU - MDW
1 stop11h 10mFrontier
Deal found 9/4$180
This CheapOair deal was found by Cheapflights users on 9/5. 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.
Sun 9/298:41 amMDW - SJU
1 stop22h 21mFrontier
Sun 10/68:30 pmSJU - MDW
1 stop11h 10mFrontier
Deal found 9/5$185
This CheapOair deal was found by Cheapflights users on 9/4. 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.
Sun 9/228:41 amMDW - SJU
1 stop22h 21mFrontier
Mon 9/309:21 amSJU - MDW
1 stop10h 47mFrontier
Deal found 9/4$186
This CheapOair deal was found by Cheapflights users on 9/4. 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.
Sun 9/228:41 amMDW - SJU
1 stop22h 21mFrontier
Fri 9/273:03 amSJU - MDW
1 stop29h 43mFrontier
Deal found 9/4$192

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 2,924,376 searches. Data last updated September 5, 2024.
Book one of these great deals on flights from Chicago to San Juan. Users should examine the flight details to ensure there are no surprises.
This Trip.com deal was found by Cheapflights users on 9/4. 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 9/1110:45 amMDW - SJU
1 stop16h 30mFrontier
Wed 9/186:30 pmSJU - MDW
1 stop17h 12mFrontier
Deal found 9/4$214
This Trip.com deal was found by Cheapflights users on 9/4. 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.
Fri 9/136:59 pmMDW - SJU
1 stop8h 16mFrontier
Sat 10/58:30 pmSJU - MDW
1 stop15h 12mFrontier
Deal found 9/4$215
This Trip.com deal was found by Cheapflights users on 9/4. 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.
Fri 9/133:41 pmMDW - SJU
1 stop9h 15mFrontier
Fri 10/43:03 amSJU - MDW
1 stop29h 43mFrontier
Deal found 9/4$221
This Frontier deal was found by Cheapflights users on 9/5. 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.
Sat 9/142:53 pmMDW - SJU
1 stop12h 22mFrontier
Mon 9/239:21 amSJU - MDW
1 stop10h 47mFrontier
Deal found 9/5$228
This Trip.com deal was found by Cheapflights users on 9/4. 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.
Tue 9/1011:14 amMDW - SJU
1 stop16h 01mFrontier
Fri 9/208:30 pmSJU - MDW
1 stop18h 28mFrontier
Deal found 9/4$246
This Trip.com deal was found by Cheapflights users on 9/4. 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.
Tue 9/1011:14 amMDW - SJU
1 stop16h 01mFrontier
Thu 9/193:03 amSJU - MDW
1 stop12h 43mFrontier
Deal found 9/4$265
This Trip.com deal was found by Cheapflights users on 9/5. 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.
Tue 9/1011:14 amMDW - SJU
1 stop16h 01mFrontier
Thu 9/193:03 amSJU - MDW
1 stop12h 43mFrontier
Deal found 9/5$266
This Frontier deal was found by Cheapflights users on 9/4. 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.
Sat 9/142:53 pmMDW - SJU
1 stop12h 22mFrontier
Mon 9/169:21 amSJU - MDW
1 stop10h 47mFrontier
Deal found 9/4$288
This eDestinos deal was found by Cheapflights users on 9/4. 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.
Wed 9/1110:45 amMDW - SJU
2 stops33h 19mMultiple Airlines
Wed 9/187:00 amSJU - MDW
2 stops28h 42mMultiple Airlines
Deal found 9/4$289

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 2,924,376 searches. Data last updated September 5, 2024.
Take a look at some of the one-way flights we've detected from Chicago to San Juan. Users can also find round-trip Chicago to San Juan flights by using the search form above.
This Cheapflightsfares deal was found by Cheapflights users on 9/5. 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.
Thu 9/198:56 amMDW - SJU
1 stop6h 51mFrontier
Deal found 9/5$63
This Frontier deal was found by Cheapflights users on 9/5. 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 9/238:03 pmMDW - SJU
1 stop13h 25mFrontier
Deal found 9/5$64
This Mytrip deal was found by Cheapflights users on 9/5. 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.
Mon 9/308:03 pmMDW - SJU
1 stop13h 25mFrontier
Deal found 9/5$65
This Mytrip deal was found by Cheapflights users on 9/5. 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.
Mon 9/238:03 pmMDW - SJU
1 stop13h 25mFrontier
Deal found 9/5$66
This Trip.com deal was found by Cheapflights users on 9/5. 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.
Sat 9/212:53 pmMDW - SJU
1 stop12h 22mFrontier
Deal found 9/5$67
This Trip.com deal was found by Cheapflights users on 9/5. 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.
Thu 10/35:30 amMDW - SJU
1 stop21h 45mFrontier
Deal found 9/5$73
This Cheapflightsfares deal was found by Cheapflights users on 9/5. 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 10/46:59 pmMDW - SJU
1 stop8h 16mFrontier
Deal found 9/5$82
This Cheapflightsfares deal was found by Cheapflights users on 9/5. 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.
Thu 9/198:56 amMDW - SJU
1 stop6h 51mFrontier
Deal found 9/5$83
This Frontier deal was found by Cheapflights users on 9/5. 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.
Fri 9/202:42 pmMDW - SJU
1 stop7h 45mFrontier
Deal found 9/5$84

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 2,924,376 searches. Data last updated September 5, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$128 - $349

Route

Depart

Return

Price

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 11/9

1 stop11h 34m

San Juan Luis Munoz Marin Intl

Tue 11/12

1 stop9h 44m

$128

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/12

1 stop11h 54m

San Juan Luis Munoz Marin Intl

Sat 10/19

1 stop15h 14m

$133

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 10/1

1 stop16h 01m

San Juan Luis Munoz Marin Intl

Thu 10/3

1 stop12h 28m

$134

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Mon 9/23

1 stop13h 25m

San Juan Luis Munoz Marin Intl

Mon 9/30

1 stop10h 47m

$138

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/21

1 stop12h 22m

San Juan Luis Munoz Marin Intl

Thu 9/26

1 stop23h 38m

$139

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/14

1 stop12h 21m

San Juan Luis Munoz Marin Intl

Fri 11/15

1 stop8h 58m

$143

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Wed 11/6

2 stops9h 55m

San Juan Luis Munoz Marin Intl

Tue 11/12

2 stops8h 40m

$210

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 10/29

2 stops26h 59m

San Juan Luis Munoz Marin Intl

Sun 11/3

2 stops22h 43m

$251

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/9

1 stop10h 52m

San Juan Luis Munoz Marin Intl

Mon 12/16

1 stop11h 44m

$349

Flights are sorted by cheapest first

Deals found on 9/5

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.

Travel insights for flights from Midway to San Juan

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

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 August 30, 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.

Find deals

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

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $92). Flying from Chicago Midway Airport to San Juan 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 SJU?

Find hourly flight availability from Midway to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 5, 2024.

It’s typically best to fly out from Chicago Midway Airport to San Juan in the evening. Doing so could potentially save you 59% on the flight price compared to flying at noon, which is usually more expensive.

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 September 1, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to San Juan flight should consider departing on Friday afternoons when fares are most often at their lowest. Monday 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 San Juan?

Our users search for these airlines the most when looking for flights from Midway to San Juan. Data last updated on September 5, 2024.

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

Frontier

Frontier

From $119

Spirit Airlines

Spirit Airlines

From $187

Delta

Delta

From $379

Rainfall in San Juan by month

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

In terms of precipitation, rainfall in San Juan 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 San Juan when rainfall is around 2.2 in.

Temperature in San Juan by month

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

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 September 5, 2024.
Read reviews from past customers who have flown Frontier, Delta and Southwest from Chicago to San Juan. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Overall

8.2

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

Reviews

1 / 10

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

Southwest
8.2
Very good
5,383 reviews
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Overall

8.2

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

Reviews

1 / 10

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

Delta
8.0
Very good
9,185 reviews
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Overall

8.2

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

Reviews

1 / 10

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

Frontier
6.2
Okay
3,731 reviews
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Overall

8.2

Boarding

8.3

Food

7.3

Crew

8.7

Entertainment

7.8

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 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 $200 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to San Juan for under $200. The cheapest flight booked recently is on Frontier for just $128, but on average you can expect to pay $148.

  • 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 $128, 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 56% less than the average price by searching for this airline.

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

    $63 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $105 and $167, respectively.

  • 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 $63. The most popular route, (Chicago Midway - San Juan Luis Munoz Marin Intl), can usually be booked for $128.

  • 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), Vieques Airport (VQS), Culebra Airport (CPX), 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 9/5.

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

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $92). Flying from Chicago Midway Airport to San Juan 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

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.

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 2,924,376 searches. Data last updated September 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$271FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$187Average$268FlexibilityNo cancel feeOn-time65%
DeltaCheapest$379Average$754FlexibilityNo cancel feeOn-timeN/A
Los Angeles to San Diego flights
Los Angeles to Amsterdam flights
Dallas to London flights
Jacksonville to New York flights
USA to Spain flights
New York to Hawaii flights
San Diego to Las Vegas flights
USA to Singapore flights
USA to India flights
San Francisco to Newark Airport flights
Chicago to Kansas City flights
Chicago Midway Airport to Prague flights

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

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to San Salvador Ilopango
Flights to Abha
Flights to Puerto Natales Teniente J. Gallardo
Flights to Salalah
Flights to Zhanjiang
Flights to Dodge City Municipal
Flights to Caxias do Sul Campo dos Bugres
Flights to Udaipur Dabok
Flights to Tirgu Mures
Flights to Sorong Jefman
Flights to Skardu
Flights to La Romana
Flights to Balmaceda Teniente Vidal
Flights to Bishop
Flights to Brașov-Ghimbav Intl
Flights to Tawau
Flights to Ilhéus Jorge Amado
Flights to Limon
Flights to Tumbes
Flights to Scottsbluff Scotts Bluff County
Flights to Alpena Phelps/Collins
Flights to Rajahmundry
Flights to Riverton
Flights to Puerto Montt El Tepual
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.
View all available airlines