HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$120+ Cheap flights from San Juan to Midway (MDW)

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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San Juan to Midway 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.

Cheapflights Tip: The best prices from San Juan to Chicago Midway are usually found in December or September, booked 45 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from San Juan to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Midway (MDW). 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 12, 2025.

Round-trip from

$203
(Priceline)

One-way from

$120
(Priceline)

Popular in

March

Cheapest in

December

Average price

$456
From San Juan to Chicago Midway
Search Deals
One-way flight from San Juan to Chicago Midway
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from San Juan to Midway

Cheapest flights from San Juan to Midway
Explore the most affordable flight options available from San Juan to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Priceline deal was found by Cheapflights users on 6/12. 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.
Thu 9/111:11 amSJU - MDW
1 stop7h 09mFrontier
Sun 9/218:15 amMDW - SJU
1 stop14h 43mFrontier
Deal found 6/12$203
This Delta deal was found by Cheapflights users on 6/12. 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.
Thu 9/1112:55 pmSJU - MDW
1 stop9h 49mDelta
Tue 9/1610:35 amMDW - SJU
1 stop10h 33mDelta
Deal found 6/12$331
This Southwest deal was found by Cheapflights users on 6/10. 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 7/315:30 amSJU - MDW
2 stops8h 30mSouthwest
Mon 8/42:10 pmMDW - SJU
1 stop8h 00mSouthwest
Deal found 6/10$379

Cheapflights Fare Finder

Customize your flight search to find flights from San Juan to Midway 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 June 12, 2025.
Use the filters below to find and compare flights from San Juan to Chicago Midway Airport that are best for you.

Fly from

San Juan

Fly to

Midway

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

1:11 am-7:20 am

1 stop7h 09m

Chicago Midway

Sun 9/21

8:15 am-11:58 pm

1 stop14h 43m

$203

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 6/26

6:30 am-1:15 pm

1 stop7h 45m

Chicago Midway

Wed 7/2

11:15 am-7:05 pm

1 stop6h 50m

$327

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

12:55 pm-9:44 pm

1 stop9h 49m

Chicago Midway

Tue 9/16

10:35 am-10:08 pm

1 stop10h 33m

$331

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 8/24

3:59 am-3:29 pm

1 stop12h 30m

$120

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 7/17

10:50 am-8:20 pm

2 stops10h 30m

$164

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/6

7:30 am-3:28 pm

1 stop8h 58m

$191

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 7/9

2:40 am-9:41 am

3 stops32h 01m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Best time to book a flight from San Juan to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San Juan 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 San Juan to Chicago Midway Airport

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

Use this chart to determine the optimal time to book a round-trip flight from San Juan to Midway. Price data was last updated on June 9, 2025.

The best time to book flights from San Juan to Chicago Midway Airport is 44 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.

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

Currently, April is the cheapest month in which you can book a flight from San Juan to Chicago Midway Airport (average of $160). Flying from San Juan to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 SJU to MDW?

Find hourly flight availability from San Juan to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

A simple way to save on the total cost of your ticket is to fly from San Juan to Chicago Midway Airport in the evening. If you’re flexible enough to do this you can expect to save up to 62% on your trip compared to booking a flight at noon.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier from San Juan to Chicago 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
4,287 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

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

  • What are the cheapest airlines flying from San Juan to Chicago Midway Airport round-trip?

    Flying on Frontier is currently your cheapest option to Chicago Midway Airport, with prices starting at $203. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $327 and $331, respectively. You may be able to fly from San Juan to Chicago Midway Airport for 47% less than the average price by searching for these airlines.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $120. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from San Juan to Chicago Midway Airport for a low price.

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

    Looking at all options, your cheapest flight can be booked for $191. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway) can be booked for $240 on average our data indicates $422 when flying from San Juan to Chicago Midway Airport.

  • Can I find deals for flights from San Juan to Midway that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from San Juan to Midway 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 San Juan to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from San Juan to Chicago Midway Airport (average of $160). Flying from San Juan to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near San Juan?

Book flights to San Juan if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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 2 airlines flying from San Juan to Midway

Discover the top 2 airlines that operate flights from San Juan to Midway. 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$234FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$312Average$446FlexibilityNo 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.