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Midway

$96+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
1 adult, Economy
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Cheap 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 December 27, 2025.

This Priceline deal was found by Cheapflights users on 12/26. 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.
Sun 12/283:54 amSJU - MDW
1 stop12h 11mFrontier
Sat 1/106:10 amMDW - SJU
1 stop8h 11mFrontier
Deal found 12/26$372
This Frontier deal was found by Cheapflights users on 12/25. 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.
Wed 12/314:16 pmSJU - MDW
1 stop7h 56mFrontier
Mon 1/58:15 amMDW - SJU
1 stop12h 00mFrontier
Deal found 12/25$393
This Frontier deal was found by Cheapflights users on 12/25. 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 12/283:54 amSJU - MDW
1 stop12h 11mFrontier
Fri 1/94:31 pmMDW - SJU
1 stop8h 19mFrontier
Deal found 12/25$407
This Frontier deal was found by Cheapflights users on 12/25. 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.
Fri 12/267:30 amSJU - MDW
1 stop7h 51mFrontier
Mon 1/53:10 pmMDW - SJU
1 stop9h 40mFrontier
Deal found 12/25$413
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/294:21 pmSJU - MDW
1 stop7h 51mFrontier
Thu 1/1511:27 amMDW - SJU
1 stop6h 32mFrontier
Deal found 12/26$422
This Frontier deal was found by Cheapflights users on 12/25. 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.
Mon 12/294:21 pmSJU - MDW
1 stop7h 51mFrontier
Fri 1/28:15 amMDW - SJU
1 stop12h 29mFrontier
Deal found 12/25$427
This CheapOair deal was found by Cheapflights users on 12/25. 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.
Wed 12/314:16 pmSJU - MDW
1 stop7h 56mFrontier
Sun 1/42:16 pmMDW - SJU
1 stop10h 34mFrontier
Deal found 12/25$428
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:30 amSJU - MDW
1 stop11h 50mDelta
Sun 1/46:00 amMDW - SJU
1 stop9h 30mDelta
Deal found 12/26$435
This Frontier deal was found by Cheapflights users on 12/25. 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.
Mon 12/294:21 pmSJU - MDW
1 stop7h 51mFrontier
Sat 1/32:16 pmMDW - SJU
1 stop10h 34mFrontier
Deal found 12/25$459
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:19 pmSJU - MDW
1 stop7h 53mFrontier
Sun 1/46:00 amMDW - SJU
1 stop7h 01mFrontier
Deal found 12/26$471
This Frontier deal was found by Cheapflights users on 12/26. 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.
Sun 12/284:21 pmSJU - MDW
1 stop7h 51mFrontier
Sat 1/32:16 pmMDW - SJU
1 stop10h 34mFrontier
Deal found 12/26$479

Find 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 December 27, 2025.

Round-trip from

$180
(Expedia)

One-way from

$96
(Priceline)

Popular in

July

Cheapest in

December

Average price

$297
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. 11% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 27, 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 1/29

4:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

Mon 2/2

1:00 pm-11:59 pm

1 stop8h 59m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

4:25 pm-2:26 pm

1 stop24h 01m

Chicago Midway

Mon 2/23

9:22 pm-12:43 am

1 stop25h 21m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/15

9:04 pm-9:09 am

1 stop14h 05m

Chicago Midway

Mon 1/19

6:10 am-3:27 pm

1 stop7h 17m

$199

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 1/11

10:47 pm-2:06 pm

1 stop17h 19m

Chicago Midway

Thu 1/15

11:27 am-2:48 am

1 stop13h 21m

$215

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-10:29 pm

1 stop8h 18m

Chicago Midway

Wed 3/11

11:19 am-10:45 pm

1 stop10h 26m

$218

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 1/13

4:35 pm-10:19 pm

1 stop7h 44m

Chicago Midway

Wed 1/21

1:20 pm-6:58 pm

2 stops27h 38m

$280

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 1/13

6:10 am-11:35 am

1 stop7h 25m

Chicago Midway

Wed 1/21

9:50 am-11:10 pm

1 stop11h 20m

$295

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/22

6:10 am-1:55 pm

2 stops9h 45m

Chicago Midway

Sun 1/25

3:15 pm-12:40 am

1 stop7h 25m

$295

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

11:52 am-6:54 pm

1 stop9h 02m

Chicago Midway

Mon 1/19

9:09 pm-3:26 pm

2 stops16h 17m

$296

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 1/25

4:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

Sun 2/1

1:00 pm-1:08 am

1 stop10h 08m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/24

Showing 1-10 of 21 results
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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

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

Currently, December is the cheapest month in which you can book a flight from San Juan to Chicago Midway Airport (average of $137). Flying from San Juan to Chicago Midway Airport in March is currently the most expensive (average of $427). 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 December 27, 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 59% on your trip compared to booking a flight at noon.

How much does it cost to fly round-trip from San Juan to Chicago Midway Airport?

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 December 27, 2025.
Read reviews from past customers who have flown Southwest from San Juan to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,258 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,258 reviews
Southwest
8.0
Very good
4,258 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from San Juan to Chicago Midway Airport?

    There are many flights that can get you from San Juan to Chicago Midway Airport in 7h 57m. Fly via Frontier to get the fastest option. San Juan and Chicago Midway Airport are separated by a distance of 2057 mi.

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

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $419.

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

    Looking at all options, your cheapest flight can be booked for $250. While the most popular route (San Juan Luis Munoz Marin Intl - Chicago Midway) can be booked for $183 on average, our data indicates $406 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, December is the cheapest month in which you can book a flight from San Juan to Chicago Midway Airport (average of $137). Flying from San Juan to Chicago Midway Airport in March is currently the most expensive (average of $427). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from San Juan to Midway

Discover the top airline 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 December 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$419Average$566FlexibilityNo cancel feeOn-time63%

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