HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$85+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MDW
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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.

The best prices from San Juan to Chicago Midway are usually found in January or February, booked 41 days in advance, depart on a Sunday or Tuesday and return on a Sunday

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 November 21, 2024.

Popular in

November

Cheapest in

January

Round-trip from

$158
(FlightHub)

One-way from

$85
(Mytrip)
High demand for flights, 25% potential price rise
Search Deals
Best time to find cheap flights, 27% potential price drop
Search Deals
From San Juan to Chicago Midway
Search Deals
One-way flight from San Juan to Chicago Midway
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 November 21, 2024.

This FlightHub deal was found by Cheapflights users on 11/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/65:03 pmSJU - MDW
1 stop9h 17mFrontier
Mon 12/97:25 amMDW - SJU
1 stop16h 32mFrontier
Deal found 11/21$158
This eDestinos deal was found by Cheapflights users on 11/20. 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.
Fri 12/65:25 amSJU - MDW
2 stops17h 37mMultiple Airlines
Mon 12/98:15 amMDW - SJU
2 stops31h 28mMultiple Airlines
Deal found 11/20$238
This Southwest deal was found by Cheapflights users on 11/20. 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 12/126:10 amSJU - MDW
2 stops12h 55mSouthwest
Mon 12/1611:55 amMDW - SJU
2 stops10h 50mSouthwest
Deal found 11/20$312
This Delta deal was found by Cheapflights users on 11/20. 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 12/57:30 amSJU - MDW
1 stop10h 45mDelta
Tue 12/106:00 amMDW - SJU
1 stop9h 15mDelta
Deal found 11/20$404

Find flights from San Juan to Midway within your budget

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/6

5:03 pm-12:20 am

1 stop9h 17m

Chicago Midway

Mon 12/9

7:25 am-1:57 am

1 stop16h 32m

$158

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/23

4:50 pm-6:01 pm

1 stop27h 11m

Chicago Midway

Mon 1/27

6:15 am-3:19 pm

2 stops31h 04m

$200

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/12

6:10 am-2:15 pm

1 stop10h 05m

Chicago Midway

Mon 12/16

11:55 am-12:45 am

2 stops10h 50m

$312

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 1/15

7:30 am-4:21 pm

1 stop10h 51m

Chicago Midway

Wed 1/22

12:44 pm-11:45 pm

1 stop9h 01m

$324

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 2/2

9:49 pm-10:28 am

1 stop14h 39m

$85

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 1/14

6:00 am-11:45 am

1 stop7h 45m

$105

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/11

2:45 am-5:18 pm

2 stops16h 33m

$132

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 1/15

7:30 am-4:21 pm

1 stop10h 51m

$162

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 1/6

7:58 pm-8:41 am

1 stop14h 43m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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.

Travel insights for flights from San Juan to Midway

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

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 November 15, 2024.

The best time to book flights from San Juan to Chicago Midway Airport is 41 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 October is currently the most expensive (average of $232). 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 November 21, 2024.

A simple way to save on the total cost of your ticket is to fly from San Juan to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 41% on your trip compared to booking a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from San Juan to Midway. Price data was last updated on November 18, 2024.

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

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 November 21, 2024.
Peruse reviews from past customers who have flown with Frontier, Southwest and Delta 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
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

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

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

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

Frontier
6.1
Okay
3,536 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

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 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 $158. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $210 and $324, respectively. You may be able to fly from San Juan to Chicago Midway Airport for 46% 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 $85. 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.

  • 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 October is currently the most expensive (average of $232). 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 San Juan to Midway

Discover the top 3 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$253FlexibilityNo cancel feeOn-time62%
DeltaCheapest$249Average$509FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$384FlexibilityNo 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.
View all available airlines