$137 Find Cheap Flights from Puerto Rico to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 6/3. 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.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flight Deals from Puerto Rico to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Puerto Rico to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Puerto Rico to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Puerto Rico to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
6:00 am - 5:30 pmSJU-MDW
12h 30m1 stop
Frontier Logo
1:19 pm - 10:01 pmMDW-SJU
7h 42m1 stop
$298Frontier
Find Deal
Sun, May 11 - Fri, May 16
Frontier Logo
3:56 am - 12:24 pmSJU-MDW
9h 28m1 stop
Frontier Logo
12:15 pm - 1:50 amMDW-SJU
12h 35m1 stop
$299Frontier
Find Deal
Thu, May 15 - Mon, May 19
Frontier Logo
3:56 am - 5:30 pmSJU-MDW
14h 34m1 stop
Frontier Logo
6:15 am - 2:47 pmMDW-SJU
7h 32m1 stop
$303Frontier
Find Deal
Sat, May 10 - Mon, May 12
Frontier Logo
6:00 am - 12:24 pmSJU-MDW
7h 24m1 stop
Frontier Logo
6:15 am - 2:47 pmMDW-SJU
7h 32m1 stop
$304Frontier
Find Deal
Fri, May 16 - Mon, May 19
Delta Logo
2:39 pm - 9:47 pmSJU-MDW
8h 08m1 stop
Delta Logo
6:00 am - 4:50 pmMDW-SJU
9h 50m1 stop
$391Delta
Find Deal
Thu, Aug 28 - Tue, Sep 2
Southwest Logo
1:20 pm - 10:30 pmSJU-MDW
10h 10m1 stop
Southwest Logo
7:30 am - 2:55 pmMDW-SJU
6h 25m1 stop
$397Southwest
Find Deal
Thu, Sep 11 - Tue, Sep 16
Southwest Logo
5:50 am - 2:00 pmSJU-MDW
9h 10m2 stops
Southwest Logo
6:05 am - 3:10 pmMDW-SJU
8h 05m1 stop
$418Southwest
Find Deal
Thu, Aug 28 - Mon, Sep 1
Delta Logo
1:06 pm - 9:41 pmSJU-MDW
9h 35m1 stop
Delta Logo
6:00 am - 4:50 pmMDW-SJU
9h 50m1 stop
$429Delta
Find Deal
Fri, Aug 8 - Mon, Aug 11
 Logo
1:59 am - 2:04 pmSJU-MDW
13h 05m2 stops
 Logo
9:12 am - 12:54 amMDW-SJU
38h 42m3 stops
Thu, May 22 - Mon, May 26
 Logo
4:46 pm - 2:04 pmSJU-MDW
22h 18m2 stops
 Logo
4:27 pm - 9:56 amMDW-SJU
40h 29m3 stops
Thu, Jul 17 - Wed, Aug 6
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KAYAK's insights & trends for flights to Midway

Get data-powered insights and trends for flights to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago Midway Airport is December, where tickets cost $252 on average for return flights. On the other hand, the most expensive months are June and March, where the average cost of tickets from Puerto Rico is $510 and $504 respectively. For one-way flights, the best month to travel is December with an average price of $252.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$137
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from San Juan to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • How far is Chicago Midway Airport from central Chicago?

    Central Chicago is 9 miles away from Chicago Midway Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $310. The cheapest price found on KAYAK in the last 2 weeks cost $132 and departed from San Juan Luis Munoz Marin Intl Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Friday where round-trip tickets can be as cheap as $154. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $610 on average.

  • How does KAYAK find such low prices on flights to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago Midway Airport?

    The cheapest time of day to fly to Chicago Midway Airport is generally at night, when round-trip flights cost $237 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $614.

  • How many direct flights to Chicago Midway Airport are there each week?

    Each week there are around 1,486 direct flights from within Puerto Rico to Chicago Midway Airport. The most common day for departures is Sunday, with 19% of flights taking off on this day.

Top tips for finding cheap flights to Chicago Midway Airport

  • Looking for cheap airfare to Chicago Midway Airport? 25% of our users found round-trip tickets to Chicago Midway Airport for the following prices or less: From San Juan Luis Munoz Marin Intl $244
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Top airlines flying from Puerto Rico to Midway

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Puerto Rico to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4294 reviews
8.2Boarding
8.6Crew
7.1Food
7.6Entertainment
8.0Comfort
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

I guess you get what you pay for. The seats are very uncomfortable and very little space. The snacks were pricey.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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