$117 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 10/21. 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
1 adult, Economy

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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Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Puerto Rico to Midway

Fri, Oct 10 - Tue, Oct 21
Frontier Logo
1:59 am - 7:25 amSJU-MDW
30h 26m1 stop
Frontier Logo
5:56 pm - 2:02 amMDW-SJU
31h 06m1 stop
$240Frontier
Find Deal
Fri, Oct 3 - Tue, Oct 7
Frontier Logo
8:00 am - 8:52 pmSJU-MDW
13h 52m2 stops
Frontier Logo
8:05 am - 2:30 amMDW-SJU
17h 25m2 stops
$249Frontier
Find Deal
Thu, Oct 2 - Tue, Oct 7
Frontier Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
Frontier Logo
8:05 am - 2:30 amMDW-SJU
17h 25m2 stops
$258Frontier
Find Deal
Fri, Oct 3 - Tue, Oct 7
Frontier Logo
3:39 am - 10:21 amSJU-MDW
7h 42m1 stop
Frontier Logo
8:05 am - 2:30 amMDW-SJU
17h 25m2 stops
$262Frontier
Find Deal
Tue, Sep 30 - Sat, Oct 4
Frontier Logo
9:26 pm - 3:58 pmSJU-MDW
19h 32m2 stops
Frontier Logo
6:15 am - 2:11 pmMDW-SJU
6h 56m1 stop
$265Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Frontier Logo
6:22 am - 11:46 pmSJU-MDW
18h 24m2 stops
Frontier Logo
10:33 am - 7:56 pmMDW-SJU
8h 23m1 stop
$268Frontier
Find Deal
Wed, Oct 1 - Sun, Oct 5
Frontier Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
Frontier Logo
6:20 am - 2:11 pmMDW-SJU
6h 51m1 stop
$269Frontier
Find Deal
Fri, Oct 24 - Mon, Oct 27
Frontier Logo
6:22 am - 11:46 pmSJU-MDW
18h 24m2 stops
Frontier Logo
6:15 am - 2:06 pmMDW-SJU
6h 51m1 stop
$270Frontier
Find Deal
Thu, Sep 25 - Fri, Oct 3
Frontier Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
Frontier Logo
6:21 am - 3:22 pmMDW-SJU
8h 01m1 stop
$272Frontier
Find Deal
Tue, Sep 30 - Thu, Oct 2
 Logo
9:26 pm - 3:58 pmSJU-MDW
19h 32m2 stops
 Logo
1:49 pm - 12:43 amMDW-SJU
9h 54m1 stop

Everything you should know

When to travel
December
Cheapest • 31% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$240
Overall average: $320
Frontier
Fri 10/10Tue 10/21
SJU - MDW • 1 stop
Cheapest non-stop
$1,029
Southwest
Sat 12/20Sat 12/27
SJU - MDW • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Booking Insights

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 $294 on average for return flights. On the other hand, the most expensive months are July and March, where the average cost of tickets from Puerto Rico is $544 and $504 respectively. For one-way flights, the best month to travel is December with an average price of $294.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$117
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 3% 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 $231. The cheapest price found on KAYAK in the last 2 weeks cost $191 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 $580 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 $610.

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

    Each week there are around 2,911 direct flights from within Puerto Rico to Chicago Midway Airport. The most common day for departures is Monday, with 15% 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 $231
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Reviews of the 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 4248 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

Was good. I miss the free 2 checked bags. That was part of what made Southwest special

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Valparaiso
Lansing
Munster
Chesterton
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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