$113 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 9/5. 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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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

Sat, Nov 1 - Sat, Nov 15
Frontier Logo
3:21 pm - 11:09 pmSJU-MDW
8h 48m1 stop
Frontier Logo
6:10 am - 3:15 pmMDW-SJU
7h 05m1 stop
$234Frontier
Find Deal
Sat, Aug 30 - Sat, Sep 6
Frontier Logo
8:23 pm - 8:22 amSJU-MDW
12h 59m1 stop
Frontier Logo
6:15 am - 2:11 pmMDW-SJU
6h 56m1 stop
$238Frontier
Find Deal
Wed, Oct 1 - Sat, Oct 4
Frontier Logo
1:06 pm - 7:11 amSJU-MDW
19h 05m1 stop
Frontier Logo
10:51 am - 2:34 amMDW-SJU
14h 43m1 stop
$239Frontier
Find Deal
Sat, Sep 27 - Mon, Sep 29
Frontier Logo
3:16 pm - 11:17 pmSJU-MDW
9h 01m1 stop
Frontier Logo
6:20 am - 2:11 pmMDW-SJU
6h 51m1 stop
$254Frontier
Find Deal
Sat, Aug 30 - Fri, Sep 5
Frontier Logo
8:23 pm - 8:22 amSJU-MDW
12h 59m1 stop
Frontier Logo
6:21 am - 3:22 pmMDW-SJU
8h 01m1 stop
$258Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
 Logo
3:19 pm - 4:43 pmSJU-MDW
26h 24m3 stops
 Logo
12:50 pm - 2:11 pmMDW-SJU
24h 21m3 stops
Thu, Sep 11 - Tue, Sep 16
Southwest Logo
1:20 pm - 10:30 pmSJU-MDW
10h 10m1 stop
Southwest Logo
7:40 am - 7:45 pmMDW-SJU
11h 05m1 stop
$351Southwest
Find Deal
Sat, Dec 6 - Wed, Dec 10
Southwest Logo
2:20 pm - 5:35 pmSJU-MDW
5h 15mnonstop
Southwest Logo
7:10 am - 9:30 pmMDW-SJU
12h 20m1 stop
$353Southwest
Find Deal
Thu, Oct 9 - Mon, Oct 13
Southwest Logo
5:50 am - 1:20 pmSJU-MDW
8h 30m2 stops
Southwest Logo
8:45 pm - 9:55 amMDW-SJU
12h 10m1 stop
$357Southwest
Find Deal
Sat, Sep 27 - Mon, Sep 29
Southwest Logo
2:20 pm - 8:45 pmSJU-MDW
7h 25m1 stop
Southwest Logo
1:45 pm - 11:30 pmMDW-SJU
8h 45m2 stops
$371Southwest
Find Deal
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 flight to Chicago Midway Airport?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Aguadilla, at $234 return. The most popular connection is from San Juan to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $234 in the last 3 days.

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 March and April, where the average cost of tickets from Puerto Rico is $504 and $489 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, which saves you about 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.


Good to know

Low seasonFebruary
Cheapest flight$113
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Aguadilla to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • What is the cheapest flight to Chicago Midway Airport?

    In the last 3 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Aguadilla, at $234 return. The most popular connection is from San Juan to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $234 in the last 3 days.

  • 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 $256. The cheapest price found on KAYAK in the last 2 weeks cost $162 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 1,562 direct flights from within Puerto Rico to Chicago Midway Airport. The most common day for departures is Friday, with 16% 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 $238
  • 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 4241 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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