$93 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 8/30. 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

Thu, Sep 25 - Sun, Sep 28
Frontier Logo
3:21 pm - 11:25 pmSJU-MDW
9h 04m1 stop
Frontier Logo
6:21 am - 3:37 pmMDW-SJU
8h 16m1 stop
$226Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5
Frontier Logo
3:21 pm - 11:25 pmSJU-MDW
9h 04m1 stop
Frontier Logo
6:21 am - 3:37 pmMDW-SJU
8h 16m1 stop
$230Frontier
Find Deal
Sat, Aug 30 - Mon, Sep 1
Frontier Logo
3:21 pm - 11:11 pmSJU-MDW
8h 50m1 stop
Frontier Logo
8:10 am - 11:43 pmMDW-SJU
14h 33m1 stop
$240Frontier
Find Deal
Thu, Jun 26 - Wed, Jul 2
Southwest Logo
6:30 am - 1:15 pmSJU-MDW
7h 45m1 stop
Southwest Logo
11:15 am - 7:05 pmMDW-SJU
6h 50m1 stop
$327Southwest
Find Deal
Thu, Sep 11 - Tue, Sep 16
Delta Logo
12:55 pm - 9:44 pmSJU-MDW
9h 49m1 stop
Delta Logo
1:05 pm - 10:08 pmMDW-SJU
8h 03m1 stop
$331Delta
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Thu, Jul 31 - Mon, Aug 4
Southwest Logo
5:30 am - 1:00 pmSJU-MDW
8h 30m2 stops
Southwest Logo
2:10 pm - 11:10 pmMDW-SJU
8h 00m1 stop
$379Southwest
Find Deal
Tue, Jul 15 - Thu, Jul 17
Southwest Logo
6:30 am - 3:15 pmSJU-MDW
9h 45m2 stops
Southwest Logo
2:10 pm - 11:10 pmMDW-SJU
8h 00m1 stop
$387Southwest
Find Deal
Fri, Dec 5 - Mon, Dec 8
Southwest Logo
6:40 am - 2:05 pmSJU-MDW
9h 25m2 stops
Southwest Logo
7:10 am - 9:30 pmMDW-SJU
12h 20m1 stop
$391Southwest
Find Deal
Wed, Sep 10 - Sun, Sep 14
Delta Logo
2:40 pm - 9:26 pmSJU-MDW
7h 46m1 stop
Delta Logo
6:00 am - 1:23 pmMDW-SJU
6h 23m1 stop
$393Delta
Find Deal
Sat, Aug 30 - Tue, Sep 2
Delta Logo
2:40 pm - 9:12 pmSJU-MDW
7h 32m1 stop
Delta Logo
6:00 am - 4:36 pmMDW-SJU
9h 36m1 stop
$419Delta
Find Deal
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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 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. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$93
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 14% 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 $478. 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 1,798 direct flights from within Puerto Rico to Chicago Midway Airport. The most common day for departures is Friday, with 18% 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 $232
  • 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 4287 reviews
7.1Food
8.2Boarding
7.6Entertainment
8.0Comfort
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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