Find flights
Insights
When to book
FAQs & Tips
Direct Flights
Airlines
Deals

Find cheap flights from Puerto Rico to Chicago Midway Airport from $73

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 5/22. 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
0 bags
Thu 6/6
Thu 6/13

Search 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
In the last 7 days travelers have searched 43,707,506 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Flights to Midway - Travel Insights & Trends

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 day to fly to Chicago?

The average price of all flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where tickets can be as cheap as $212. On the other hand, the most expensive day to fly is Monday, where prices are $322 on average.

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 September, where tickets cost $165 on average for one-way flights. On the other hand, the most expensive months are April and March, where the average cost of tickets from Puerto Rico is $329 and $288 respectively. For return trips, the best month to travel is September with an average price of $165.

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

The average price for all flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago Midway Airport is generally in the evening, when flights cost $181 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 $258.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
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 70 days before departure.

Which airline offers the most flights to Chicago Midway Airport?

Of the 5 airlines that fly to Chicago Midway Airport, Southwest offers the most flights, with around 2,686 per week, followed by Frontier with 110 flights per week.

How long is the flight to Chicago Midway Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from San Juan, which takes 5h 08m, Culebra, which takes 11h 09m, and Aguadilla, which takes 16h 17m.

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

There are around 418 direct flights from within Puerto Rico to Chicago Midway Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 45% of flights departing in the morning.

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

Each week there are around 2,923 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.

How many long-haul flights are there to Chicago Midway Airport each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago Midway Airport. Instead, there are 3 medium-haul flights (3-6 hour flight duration), with the most arriving from San Juan Luis Munoz Marin Intl Airport.

How many cities have direct flights to Chicago Midway Airport?

From Puerto Rico, there are direct flights to Chicago Midway Airport from 1 city. This city is San Juan Luis Munoz Marin Intl Airport and there are 3 direct flights each week.

Good to know

Low season

March

High season

December

Cheapest flight

$73
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly with an average 4% 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 $122. The cheapest price found on KAYAK in the last 2 weeks cost $75 and departed from San Juan Luis Munoz Marin Intl Airport.

  • 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.

See more FAQs

Top tips for finding cheap flights to Chicago Midway Airport

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Prefer to fly non-stop to Chicago Midway?

Find which airlines fly direct to Midway, which days they fly and book direct flights.

Nonstop departures

Puerto Rico to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights

Nonstop returns

Chicago Midway to Puerto Rico

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights
See more direct flights

Top 3 airlines serving 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
DeltaOverall score based on 10810 reviews
8.2Boarding
8.0Entertainment
7.4Food
7.9Comfort
8.6Crew
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

The flight was fine. The itinerary change from original booking was not good. We were originally leaving at 12:50 pm. The change to 8:29pm put us getting home in the early morning hours the next day. Then having to wait over an hour on the ground for a parking place to get off the plane was exhausting.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

Book cheap flights from Puerto Rico to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
5/17Fri
1 stopFrontier
10h 03mSJU-MDW
5/20Mon
1 stopFrontier
12h 21mMDW-SJU
$175
5/17Fri
1 stopFrontier
10h 03mSJU-MDW
5/20Mon
1 stopFrontier
12h 21mMDW-SJU
$178
5/18Sat
1 stopFrontier
9h 36mSJU-MDW
5/21Tue
1 stopFrontier
11h 49mMDW-SJU
$180
5/17Fri
1 stopFrontier
10h 03mSJU-MDW
5/21Tue
1 stopFrontier
12h 38mMDW-SJU
$186
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
5/28Tue
1 stopFrontier
12h 38mMDW-SJU
$211
8/20Tue
1 stopFrontier
13h 46mSJU-MDW
9/4Wed
1 stopFrontier
11h 34mMDW-SJU
$214
8/17Sat
1 stopDelta
9h 59mSJU-MDW
8/20Tue
1 stopDelta
10h 58mMDW-SJU
$473
10/17Thu
1 stopDelta
9h 50mSJU-MDW
10/20Sun
1 stopDelta
9h 04mMDW-SJU
$604
10/22Tue
1 stopDelta
8h 19mSJU-MDW
10/26Sat
1 stopDelta
10h 52mMDW-SJU
$619
5/21Tue
3 stops
16h 18mSJU-MDW
5/29Wed
2 stops
15h 25mMDW-SJU
$697

Search by stops

Search by airline

Search by price

Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
$73
5/15Wed
1 stopFrontier
9h 53mSJU-MDW
$109
5/14Tue
1 stopFrontier
28h 46mSJU-MDW
$119
5/16Thu
1 stopFrontier
29h 30mSJU-MDW
$120
5/14Tue
1 stopFrontier
27h 46mSJU-MDW
$128
5/14Tue
1 stopFrontier
9h 49mSJU-MDW
$129
5/29Wed
3 stops
31h 51mSJU-MDW
$295
6/8Sat
1 stopDelta
9h 56mSJU-MDW
$452
6/8Sat
1 stopDelta
9h 56mSJU-MDW
$467
5/20Mon
1 stopDelta
8h 25mSJU-MDW
$1,027

Search by stops

Search by airline

Search by price

Last minute flights to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
5/9Thu
multi-stopFrontier
9h 49mSJU-MDW
5/14Tue
multi-stopFrontier
10h 16mMDW-SJU
$277
5/8Wed
multi-stopFrontier
9h 44mSJU-MDW
5/13Mon
multi-stopFrontier
9h 12mMDW-SJU
$278
5/11Sat
multi-stopFrontier
8h 50mSJU-MDW
5/18Sat
multi-stopFrontier
8h 35mMDW-SJU
$279
5/12Sun
multi-stopFrontier
20h 28mSJU-MDW
5/15Wed
multi-stopFrontier
12h 27mMDW-SJU
$284
5/8Wed
multi-stopFrontier
9h 53mSJU-MDW
5/15Wed
multi-stopFrontier
12h 31mMDW-SJU
$298
5/8Wed
multi-stopFrontier
9h 53mSJU-MDW
5/15Wed
multi-stopFrontier
9h 38mMDW-SJU
$299
5/9Thu
multi-stopFrontier
20h 23mSJU-MDW
5/13Mon
multi-stopFrontier
21h 28mMDW-SJU
$303
5/8Wed
multi-stopFrontier
9h 44mSJU-MDW
5/14Tue
multi-stopFrontier
10h 16mMDW-SJU
$306
5/11Sat
multi-stopDelta
7h 06mSJU-MDW
5/14Tue
multi-stopDelta
13h 20mMDW-SJU
$3,248
5/8Wed
multi-stopDelta
10h 12mSJU-MDW
5/15Wed
multi-stopDelta
13h 20mMDW-SJU
$3,795

Search by stops

Search by airline

Search by price

Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Puerto Rico

Cabin classes:

$141