$84 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 11/15. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$196
Overall average: $299
Frontier
Thu 12/4Mon 12/8
SJU - MDW • 1 stop
Cheapest non-stop
$855
Southwest
Sat 12/27Sat 1/3
SJU - MDW • Non-stop
Top routes
BQN-MDW
Cheapest
SJU-MDW
Most popular
Insights
Insights
Insights
Insights
When to travel
December
Cheapest • 28% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
Flight Deals
Booking Insights
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

Thu, Dec 4 - Mon, Dec 8
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Frontier Logo
6:15 am - 3:11 pmMDW-SJU
6h 56m1 stop
$196Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Frontier Logo
8:42 pm - 6:23 pmMDW-SJU
19h 41m2 stops
$210Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
4:31 pm - 10:12 pmSJU-MDW
7h 41m1 stop
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$215Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
4:31 pm - 10:12 pmSJU-MDW
7h 41m1 stop
Frontier Logo
2:59 pm - 9:37 amMDW-SJU
16h 38m1 stop
$216Frontier
Find Deal
Sat, Nov 22 - Thu, Nov 27
Frontier Logo
3:59 am - 4:30 pmSJU-MDW
14h 31m1 stop
Frontier Logo
5:30 pm - 2:54 amMDW-SJU
7h 24m1 stop
$217Frontier
Find Deal
Wed, Dec 24 - Sat, Jan 3
Frontier Logo
4:16 pm - 10:12 pmSJU-MDW
7h 56m1 stop
Frontier Logo
2:24 pm - 2:39 amMDW-SJU
10h 15m1 stop
$223Frontier
Find Deal
Fri, Jan 23 - Tue, Feb 3
Delta Logo
7:30 am - 12:01 pmSJU-MDW
6h 31m1 stop
Delta Logo
12:48 pm - 8:57 pmMDW-SJU
6h 09m1 stop
$227Delta
Find Deal
Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Multiple Airlines Logo
2:16 pm - 7:50 pmMDW-SJU
27h 34m1 stop
$253Multiple Airlines
Find Deal
Thu, Dec 4 - Fri, Dec 12
Multiple Airlines Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Multiple Airlines Logo
2:59 pm - 11:25 pmMDW-SJU
30h 26m1 stop
$254Multiple Airlines
Find Deal
Fri, Dec 5 - Tue, Dec 9
Southwest Logo
9:40 am - 7:30 pmSJU-MDW
11h 50m1 stop
Southwest Logo
9:20 am - 11:20 pmMDW-SJU
12h 00m1 stop
$317Southwest
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.

The cheapest airline ticket to Chicago Midway Airport from the Puerto Rico in the last 72 hours was $84 one-way, and $196 round-trip on the route from Aguadilla to Chicago Midway Airport. The most popular route is from San Juan to Chicago Midway Airport and the cheapest ticket found on this route in the last 72 hours was $196 round-trip.

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 $299 on average for one-way flights. On the other hand, the most expensive months are July and April, where the average cost of tickets from Puerto Rico is $544 and $489 respectively. For return trips, the best month to travel is December with an average price of $299.

Good to know

Low seasonFebruary
Cheapest flight$84
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 17% 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?

    The cheapest airline ticket to Chicago Midway Airport from the Puerto Rico in the last 72 hours was $84 one-way, and $196 round-trip on the route from Aguadilla to Chicago Midway Airport. The most popular route is from San Juan to Chicago Midway Airport and the cheapest ticket found on this route in the last 72 hours was $196 round-trip.

  • How far is Chicago Midway Airport from central Chicago?

    Central Chicago is 9 miles away from Chicago Midway 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 2 direct flights each week.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Friday where tickets can be as cheap as $154. On the other hand, the most expensive day to fly is Saturday, where 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 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 $580.

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.

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 4242 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Traveling to a place near Midway?

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