$99 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 2/12. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$190
Overall average: $425
Frontier
Wed 2/18Mon 2/23
SJU - MDW • 1 stop
Cheapest one-way
$99
Typical prices: $228-$343
Multiple Airlines
Thu 2/12
SJU - MDW • 1 stop
When to travel
December
Cheapest • 30% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Wed, Feb 18 - Mon, Feb 23
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m
1 stop
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m
1 stop
$190Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m
1 stop
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m
1 stop
$203Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m
1 stop
Frontier Logo
6:00 am - 3:02 pm
MDW
-
SJU
7h 02m
1 stop
$214Frontier
Wed, Feb 25 - Sun, Mar 1
Frontier Logo
3:53 am - 2:26 pm
SJU
-
MDW
12h 33m
1 stop
Frontier Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
$217Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
Frontier Logo
9:51 pm - 10:12 am
MDW
-
SJU
11h 21m
1 stop
$220Frontier
Wed, May 6 - Mon, May 11
Frontier Logo
3:08 am - 8:04 am
SJU
-
MDW
29h 56m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$222Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
$229Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 2:06 pm
MDW
-
SJU
27h 52m
1 stop
$232Frontier
Wed, Feb 11 - Mon, Feb 16
Frontier Logo
4:06 pm - 11:27 am
SJU
-
MDW
21h 21m
1 stop
Frontier Logo
6:00 am - 1:24 am
MDW
-
SJU
41h 24m
2 stops
$237Frontier
Thu, Apr 9 - Sun, Apr 12
Frontier Logo
6:07 pm - 2:01 pm
SJU
-
MDW
20h 54m
1 stop
Frontier Logo
9:20 am - 2:01 am
MDW
-
SJU
15h 41m
1 stop
$238Frontier
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 $302 on average for one-way flights. On the other hand, the most expensive months are July and January, where the average cost of tickets from Puerto Rico is $544 and $501 respectively. For return trips, the best month to travel is December with an average price of $302.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$99
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 13% 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 $393. The cheapest price found on KAYAK in the last 2 weeks cost $280 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 tickets can be as cheap as $154. On the other hand, the most expensive day to fly is Saturday, where prices are $610 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 in the afternoon, when flights cost $610 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.

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 $280
  • 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 airline 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 4267 reviews
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

Chicago Midway Airport (MDW)