$118 Find Cheap Flights from Puerto Rico to Chicago Midway Airport - Compare and Save

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 8/16. 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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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

Sun, Aug 23 - Thu, Aug 27
Southwest Logo
9:25 pm - 10:00 am
SJU
-
MDW
13h 35m
1 stop
Southwest Logo
1:00 pm - 10:50 pm
MDW
-
SJU
8h 50m
2 stops
$236Southwest
Wed, Aug 26 - Sat, Aug 29
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
$246Delta
Fri, Aug 21 - Sun, Aug 23
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
Southwest Logo
8:05 pm - 9:10 am
MDW
-
SJU
12h 05m
1 stop
$256Southwest
Wed, Aug 19 - Mon, Aug 24
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
$266Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
$276Delta
Fri, Aug 7 - Sun, Aug 9
Southwest Logo
8:55 pm - 8:55 am
SJU
-
MDW
13h 00m
1 stop
Southwest Logo
8:05 pm - 9:10 am
MDW
-
SJU
12h 05m
1 stop
$286Southwest
Wed, Aug 19 - Mon, Aug 24
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 1:42 pm
MDW
-
SJU
6h 37m
1 stop
$296Delta
Thu, Aug 6 - Tue, Aug 11
Southwest Logo
8:55 pm - 8:45 am
SJU
-
MDW
12h 50m
1 stop
Southwest Logo
12:20 pm - 9:05 pm
MDW
-
SJU
7h 45m
1 stop
$301Southwest
Sun, Jul 5 - Sun, Jul 12
Frontier Logo
3:10 am - 11:07 am
BQN
-
MDW
32h 57m
2 stops
Frontier Logo
6:05 am - 2:10 am
MDW
-
BQN
19h 05m
2 stops
$565Frontier
Sat, Jul 4 - Sun, Jul 12
Frontier Logo
12:19 pm - 10:03 pm
BQN
-
MDW
34h 44m
2 stops
Frontier Logo
6:05 am - 2:10 am
MDW
-
BQN
19h 05m
2 stops
$605Frontier
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 day to fly to Chicago?

The average price of all round-trip 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 Saturday where round-trip tickets can be as cheap as $616. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $616 on average.

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

The average price for all round-trip 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 afternoon, when round-trip flights cost $616 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 $616.

Good to know

Low seasonDecember
Cheapest flight$118
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 20% lower on average.
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 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.

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 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.
7.9
SouthwestOverall score based on 4235 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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
Schererville
Munster
Chesterton
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