$279 Find Cheap Flights from Costa Rica 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 Chicago departing on 10/7. 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 Costa Rica to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Costa Rica to Chicago 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 Costa Rica to Chicago

Tue, Sep 15 - Fri, Sep 25
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
$404Southwest
Mon, Sep 28 - Thu, Oct 1
Southwest Logo
9:00 am - 10:20 pm
SJO
-
MDW
12h 20m
2 stops
Southwest Logo
5:05 am - 12:00 pm
MDW
-
SJO
7h 55m
1 stop
$408Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$414Southwest
Tue, Sep 15 - Sun, Sep 20
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
7:10 am - 6:40 pm
MDW
-
SJO
12h 30m
2 stops
$415Southwest
Thu, Sep 17 - Tue, Sep 22
Southwest Logo
9:00 am - 9:55 pm
SJO
-
MDW
11h 55m
2 stops
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$419Southwest
Fri, Sep 18 - Thu, Sep 24
Southwest Logo
9:00 am - 9:00 pm
SJO
-
MDW
11h 00m
2 stops
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
1 stop
$420Southwest
Sat, Sep 12 - Tue, Sep 15
Southwest Logo
1:15 pm - 10:00 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
$430Southwest
Thu, Oct 8 - Tue, Oct 13
Southwest Logo
1:30 pm - 12:45 am
SJO
-
MDW
10h 15m
2 stops
Southwest Logo
8:35 pm - 6:00 am
MDW
-
SJO
10h 25m
1 stop
$435Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
9:00 am - 8:10 pm
SJO
-
MDW
10h 10m
2 stops
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$438Southwest
Tue, Sep 15 - Mon, Sep 21
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$439Southwest
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

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 Liberia, which takes 5h 19m, and San José, which takes 5h 30m.

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

There are around 270 direct flights from within Costa Rica to Chicago Midway Airport every day. Most flights depart in the morning, with 40% of flights departing in the morning.

Good to know

Cheapest flight$279
Most popular time to fly with an average 53% increase in price.
Flight from San José to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • How far is Chicago Midway Airport from central Chicago?

    You’ll need to travel 9 miles to reach the Chicago city center 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.

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

    Each week there are around 1,889 direct flights from within Costa Rica to Chicago Midway Airport. The most common day for departures is Monday, with 15% of flights taking off on this day.

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 Costa Rica to Chicago

 
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 Costa Rica 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 Chicago? 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 4237 reviews
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

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

Traveling to a place near Chicago?

Book flights to Chicago 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 Chicago

Information on the airport you'll fly into in Chicago