$161 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 3/14. 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
$332
Multiple Airlines
Wed 3/11Wed 3/18
SJO - MDW • 2 stops
Cheapest one-way
$161
Multiple Airlines
Sat 3/14
SJO - MDW • 1 stop
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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 Chicago!
Flight Deals
Booking Insights
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

Wed, Mar 11 - Wed, Mar 18
Multiple Airlines Logo
3:05 pm - 1:41 pm
SJO
-
MDW
21h 36m
2 stops
Multiple Airlines Logo
11:19 am - 10:42 am
MDW
-
SJO
24h 23m
1 stop
$332Multiple Airlines
Fri, Mar 6 - Tue, Mar 10
Multiple Airlines Logo
12:35 pm - 8:53 pm
SJO
-
MDW
8h 18m
1 stop
Multiple Airlines Logo
7:30 am - 10:38 am
MDW
-
SJO
28h 08m
2 stops
$365Multiple Airlines
Thu, Apr 23 - Sun, Apr 26
Southwest Logo
9:00 am - 10:45 pm
SJO
-
MDW
12h 45m
2 stops
Southwest Logo
6:50 am - 1:00 pm
MDW
-
SJO
7h 10m
1 stop
$384Southwest
Thu, Feb 19 - Wed, Feb 25
Southwest Logo
1:45 pm - 10:25 pm
SJO
-
MDW
8h 40m
1 stop
Southwest Logo
5:00 am - 12:50 pm
MDW
-
SJO
7h 50m
1 stop
$395Southwest
Fri, Mar 6 - Tue, Mar 10
Southwest Logo
9:45 am - 7:05 pm
SJO
-
MDW
9h 20m
1 stop
Southwest Logo
6:00 am - 12:55 pm
MDW
-
SJO
7h 55m
1 stop
$406Southwest
Fri, May 1 - Sun, May 3
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
6:50 am - 1:00 pm
MDW
-
SJO
7h 10m
1 stop
$419Southwest
Fri, Feb 13 - Tue, Feb 17
LATAM Airlines Logo
7:00 am - 10:31 pm
SJO
-
MDW
15h 31m
1 stop
LATAM Airlines Logo
12:45 pm - 10:02 pm
MDW
-
SJO
9h 17m
1 stop
$423LATAM Airlines
Thu, Apr 23 - Sun, Apr 26
Southwest Logo
9:00 am - 10:45 pm
SJO
-
MDW
12h 45m
2 stops
Southwest Logo
5:00 am - 1:00 pm
MDW
-
SJO
9h 00m
2 stops
$427Southwest
Sat, Feb 28 - Wed, Mar 4
Southwest Logo
1:15 pm - 9:50 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
5:00 am - 12:50 pm
MDW
-
SJO
7h 50m
1 stop
$437Southwest
Fri, Feb 20 - Mon, Feb 23
LATAM Airlines Logo
2:25 pm - 10:31 pm
SJO
-
MDW
8h 06m
1 stop
LATAM Airlines Logo
6:00 am - 10:02 pm
MDW
-
SJO
16h 02m
1 stop
$441LATAM Airlines
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 24m.

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

There are around 251 direct flights from within Costa Rica to Chicago Midway Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 50% of flights departing in the morning.

Find deals

Good to know

Low seasonMarch
Cheapest flight$161
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 13% lower on average.
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 1,751 direct flights from within Costa Rica to Chicago Midway Airport. The most common day for departures is Sunday, with 17% 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.
8.0
SouthwestOverall score based on 4268 reviews
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
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 Chicago?

Book flights to Chicago 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 Chicago

Information on the airport you'll fly into in Chicago

Chicago Midway Airport (MDW)