$142 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 12/6. 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

Fri, Nov 7 - Sun, Nov 16
Delta Logo
2:15 pm - 10:14 pmSJO-MDW
7h 59m1 stop
Delta Logo
10:47 am - 10:07 pmMDW-SJO
11h 20m1 stop
$331Delta
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Thu, Feb 5 - Sun, Feb 22
Delta Logo
7:00 am - 9:46 pmSJO-MDW
14h 46m1 stop
Delta Logo
9:30 am - 10:15 pmMDW-SJO
12h 45m2 stops
$333Delta
Find Deal
Sat, Dec 6 - Mon, Dec 8
Delta Logo
7:00 am - 6:06 pmSJO-MDW
11h 06m2 stops
Delta Logo
9:34 am - 10:20 pmMDW-SJO
12h 46m2 stops
$339Delta
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Wed, Nov 12 - Sat, Nov 15
Delta Logo
2:31 pm - 11:40 pmSJO-MDW
9h 09m1 stop
Delta Logo
9:32 am - 10:07 pmMDW-SJO
12h 35m2 stops
$341Delta
Find Deal
Sat, Jan 24 - Wed, Jan 28
Delta Logo
7:00 am - 3:25 pmSJO-MDW
8h 25m1 stop
Delta Logo
1:05 pm - 10:15 pmMDW-SJO
9h 10m1 stop
$343Delta
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Thu, Nov 27 - Mon, Dec 1
Multiple Airlines Logo
1:20 pm - 2:40 pmSJO-MDW
25h 20m2 stops
Multiple Airlines Logo
5:47 pm - 10:19 amMDW-SJO
16h 32m1 stop
$367Multiple Airlines
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Tue, Jan 20 - Tue, Jan 27
Southwest Logo
9:40 am - 10:55 pmSJO-MDW
13h 15m1 stop
Southwest Logo
8:55 am - 7:30 pmMDW-SJO
10h 35m1 stop
$369Southwest
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Thu, Dec 11 - Sun, Dec 14
Multiple Airlines Logo
7:45 am - 9:53 pmSJO-MDW
14h 08m1 stop
Multiple Airlines Logo
2:01 pm - 11:42 amMDW-SJO
21h 41m2 stops
$370Multiple Airlines
Find Deal
Tue, Jan 20 - Tue, Jan 27
Southwest Logo
9:40 am - 8:40 pmSJO-MDW
11h 00m2 stops
Southwest Logo
6:15 am - 7:30 pmMDW-SJO
13h 15m1 stop
$374Southwest
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Wed, Dec 24 - Wed, Dec 31
Frontier Logo
2:52 pm - 5:38 pmSJO-MDW
26h 46m1 stop
Frontier Logo
6:12 am - 1:42 pmMDW-SJO
7h 30m1 stop
$421Frontier
Find Deal

Everything you should know

Cheapest round-trip
$331
Typical prices: $609-$639
Delta
Fri 11/7Sun 11/16
SJO - MDW • 1 stop
Cheapest one-way
$142
Multiple Airlines
Sat 12/6
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!
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 279 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 51% of flights departing in the morning.

Good to know

Low seasonAugust
Cheapest flight$142
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 4% 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.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where tickets can be as cheap as $599. On the other hand, the most expensive day to fly is Saturday, where prices are $976 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 morning, 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 $896.

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

    Each week there are around 1,950 direct flights from within Costa Rica to Chicago Midway Airport. The most common day for departures is Saturday, with 24% 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 4237 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

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

10.0 ExcellentStacy, Oct 2025SMF - DEN
Read more Southwest reviews

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

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

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
Munster
Schererville
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

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