$241 Find Cheap Flights from Costa Rica 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 Chicago departing on 9/24. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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, Sep 23 - Mon, Sep 28
Southwest Logo
1:40 pm - 11:15 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$422Southwest
Wed, Sep 23 - Mon, Sep 28
Southwest Logo
1:40 pm - 11:15 pm
SJO
-
MDW
8h 35m
1 stop
Southwest Logo
9:20 am - 6:45 pm
MDW
-
SJO
10h 25m
2 stops
$438Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
1:40 pm - 10:20 pm
SJO
-
MDW
7h 40m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$453Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
1:40 pm - 10:20 pm
SJO
-
MDW
7h 40m
1 stop
Southwest Logo
7:55 am - 6:45 pm
MDW
-
SJO
11h 50m
2 stops
$458Southwest
Thu, Sep 24 - Sun, Oct 4
Southwest Logo
1:40 pm - 10:20 pm
SJO
-
MDW
7h 40m
1 stop
Southwest Logo
9:55 am - 7:40 pm
MDW
-
SJO
10h 45m
2 stops
$468Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
9:00 am - 9:35 pm
SJO
-
MDW
11h 35m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$468Southwest
Wed, Sep 23 - Mon, Sep 28
Southwest Logo
9:00 am - 10:25 pm
SJO
-
MDW
12h 25m
2 stops
Southwest Logo
7:55 am - 6:45 pm
MDW
-
SJO
11h 50m
2 stops
$470Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
9:00 am - 9:00 pm
SJO
-
MDW
11h 00m
2 stops
Southwest Logo
7:55 am - 6:45 pm
MDW
-
SJO
11h 50m
2 stops
$473Southwest
Wed, Sep 9 - Sun, Sep 20
JetBlue Logo
9:00 am - 7:15 pm
SJO
-
MDW
9h 15m
1 stop
JetBlue Logo
8:05 am - 6:40 pm
MDW
-
SJO
11h 35m
1 stop
$488JetBlue
Thu, Sep 17 - Sun, Sep 20
JetBlue Logo
9:00 am - 10:40 pm
SJO
-
MDW
12h 40m
1 stop
JetBlue Logo
8:05 pm - 12:45 pm
MDW
-
SJO
17h 40m
1 stop
$488JetBlue
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 368 direct flights from within Costa Rica to Chicago Midway Airport every day. Most flights depart in the morning, with 43% of flights departing in the morning.

Find deals

Good to know

Low season

March

Cheapest flight

$241
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 16% 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 2,572 direct flights from within Costa Rica to Chicago Midway Airport. The most common day for departures is Friday, with 20% 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.

Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago

Chicago Midway Airport (MDW)