$181 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 10/9. 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

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

sáb., oct. 18 - sáb., oct. 25
Frontier Logo
1:49 pm - 11:25 pmSJO-MDW
8h 36m1 stop
Frontier Logo
6:15 am - 12:34 pmMDW-SJO
7h 19m1 stop
$310Frontier
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vie., oct. 10 - lun., oct. 13
Logo
11:37 am - 3:11 pmSJO-MDW
26h 34m1 stop
Logo
5:28 pm - 10:41 amMDW-SJO
18h 13m1 stop
$354
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vie., oct. 3 - dom., oct. 12
Logo
11:37 am - 9:51 amSJO-MDW
21h 14m1 stop
Logo
12:39 pm - 10:42 amMDW-SJO
23h 03m1 stop
$357
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mié., sep. 24 - mar., sep. 30
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
Southwest Logo
6:25 am - 6:55 pmMDW-SJO
13h 30m1 stop
$384Southwest
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mié., sep. 24 - mar., sep. 30
Southwest Logo
8:50 am - 7:45 pmSJO-MDW
9h 55m2 stops
Southwest Logo
6:25 am - 6:55 pmMDW-SJO
13h 30m1 stop
$388Southwest
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jue., oct. 9 - lun., oct. 13
Logo
5:55 pm - 4:20 pmSJO-MDW
21h 25m2 stops
Logo
5:28 pm - 10:42 amMDW-SJO
18h 14m1 stop
$410
Find Deal
jue., oct. 9 - mar., oct. 14
Southwest Logo
1:30 pm - 12:45 amSJO-MDW
10h 15m1 stop
Southwest Logo
5:15 am - 11:40 amMDW-SJO
7h 25m1 stop
$412Southwest
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vie., sep. 5 - sáb., sep. 13
Southwest Logo
8:50 am - 6:15 pmSJO-MDW
8h 25m1 stop
Southwest Logo
6:15 am - 12:15 pmMDW-SJO
7h 00m1 stop
$415Southwest
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mar., sep. 23 - sáb., sep. 27
Delta Logo
1:35 pm - 8:40 amSJO-MDW
18h 05m2 stops
Delta Logo
6:00 am - 12:08 pmMDW-SJO
7h 08m1 stop
$470Delta
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vie., nov. 7 - dom., nov. 16
Delta Logo
2:15 pm - 10:14 pmSJO-MDW
7h 59m1 stop
Delta Logo
10:35 am - 10:15 pmMDW-SJO
11h 40m1 stop
$574Delta
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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 San José, which takes 5h 30m, and Liberia, which takes 8h 21m.

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

There are around 227 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 57% of flights departing in the morning.

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Good to know

Low seasonAugust
Cheapest flight$181
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 1% 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.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as $599. On the other hand, the most expensive day to fly is Saturday, where round-trip 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 round-trip 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 1,588 direct flights from within Costa Rica to Chicago Midway Airport. The most common day for departures is Sunday, with 18% 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Valparaiso
Lansing
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

Chicago Midway Airport (MDW)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.