$237 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 9/10. 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.
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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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Cheap Flight Deals 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.

Recent round-trip flight deals from Costa Rica to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Costa Rica to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
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5:52 am - 7:31 pmSJO-MDW
12h 39m2 stops
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9:12 pm - 10:27 amMDW-SJO
14h 15m1 stop
$364
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Mon, Jun 2 - Mon, Jun 9
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8:46 am - 8:17 pmSJO-MDW
10h 31m2 stops
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9:12 pm - 10:27 amMDW-SJO
14h 15m1 stop
$402
Find Deal
Sun, Jun 1 - Mon, Jun 9
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8:46 am - 8:17 pmSJO-MDW
10h 31m2 stops
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9:12 pm - 10:27 amMDW-SJO
14h 15m1 stop
$431
Find Deal
Thu, May 22 - Mon, May 26
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8:46 am - 8:17 pmSJO-MDW
10h 31m2 stops
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8:15 pm - 10:27 amMDW-SJO
15h 12m1 stop
$436
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Thu, May 22 - Sat, Jun 7
Delta Logo
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
Delta Logo
6:00 am - 11:53 amMDW-SJO
6h 53m1 stop
$438Delta
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Thu, Sep 25 - Tue, Sep 30
Southwest Logo
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
Southwest Logo
9:15 am - 6:55 pmMDW-SJO
10h 40m2 stops
$441Southwest
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Thu, Sep 11 - Thu, Sep 18
Southwest Logo
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
Southwest Logo
11:25 am - 6:55 pmMDW-SJO
8h 30m2 stops
$471Southwest
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Thu, Sep 25 - Tue, Sep 30
Delta Logo
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
Delta Logo
6:00 am - 11:48 amMDW-SJO
6h 48m1 stop
$478Delta
Find Deal
Wed, Oct 1 - Tue, Oct 7
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
Southwest Logo
5:15 am - 11:40 amMDW-SJO
7h 25m1 stop
$487Southwest
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Wed, Oct 1 - Wed, Oct 8
Delta Logo
1:18 pm - 9:44 pmSJO-MDW
7h 26m1 stop
Delta Logo
6:00 am - 11:48 amMDW-SJO
6h 48m1 stop
$518Delta
Find Deal
Sat, Oct 4 - Tue, Oct 7
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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 25m, and San José, which takes 5h 34m.

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

There are around 212 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.

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Good to know

Low seasonMarch
High seasonOctober
Cheapest flight$237
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 3% 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 1,479 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.

Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago

Chicago Midway Airport (MDW)

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