$210 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 5/8. 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

Thu, Apr 9 - Tue, Apr 14
Multiple Airlines Logo
11:38 am - 9:21 pm
SJO
-
MDW
8h 43m
1 stop
Multiple Airlines Logo
7:30 am - 10:38 am
MDW
-
SJO
28h 08m
2 stops
$428Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
Multiple Airlines Logo
11:38 am - 3:59 pm
SJO
-
MDW
27h 21m
2 stops
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
$441Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
Multiple Airlines Logo
11:38 am - 9:21 pm
SJO
-
MDW
8h 43m
1 stop
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
$447Multiple Airlines
Tue, Apr 21 - Mon, Apr 27
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
10:15 am - 7:00 pm
MDW
-
SJO
9h 45m
1 stop
$474Southwest
Sat, May 2 - Sat, May 9
Delta Logo
1:21 pm - 10:28 pm
SJO
-
MDW
8h 07m
1 stop
Delta Logo
6:23 am - 1:15 pm
MDW
-
SJO
7h 52m
1 stop
$476Delta
Sat, May 2 - Sat, May 9
Multiple Airlines Logo
7:00 am - 7:04 pm
SJO
-
MDW
35h 04m
2 stops
Multiple Airlines Logo
3:07 pm - 11:59 pm
MDW
-
SJO
33h 52m
2 stops
$477Multiple Airlines
Tue, Apr 21 - Mon, Apr 27
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
7:30 am - 7:00 pm
MDW
-
SJO
12h 30m
2 stops
$479Southwest
Tue, May 5 - Sat, May 9
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
5:00 am - 12:15 pm
MDW
-
SJO
8h 15m
1 stop
$480Southwest
Thu, Apr 16 - Sun, Apr 19
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
8:15 am - 7:00 pm
MDW
-
SJO
11h 45m
2 stops
$484Southwest
Fri, May 1 - Thu, May 7
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$485Southwest
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.

What is the cheapest flight to Chicago Midway Airport?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago Midway Airport was found on the route from San José, at $428 return. The most popular connection is from Minneapolis to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $112 in the last 3 days.

Find deals

Good to know

Cheapest flight$210
Most popular time to fly with an average 51% increase in price.
Flight from San José to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • What is the cheapest flight to Chicago Midway Airport?

    In the last 3 days, the cheapest flight deal to Chicago Midway Airport was found on the route from San José, at $428 return. The most popular connection is from Minneapolis to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $112 in the last 3 days.

  • 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 2,966 direct flights from within Costa Rica to Chicago Midway Airport. The most common day for departures is Monday, with 15% 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 4318 reviews
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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
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)