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Cheap flights from Costa Rica to Chicago from $207

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Costa Rica to Chicago departing on 4/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Costa Rica to Chicago

Recent round-trip flight deals from Costa Rica to Chicago

Enter your travel dates to find the best prices.
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
$400Multiple Airlines
Thu, Apr 9 - Tue, Apr 14
Southwest Logo
9:00 am - 5:30 pm
SJO
-
MDW
7h 30m
1 stop
Southwest Logo
5:35 am - 12:10 pm
MDW
-
SJO
7h 35m
1 stop
$411Southwest
Wed, May 13 - Mon, May 18
Southwest Logo
9:00 am - 9:45 pm
SJO
-
MDW
11h 45m
2 stops
Southwest Logo
5:35 am - 12:10 pm
MDW
-
SJO
7h 35m
1 stop
$416Southwest
Wed, May 13 - Mon, May 18
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$443Southwest
Tue, Apr 14 - Mon, Apr 20
Frontier Logo
10:00 am - 7:00 am
SJO
-
MDW
20h 00m
2 stops
Frontier Logo
8:05 am - 8:45 am
MDW
-
SJO
25h 40m
2 stops
$445Frontier
Mon, Jun 1 - Sat, Jun 6
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
$447Southwest
Tue, Apr 14 - Mon, Apr 20
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
$448Southwest
Wed, May 13 - Tue, May 19
Southwest Logo
9:00 am - 7:00 pm
SJO
-
MDW
9h 00m
1 stop
Southwest Logo
10:05 am - 7:00 pm
MDW
-
SJO
9h 55m
2 stops
$453Southwest
Thu, Apr 16 - Tue, Apr 21
Multiple Airlines Logo
11:38 am - 9:58 pm
SJO
-
MDW
9h 20m
1 stop
Multiple Airlines Logo
7:30 am - 10:38 am
MDW
-
SJO
28h 08m
2 stops
$454Multiple Airlines
Fri, Apr 10 - Tue, Apr 14
Southwest Logo
9:00 am - 10:45 pm
SJO
-
MDW
12h 45m
2 stops
Southwest Logo
9:50 am - 7:00 pm
MDW
-
SJO
10h 10m
2 stops
$458Southwest
Thu, Apr 16 - Tue, Apr 21

Southwest flights from Costa Rica to Chicago Midway Airport

Our best Southwest deals on Costa Rica to Chicago Midway Airport flight tickets
Southwest
May 13
SJO9:00 amSan José Juan Santamaria Intl
7h 30m
1 stop
MDW5:30 pmChicago Midway
May 18
MDW5:35 amChicago Midway
7h 35m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
$411
Southwest
May 13
SJO9:00 amSan José Juan Santamaria Intl
11h 45m
2 stops
MDW9:45 pmChicago Midway
May 18
MDW5:35 amChicago Midway
7h 35m
1 stop
SJO12:10 pmSan José Juan Santamaria Intl
$416
Southwest
Apr 14
SJO1:10 pmSan José Juan Santamaria Intl
8h 55m
1 stop
MDW11:05 pmChicago Midway
Apr 20
MDW12:10 pmChicago Midway
7h 50m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
$443

Delta flights from Costa Rica to Chicago Midway Airport

Our best Delta deals on Costa Rica to Chicago Midway Airport flight tickets
Delta
Feb 28
SJO2:25 pmSan José Juan Santamaria Intl
8h 06m
1 stop
MDW10:31 pmChicago Midway
Mar 5
MDW6:00 amChicago Midway
16h 02m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
$471
Delta
Mar 11
SJO7:00 amSan José Juan Santamaria Intl
9h 54m
2 stops
MDW5:54 pmChicago Midway
Mar 22
MDW12:47 pmChicago Midway
9h 28m
1 stop
SJO9:15 pmSan José Juan Santamaria Intl
$492
Delta
Mar 18
SJO1:20 pmSan José Juan Santamaria Intl
8h 11m
1 stop
MDW10:31 pmChicago Midway
Mar 21
MDW9:35 amChicago Midway
12h 40m
2 stops
SJO9:15 pmSan José Juan Santamaria Intl
$503

momondo Fare Finder

 
Customize your flight search to find flights from Costa Rica to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 27, 2026.
Use the filters below to find and compare flights from Costa Rica to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/9

11:38 am-9:21 pm

1 stop8h 43m

Chicago Midway

Tue 4/14

7:30 am-10:38 am

2 stops28h 08m

$400

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 5/13

9:00 am-5:30 pm

1 stop7h 30m

Chicago Midway

Mon 5/18

5:35 am-12:10 pm

1 stop7h 35m

$411

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 5/13

9:00 am-9:45 pm

2 stops11h 45m

Chicago Midway

Mon 5/18

5:35 am-12:10 pm

1 stop7h 35m

$416

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 4/14

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Mon 4/20

12:10 pm-7:00 pm

1 stop7h 50m

$443

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 6/1

10:00 am-7:00 am

2 stops20h 00m

Chicago Midway

Sat 6/6

8:05 am-8:45 am

2 stops25h 40m

$445

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 4/14

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Mon 4/20

7:30 am-7:00 pm

2 stops12h 30m

$447

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 5/13

1:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Tue 5/19

12:15 pm-7:00 pm

1 stop7h 45m

$448

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/16

9:00 am-7:00 pm

1 stop9h 00m

Chicago Midway

Tue 4/21

10:05 am-7:00 pm

2 stops9h 55m

$453

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 4/10

11:38 am-9:58 pm

1 stop9h 20m

Chicago Midway

Tue 4/14

7:30 am-10:38 am

2 stops28h 08m

$454

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 4/16

9:00 am-10:45 pm

2 stops12h 45m

Chicago Midway

Tue 4/21

9:50 am-7:00 pm

2 stops10h 10m

$458

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Costa Rica to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Costa Rica to Chicago Midway Airport flights?

You could potentially save up to 71% on your flight if you consider stops on a Costa Rica to Chicago Midway Airport flight.

Cheap Costa Rica to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Costa Rica to Chicago Midway Airport

Fastest flight time

7h 54m

Direct flights

None
The fastest flight from Costa Rica to Chicago Midway Airport takes 7h 54m
There are no direct flights from Costa Rica to Chicago Midway Airport. There are no popular flight routes from Costa Rica to Chicago Midway Airport.
Search flight deals

  • When did momondo last update prices for flights from Costa Rica to Chicago Midway Airport?

    Prices for flights from Costa Rica to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Costa Rica to Chicago Midway Airport?

  • How old do you have to be to fly from Costa Rica to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Costa Rica to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Costa Rica to Chicago Midway Airport

Compare and see reviews for airlines that fly from Costa Rica to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $463Free CancellationRating
8.0
4,303 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Costa Rica to Chicago?

Finding the right flight to Chicago from Costa Rica is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Costa Rica to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Costa Rica with this policy.

How can momondo help me find flights from Costa Rica to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Costa Rica.

I’m not ready to book a flight from Costa Rica to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Costa Rica and alert you when they change.

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