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Cheap flights from Costa Rica to Chicago from $200

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 2/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
3:12 pm - 8:03 am
SJO
-
MDW
16h 51m1 stop
Multiple Airlines Logo
5:01 pm - 12:22 pm
MDW
-
SJO
19h 21m2 stops
$335Multiple Airlines
Sat, Jan 17 - Thu, Jan 22
Delta Logo
2:31 pm - 12:48 pm
SJO
-
MDW
22h 17m2 stops
Delta Logo
9:33 am - 10:15 pm
MDW
-
SJO
12h 42m2 stops
$346Delta
Wed, Jan 14 - Wed, Jan 28
Delta Logo
2:31 pm - 10:22 pm
SJO
-
MDW
7h 51m1 stop
Delta Logo
9:34 am - 10:02 pm
MDW
-
SJO
12h 28m2 stops
$373Delta
Wed, Feb 11 - Wed, Feb 18
Delta Logo
8:25 am - 12:48 pm
SJO
-
MDW
28h 23m2 stops
Delta Logo
6:00 am - 10:15 pm
MDW
-
SJO
16h 15m1 stop
$377Delta
Sat, Jan 17 - Mon, Jan 26
Multiple Airlines Logo
12:33 pm - 7:52 pm
SJO
-
MDW
31h 19m1 stop
Multiple Airlines Logo
12:25 pm - 12:22 pm
MDW
-
SJO
23h 57m2 stops
$385Multiple Airlines
Thu, Feb 5 - Thu, Feb 12
Delta Logo
7:00 am - 10:07 pm
SJO
-
MDW
15h 07m1 stop
Delta Logo
6:00 am - 10:15 pm
MDW
-
SJO
16h 15m1 stop
$388Delta
Tue, Jan 13 - Mon, Jan 26
Delta Logo
2:31 pm - 10:22 pm
SJO
-
MDW
7h 51m1 stop
Delta Logo
10:49 am - 10:02 pm
MDW
-
SJO
11h 13m1 stop
$400Delta
Fri, Jan 30 - Sun, Mar 1
Southwest Logo
9:40 am - 10:55 pm
SJO
-
MDW
13h 15m1 stop
Southwest Logo
10:05 am - 7:30 pm
MDW
-
SJO
9h 25m2 stops
$401Southwest
Thu, Jan 29 - Tue, Feb 3
Southwest Logo
9:40 am - 10:55 pm
SJO
-
MDW
13h 15m1 stop
Southwest Logo
6:15 am - 7:30 pm
MDW
-
SJO
13h 15m1 stop
$406Southwest
Wed, Jan 28 - Wed, Feb 4
Multiple Airlines Logo
12:33 pm - 7:52 pm
SJO
-
MDW
31h 19m1 stop
Multiple Airlines Logo
7:30 am - 11:40 am
MDW
-
SJO
28h 10m1 stop
$414Multiple Airlines
Thu, Feb 5 - Thu, Feb 12

Southwest flights from Costa Rica to Chicago Midway Airport

Our best Southwest deals on Costa Rica to Chicago Midway Airport flight tickets
Southwest
Jan 29
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
Feb 3
MDW10:05 amChicago Midway
9h 25m
2 stops
SJO7:30 pmSan José Juan Santamaria Intl
$401
Find similar
Southwest
Jan 28
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
Feb 4
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
$406
Find similar
Southwest
Jan 28
SJO9:40 amSan José Juan Santamaria Intl
12h 25m
2 stops
MDW10:05 pmChicago Midway
Feb 4
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
$442
Find similar

Delta flights from Costa Rica to Chicago Midway Airport

Our best Delta deals on Costa Rica to Chicago Midway Airport flight tickets
Delta
Jan 14
SJO2:31 pmSan José Juan Santamaria Intl
22h 17m
2 stops
MDW12:48 pmChicago Midway
Jan 28
MDW9:33 amChicago Midway
12h 42m
2 stops
SJO10:15 pmSan José Juan Santamaria Intl
$346
Find similar
Delta
Feb 11
SJO2:31 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:22 pmChicago Midway
Feb 18
MDW9:34 amChicago Midway
12h 28m
2 stops
SJO10:02 pmSan José Juan Santamaria Intl
$373
Find similar
Delta
Jan 17
SJO8:25 amSan José Juan Santamaria Intl
28h 23m
2 stops
MDW12:48 pmChicago Midway
Jan 26
MDW6:00 amChicago Midway
16h 15m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
$377
Find similar

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 December 23, 2025.
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

Sat 1/17

3:12 pm-8:03 am

1 stop16h 51m

Chicago Midway

Thu 1/22

5:01 pm-12:22 pm

2 stops19h 21m

$335

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 1/14

2:31 pm-12:48 pm

2 stops22h 17m

Chicago Midway

Wed 1/28

9:33 am-10:15 pm

2 stops12h 42m

$346

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 2/11

2:31 pm-10:22 pm

1 stop7h 51m

Chicago Midway

Wed 2/18

9:34 am-10:02 pm

2 stops12h 28m

$373

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/17

8:25 am-12:48 pm

2 stops28h 23m

Chicago Midway

Mon 1/26

6:00 am-10:15 pm

1 stop16h 15m

$377

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 2/5

12:33 pm-7:52 pm

1 stop31h 19m

Chicago Midway

Thu 2/12

12:25 pm-12:22 pm

2 stops23h 57m

$385

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 1/13

7:00 am-10:07 pm

1 stop15h 07m

Chicago Midway

Mon 1/26

6:00 am-10:15 pm

1 stop16h 15m

$388

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 1/30

2:31 pm-10:22 pm

1 stop7h 51m

Chicago Midway

Sun 3/1

10:49 am-10:02 pm

1 stop11h 13m

$400

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 1/29

9:40 am-10:55 pm

1 stop13h 15m

Chicago Midway

Tue 2/3

10:05 am-7:30 pm

2 stops9h 25m

$401

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 1/28

9:40 am-10:55 pm

1 stop13h 15m

Chicago Midway

Wed 2/4

6:15 am-7:30 pm

1 stop13h 15m

$406

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 2/5

12:33 pm-7:52 pm

1 stop31h 19m

Chicago Midway

Thu 2/12

7:30 am-11:40 am

1 stop28h 10m

$414

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

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Costa Rica. The lowest ticket price found for a Thursday departure recently was $599. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Costa Rica because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $976.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Costa Rica in the morning is the least expensive time of day to depart. momondo users have found prices as low as $610 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $896. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You could potentially save up to 78% 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 40m

Direct flights

None
The fastest flight from Costa Rica to Chicago Midway Airport takes 7h 40m
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
4,253 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
Valparaiso
Schererville
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.

An easier way to manage your Chicago Midway Airport trip

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