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Cheap flights from Costa Rica to Chicago from $196

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 5/15. 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
7:00 am - 4:13 pm
SJO
-
MDW
8h 13m
1 stop
Multiple Airlines Logo
11:59 am - 11:45 am
MDW
-
SJO
24h 46m
2 stops
$432Multiple Airlines
Sat, May 2 - Sat, May 16
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
11h 27m
2 stops
Frontier Logo
3:07 pm - 8:19 am
MDW
-
SJO
18h 12m
2 stops
$453Frontier
Thu, May 28 - Wed, Jun 3
Frontier Logo
9:35 am - 10:11 pm
SJO
-
MDW
11h 36m
2 stops
Frontier Logo
3:02 pm - 8:20 am
MDW
-
SJO
18h 18m
2 stops
$454Frontier
Sat, Aug 29 - Sun, Sep 6
Multiple Airlines Logo
7:00 am - 10:02 pm
SJO
-
MDW
14h 02m
2 stops
Multiple Airlines Logo
4:52 pm - 3:18 pm
MDW
-
SJO
23h 26m
1 stop
$456Multiple Airlines
Wed, May 13 - Mon, May 18
Multiple Airlines Logo
7:00 am - 10:02 pm
SJO
-
MDW
14h 02m
2 stops
Multiple Airlines Logo
4:52 pm - 3:18 pm
MDW
-
SJO
23h 26m
1 stop
$458Multiple Airlines
Wed, May 13 - Mon, May 18
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
11h 27m
2 stops
Frontier Logo
3:07 pm - 8:19 am
MDW
-
SJO
18h 12m
2 stops
$462Frontier
Thu, May 21 - Wed, Jun 3
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
$468Southwest
Fri, Sep 25 - Tue, Sep 29
Southwest Logo
9:00 am - 9:00 pm
SJO
-
MDW
11h 00m
2 stops
Southwest Logo
7:40 am - 6:40 pm
MDW
-
SJO
12h 00m
2 stops
$473Southwest
Fri, Sep 25 - Tue, Sep 29
Delta Logo
1:16 pm - 10:15 pm
SJO
-
MDW
7h 59m
1 stop
Delta Logo
6:05 am - 11:51 am
MDW
-
SJO
6h 46m
1 stop
$476Delta
Thu, Jul 23 - Tue, Jul 28
Frontier Logo
9:35 am - 10:11 pm
SJO
-
MDW
11h 36m
2 stops
Frontier Logo
3:02 pm - 8:20 am
MDW
-
SJO
18h 18m
2 stops
$477Frontier
Thu, Aug 20 - Sun, Aug 30

Southwest flights from Costa Rica to Chicago Midway Airport

Our best Southwest deals on Costa Rica to Chicago Midway Airport flight tickets
Southwest
Sep 25
SJO9:00 amSan José Juan Santamaria Intl
11h 30m
1 stop
MDW9:30 pmChicago Midway
Sep 29
MDW6:15 amChicago Midway
7h 30m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
$468
Southwest
Sep 25
SJO9:00 amSan José Juan Santamaria Intl
11h 00m
2 stops
MDW9:00 pmChicago Midway
Sep 29
MDW7:40 amChicago Midway
12h 00m
2 stops
SJO6:40 pmSan José Juan Santamaria Intl
$473
Southwest
May 8
SJO9:00 amSan José Juan Santamaria Intl
9h 00m
1 stop
MDW7:00 pmChicago Midway
May 11
MDW12:10 pmChicago Midway
7h 50m
1 stop
SJO7:00 pmSan José Juan Santamaria Intl
$480

Delta flights from Costa Rica to Chicago Midway Airport

Our best Delta deals on Costa Rica to Chicago Midway Airport flight tickets
Delta
Jul 23
SJO1:16 pmSan José Juan Santamaria Intl
7h 59m
1 stop
MDW10:15 pmChicago Midway
Jul 28
MDW6:05 amChicago Midway
6h 46m
1 stop
SJO11:51 amSan José Juan Santamaria Intl
$476
Delta
Jul 19
SJO1:16 pmSan José Juan Santamaria Intl
7h 59m
1 stop
MDW10:15 pmChicago Midway
Jul 25
MDW6:05 amChicago Midway
6h 46m
1 stop
SJO11:51 amSan José Juan Santamaria Intl
$497
Delta
Aug 4
SJO1:16 pmSan José Juan Santamaria Intl
7h 59m
1 stop
MDW10:15 pmChicago Midway
Aug 12
MDW6:00 amChicago Midway
6h 56m
1 stop
SJO11:56 amSan José Juan Santamaria Intl
$532

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 April 17, 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

Cheapest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 5/2

7:00 am-4:13 pm

1 stop8h 13m

Chicago Midway

Sat 5/16

11:59 am-11:45 am

2 stops24h 46m

$432

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/28

9:35 am-10:02 pm

2 stops11h 27m

Chicago Midway

Wed 6/3

3:07 pm-8:19 am

2 stops18h 12m

$453

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 8/29

9:35 am-10:11 pm

2 stops11h 36m

Chicago Midway

Sun 9/6

3:02 pm-8:20 am

2 stops18h 18m

$454

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 5/13

7:00 am-10:02 pm

2 stops14h 02m

Chicago Midway

Mon 5/18

4:52 pm-3:18 pm

1 stop23h 26m

$456

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 5/13

7:00 am-10:02 pm

2 stops14h 02m

Chicago Midway

Mon 5/18

4:52 pm-3:18 pm

1 stop23h 26m

$458

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/21

9:35 am-10:02 pm

2 stops11h 27m

Chicago Midway

Wed 6/3

3:07 pm-8:19 am

2 stops18h 12m

$462

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/25

9:00 am-9:30 pm

1 stop11h 30m

Chicago Midway

Tue 9/29

6:15 am-12:45 pm

1 stop7h 30m

$468

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 9/25

9:00 am-9:00 pm

2 stops11h 00m

Chicago Midway

Tue 9/29

7:40 am-6:40 pm

2 stops12h 00m

$473
Quickest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 7/23

1:16 pm-10:15 pm

1 stop7h 59m

Chicago Midway

Tue 7/28

6:05 am-11:51 am

1 stop6h 46m

$476

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 8/20

9:35 am-10:11 pm

2 stops11h 36m

Chicago Midway

Sun 8/30

3:02 pm-8:20 am

2 stops18h 18m

$477

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 83% 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 21m

Direct flights

None
The fastest flight from Costa Rica to Chicago Midway Airport takes 7h 21m
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

Frequently asked questions about flying from Costa Rica to Chicago Midway Airport

  • 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
4,328 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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