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Cheap flights from Costa Rica to Chicago from $287

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 9/1. 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
1 adult, Economy, 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.
Southwest Logo
9:00 am - 6:00 pm
SJO
-
MDW
8h 00m
1 stop
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
1 stop
$390Southwest
Fri, Aug 28 - Mon, Aug 31
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$404Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
1:40 pm - 10:15 pm
SJO
-
MDW
7h 35m
1 stop
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
$405Southwest
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$430Southwest
Tue, Sep 1 - Tue, Sep 15
Southwest Logo
1:00 pm - 11:00 pm
SJO
-
MDW
9h 00m
1 stop
Southwest Logo
6:05 am - 12:05 pm
MDW
-
SJO
7h 00m
1 stop
$431Southwest
Wed, Oct 7 - Tue, Oct 13
Southwest Logo
9:00 am - 10:20 pm
SJO
-
MDW
12h 20m
2 stops
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
2 stops
$444Southwest
Fri, Aug 28 - Mon, Aug 31
Southwest Logo
1:00 pm - 11:00 pm
SJO
-
MDW
9h 00m
1 stop
Southwest Logo
6:05 am - 12:05 pm
MDW
-
SJO
7h 00m
1 stop
$448Southwest
Wed, Oct 7 - Wed, Oct 14
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
Southwest Logo
7:55 am - 6:40 pm
MDW
-
SJO
11h 45m
2 stops
$453Southwest
Mon, Sep 14 - Fri, Sep 18
Southwest Logo
2:10 pm - 1:05 am
SJO
-
MDW
10h 55m
1 stop
Southwest Logo
5:15 am - 1:15 pm
MDW
-
SJO
8h 00m
1 stop
$462Southwest
Fri, Nov 6 - Tue, Nov 10
Southwest Logo
9:00 am - 6:20 pm
SJO
-
MDW
9h 20m
2 stops
Southwest Logo
5:15 am - 1:15 pm
MDW
-
SJO
8h 00m
1 stop
$466Southwest
Fri, Nov 6 - Tue, Nov 10

Southwest flights from Costa Rica to Chicago Midway Airport

Our best Southwest deals on Costa Rica to Chicago Midway Airport flight tickets
Southwest
Aug 28
SJO9:00 amSan José Juan Santamaria Intl
8h 00m
1 stop
MDW6:00 pmChicago Midway
Aug 31
MDW10:05 amChicago Midway
9h 35m
2 stops
SJO6:40 pmSan José Juan Santamaria Intl
$390
Southwest
Sep 16
SJO1:40 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW11:10 pmChicago Midway
Sep 22
MDW10:10 amChicago Midway
9h 30m
2 stops
SJO6:40 pmSan José Juan Santamaria Intl
$404
Southwest
Aug 27
SJO1:40 pmSan José Juan Santamaria Intl
7h 35m
1 stop
MDW10:15 pmChicago Midway
Aug 31
MDW10:05 amChicago Midway
9h 35m
2 stops
SJO6:40 pmSan José Juan Santamaria Intl
$405

Delta flights from Costa Rica to Chicago Midway Airport

Our best Delta deals on Costa Rica to Chicago Midway Airport flight tickets
Delta
Sep 3
SJO1:14 pmSan José Juan Santamaria Intl
8h 22m
1 stop
MDW10:36 pmChicago Midway
Sep 13
MDW6:00 amChicago Midway
6h 54m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
$476
Delta
Sep 16
SJO1:25 pmSan José Juan Santamaria Intl
8h 00m
1 stop
MDW10:25 pmChicago Midway
Sep 21
MDW6:05 amChicago Midway
6h 49m
1 stop
SJO11:54 amSan José Juan Santamaria Intl
$497
Delta
Nov 3
SJO2:23 pmSan José Juan Santamaria Intl
7h 47m
1 stop
MDW10:10 pmChicago Midway
Nov 9
MDW10:35 amChicago Midway
11h 40m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
$508

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 June 6, 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

Fri 8/28

9:00 am-6:00 pm

1 stop8h 00m

Chicago Midway

Mon 8/31

10:05 am-6:40 pm

1 stop9h 35m

$390

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 9/16

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Tue 9/22

10:10 am-6:40 pm

2 stops9h 30m

$404

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 8/27

1:40 pm-10:15 pm

1 stop7h 35m

Chicago Midway

Mon 8/31

10:05 am-6:40 pm

2 stops9h 35m

$405

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 9/1

1:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Tue 9/15

10:10 am-6:40 pm

2 stops9h 30m

$430
Quickest round-trip

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 10/7

1:00 pm-11:00 pm

1 stop9h 00m

Chicago Midway

Tue 10/13

6:05 am-12:05 pm

1 stop7h 00m

$431

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 8/28

9:00 am-10:20 pm

2 stops12h 20m

Chicago Midway

Mon 8/31

10:05 am-6:40 pm

2 stops9h 35m

$444

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 10/7

1:00 pm-11:00 pm

1 stop9h 00m

Chicago Midway

Wed 10/14

6:05 am-12:05 pm

1 stop7h 00m

$448

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 9/14

9:00 am-9:30 pm

1 stop11h 30m

Chicago Midway

Fri 9/18

7:55 am-6:40 pm

2 stops11h 45m

$453

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 11/6

2:10 pm-1:05 am

1 stop10h 55m

Chicago Midway

Tue 11/10

5:15 am-1:15 pm

1 stop8h 00m

$462

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 11/6

9:00 am-6:20 pm

2 stops9h 20m

Chicago Midway

Tue 11/10

5:15 am-1:15 pm

1 stop8h 00m

$466

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 month to fly to Chicago Midway Airport?

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Costa Rica, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Costa Rica during the month June is also very affordable. Most momondo users find prices during this month for around $0.

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

You could potentially save up to 72% 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 22m

Direct flights

None
The fastest flight from Costa Rica to Chicago Midway Airport takes 7h 22m
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
4,258 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
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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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