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Cheap flights from Costa Rica to Chicago from $166

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 11/14. 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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Find the cheapest flights from Costa Rica to Chicago

Recent round-trip flight deals from Costa Rica to Chicago

Delta Logo
7:00 am - 4:36 pmSJO-MDW
9h 36m1 stop
Delta Logo
12:50 pm - 10:12 pmMDW-SJO
9h 22m1 stop
$328Delta
Find Deal
Fri, Dec 5 - Mon, Dec 8
Delta Logo
1:23 pm - 10:14 pmSJO-MDW
7h 51m1 stop
Delta Logo
6:00 am - 11:58 amMDW-SJO
6h 58m1 stop
$330Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
7:00 am - 3:25 pmSJO-MDW
8h 25m1 stop
Delta Logo
1:00 pm - 10:15 pmMDW-SJO
9h 15m2 stops
$332Delta
Find Deal
Sat, Jan 24 - Wed, Jan 28
Multiple Airlines Logo
12:35 pm - 1:38 pmSJO-MDW
48h 03m2 stops
Multiple Airlines Logo
12:17 pm - 12:50 amMDW-SJO
13h 33m1 stop
$333Multiple Airlines
Find Deal
Mon, Oct 20 - Mon, Oct 27
Multiple Airlines Logo
5:25 pm - 11:27 amSJO-MDW
17h 02m2 stops
Multiple Airlines Logo
4:24 pm - 7:50 amMDW-SJO
16h 26m2 stops
$358Multiple Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
Multiple Airlines Logo
5:25 pm - 11:27 amSJO-MDW
17h 02m2 stops
Multiple Airlines Logo
4:24 pm - 7:50 amMDW-SJO
16h 26m2 stops
$359Multiple Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
Delta Logo
2:31 pm - 11:40 pmSJO-MDW
9h 09m1 stop
Delta Logo
9:34 am - 10:07 pmMDW-SJO
12h 33m2 stops
$362Delta
Find Deal
Fri, Nov 14 - Tue, Nov 18
Southwest Logo
9:00 am - 8:35 pmSJO-MDW
11h 35m1 stop
Southwest Logo
5:25 am - 1:15 pmMDW-SJO
7h 50m1 stop
$389Southwest
Find Deal
Wed, Nov 26 - Sun, Nov 30
Southwest Logo
1:30 pm - 8:30 amSJO-MDW
18h 00m2 stops
Southwest Logo
6:45 am - 12:40 pmMDW-SJO
6h 55m1 stop
$394Southwest
Find Deal
Thu, Oct 23 - Sun, Oct 26
Frontier Logo
2:58 pm - 11:25 pmSJO-MDW
8h 27m1 stop
Frontier Logo
6:00 am - 1:39 pmMDW-SJO
7h 39m1 stop
$479Frontier
Find Deal
Sat, Jan 10 - Sat, Jan 17

Delta flights from Costa Rica to Chicago Midway Airport

Our best Delta deals on Costa Rica to Chicago Midway Airport flight tickets
Delta
Dec 5
SJO7:00 amSan José Juan Santamaria Intl
9h 36m
1 stop
MDW4:36 pmChicago Midway
Dec 8
MDW12:50 pmChicago Midway
9h 22m
1 stop
SJO10:12 pmSan José Juan Santamaria Intl
$328
Find similar
Delta
Oct 23
SJO1:23 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:14 pmChicago Midway
Oct 27
MDW6:00 amChicago Midway
6h 58m
1 stop
SJO11:58 amSan José Juan Santamaria Intl
$330
Find similar
Delta
Jan 24
SJO7:00 amSan José Juan Santamaria Intl
8h 25m
1 stop
MDW3:25 pmChicago Midway
Jan 28
MDW1:00 pmChicago Midway
9h 15m
2 stops
SJO10:15 pmSan José Juan Santamaria Intl
$332
Find similar

Southwest flights from Costa Rica to Chicago Midway Airport

Our best Southwest deals on Costa Rica to Chicago Midway Airport flight tickets
Southwest
Nov 26
SJO9:00 amSan José Juan Santamaria Intl
11h 35m
1 stop
MDW8:35 pmChicago Midway
Nov 30
MDW5:25 amChicago Midway
7h 50m
1 stop
SJO1:15 pmSan José Juan Santamaria Intl
$389
Find similar
Southwest
Oct 23
SJO1:30 pmSan José Juan Santamaria Intl
18h 00m
2 stops
MDW8:30 amChicago Midway
Oct 26
MDW6:45 amChicago Midway
6h 55m
1 stop
SJO12:40 pmSan José Juan Santamaria Intl
$394
Find similar
Southwest
Nov 8
SJO9:00 amSan José Juan Santamaria Intl
11h 25m
1 stop
MDW8:25 pmChicago Midway
Nov 12
MDW5:05 amChicago Midway
8h 10m
1 stop
SJO1:15 pmSan José Juan Santamaria Intl
$409
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 September 22, 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

Fri 12/5

7:00 am-4:36 pm

1 stop9h 36m

Chicago Midway

Mon 12/8

12:50 pm-10:12 pm

1 stop9h 22m

$328

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 10/23

1:23 pm-10:14 pm

1 stop7h 51m

Chicago Midway

Mon 10/27

6:00 am-11:58 am

1 stop6h 58m

$330

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/24

7:00 am-3:25 pm

1 stop8h 25m

Chicago Midway

Wed 1/28

1:00 pm-10:15 pm

2 stops9h 15m

$332

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 10/20

12:35 pm-1:38 pm

2 stops48h 03m

Chicago Midway

Mon 10/27

12:17 pm-12:50 am

1 stop13h 33m

$333

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 10/9

5:25 pm-11:27 am

2 stops17h 02m

Chicago Midway

Mon 10/13

4:24 pm-7:50 am

2 stops16h 26m

$358

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 10/9

5:25 pm-11:27 am

2 stops17h 02m

Chicago Midway

Mon 10/13

4:24 pm-7:50 am

2 stops16h 26m

$359

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 11/14

2:31 pm-11:40 pm

1 stop9h 09m

Chicago Midway

Tue 11/18

9:34 am-10:07 pm

2 stops12h 33m

$362

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 11/26

9:00 am-8:35 pm

1 stop11h 35m

Chicago Midway

Sun 11/30

5:25 am-1:15 pm

1 stop7h 50m

$389

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 10/23

1:30 pm-8:30 am

2 stops18h 00m

Chicago Midway

Sun 10/26

6:45 am-12:40 pm

1 stop6h 55m

$394

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/10

2:58 pm-11:25 pm

1 stop8h 27m

Chicago Midway

Sat 1/17

6:00 am-1:39 pm

1 stop7h 39m

$479

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

Direct flights

None
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
4,244 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
Crown Point
Munster
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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