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Cheap flights from Costa Rica to Chicago from $217

1 adult
1 adult, Economy, 0 bags

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.
Delta Logo
2:37 pm - 6:04 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
27h 27m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
27h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Mon, Nov 9 - Sat, Nov 14
Delta Logo
7:00 am - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 54m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:44 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
27h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Thu, Nov 12 - Sat, Nov 14
Delta Logo
2:37 pm - 9:42 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
19h 05m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
27h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Wed, Nov 11 - Sat, Nov 14
Delta Logo
7:00 am - 4:18 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 18m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:44 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
27h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Fri, Nov 13 - Sat, Nov 14
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:44 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
27h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Mon, Nov 9 - Sat, Nov 14
Delta Logo
2:37 pm - 12:51 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
22h 14m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
27h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Tue, Nov 10 - Sat, Nov 14
Delta Logo
7:00 am - 12:51 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
29h 51m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
27h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Thu, Nov 12 - Sat, Nov 14
Delta Logo
7:00 am - 4:18 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 18m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:44 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
27h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$366Delta
Wed, Nov 11 - Sat, Nov 14
Southwest Logo
9:00 am - 8:20 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
10h 20m1 stop Orlando
Southwest Logo
5:15 am - 12:20 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 05m1 stop Houston Hobby
$393Southwest
Thu, Oct 29 - Sun, Nov 1
Southwest Logo
1:30 pm - 10:20 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
7h 50m1 stop Houston Hobby
Southwest Logo
5:15 am - 12:20 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 05m1 stop Houston Hobby
$393Southwest
Thu, Oct 29 - Sun, Nov 8

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Delta flights from Costa Rica to Chicago Midway Airport

Our best Delta deals on Costa Rica to Chicago Midway Airport flight tickets
Delta
Nov 9
SJO2:37 pmSan José Juan Santamaria Intl
8h 17m
1 stop
MDW10:54 pmChicago Midway
Nov 14
MDW6:44 pmChicago Midway
27h 31m
2 stops
SJO10:15 pmSan José Juan Santamaria Intl
$366
Delta
Jan 28
SJO7:05 amSan José Juan Santamaria Intl
11h 32m
2 stops
MDW6:37 pmChicago Midway
Feb 3
MDW9:30 amChicago Midway
12h 35m
2 stops
SJO10:05 pmSan José Juan Santamaria Intl
$416
Delta
Jan 13
SJO2:10 pmSan José Juan Santamaria Intl
8h 00m
1 stop
MDW10:10 pmChicago Midway
Jan 20
MDW10:35 amChicago Midway
11h 30m
1 stop
SJO10:05 pmSan José Juan Santamaria Intl
$465

Southwest flights from Costa Rica to Chicago Midway Airport

Our best Southwest deals on Costa Rica to Chicago Midway Airport flight tickets
Southwest
Oct 29
SJO9:00 amSan José Juan Santamaria Intl
10h 20m
1 stop
MDW8:20 pmChicago Midway
Nov 1
MDW5:15 amChicago Midway
7h 05m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
$393
Southwest
Nov 11
SJO2:15 pmSan José Juan Santamaria Intl
8h 50m
1 stop
MDW11:05 pmChicago Midway
Nov 15
MDW5:15 amChicago Midway
7h 05m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
$411
Southwest
Oct 29
SJO9:00 amSan José Juan Santamaria Intl
10h 10m
2 stops
MDW8:10 pmChicago Midway
Nov 8
MDW5:15 amChicago Midway
7h 05m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
$414

momondo Fare Finder

 
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 San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Mon 11/9

2:37 pm-6:04 pm

2 stops27h 27m

Chicago Midway

Sat 11/14

6:44 pm-10:15 pm

2 stops27h 31m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 11/12

7:00 am-10:54 pm

1 stop15h 54m

Chicago Midway

Sat 11/14

6:44 pm-10:15 pm

2 stops27h 31m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Wed 11/11

2:37 pm-9:42 am

2 stops19h 05m

Chicago Midway

Sat 11/14

6:44 pm-10:15 pm

2 stops27h 31m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Fri 11/13

7:00 am-4:18 pm

1 stop9h 18m

Chicago Midway

Sat 11/14

6:44 pm-10:15 pm

2 stops27h 31m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Mon 11/9

2:37 pm-10:54 pm

1 stop8h 17m

Chicago Midway

Sat 11/14

6:44 pm-10:15 pm

2 stops27h 31m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Tue 11/10

2:37 pm-12:51 pm

2 stops22h 14m

Chicago Midway

Sat 11/14

6:44 pm-10:15 pm

2 stops27h 31m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 11/12

7:00 am-12:51 pm

2 stops29h 51m

Chicago Midway

Sat 11/14

6:44 pm-10:15 pm

2 stops27h 31m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Wed 11/11

7:00 am-4:18 pm

1 stop9h 18m

Chicago Midway

Sat 11/14

6:44 pm-10:15 pm

2 stops27h 31m

$366

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 10/29

9:00 am-8:20 pm

1 stop10h 20m

Chicago Midway

Sun 11/1

5:15 am-12:20 pm

1 stop7h 05m

$393
Quickest round-trip

San JoséChicago

SJO San José Juan Santamaria Intl - MDW Chicago Midway

SJOMDW

San José Juan Santamaria Intl

Thu 10/29

1:30 pm-10:20 pm

1 stop7h 50m

Chicago Midway

Sun 11/8

5:15 am-12:20 pm

1 stop7h 05m

$393

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Costa Rica, with most prices found around $385. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Costa Rica during the month March is also very affordable. Most momondo users find prices during this month for around $401.

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

Best Price Found

$217

Fastest flight time

7h 41m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Costa Rica in the past 72 hours is $217. The best round-trip flight deal from Costa Rica to Chicago Midway Airport found on momondo in the last 72 hours is $366.
The fastest flight from Costa Rica to Chicago Midway Airport takes 7h 41m
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 $390Free CancellationRating
8.0
4,198 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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