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Cheap flights from Chicago Midway Airport to Costa Rica from $138

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Costa Rica departing on 1/19. 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 Chicago Midway Airport to Costa Rica

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:15 am - 6:55 pm
MDW
-
SJO
12h 40m2 stops
Multiple Airlines Logo
12:35 pm - 8:32 pm
SJO
-
MDW
7h 57m1 stop
$341Multiple Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
6:15 am - 3:30 pm
MDW
-
SJO
9h 15m1 stop
Multiple Airlines Logo
12:35 pm - 8:32 pm
SJO
-
MDW
7h 57m1 stop
$344Multiple Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
3:02 pm - 11:40 am
MDW
-
SJO
20h 38m2 stops
Multiple Airlines Logo
3:07 pm - 11:42 pm
SJO
-
MDW
8h 35m1 stop
$345Multiple Airlines
Sun, Mar 1 - Sat, Mar 7
Multiple Airlines Logo
1:00 pm - 11:37 am
MDW
-
SJO
22h 37m1 stop
Multiple Airlines Logo
2:33 pm - 7:59 pm
SJO
-
MDW
29h 26m1 stop
$348Multiple Airlines
Sun, Feb 8 - Sat, Feb 14
Delta Logo
6:00 am - 10:20 pm
MDW
-
SJO
16h 20m1 stop
Delta Logo
2:21 pm - 10:22 pm
SJO
-
MDW
8h 01m1 stop
$349Delta
Mon, Dec 15 - Tue, Dec 23
Southwest Logo
5:30 am - 12:50 pm
MDW
-
SJO
7h 20m1 stop
Southwest Logo
9:40 am - 10:55 pm
SJO
-
MDW
13h 15m1 stop
$359Southwest
Mon, Jan 19 - Thu, Jan 22
Southwest Logo
6:15 am - 2:20 pm
MDW
-
LIR
8h 05m1 stop
Southwest Logo
3:10 pm - 10:55 pm
LIR
-
MDW
7h 45m1 stop
$440Southwest
Sun, Jan 18 - Fri, Jan 23
Southwest Logo
6:15 am - 2:30 pm
MDW
-
LIR
8h 15m1 stop
Southwest Logo
2:55 pm - 9:15 am
LIR
-
MDW
18h 20m2 stops
$457Southwest
Tue, Feb 24 - Mon, Mar 2
Southwest Logo
7:25 am - 1:15 pm
MDW
-
LIR
6h 50m1 stop
Southwest Logo
2:10 pm - 5:00 am
LIR
-
MDW
13h 50m2 stops
$462Southwest
Wed, Apr 8 - Wed, Apr 15
Delta Logo
6:45 am - 1:50 pm
MDW
-
LIR
7h 05m1 stop
Delta Logo
2:05 pm - 10:07 pm
LIR
-
MDW
8h 02m1 stop
$513Delta
Sat, Jan 10 - Wed, Jan 14

Southwest flights from Chicago Midway Airport to Costa Rica

Our best Southwest deals on Chicago Midway Airport to Costa Rica flight tickets
Southwest
Jan 19
MDW5:30 amChicago Midway
7h 20m
1 stop
SJO12:50 pmSan José Juan Santamaria Intl
Jan 22
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
$359
Find similar
Southwest
Jan 26
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
Jan 31
SJO9:30 amSan José Juan Santamaria Intl
9h 15m
2 stops
MDW6:45 pmChicago Midway
$385
Find similar
Southwest
Jan 18
MDW5:00 amChicago Midway
7h 50m
1 stop
SJO12:50 pmSan José Juan Santamaria Intl
Jan 22
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
$389
Find similar

Frontier flights from Chicago Midway Airport to Costa Rica

Our best Frontier deals on Chicago Midway Airport to Costa Rica flight tickets
Frontier
Jan 5
MDW6:12 amChicago Midway
7h 30m
1 stop
SJO1:42 pmSan José Juan Santamaria Intl
Jan 10
SJO1:35 pmSan José Juan Santamaria Intl
8h 52m
1 stop
MDW10:27 pmChicago Midway
$447
Find similar
Frontier
Dec 24
MDW6:12 amChicago Midway
7h 30m
1 stop
SJO1:42 pmSan José Juan Santamaria Intl
Dec 31
SJO2:52 pmSan José Juan Santamaria Intl
26h 46m
1 stop
MDW5:38 pmChicago Midway
$672
Find similar
Frontier
Dec 19
MDW6:12 amChicago Midway
7h 30m
1 stop
SJO1:42 pmSan José Juan Santamaria Intl
Dec 27
SJO10:36 amSan José Juan Santamaria Intl
10h 28m
1 stop
MDW9:04 pmChicago Midway
$740
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Costa Rica 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 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Costa Rica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/19

6:15 am-6:55 pm

2 stops12h 40m

San José Juan Santamaria Intl

Mon 2/23

12:35 pm-8:32 pm

1 stop7h 57m

$341

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 2/19

6:15 am-3:30 pm

1 stop9h 15m

San José Juan Santamaria Intl

Mon 2/23

12:35 pm-8:32 pm

1 stop7h 57m

$344

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 3/1

3:02 pm-11:40 am

2 stops20h 38m

San José Juan Santamaria Intl

Sat 3/7

3:07 pm-11:42 pm

1 stop8h 35m

$345

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 2/8

1:00 pm-11:37 am

1 stop22h 37m

San José Juan Santamaria Intl

Sat 2/14

2:33 pm-7:59 pm

1 stop29h 26m

$348

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 12/15

6:00 am-10:20 pm

1 stop16h 20m

San José Juan Santamaria Intl

Tue 12/23

2:21 pm-10:22 pm

1 stop8h 01m

$349

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 1/19

5:30 am-12:50 pm

1 stop7h 20m

San José Juan Santamaria Intl

Thu 1/22

9:40 am-10:55 pm

1 stop13h 15m

$359

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sun 1/18

6:15 am-2:20 pm

1 stop8h 05m

Liberia

Fri 1/23

3:10 pm-10:55 pm

1 stop7h 45m

$440

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 2/24

6:15 am-2:30 pm

1 stop8h 15m

Liberia

Mon 3/2

2:55 pm-9:15 am

2 stops18h 20m

$457

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Wed 4/8

7:25 am-1:15 pm

1 stop6h 50m

Liberia

Wed 4/15

2:10 pm-5:00 am

2 stops13h 50m

$462

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sat 1/10

6:45 am-1:50 pm

1 stop7h 05m

Liberia

Wed 1/14

2:05 pm-10:07 pm

1 stop8h 02m

$513

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 Costa Rica from

How to get the cheapest flight ticket from Chicago Midway Airport to Costa Rica

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 Costa Rica?

According to our data, Thursday is the cheapest day to fly to Costa Rica from Chicago Midway Airport. The lowest ticket price found for a Thursday departure recently was $633. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $1,128. These prices are subject to change though, so be sure to set up a Price Alert for flights to Costa Rica.

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

You could potentially save up to 1% on your flight if you consider stops on a Chicago Midway Airport to Costa Rica flight.

Cheap Chicago Midway Airport to Costa Rica flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Costa Rica

Fastest flight time

6h 50m

Direct flights

None
The fastest flight from Chicago Midway Airport to Costa Rica takes 6h 50m
There are no direct flights from Chicago Midway Airport to Costa Rica. There are no popular flight routes from Chicago Midway Airport to Costa Rica.
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Costa Rica?

    Prices for flights from Chicago Midway Airport to Costa Rica are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Costa Rica?

  • How old do you have to be to fly from Chicago Midway Airport to Costa Rica?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Costa Rica.

  • What documentation or ID do you need to fly to Costa Rica?

    The travel and health documents you'll need for your trip to Costa Rica may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Costa Rica. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago Midway Airport to Costa Rica

Compare and see reviews for airlines that fly from Chicago Midway Airport to Costa Rica with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
7.9
4,253 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Costa Rica?

It is quick and easy to find Chicago to Costa Rica flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Costa Rica that suits you.

Can I find flights from Chicago to Costa Rica with flexible booking policies on momondo?

Yes. All flights to Costa Rica from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Costa Rica?

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 Costa Rica from Chicago.

I’m not ready to book a flight from Chicago to Costa Rica right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Costa Rica, momondo offers a useful price alert feature which will track prices for flights to Costa Rica from Chicago and alert you when they change.

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