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Cheap flights from Chicago Midway Airport to Costa Rica from $178

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 6/20. 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

Find the cheapest flights from Chicago Midway Airport to Costa Rica

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:25 pm - 9:46 pm
SJO
-
MDW
7h 21m
1 stop
$438Delta
Tue, Sep 22 - Tue, Sep 29
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:25 pm - 8:42 am
SJO
-
MDW
18h 17m
2 stops
$443Delta
Tue, Sep 22 - Wed, Sep 23
Frontier Logo
3:07 pm - 8:19 am
MDW
-
SJO
18h 12m
2 stops
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
11h 27m
2 stops
$449Frontier
Wed, May 27 - Thu, Jun 4
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$476Southwest
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
9:05 am - 6:40 pm
MDW
-
SJO
10h 35m
2 stops
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$480Southwest
Tue, Sep 8 - Tue, Sep 15
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$484Southwest
Tue, Sep 8 - Tue, Sep 15
Delta Logo
6:00 am - 11:54 am
MDW
-
SJO
6h 54m
1 stop
Delta Logo
1:25 pm - 9:46 pm
SJO
-
MDW
7h 21m
1 stop
$493Delta
Mon, Sep 21 - Wed, Sep 23
Frontier Logo
3:07 pm - 8:19 am
MDW
-
SJO
18h 12m
2 stops
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
11h 27m
2 stops
$502Frontier
Wed, May 27 - Thu, Jun 4
Frontier Logo
4:10 pm - 8:20 am
MDW
-
SJO
17h 10m
2 stops
Frontier Logo
9:35 am - 10:11 pm
SJO
-
MDW
11h 36m
2 stops
$509Frontier
Fri, Jun 12 - Sat, Jun 27
Southwest Logo
5:00 am - 11:15 am
MDW
-
LIR
7h 15m
1 stop
Southwest Logo
11:50 am - 11:05 pm
LIR
-
MDW
10h 15m
2 stops
$630Southwest
Sat, Jun 20 - Sat, Jun 27

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Frontier flights from Chicago Midway Airport to Costa Rica

Our best Frontier deals on Chicago Midway Airport to Costa Rica flight tickets
Frontier
May 27
MDW3:07 pmChicago Midway
18h 12m
2 stops
SJO8:19 amSan José Juan Santamaria Intl
Jun 4
SJO9:35 amSan José Juan Santamaria Intl
11h 27m
2 stops
MDW10:02 pmChicago Midway
$449
Frontier
May 27
MDW3:07 pmChicago Midway
18h 12m
2 stops
SJO8:19 amSan José Juan Santamaria Intl
Jun 4
SJO9:35 amSan José Juan Santamaria Intl
11h 27m
2 stops
MDW10:02 pmChicago Midway
$502
Frontier
Jun 12
MDW4:10 pmChicago Midway
17h 10m
2 stops
SJO8:20 amSan José Juan Santamaria Intl
Jun 27
SJO9:35 amSan José Juan Santamaria Intl
11h 36m
2 stops
MDW10:11 pmChicago Midway
$509

Southwest flights from Chicago Midway Airport to Costa Rica

Our best Southwest deals on Chicago Midway Airport to Costa Rica flight tickets
Southwest
Sep 9
MDW6:15 amChicago Midway
7h 30m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
Sep 16
SJO1:40 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW11:10 pmChicago Midway
$476
Southwest
Sep 8
MDW9:05 amChicago Midway
10h 35m
2 stops
SJO6:40 pmSan José Juan Santamaria Intl
Sep 15
SJO1:40 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW11:10 pmChicago Midway
$480
Southwest
Sep 8
MDW6:15 amChicago Midway
7h 30m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
Sep 15
SJO1:40 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW11:10 pmChicago Midway
$484

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 April 30, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/22

6:00 am-11:54 am

1 stop6h 54m

San José Juan Santamaria Intl

Tue 9/29

1:25 pm-9:46 pm

1 stop7h 21m

$438

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/22

6:00 am-11:54 am

1 stop6h 54m

San José Juan Santamaria Intl

Wed 9/23

1:25 pm-8:42 am

2 stops18h 17m

$443

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/27

3:07 pm-8:19 am

2 stops18h 12m

San José Juan Santamaria Intl

Thu 6/4

9:35 am-10:02 pm

2 stops11h 27m

$449

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 9/9

6:15 am-12:45 pm

1 stop7h 30m

San José Juan Santamaria Intl

Wed 9/16

1:40 pm-11:10 pm

1 stop8h 30m

$476

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/8

9:05 am-6:40 pm

2 stops10h 35m

San José Juan Santamaria Intl

Tue 9/15

1:40 pm-11:10 pm

1 stop8h 30m

$480

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/8

6:15 am-12:45 pm

1 stop7h 30m

San José Juan Santamaria Intl

Tue 9/15

1:40 pm-11:10 pm

1 stop8h 30m

$484

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 9/21

6:00 am-11:54 am

1 stop6h 54m

San José Juan Santamaria Intl

Wed 9/23

1:25 pm-9:46 pm

1 stop7h 21m

$493

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 5/27

3:07 pm-8:19 am

2 stops18h 12m

San José Juan Santamaria Intl

Thu 6/4

9:35 am-10:02 pm

2 stops11h 27m

$502

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 6/12

4:10 pm-8:20 am

2 stops17h 10m

San José Juan Santamaria Intl

Sat 6/27

9:35 am-10:11 pm

2 stops11h 36m

$509

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sat 6/20

5:00 am-11:15 am

1 stop7h 15m

Liberia

Sat 6/27

11:50 am-11:05 pm

2 stops10h 15m

$630

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

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

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

You could potentially save up to 16% 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 45m

Direct flights

None
The fastest flight from Chicago Midway Airport to Costa Rica takes 6h 45m
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.
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Frequently asked questions about flying from Chicago Midway Airport to Costa Rica

  • 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
8.0
4,314 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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