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Cheap flights from Chicago Midway Airport to Costa Rica from $154

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 5/28. 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

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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
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
Multiple Airlines Logo
7:48 pm - 1:00 pm
SJO
-
MDW
16h 12m
2 stops
$391Multiple Airlines
Mon, Apr 13 - Tue, Apr 21
Southwest Logo
10:15 am - 7:00 pm
MDW
-
SJO
9h 45m
1 stop
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
$403Southwest
Thu, Apr 30 - Tue, May 5
Multiple Airlines Logo
9:51 pm - 10:42 am
MDW
-
SJO
13h 51m
1 stop
Multiple Airlines Logo
12:19 pm - 10:19 pm
SJO
-
MDW
33h 00m
2 stops
$410Multiple Airlines
Mon, Mar 30 - Mon, Apr 6
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
$412Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
Southwest Logo
1:10 pm - 11:05 pm
SJO
-
MDW
8h 55m
1 stop
$421Southwest
Mon, Apr 13 - Tue, Apr 21
Multiple Airlines Logo
6:30 am - 3:05 pm
MDW
-
SJO
9h 35m
1 stop
Multiple Airlines Logo
7:45 am - 10:22 pm
SJO
-
MDW
13h 37m
2 stops
$430Multiple Airlines
Sat, Apr 11 - Thu, Apr 16
Southwest Logo
12:15 pm - 7:00 pm
MDW
-
SJO
7h 45m
1 stop
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
$436Southwest
Tue, Apr 21 - Fri, May 1
Delta Logo
6:23 am - 1:15 pm
MDW
-
LIR
7h 52m
1 stop
Delta Logo
1:25 pm - 12:42 pm
LIR
-
MDW
22h 17m
2 stops
$493Delta
Sat, May 9 - Wed, May 13
Delta Logo
1:22 pm - 12:00 pm
MDW
-
LIR
23h 38m
2 stops
Delta Logo
1:25 pm - 8:43 am
LIR
-
MDW
18h 18m
2 stops
$510Delta
Sun, May 17 - Thu, May 28
Delta Logo
1:22 pm - 12:00 pm
MDW
-
LIR
23h 38m
2 stops
Delta Logo
1:25 pm - 12:42 pm
LIR
-
MDW
22h 17m
2 stops
$512Delta
Tue, May 12 - Thu, May 14

Delta flights from Chicago Midway Airport to Costa Rica

Our best Delta deals on Chicago Midway Airport to Costa Rica flight tickets
Delta
Apr 25
MDW6:00 amChicago Midway
6h 56m
1 stop
SJO11:56 amSan José Juan Santamaria Intl
May 2
SJO1:21 pmSan José Juan Santamaria Intl
8h 07m
1 stop
MDW10:28 pmChicago Midway
$442
Delta
Apr 28
MDW6:00 amChicago Midway
6h 56m
1 stop
SJO11:56 amSan José Juan Santamaria Intl
May 8
SJO1:20 pmSan José Juan Santamaria Intl
18h 23m
2 stops
MDW8:43 amChicago Midway
$447
Delta
Mar 30
MDW12:47 pmChicago Midway
9h 28m
1 stop
SJO9:15 pmSan José Juan Santamaria Intl
Apr 7
SJO7:00 amSan José Juan Santamaria Intl
9h 22m
1 stop
MDW5:22 pmChicago Midway
$475

Frontier flights from Chicago Midway Airport to Costa Rica

Our best Frontier deals on Chicago Midway Airport to Costa Rica flight tickets
Frontier
May 24
MDW7:41 pmChicago Midway
14h 04m
1 stop
SJO8:45 amSan José Juan Santamaria Intl
May 28
SJO10:00 amSan José Juan Santamaria Intl
20h 00m
2 stops
MDW7:00 amChicago Midway
$463
Frontier
Aug 9
MDW7:41 pmChicago Midway
14h 04m
1 stop
SJO8:45 amSan José Juan Santamaria Intl
Aug 14
SJO10:00 amSan José Juan Santamaria Intl
20h 00m
2 stops
MDW7:00 amChicago Midway
$508

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 March 3, 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

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 4/13

6:30 am-3:05 pm

1 stop9h 35m

San José Juan Santamaria Intl

Tue 4/21

7:48 pm-1:00 pm

2 stops16h 12m

$391

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 4/30

10:15 am-7:00 pm

1 stop9h 45m

San José Juan Santamaria Intl

Tue 5/5

1:10 pm-11:05 pm

1 stop8h 55m

$403

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 3/30

9:51 pm-10:42 am

1 stop13h 51m

San José Juan Santamaria Intl

Mon 4/6

12:19 pm-10:19 pm

2 stops33h 00m

$410

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 4/14

12:15 pm-7:00 pm

1 stop7h 45m

San José Juan Santamaria Intl

Tue 4/21

1:10 pm-11:05 pm

1 stop8h 55m

$412

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 4/13

12:10 pm-7:00 pm

1 stop7h 50m

San José Juan Santamaria Intl

Tue 4/21

1:10 pm-11:05 pm

1 stop8h 55m

$421

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 4/11

6:30 am-3:05 pm

1 stop9h 35m

San José Juan Santamaria Intl

Thu 4/16

7:45 am-10:22 pm

2 stops13h 37m

$430

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 4/21

12:15 pm-7:00 pm

1 stop7h 45m

San José Juan Santamaria Intl

Fri 5/1

1:10 pm-9:55 pm

1 stop7h 45m

$436

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sat 5/9

6:23 am-1:15 pm

1 stop7h 52m

Liberia

Wed 5/13

1:25 pm-12:42 pm

2 stops22h 17m

$493

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sun 5/17

1:22 pm-12:00 pm

2 stops23h 38m

Liberia

Thu 5/28

1:25 pm-8:43 am

2 stops18h 18m

$510

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Tue 5/12

1:22 pm-12:00 pm

2 stops23h 38m

Liberia

Thu 5/14

1:25 pm-12:42 pm

2 stops22h 17m

$512

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 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 35% 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.
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  • 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
4,302 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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