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Cheap flights from Chicago Midway Airport to Costa Rica from $132

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 1/7. 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.
Frontier Logo
6:12 am - 1:42 pmMDW-SJO
31h 30m1 stop
Frontier Logo
2:58 pm - 11:25 pmSJO-MDW
8h 27m1 stop
$303Frontier
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Thu, Jan 1 - Fri, Jan 9
Multiple Airlines Logo
8:42 pm - 1:52 pmMDW-SJO
17h 10m1 stop
Multiple Airlines Logo
12:39 pm - 9:58 pmSJO-MDW
9h 19m1 stop
$312Multiple Airlines
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Fri, Dec 5 - Mon, Dec 15
Multiple Airlines Logo
6:37 pm - 11:42 amMDW-SJO
17h 05m1 stop
Multiple Airlines Logo
12:39 pm - 9:58 pmSJO-MDW
9h 19m1 stop
$314Multiple Airlines
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Sun, Dec 7 - Thu, Dec 11
Multiple Airlines Logo
8:29 pm - 12:15 pmMDW-SJO
15h 46m2 stops
Multiple Airlines Logo
2:43 pm - 10:43 pmSJO-MDW
8h 00m1 stop
$315Multiple Airlines
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Sat, Nov 22 - Wed, Nov 26
Multiple Airlines Logo
5:47 pm - 10:19 amMDW-SJO
16h 32m1 stop
Multiple Airlines Logo
1:31 pm - 8:46 amSJO-MDW
19h 15m2 stops
$317Multiple Airlines
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Mon, Dec 1 - Mon, Dec 8
Delta Logo
6:00 am - 10:07 pmMDW-SJO
16h 07m1 stop
Delta Logo
2:31 pm - 11:47 pmSJO-MDW
9h 16m1 stop
$331Delta
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Fri, Nov 28 - Thu, Dec 4
Delta Logo
6:00 am - 10:20 pmMDW-SJO
16h 20m1 stop
Delta Logo
7:00 am - 4:34 pmSJO-MDW
9h 34m1 stop
$342Delta
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Sun, Dec 7 - Mon, Dec 15
Delta Logo
9:29 am - 10:20 pmMDW-SJO
12h 51m2 stops
Delta Logo
7:00 am - 4:31 pmSJO-MDW
9h 31m1 stop
$346Delta
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Sat, Dec 6 - Thu, Dec 18
Southwest Logo
6:15 am - 7:30 pmMDW-SJO
13h 15m1 stop
Southwest Logo
9:40 am - 10:55 pmSJO-MDW
13h 15m1 stop
$347Southwest
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Wed, Feb 4 - Tue, Feb 10
Southwest Logo
6:15 am - 7:30 pmMDW-SJO
13h 15m1 stop
Southwest Logo
9:40 am - 10:55 pmSJO-MDW
13h 15m1 stop
$412Southwest
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Wed, Jan 14 - Tue, Jan 20

Southwest flights from Chicago Midway Airport to Costa Rica

Our best Southwest deals on Chicago Midway Airport to Costa Rica flight tickets
Southwest
Feb 4
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
Feb 10
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
$347
Find similar
Southwest
Jan 14
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
Jan 20
SJO9:40 amSan José Juan Santamaria Intl
13h 15m
1 stop
MDW10:55 pmChicago Midway
$412
Find similar
Southwest
Jan 14
MDW6:15 amChicago Midway
13h 15m
1 stop
SJO7:30 pmSan José Juan Santamaria Intl
Jan 20
SJO9:40 amSan José Juan Santamaria Intl
12h 25m
2 stops
MDW10:05 pmChicago Midway
$417
Find similar

Delta flights from Chicago Midway Airport to Costa Rica

Our best Delta deals on Chicago Midway Airport to Costa Rica flight tickets
Delta
Nov 28
MDW6:00 amChicago Midway
16h 07m
1 stop
SJO10:07 pmSan José Juan Santamaria Intl
Dec 4
SJO2:31 pmSan José Juan Santamaria Intl
9h 16m
1 stop
MDW11:47 pmChicago Midway
$331
Find similar
Delta
Dec 7
MDW6:00 amChicago Midway
16h 20m
1 stop
SJO10:20 pmSan José Juan Santamaria Intl
Dec 15
SJO7:00 amSan José Juan Santamaria Intl
9h 34m
1 stop
MDW4:34 pmChicago Midway
$342
Find similar
Delta
Dec 6
MDW9:29 amChicago Midway
12h 51m
2 stops
SJO10:20 pmSan José Juan Santamaria Intl
Dec 18
SJO7:00 amSan José Juan Santamaria Intl
9h 31m
1 stop
MDW4:31 pmChicago Midway
$346
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 November 5, 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 1/1

6:12 am-1:42 pm

1 stop31h 30m

San José Juan Santamaria Intl

Fri 1/9

2:58 pm-11:25 pm

1 stop8h 27m

$303

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 12/5

8:42 pm-1:52 pm

1 stop17h 10m

San José Juan Santamaria Intl

Mon 12/15

12:39 pm-9:58 pm

1 stop9h 19m

$312

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 12/7

6:37 pm-11:42 am

1 stop17h 05m

San José Juan Santamaria Intl

Thu 12/11

12:39 pm-9:58 pm

1 stop9h 19m

$314

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 11/22

8:29 pm-12:15 pm

2 stops15h 46m

San José Juan Santamaria Intl

Wed 11/26

2:43 pm-10:43 pm

1 stop8h 00m

$315

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 12/1

5:47 pm-10:19 am

1 stop16h 32m

San José Juan Santamaria Intl

Mon 12/8

1:31 pm-8:46 am

2 stops19h 15m

$317

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 11/28

6:00 am-10:07 pm

1 stop16h 07m

San José Juan Santamaria Intl

Thu 12/4

2:31 pm-11:47 pm

1 stop9h 16m

$331

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sun 12/7

6:00 am-10:20 pm

1 stop16h 20m

San José Juan Santamaria Intl

Mon 12/15

7:00 am-4:34 pm

1 stop9h 34m

$342

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 12/6

9:29 am-10:20 pm

2 stops12h 51m

San José Juan Santamaria Intl

Thu 12/18

7:00 am-4:31 pm

1 stop9h 31m

$346

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 2/4

6:15 am-7:30 pm

1 stop13h 15m

San José Juan Santamaria Intl

Tue 2/10

9:40 am-10:55 pm

1 stop13h 15m

$347

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 1/14

6:15 am-7:30 pm

1 stop13h 15m

San José Juan Santamaria Intl

Tue 1/20

9:40 am-10:55 pm

1 stop13h 15m

$412

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 month to fly to Costa Rica?

The cheapest month to fly to Costa Rica from Chicago Midway Airport is in August. Flight prices, which tend to average around $477, are often lower during this time because this is during the off-season. If you’re not able to fly to Costa Rica in August, then September is your next best option. Flight prices from Chicago Midway Airport to Costa Rica during September average around $477.

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 48% 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

Direct flights

None
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
8.0
4,240 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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