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Cheap flights from Chicago Midway Airport to Costa Rica from $144

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 10/5. 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

Delta Logo
6:00 am - 10:07 pmMDW-SJO
16h 07m1 stop
Delta Logo
7:00 am - 11:32 pmSJO-MDW
16h 32m1 stop
$344Delta
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Tue, Nov 18 - Wed, Nov 26
Delta Logo
9:32 am - 10:07 pmMDW-SJO
12h 35m2 stops
Delta Logo
7:00 am - 6:08 pmSJO-MDW
11h 08m2 stops
$348Delta
Find Deal
Tue, Nov 18 - Tue, Nov 25
Southwest Logo
6:15 am - 12:45 pmMDW-SJO
7h 30m1 stop
Southwest Logo
12:20 pm - 9:00 pmSJO-MDW
7h 40m1 stop
$381Southwest
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Tue, Sep 30 - Sat, Oct 11
Multiple Airlines Logo
4:24 pm - 7:50 amMDW-SJO
16h 26m2 stops
Multiple Airlines Logo
5:00 am - 8:31 pmSJO-MDW
15h 31m2 stops
$382Multiple Airlines
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Mon, Oct 13 - Thu, Nov 13
Southwest Logo
5:50 am - 1:15 pmMDW-SJO
7h 25m1 stop
Southwest Logo
9:00 am - 10:35 pmSJO-MDW
13h 35m2 stops
$397Southwest
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Thu, Nov 6 - Tue, Nov 11
Southwest Logo
7:00 am - 8:30 pmMDW-SJO
13h 30m1 stop
Southwest Logo
9:00 am - 8:35 pmSJO-MDW
11h 35m1 stop
$404Southwest
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Wed, Nov 19 - Tue, Nov 25
Delta Logo
6:00 am - 11:58 amMDW-SJO
6h 58m1 stop
Delta Logo
1:23 pm - 10:14 pmSJO-MDW
7h 51m1 stop
$408Delta
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Wed, Oct 15 - Wed, Oct 22
Delta Logo
10:47 am - 10:07 pmMDW-SJO
11h 20m1 stop
Delta Logo
7:00 am - 11:32 pmSJO-MDW
16h 32m1 stop
$410Delta
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Wed, Nov 19 - Tue, Nov 25
Multiple Airlines Logo
6:05 am - 12:50 amMDW-SJO
18h 45m2 stops
Multiple Airlines Logo
2:43 pm - 10:43 pmSJO-MDW
8h 00m1 stop
$537Multiple Airlines
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Thu, Nov 20 - Wed, Nov 26
WestJet Logo
9:20 am - 12:21 pmMDW-LIR
28h 01m2 stops
WestJet Logo
7:25 am - 10:30 amLIR-MDW
26h 05m3 stops
$1,072WestJet
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Fri, Oct 3 - Fri, Oct 10

Southwest flights from Chicago Midway Airport to Costa Rica

Our best Southwest deals on Chicago Midway Airport to Costa Rica flight tickets
Southwest
Sep 30
MDW6:15 amChicago Midway
7h 30m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
Oct 11
SJO12:20 pmSan José Juan Santamaria Intl
7h 40m
1 stop
MDW9:00 pmChicago Midway
$381
Find similar
Southwest
Nov 6
MDW5:50 amChicago Midway
7h 25m
1 stop
SJO1:15 pmSan José Juan Santamaria Intl
Nov 11
SJO9:00 amSan José Juan Santamaria Intl
13h 35m
2 stops
MDW10:35 pmChicago Midway
$397
Find similar
Southwest
Nov 19
MDW7:00 amChicago Midway
13h 30m
1 stop
SJO8:30 pmSan José Juan Santamaria Intl
Nov 25
SJO9:00 amSan José Juan Santamaria Intl
11h 35m
1 stop
MDW8:35 pmChicago Midway
$404
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
Sep 30
MDW6:00 amChicago Midway
7h 00m
1 stop
LIR12:00 pmLiberia
Oct 3
LIR1:25 pmLiberia
7h 11m
1 stop
MDW9:36 pmChicago Midway
$309
Find similar
Delta
Sep 30
MDW6:00 amChicago Midway
7h 00m
1 stop
LIR12:00 pmLiberia
Oct 9
LIR1:25 pmLiberia
18h 15m
2 stops
MDW8:40 amChicago Midway
$313
Find similar
Delta
Nov 18
MDW6:00 amChicago Midway
16h 07m
1 stop
SJO10:07 pmSan José Juan Santamaria Intl
Nov 26
SJO7:00 amSan José Juan Santamaria Intl
16h 32m
1 stop
MDW11:32 pmChicago Midway
$344
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 September 18, 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

Tue 11/18

6:00 am-10:07 pm

1 stop16h 07m

San José Juan Santamaria Intl

Wed 11/26

7:00 am-11:32 pm

1 stop16h 32m

$344

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 11/18

9:32 am-10:07 pm

2 stops12h 35m

San José Juan Santamaria Intl

Tue 11/25

7:00 am-6:08 pm

2 stops11h 08m

$348

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 9/30

6:15 am-12:45 pm

1 stop7h 30m

San José Juan Santamaria Intl

Sat 10/11

12:20 pm-9:00 pm

1 stop7h 40m

$381

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 10/13

4:24 pm-7:50 am

2 stops16h 26m

San José Juan Santamaria Intl

Thu 11/13

5:00 am-8:31 pm

2 stops15h 31m

$382

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 11/6

5:50 am-1:15 pm

1 stop7h 25m

San José Juan Santamaria Intl

Tue 11/11

9:00 am-10:35 pm

2 stops13h 35m

$397

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 11/19

7:00 am-8:30 pm

1 stop13h 30m

San José Juan Santamaria Intl

Tue 11/25

9:00 am-8:35 pm

1 stop11h 35m

$404

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 10/15

6:00 am-11:58 am

1 stop6h 58m

San José Juan Santamaria Intl

Wed 10/22

1:23 pm-10:14 pm

1 stop7h 51m

$408

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 11/19

10:47 am-10:07 pm

1 stop11h 20m

San José Juan Santamaria Intl

Tue 11/25

7:00 am-11:32 pm

1 stop16h 32m

$410

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 11/20

6:05 am-12:50 am

2 stops18h 45m

San José Juan Santamaria Intl

Wed 11/26

2:43 pm-10:43 pm

1 stop8h 00m

$537

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Fri 10/3

9:20 am-12:21 pm

2 stops28h 01m

Liberia

Fri 10/10

7:25 am-10:30 am

3 stops26h 05m

$1,072

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

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 38% 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.
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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
4,242 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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