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Cheap flights from Chicago Midway Airport to Costa Rica from $198

1 adult
1 adult, Economy, 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
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$439Delta
Sat, Nov 14 - Fri, Nov 20
Southwest Logo
5:20 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 25m1 stop Houston Hobby
Southwest Logo
2:45 pm - 11:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 10m1 stop Orlando
$440Southwest
Thu, Jan 28 - Thu, Feb 11
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$443Delta
Sat, Nov 14 - Fri, Nov 20
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$463Delta
Sat, Nov 14 - Fri, Nov 20
Southwest Logo
5:25 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 20m1 stop Houston Hobby
Southwest Logo
2:45 pm - 10:45 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 00m1 stop Houston Hobby
$470Southwest
Thu, Jan 21 - Thu, Feb 18
Delta Logo
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$473Delta
Sat, Nov 14 - Fri, Nov 20
Delta Logo
9:30 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
12h 45m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$477Delta
Sat, Nov 14 - Fri, Nov 20
Southwest Logo
5:20 am - 1:45 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 25m1 stop Houston Hobby
Southwest Logo
1:50 pm - 10:50 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 00m1 stop Orlando
$480Southwest
Wed, Jan 27 - Wed, Feb 3
Delta Logo
1:05 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
9h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$486Delta
Tue, Nov 17 - Thu, Nov 26
Delta Logo
6:00 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$486Delta
Tue, Nov 17 - Fri, Dec 4

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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
Dec 24
MDW1:11 pmChicago Midway
25h 05m
1 stop
SJO2:16 pmSan José Juan Santamaria Intl
Dec 28
SJO3:31 pmSan José Juan Santamaria Intl
8h 30m
1 stop
MDW12:01 amChicago Midway
$611
Frontier
Dec 17
MDW8:35 pmChicago Midway
16h 06m
1 stop
SJO12:41 pmSan José Juan Santamaria Intl
Dec 23
SJO3:31 pmSan José Juan Santamaria Intl
20h 39m
1 stop
MDW12:10 pmChicago Midway
$649
Frontier
Dec 24
MDW6:52 amChicago Midway
31h 24m
1 stop
SJO2:16 pmSan José Juan Santamaria Intl
Dec 28
SJO1:56 pmSan José Juan Santamaria Intl
29h 34m
1 stop
MDW7:30 pmChicago Midway
$656

Southwest flights from Chicago Midway Airport to Costa Rica

Our best Southwest deals on Chicago Midway Airport to Costa Rica flight tickets
Southwest
Jan 21
MDW5:25 amChicago Midway
8h 20m
1 stop
SJO1:45 pmSan José Juan Santamaria Intl
Feb 18
SJO2:45 pmSan José Juan Santamaria Intl
8h 00m
1 stop
MDW10:45 pmChicago Midway
$470
Southwest
Jan 8
MDW5:20 amChicago Midway
8h 25m
1 stop
SJO1:45 pmSan José Juan Santamaria Intl
Jan 15
SJO1:50 pmSan José Juan Santamaria Intl
9h 10m
1 stop
MDW11:00 pmChicago Midway
$487
Southwest
Jan 21
MDW5:20 amChicago Midway
8h 25m
1 stop
SJO1:45 pmSan José Juan Santamaria Intl
Jan 28
SJO1:50 pmSan José Juan Santamaria Intl
9h 00m
1 stop
MDW10:50 pmChicago Midway
$504

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to Costa Rica that are best for you.

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Route

Depart

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Price

Cheapest round-trip

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 11/14

11:27 am-10:15 pm

1 stop10h 48m

San José Juan Santamaria Intl

Fri 11/20

2:37 pm-10:54 pm

1 stop8h 17m

$439

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Thu 1/28

5:20 am-1:45 pm

1 stop8h 25m

San José Juan Santamaria Intl

Thu 2/11

2:45 pm-11:55 pm

1 stop9h 10m

$440

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 11/14

9:30 am-10:15 pm

2 stops12h 45m

San José Juan Santamaria Intl

Fri 11/20

2:37 pm-10:54 pm

1 stop8h 17m

$443

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 11/14

9:30 am-10:15 pm

2 stops12h 45m

San José Juan Santamaria Intl

Fri 11/20

2:37 pm-10:54 pm

1 stop8h 17m

$463
Quickest round-trip

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Thu 1/21

5:25 am-1:45 pm

1 stop8h 20m

San José Juan Santamaria Intl

Thu 2/18

2:45 pm-10:45 pm

1 stop8h 00m

$470

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 11/14

11:27 am-10:15 pm

1 stop10h 48m

San José Juan Santamaria Intl

Fri 11/20

2:37 pm-10:54 pm

1 stop8h 17m

$473

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 11/14

9:30 am-10:15 pm

2 stops12h 45m

San José Juan Santamaria Intl

Fri 11/20

2:37 pm-10:54 pm

1 stop8h 17m

$477

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 1/27

5:20 am-1:45 pm

1 stop8h 25m

San José Juan Santamaria Intl

Wed 2/3

1:50 pm-10:50 pm

1 stop9h 00m

$480

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Tue 11/17

1:05 pm-10:15 pm

1 stop9h 10m

San José Juan Santamaria Intl

Thu 11/26

2:37 pm-10:54 pm

1 stop8h 17m

$486

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Tue 11/17

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Fri 12/4

2:37 pm-10:54 pm

1 stop8h 17m

$486

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 15% 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

Best Price Found

$198

Fastest flight time

6h 41m

Direct flights

None
The best one-way flight to Costa Rica from Chicago Midway Airport in the past 72 hours is $198. The best round-trip flight deal from Chicago Midway Airport to Costa Rica found on momondo in the last 72 hours is $439.
The fastest flight from Chicago Midway Airport to Costa Rica takes 6h 41m
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

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 $420Free CancellationRating
7.9
4,219 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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