Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Costa Rica from $188

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
10:35 am - 10:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
11h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:55 pm - 9:52 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
17h 57m1 stop Atlanta Hartsfield-Jackson
$398Delta
Sat, Jan 30 - Sat, Feb 6
Delta Logo
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 54m1 stop Atlanta Hartsfield-Jackson
$398Delta
Wed, Nov 11 - Fri, Nov 13
Delta Logo
6:00 am - 10:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 05m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:05 am - 10:10 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 05m1 stop Atlanta Hartsfield-Jackson
$398Delta
Sat, Jan 30 - Fri, Feb 5
Delta Logo
6:00 am - 10:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 05m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:05 am - 4:25 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 20m1 stop Atlanta Hartsfield-Jackson
$398Delta
Sat, Jan 30 - Thu, Feb 4
Delta Logo
6:00 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 54m1 stop Atlanta Hartsfield-Jackson
$398Delta
Wed, Nov 11 - Mon, Nov 16
Delta Logo
10:35 am - 10:05 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
11h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:10 pm - 10:10 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 00m1 stop Atlanta Hartsfield-Jackson
$398Delta
Wed, Jan 20 - Wed, Feb 3
Delta Logo
6:04 am - 12:00 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
6h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:25 pm - 10:33 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 08m1 stop Atlanta Hartsfield-Jackson
$398Delta
Thu, Oct 29 - Sun, Nov 1
Southwest Logo
11:50 am - 7:40 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 50m1 stop Houston Hobby
Southwest Logo
9:00 am - 8:10 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
10h 10m2 stops Orlando Norfolk
$437Southwest
Thu, Oct 22 - Thu, Oct 29
Southwest Logo
11:50 am - 7:40 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
8h 50m1 stop Houston Hobby
Southwest Logo
9:00 am - 8:20 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
10h 20m1 stop Orlando
$437Southwest
Thu, Oct 22 - Thu, Oct 29
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 - 11:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 10m1 stop Orlando
$444Southwest
Thu, Jan 28 - Thu, Feb 11

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Delta flights from Chicago Midway Airport to Costa Rica

Our best Delta deals on Chicago Midway Airport to Costa Rica flight tickets
Delta
Jan 30
MDW10:35 amChicago Midway
11h 30m
1 stop
SJO10:05 pmSan José Juan Santamaria Intl
Feb 6
SJO3:55 pmSan José Juan Santamaria Intl
17h 57m
1 stop
MDW9:52 amChicago Midway
$398
Delta
Jan 30
MDW9:30 amChicago Midway
12h 35m
2 stops
SJO10:05 pmSan José Juan Santamaria Intl
Feb 5
SJO7:05 amSan José Juan Santamaria Intl
11h 32m
2 stops
MDW6:37 pmChicago Midway
$403
Delta
Nov 23
MDW6:00 amChicago Midway
16h 15m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Dec 4
SJO7:00 amSan José Juan Santamaria Intl
15h 55m
1 stop
MDW10:55 pmChicago Midway
$467

Southwest flights from Chicago Midway Airport to Costa Rica

Our best Southwest deals on Chicago Midway Airport to Costa Rica flight tickets
Southwest
Oct 22
MDW11:50 amChicago Midway
8h 50m
1 stop
SJO7:40 pmSan José Juan Santamaria Intl
Oct 29
SJO9:00 amSan José Juan Santamaria Intl
10h 20m
1 stop
MDW8:20 pmChicago Midway
$437
Southwest
Jan 28
MDW5:25 amChicago Midway
8h 20m
1 stop
SJO1:45 pmSan José Juan Santamaria Intl
Feb 10
SJO1:50 pmSan José Juan Santamaria Intl
9h 00m
1 stop
MDW10:50 pmChicago Midway
$444
Southwest
Jan 25
MDW5:25 amChicago Midway
8h 20m
1 stop
SJO1:45 pmSan José Juan Santamaria Intl
Feb 3
SJO1:50 pmSan José Juan Santamaria Intl
9h 00m
1 stop
MDW10:50 pmChicago Midway
$445

momondo Fare Finder

 
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

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 1/30

10:35 am-10:05 pm

1 stop11h 30m

San José Juan Santamaria Intl

Sat 2/6

3:55 pm-9:52 am

1 stop17h 57m

$398

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 11/11

11:27 am-10:15 pm

1 stop10h 48m

San José Juan Santamaria Intl

Fri 11/13

7:00 am-10:54 pm

1 stop15h 54m

$398

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 1/30

6:00 am-10:05 pm

1 stop16h 05m

San José Juan Santamaria Intl

Fri 2/5

7:05 am-10:10 pm

1 stop15h 05m

$398

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 1/30

6:00 am-10:05 pm

1 stop16h 05m

San José Juan Santamaria Intl

Thu 2/4

7:05 am-4:25 pm

1 stop9h 20m

$398

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 11/11

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Mon 11/16

7:00 am-10:54 pm

1 stop15h 54m

$398

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 1/20

10:35 am-10:05 pm

1 stop11h 30m

San José Juan Santamaria Intl

Wed 2/3

2:10 pm-10:10 pm

1 stop8h 00m

$398
Quickest round-trip

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Thu 10/29

6:04 am-12:00 pm

1 stop6h 56m

San José Juan Santamaria Intl

Sun 11/1

2:25 pm-10:33 pm

1 stop8h 08m

$398

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Thu 10/22

11:50 am-7:40 pm

1 stop8h 50m

San José Juan Santamaria Intl

Thu 10/29

9:00 am-8:10 pm

2 stops10h 10m

$437

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Thu 10/22

11:50 am-7:40 pm

1 stop8h 50m

San José Juan Santamaria Intl

Thu 10/29

9:00 am-8:20 pm

1 stop10h 20m

$437

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Thu 1/28

5:25 am-1:45 pm

1 stop8h 20m

San José Juan Santamaria Intl

Thu 2/11

2:45 pm-11:55 pm

1 stop9h 10m

$444

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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 8% 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

$188

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 $188. The best round-trip flight deal from Chicago Midway Airport to Costa Rica found on momondo in the last 72 hours is $398.
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
8.0
4,192 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.

An easier way to manage your Costa Rica trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 10/12
Mon 10/19
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Costa Rica

Popular cities in Costa Rica

Flights to San Joséfrom $212
Flights to Liberiafrom $303
Flights to Limon
Flights to Tamarindo
Flights to Tortuguero
Flights to Golfito
Flights to Tambor