Cheap flights from Chicago to Costa Rica from $64

Round-trip
1 adult
Economy
From?
To?
Sat 10/23
Sat 10/30

Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from Chicago to Costa Rica.
View current Costa Rica travel restrictions

Flight information for Chicago to Costa Rica

Find info about flight duration, direct flights, and airports for your flight from Chicago to Costa Rica
Best Price Found$149The best flight deal from Chicago to Costa Rica found on momondo in the last 72 hours is $149
Fastest flight time5h 00mThe fastest flight from Chicago to Costa Rica takes 5h 00m
Direct flightsNoneThere are no direct flights from Chicago to Costa Rica. Popular non-direct routes for this connection are Chicago O'Hare Intl Airport - Liberia Airport, Chicago O'Hare Intl Airport - San José Juan Santamaria Intl Airport and Chicago Midway Airport - San José Juan Santamaria Intl Airport.

How to get the cheapest flight ticket from Chicago 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 airline that flies to Costa Rica from Chicago?

JetBlue

Air Canada, Copa Airlines, and Interjet are the most popular carriers operating from Chicago to Costa Rica

What is the cheapest Chicago to Costa Rica flight route?

Chicago O'Hare Intl - San José Juan Santamaria Intl

Fly from Chicago O'Hare Intl to San José Juan Santamaria Intl for the best Chicago - Costa Rica flight prices


Easily compare round-trip flights from Chicago to Costa Rica

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Costa Rica by changing tabs
Spirit Airlines
Nov 2
ORD3:10 pmChicago O'Hare Intl
17h 35m
1 stop
SJO8:45 amSan José Juan Santamaria Intl
Nov 9
SJO8:53 amSan José Juan Santamaria Intl
10h 10m
1 stop
ORD7:03 pmChicago O'Hare Intl
Multiple Airlines
Nov 2
ORD1:44 amChicago O'Hare Intl
8h 24m
1 stop
SJO10:08 amSan José Juan Santamaria Intl
Nov 3
SJO8:54 amSan José Juan Santamaria Intl
10h 09m
1 stop
ORD7:03 pmChicago O'Hare Intl
Frontier
Nov 13
ORD8:57 amChicago O'Hare Intl
23h 46m
1 stop
SJO8:43 amSan José Juan Santamaria Intl
Nov 18
SJO9:48 amSan José Juan Santamaria Intl
9h 22m
1 stop
ORD7:10 pmChicago O'Hare Intl
Spirit Airlines
Nov 13
ORD2:10 pmChicago O'Hare Intl
17h 35m
1 stop
SJO7:45 amSan José Juan Santamaria Intl
Nov 20
SJO8:52 amSan José Juan Santamaria Intl
10h 32m
1 stop
ORD7:24 pmChicago O'Hare Intl
Frontier
Nov 14
ORD1:12 amChicago O'Hare Intl
7h 31m
1 stop
SJO8:43 amSan José Juan Santamaria Intl
Nov 18
SJO9:48 amSan José Juan Santamaria Intl
9h 22m
1 stop
ORD7:10 pmChicago O'Hare Intl
Spirit Airlines
Dec 4
ORD12:25 amChicago O'Hare Intl
7h 27m
1 stop
SJO7:52 amSan José Juan Santamaria Intl
Dec 7
SJO8:54 amSan José Juan Santamaria Intl
10h 26m
1 stop
ORD7:20 pmChicago O'Hare Intl

Find the cheapest one-way flights from Chicago to Costa Rica

If you're looking for one-way flights from Chicago to Costa Rica, view some of our deals below provided by Delta, Frontier and JetBlue
Spirit Airlines
Nov 2
ORD1:10 amChicago O'Hare Intl
7h 35m
1 stop
SJO8:45 amSan José Juan Santamaria Intl
Frontier
Jan 7
ORD11:33 amChicago O'Hare Intl
16h 02m
1 stop
SJO3:35 amSan José Juan Santamaria Intl
JetBlue
Oct 27
ORD1:40 amChicago O'Hare Intl
7h 00m
1 stop
SJO8:40 amSan José Juan Santamaria Intl

Search last-minute flights to Costa Rica from Chicago

Find and compare flight prices for your last-minute flight from Chicago to Costa Rica
Spirit Airlines
Oct 27
ORD1:10 amChicago O'Hare Intl
7h 35m
1 stop
SJO8:45 amSan José Juan Santamaria Intl
Nov 2
SJO8:54 amSan José Juan Santamaria Intl
10h 09m
1 stop
ORD7:03 pmChicago O'Hare Intl
Multiple Airlines
Oct 28
ORD1:10 amChicago O'Hare Intl
7h 35m
1 stop
SJO8:45 amSan José Juan Santamaria Intl
Oct 31
SJO10:13 amSan José Juan Santamaria Intl
16h 57m
1 stop
ORD3:10 amChicago O'Hare Intl
JetBlue
Oct 23
ORD1:40 amChicago O'Hare Intl
7h 00m
1 stop
SJO8:40 amSan José Juan Santamaria Intl
Oct 26
SJO8:45 amSan José Juan Santamaria Intl
9h 13m
1 stop
ORD5:58 pmChicago O'Hare Intl
Spirit Airlines
Oct 26
ORD3:10 pmChicago O'Hare Intl
17h 35m
1 stop
SJO8:45 amSan José Juan Santamaria Intl
Oct 29
SJO8:49 amSan José Juan Santamaria Intl
10h 14m
1 stop
ORD7:03 pmChicago O'Hare Intl
Multiple Airlines
Oct 24
ORD1:10 amChicago O'Hare Intl
7h 35m
1 stop
SJO8:45 amSan José Juan Santamaria Intl
Oct 31
SJO10:13 amSan José Juan Santamaria Intl
16h 57m
1 stop
ORD3:10 amChicago O'Hare Intl
Spirit Airlines
Oct 25
ORD3:10 pmChicago O'Hare Intl
17h 35m
1 stop
SJO8:45 amSan José Juan Santamaria Intl
Oct 28
SJO8:49 amSan José Juan Santamaria Intl
10h 14m
1 stop
ORD7:03 pmChicago O'Hare Intl

Best airlines flying from Chicago to Costa Rica

Compare and see reviews for airlines that fly from Chicago to Costa Rica with momondo
AirlineRatingFree CancellationPrice
JetBlue
PriceFrom $148
Free Cancellation
Rating
7.0
7.3

Boarding

7.6

Comfort

7.9

Crew

7.2

Entertainment

6.8

Food

Reviews

Outdated media

1 / 10
Spirit Airlines
PriceFrom $179
Free Cancellation
Rating
6.3
6.4

Boarding

5.9

Comfort

6.9

Crew

4.8

Entertainment

5.2

Food

Reviews

Overpricing luggage and delayed flights

1 / 10
United Airlines
PriceFrom $203
Free Cancellation
Rating
6.8
7.2

Boarding

6.7

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Pros: Everything! From ticketing agent to all the crew on our flight back were awesome. Thank you!

1 / 10
Interjet
PriceFrom $262
Free Cancellation
Rating
6.8
6.9

Boarding

7.0

Comfort

7.5

Crew

5.8

Entertainment

6.5

Food

Reviews

Pros: I was really happy with the over all flight. Everything was fast and smooth

1 / 10
Air Canada
PriceFrom $271
Free Cancellation
Rating
7.5
7.8

Boarding

7.3

Comfort

8.1

Crew

7.3

Entertainment

5.9

Food

Reviews

The food selection has been better in the past but due to Covid it is understandable. This particular flight did not have any entertainment and the Air Canada App did not work to access movies.

1 / 10
American Airlines
PriceFrom $276
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.8

Crew

7.1

Entertainment

6.8

Food

Reviews

Flight attendant for first class is definitely not a morning person. Oh and the WiFi DID NOT WORK!

1 / 10
Delta
PriceFrom $283
Free Cancellation
Rating
8.2
8.2

Boarding

8.4

Comfort

8.3

Crew

8.1

Entertainment

8.0

Food

Reviews

Great

1 / 10
Copa Airlines
PriceFrom $292
Free Cancellation
Rating
7.9
8.1

Boarding

7.8

Comfort

8.3

Crew

7.3

Entertainment

7.6

Food

Reviews

Reasonable

1 / 10
Avianca
PriceFrom $326
Free Cancellation
Rating
8.4
8.3

Boarding

8.5

Comfort

8.7

Crew

8.1

Entertainment

8.0

Food

Reviews

Entertainment and seat space was great . Meal was not tasty , plain , no vegetable at all, all wheat .

1 / 10
Aeromexico
PriceFrom $421
Free Cancellation
Rating
7.3
7.1

Boarding

7.4

Comfort

7.8

Crew

7.0

Entertainment

6.5

Food

Reviews

I paid for my seat next 2 seats were opened and they moved 2 other guest into the premium seats without charging them.. I asked if these seats were premium and the said no seat 15 D E F so why do I pay when others didn’t pay for the premium seats

1 / 10

  • Are airlines flying from Chicago to Costa Rica offering flexible cancellation due to COVID-19?

    To ease the stress of booking flights, some of our airline partners flying from Chicago to Costa Rica are responding to the global pandemic. The following airlines may have a flexible cancellation policy to help accommodate travelers: United Airlines, Copa Airlines, and Spirit Airlines.


Can I fly to Costa Rica from Chicago right now?

Information is based on travel restrictions from Chicago to Costa Rica

Most visitors from Chicago can enter Costa Rica without restrictions.

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Costa Rica.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Costa Rica.

Documents
Epidemiological Health Pass Form - The Health Pass can only be completed within 72 hours of arriving in the country. One form must be completed per person, including minors, without exception.

Health Insurance - Tourists may get an insurance from Costa Rican insurance companies that are registered and authorized by the General Superintendence of Insurance of Costa Rica.


Can I fly back to Chicago from Costa Rica?

Returning to Chicago from Costa Rica

COVID-19 testing requirements
Visitors from Costa Rica must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Costa Rica are not required to quarantine after entering Chicago.

If you are planning to travel to Costa Rica at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

Alternative routes for Chicago to Costa Rica

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Chicago to San José, San José Province Flights
Fastest flight time5h 09m
Cheapest price$149