There are 7 ways to get from Chicago to Guanacaste by plane, bus (Greyhound, Flixbus), car, shuttle, train, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago O'Hare International Airport to Liberia International Airport
best- Fly from Chicago O'Hare International Airport (ORD) to Liberia International Airport (LIR)plane ORD - LIR
8h 42m$288–974Bus
- Take the bus from Chicago Bus Station to Memphis Bus Stationbus
- Take the bus from Memphis Bus Station to Downtown Houstonbus
- Take the bus from Houston to San Salvadorbus
- Take the bus from Terminal Tica Bus San Salvador to Liberiabus
4d 19h$436–793Drive 5,123.2 km
- Drive from Chicago to Liberiacar 5,123.2 km
2d 14h$687–993Fly Chicago Midway International Airport to Liberia International Airport
- Fly from Chicago Midway International Airport (MDW) to Liberia International Airport (LIR)plane MDW - LIR
10h 31m$368–1,374Fly Chicago O'Hare International Airport to Juan Santamaría International Airport, shuttle
- Fly from Chicago O'Hare International Airport (ORD) to Juan Santamaría International Airport (SJO)plane ORD - SJO
- Take a shuttle bus from Alajuela to Monteverde
- Take a shuttle bus from Monteverde to Cañas
11h 4m$766–1,070Fly Chicago Midway International Airport to Juan Santamaría International Airport, shuttle
- Fly from Chicago Midway International Airport (MDW) to Juan Santamaría International Airport (SJO)plane MDW - SJO
- Take a shuttle bus from Alajuela to Monteverde
- Take a shuttle bus from Monteverde to Cañas
12h 14m$776–1,390Train, bus
- Take the train from Chicago Union Station to Longviewtrain
- Take the bus from Longview Bus Station to Houston Bus Stationbus
- Take the bus from Houston to San Salvadorbus
- Take the bus from Terminal Tica Bus San Salvador to Liberiabus
4d 20h$499–1,027
Chicago O'Hare International Airport (ORD) to Liberia International Airport (LIR) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Guanacaste is to fly which costs $280 - $1,000 and takes 8h 42m.
The fastest way to get from Chicago to Guanacaste is to fly which takes 8h 42m and costs $280 - $1,000.
No, there is no direct bus from Chicago station to Guanacaste. However, there are services departing from Chicago Bus Station and arriving at Liberia via Memphis Bus Station, Smith St @ Pierce St, Houston and Terminal Tica Bus San Salvador. The journey, including transfers, takes approximately 4 days 19h.
The distance between Chicago and Guanacaste is 3539 km. The road distance is 5123.2 km.
The best way to get from Chicago to Guanacaste without a car is to bus which takes 4 days 19h and costs $430 - $800.
It takes approximately 8h 42m to get from Chicago to Guanacaste, including transfers.
Chicago to Guanacaste bus services, operated by Greyhound USA, depart from Chicago Bus Station.
The best way to get from Chicago to Guanacaste is to fly which takes 8h 42m and costs $280 - $1,000. Alternatively, you can bus, which costs $430 - $800 and takes 4 days 19h.
Chicago to Guanacaste bus services, operated by Greyhound USA, arrive at Memphis Bus Station.
Guanacaste is 1h behind Chicago. It is currently 1:55 AM in Chicago and 12:55 AM in Guanacaste.
What companies run services between Chicago, IL, USA and Guanacaste, Costa Rica?
American Airlines, United Airlines, and Delta fly from Chicago O'Hare International Airport (ORD) to Liberia International Airport (LIR) 5 times a day. Alternatively, you can take a bus from Chicago Bus Station to Liberia via Memphis Bus Station, Downtown Houston, Smith St @ Pierce St, West Bellfort Park & Ride, Houston, San Salvador, and Terminal Tica Bus San Salvador in around 4d 19h.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Liberia International Airport
- Ave. Duration
- 4h 59m
- When
- Saturday
- Estimated price
- $220–900
Flights from Chicago O'Hare International Airport to Liberia International Airport via Miami
- Ave. Duration
- 7h 14m
- When
- Every day
- Estimated price
- $230–950
Flights from Chicago O'Hare International Airport to Liberia International Airport via Dallas/Ft.Worth
- Ave. Duration
- 7h 47m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $240–1,000
Flights from Chicago O'Hare International Airport to Juan Santamaría International Airport via Miami
- Ave. Duration
- 7h 6m
- When
- Every day
- Estimated price
- $140–600
Flights from Chicago Midway International Airport to Juan Santamaría International Airport via Miami
- Ave. Duration
- 8h 17m
- When
- Monday, Thursday, and Friday
- Estimated price
- $190–800
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Longview
- Ave. Duration
- 18h 50m
- Frequency
- Once daily
- Estimated price
- $220–500
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Chicago Bus Station to Memphis Bus Station
- Ave. Duration
- 9h 35m
- Frequency
- Once daily
- Estimated price
- $85–140
- Website
- Greyhound
Bus from Longview Bus Station to Houston Bus Station
- Ave. Duration
- 5h
- Frequency
- Once daily
- Estimated price
- $30–55
- Website
- Greyhound
Want to know more about travelling around Costa Rica
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Booking & Getting There
Yes, the driving distance between Chicago to Guanacaste is 5123 km. It takes approximately 2 days 14h to drive from Chicago to Guanacaste.
There are 103+ hotels available in Guanacaste.








