There are 4 ways to get from Havana to Chicago by plane, bus, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly José Martí International Airport to Chicago Midway International Airport
best- Fly from José Martí International Airport (HAV) to Chicago Midway International Airport (MDW)plane HAV - MDW
8h 31m$248–1,116Bus to Juan Gualberto Gómez International Airport, fly to Chicago O'Hare International Airport
cheapest- Take the bus from Terminal de Ómnibus Nacionales La Habana to Varadero Airportbus
- Fly from Juan Gualberto Gómez International Airport (VRA) to Chicago O'Hare International Airport (ORD)plane VRA - ORD
10h 35m$109–464Fly José Martí International Airport to Chicago O'Hare International Airport
- Fly from José Martí International Airport (HAV) to Chicago O'Hare International Airport (ORD)plane HAV - ORD
9h 13m$218–966Fly José Martí International Airport to General Mitchell International Airport, train
- Fly from José Martí International Airport (HAV) to General Mitchell International Airport (MKE)plane HAV - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
12h 20m$390–1,775
José Martí International Airport (HAV) to Chicago Midway International Airport (MDW) flights
Comparing Your Travel Options
The cheapest way to get from Havana to Chicago is to bus and fly which costs $100 - $470 and takes 10h 35m.
The fastest way to get from Havana to Chicago is to fly which takes 8h 31m and costs $240 - $1,200.
The distance between Havana and Chicago is 1364 miles.
It takes approximately 8h 31m to get from Havana to Chicago, including transfers.
Chicago is 1h behind Havana. It is currently 12:44 PM in Havana and 11:44 AM in Chicago.
There are 1285+ hotels available in Chicago.
What companies run services between Havana, Cuba and Chicago, IL, USA?
Southwest Airlines, American Airlines, and Viva Aerobus fly from José Martí International Airport (HAV) to Chicago Midway International Airport (MDW) twice daily.
- Website
- aa.com
Flights from José Martí International Airport to Chicago O'Hare International Airport via Miami
- Ave. Duration
- 6h 5m
- When
- Every day
- Estimated price
- $210–950
Flights from Juan Gualberto Gómez International Airport to Chicago O'Hare International Airport via Miami
- Ave. Duration
- 6h
- When
- Every day
- Estimated price
- $95–440
Flights from Juan Gualberto Gómez International Airport to Chicago O'Hare International Airport via Montreal
- Ave. Duration
- 7h 54m
- When
- Sunday
- Estimated price
- $210–900
Flights from José Martí International Airport to General Mitchell International Airport via Miami
- Ave. Duration
- 6h 52m
- When
- Saturday
- Estimated price
- $380–1,700
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–50
- Website
- Amtrak
#mediaviewer/File:Super_Dome_car.jpg "Hiawatha dome car")
- Phone
- +53 59 89 0616
- [email protected]
- Website
- Viazul
Bus from Terminal de Ómnibus Nacionales La Habana to Varadero Airport
- Ave. Duration
- 1h 50m
- Frequency
- 4 times a day
- Estimated price
- $12–20
- Website
- Viazul
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