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Chicago, IL, USA to Havana from $260: 3 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
Havana, Cuba

How to Get from Chicago to Havana: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$260 - PlaneBest price
2153 kmDistance
8h 7m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Havana with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Plane
Average Duration
8h  13m
Estimated price
$140-436
Recommended
route map
Distance: 2153 km
Duration: 8h 7m

See more options

Company
various
Plane
Average Duration
8h  7m
Estimated price
$260-496
Company
Amtrak and various
Plane
Average Duration
10h  3m
Estimated price
$263-762
Browse car rentalsExplore flights

Traveling From Chicago to Havana

The vibrant cityscape of Chicago, with its iconic skyline and bustling culture, stands in stark contrast to the colorful streets and rich history of Havana, where classic cars and colonial architecture come together to create a captivating atmosphere.

Best Neighbourhoods in Havana

Havana's neighborhoods each offer a distinct vibe and charm, enriching your travel experience.

Old Havana (Habana Vieja)
• Home to historic architecture and lively plazas.
• Renowned for vibrant street art and local markets.
Vedado
• Features modernist buildings and upscale dining options.
• Popular nightlife scene with bars and clubs.
Miramar
• Coastal neighborhood known for luxury accommodations.
• Offers beautiful seaside views and serene parks.

Best Times To Visit Havana's Attractions

Maximize your enjoyment of Havana's rich attractions by timing your visits wisely.

Malecón
Visit at sunset for breathtaking views and a quieter atmosphere.
The Cathedral of Havana
Early mornings are ideal to avoid crowds and appreciate its beauty.
Museum of the Revolution
Weekdays offer a more relaxed experience and fewer visitors.

Havana Weather: What to Expect Year-Round

Havana enjoys a tropical climate with warm temperatures year-round, but the best time to visit is during the dry season from November to April. Understanding the weather patterns can help you plan your activities, whether you're exploring vibrant streets or lounging on the beach.

Dining in Havana: A Flavorful Journey

Savoring Ropa Vieja at La Guarida, one of Havana's iconic restaurants, immerses you in the rich flavors of slow-cooked shredded beef, which contrasts beautifully with Chicago's iconic deep-dish pizza. The lively atmosphere, complemented by local ingredients and passionate culinary traditions, creates a dining experience that feels both vibrant and authentically Cuban.

Chicago - Havana operators

Explore transport companies operating between Chicago and Havana, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane Show flights
Website
southwest.com

Plane from Chicago Midway to Havana

Average Duration
7h 25m
Estimated price
$220-1400

Plane from Chicago Midway to Havana

Average Duration
6h
Estimated price
$270-1401

Plane from Chicago Midway to Havana

Average Duration
6h 50m
Estimated price
$270-1401

Plane from Chicago O'Hare to Havana

Average Duration
5h 25m
Estimated price
$1402-1403
Website
aa.com

Plane from Chicago Midway to Havana

Average Duration
5h 30m
Estimated price
$270-1401

Plane from Chicago O'Hare to Havana

Average Duration
5h 43m
Estimated price
$270-1404

Plane from Milwaukee to Havana

Average Duration
6h 8m
Estimated price
$200-1405
Website
delta.com

Plane from Chicago Midway to Havana

Average Duration
5h 24m
Estimated price
$1406-1407
Website
united.com

Plane from Chicago O'Hare to Havana

Average Duration
7h 44m
Estimated price
$290-1408

Plane from Chicago O'Hare to Havana

Average Duration
5h 3m
Estimated price
$290-1408
Train
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Chicago Union Station to Milwaukee

Average Duration
1h 29m
Estimated price
$1409-4360

Chicago to Havana: Overview of Bus, Train, Flight, and Car Trips

Traveling between Chicago and Havana offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🛫 Traveling from Chicago to Havana involves taking a flight with one stopover, as there are no direct flights offered from Chicago Midway Airport to Havana Airport. The quickest route typically takes around 5 hours and 30 minutes. ✈️ Major airlines such as Delta, American Airlines, Frontier Airlines, and Southwest Airlines provide options for flights between Chicago Midway Airport and Havana Airport. The journey from Chicago to Havana by plane typically lasts around 8 hours and 13 minutes. 💸 The cost of a flight from Chicago to Havana can vary, with prices ranging from $140 to $436.
Departure Point
Chicago Midway Airport
Arrival Point
Havana Airport. The quickest flight takes 5h 30m and has one stopover

Frequently asked questions

Find out more about the route from Chicago to Havana.

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The distance between Chicago and Havana is approximately 1338 miles. The typical travel time varies depending on the mode of transportation. If you choose to take a train from Chicago to Milwaukee and then fly to Havana, it would take around 11 hours and 9 minutes. Alternatively, if you opt for a direct flight from Chicago to Havana, the travel time is approximately 9 hours.
The most cost-effective and time-efficient transportation option for traveling from Chicago to Havana is by flying. Flying from Chicago to Havana typically takes around 9 hours and costs between $200 and $700. This is not only the quickest mode of transportation but also relatively affordable. Taking a train to Milwaukee and then flying to Havana is another option, but it takes longer and may not be as cost-effective.
The flight from Chicago to Havana typically has a duration of around 6 hours and 5 minutes with one stopover. However, there is no direct flight available between the two cities. The cost for a flight between Havana and Chicago can range from $204 to $660, depending on the airline and the time of booking.

Trips from Chicago