Compare 2 ways to go from Chicago to Winter Haven.
Busbud recommends taking the bus from Chicago to Winter HavenAmong the sustainable travel choices, the bus stands out as the good way to reach Winter Haven. The journey takes about 1 day, 14 hours 55 minutes and with fares starting at just $166, it presents an excellent value for a comfortable ride.
Train Chicago to Winter Haven: Trip Overview
Please note, this information is subject to change.
Train Companies
Based on 5103 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $277.00
Chicago to Winter Haven Train
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Discover how much the train trip from Chicago to Winter Haven will cost you. Use our filters and sorting features to find the cheapest train tickets or high-end trains.
Frequently asked questions for your trip Chicago - Winter Haven
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Chicago to Winter Haven was searched and found on May 7, 2025 with a price of $321To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Chicago to Winter Haven, as early as possible.
About Train Travel
Train Travel Tips
Taking the fastest trains allows you to travel at speeds greater than 300 km/h. Taking a trip from Chicago to Winter Haven is not only much quicker but more comfortable too! You can usually travel directly to the city centre and save time while you're at it.
Regional train? High-speed train? Whichever train to Winter Haven you take, you’ll help reduce the environmental impact and carbon footprint of your trip. As you watch the landscapes unfold before your eyes, you can tell yourself that with this choice, you are making sure they remain protected.
With up to 30x less CO2 emissions for your train journey between Chicago and Winter Haven, the train is an ecological alternative to flights or personal cars.
Make a music playlist for your train ride from Chicago to Winter Haven, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
One of the deepest train stations in the world is in Kiev. Located at a depth of 105 m, it was designed in this way to serve as a shelter in the event of an attack. The second deepest station is in China. Badaling station is located 60 m under the Great Wall of China!
The longest train journey in the world is between Europe and Asia. This long journey starts from Porto in Portugal and crosses the whole European continent to reach Hanoi in Vietnam in 12 days while traveling more than 17,000 km.
Japanese trains are always on time, it is extremely infrequent to see breakdowns during peak periods. In the event of a delay of more than 5 minutes, the crew will personally apologize to each passenger.
Top Traveled Train Routes
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Popular Trains Connecting Winter Haven
Trains Going to Winter Haven
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