Compare 2 ways to go from Winter Haven to Chicago.
Busbud recommends taking the bus from Winter Haven to ChicagoAmong the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 7 hours and with fares starting at just $159, it presents an excellent value for a comfortable ride.
Train Winter Haven to Chicago: Trip Overview
Please note, this information is subject to change.
Train Companies
Based on 5095 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 $270.00
Winter Haven to Chicago Train
Busbud helps you find a train from Winter Haven to Chicago. Get the best fare and schedule, book a round trip ticket or find trains with WiFi and electrical outlets.
Train service from Winter Haven to Chicago will be provided by the most trusted companies.
Discover how much the train trip from Winter Haven to Chicago 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 Winter Haven - Chicago
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Winter Haven to Chicago was searched and found on May 4, 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 Winter Haven to Chicago, as early as possible.
About Train Travel
Train Travel Tips
There are many train stations in the world, check it station pages on Busbud to get all information you need.
No matter if you plan to take a regional or high-speed train to Chicago, the planet will thank you. You’ll help to protect the beautiful landscapes that will unfold before your very eyes.
With up to 30x less CO2 emissions for your train journey between Winter Haven and Chicago, the train is an ecological alternative to flights or personal cars.
Make a music playlist for your train ride from Winter Haven to Chicago, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
The magnetic levitation train (Maglev for short) is currently the fastest train in the world. With a speed of 603 km/ h, it is closely followed by the French high-speed train (574.8 km / h) which remains in 2020, the fastest train to date
You can find dogs as passengers on the trains of Moscow, where there is a large number of stray dogs. Over time, the dogs have learned the inner workings of the rail system and it is not uncommon to find one traveling between the city and the suburbs.
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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