Next departures to Winter Haven
One passenger / one way
- This trip is recommended because it is: Cheapest + FastestDeparture time: June 24 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: June 26 atDestination city: Winter HavenDestination location: Winter Haven StationOperated by: Amtrak
Vehicle: BusDuration: - Departure time: June 24 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: June 26 atDestination city: Winter HavenDestination location: Winter Haven StationOperated by: AmtrakVehicle: BusDuration:
- Departure time: June 24 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: June 26 atDestination city: Winter HavenDestination location: Winter Haven StationOperated by: AmtrakVehicle: BusDuration:
- Departure time: June 24 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: June 26 atDestination city: Winter HavenDestination location: Winter Haven StationOperated by: AmtrakVehicle: BusDuration:
- Departure time: June 24 atDeparture city: ChicagoDeparture location: Chicago (Union Station), ILArrival time: June 26 atDestination city: Winter HavenDestination location: Winter Haven StationOperated by: AmtrakVehicle: BusDuration:
Accepted payments
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 20 minutes and with fares starting at just $161, 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 5223 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 $344
Chicago to Winter Haven Train
With Busbud, comparing and booking tickets for a train from Chicago to Winter Haven is a breeze. Browse through an extensive selection of train fares and train schedules to find the best deals.
We make sure you can find a train service from Chicago to Winter Haven from the most reliable train companies operating this trip.
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 Jun 25, 2025 with a price of $403To 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.
You can expect to pay from $403 to $2,301 for a train ticket from Chicago to Winter Haven based on the last 2 days. You can expect to find the cheapest price for the trip at $403 which is on 2025-06-25.
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
Why choose Busbud?
The Best Way To Book Bus and Train Tickets
Busbud makes bus travel easy. We help travelers find a bus, plot routes, and book intercity bus tickets all over the world. Use Busbud to book your trip online, in your own language and currency, wherever you are. Busbud prides itself on its worldwide partnerships. We make it possible for you to buy tickets with its large network of trustworthy bus partners like Greyhound, Eurolines, ALSA, OUIBUS (BlaBlaBus), National Express and many others.
People from around the world trust Busbud
Popular Trains Connecting Chicago
Trains Leaving from Chicago
Popular Trains Connecting Winter Haven
Trains Going to Winter Haven
Popular train trips
Top Routes Worldwide
- Train from Wells to Fargo
- Train from Richmond to Richmond
- Train from Detroit to Red Wing
- Train from Wilmington to Wilmington
- Train from Los Angeles to Glendale
- Train from Niagara Falls to Ontario
- Train from Washington to Leavenworth
- Train from Waterloo to Buffalo
- Train from New York to Saratoga Springs
- Train from Saratoga Springs to New York
- Train from Washington to Everett
- Train from Seattle to Washington
- Train from Salem to Washington
- Train from Jacksonville to Jacksonville
- Train from Vancouver to Washington