Trains tickets from Chicago to Winter Haven

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Today24 May
from US$344
Tomorrow25 May
Mon26 May
Tue27 May
Wed28 May
Thu29 May
Fri30 May
Sat31 May

Next departures to Winter Haven

One passenger / one way

  • This trip is recommended because it is the: Cheapest + Fastest
    Departure time: 24 May at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: 26 May at
    Destination city: Winter Haven
    Destination location: Winter Haven Station
    Operated by: AmtrakAmtrak
    Vehicle: BusDuration:
  • Departure time: 24 May at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: 26 May at
    Destination city: Winter Haven
    Destination location: Winter Haven Station
    Operated by: AmtrakAmtrak
    Vehicle: BusDuration:
  • Departure time: 24 May at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: 26 May at
    Destination city: Winter Haven
    Destination location: Winter Haven Station
    Operated by: AmtrakAmtrak
    Vehicle: BusDuration:
  • Departure time: 24 May at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: 26 May at
    Destination city: Winter Haven
    Destination location: Winter Haven Station
    Operated by: AmtrakAmtrak
    Vehicle: BusDuration:
  • Departure time: 24 May at
    Departure city: Chicago
    Departure location: Chicago (Union Station), IL
    Arrival time: 26 May at
    Destination city: Winter Haven
    Destination location: Winter Haven Station
    Operated by: AmtrakAmtrak
    Vehicle: BusDuration:

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Compare 2 ways to travel from Chicago to Winter Haven

Bus
Average priceUS$166 - US$285Average duration1d 14h
41kg CO₂e5 out of 5 stars
CheapestFastestMost eco-friendly
Train
Average priceUS$277 - US$477Average duration1d 17h
149kg CO₂e1 out of 5 stars
busbud logoBusbud recommends taking the bus from Chicago to Winter Haven

Among the sustainable travel choices, the bus stands out as a good way to reach Winter Haven. The journey takes about 1 day, 14 hours 20 minutes and with fares starting at just US$166, it presents an excellent value for a comfortable ride.

3bus per day
1d 14hAverage duration
US$166Cheapest ticket
41kgCO₂ emissions

Train Chicago to Winter Haven: Trip Overview

Please note, this information is subject to change.

Average ticket priceUS$334
Average train trip duration1d 17h
Number of daily trains2
Earliest train departure18:40
Distance1013 miles

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 on the trip Chicago - Winter Haven

  1. How much does a cheap train ticket from Chicago to Winter Haven cost?

    The average train ticket price from Chicago to Winter Haven is US$334. The best way to find cheap train tickets from Chicago to Winter Haven is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!

  2. How long is the train trip from Chicago to Winter Haven?

    A train trip between Chicago and Winter Haven is around 1d 17h, although the fastest train will take about 1d 17h. This is the time it takes to travel the 1011 miles that separates the two cities.

  3. How many daily train are there between Chicago and Winter Haven?

    The number of trains from Chicago to Winter Haven can differ depending on the day of the week. On average, there are 2. Some trains are direct while others include transferring trains. Simplify your train trip from Chicago to Winter Haven by comparing and selecting the train that fits your travel style and budget on Busbud.

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found
22/05
No data
23/05
No data
Today
US$331
25/05
No data
26/05
No data
27/05
No data
28/05
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29/05
No data
busbud logoThe cheapest trip from Chicago to Winter Haven was searched and found on 24 May 2025 with a price of US$331

To 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 105m, 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 60m 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 travelling 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 apologise to each passenger.

Will you be returning to Chicago by train?

Train from Winter Haven to Chicago

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