Previously seen journeys
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Chicago (Union Station), IL | Winter Haven Station | No tags | ||||
| Train | Chicago (Union Station), IL | Winter Haven Station | No tags | ||||
| Train | Chicago (Union Station), IL | Winter Haven Station | No tags | ||||
| Train | Chicago (Union Station), IL | Winter Haven Station | No tags | ||||
| Train | Chicago (Union Station), IL | Winter Haven Station | No tags |
Compare 2 ways to travel 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 R 2 850, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5582 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at R 5 008
Frequently asked questions on the trip Chicago - Winter Haven
How much does a cheap train ticket from Chicago to Winter Haven cost?
The average train ticket price from Chicago to Winter Haven is R 7 329. 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!
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 1630 km that separates the two cities.
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.
Which train companies travel from Chicago to Winter Haven?
When taking the train from Chicago to Winter Haven, you can travel comfortably and safely with Amtrak.
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 12 Nov 2025 with a price of R 5 799To 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.
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