Next departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Chicago (Union Station), IL | Winter Haven Station | CheapestFastest | |||||
| Chicago (Union Station), IL | Winter Haven Station | No tags | |||||
| Chicago (Union Station), IL | Winter Haven Station | No tags | |||||
| Chicago (Union Station), IL | Winter Haven Station | No tags |
Last refresh of the prices: Today at 9:27 AM CST.
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 2 427, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5639 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 4 126
Frequently asked questions about travelling from Chicago to Winter Haven by train
Please note that timetables, routes, or operator details shown here may be updated or differ at the time of your trip.
How much is the train ticket from Chicago to Winter Haven?
The cheapest train tickets from Chicago to Winter Haven start from R 4 126. The average price for this train route is around R 7 819. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from Chicago to Winter Haven?
The average train journey time from Chicago to Winter Haven is 1d 18h, covering a distance of 1634 km. The quickest train can get you there in 1d 17h and is operated by Amtrak.
Which train operators serve the Chicago to Winter Haven route?
Several major train operators run on this route, with 1 trains available per day.
What are the earliest and latest departure times for the train from Chicago to Winter Haven?
The earliest train from Chicago to Winter Haven departs at 18:40. And the latest train departs at 18:40.
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 11 Dec 2025 with a price of R 4 763To 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 R 4 763 to R 32 041 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 R 5 733, which is on 2025-12-16.
