Next train departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Winter Haven Station | Chicago (Union Station), IL | CheapestFastest | ||||
| Train | Winter Haven Station | Chicago (Union Station), IL | No tags | ||||
| Train | Winter Haven Station | Chicago (Union Station), IL | No tags | ||||
| Train | Winter Haven Station | Chicago (Union Station), IL | No tags | ||||
| Train | Winter Haven Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Today at 9:44 AM EST.
Compare 2 ways to travel from Winter Haven to Chicago
Among the sustainable travel choices, the bus stands out as a good way to reach Chicago. The journey takes about 1 day, 7 hours and with fares starting at just R 2 353, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5645 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 2 793
Frequently asked questions about travelling from Winter Haven to Chicago 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 Winter Haven to Chicago?
The cheapest train tickets from Winter Haven to Chicago start from R 2 793. The average price for this train route is around R 7 229. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from Winter Haven to Chicago?
The average train journey time from Winter Haven to Chicago is 1d 21h, covering a distance of 1634 km. The quickest train can get you there in 1d 18h and is operated by Amtrak.
Which train operators serve the Winter Haven to Chicago route?
Several major train operators run on this route, with 3 trains available per day.
What are the earliest and latest departure times for the train from Winter Haven to Chicago?
The earliest train from Winter Haven to Chicago departs at 12:08. And the latest train departs at 14:56.
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 13 Dec 2025 with a price of R 4 752To 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.
You can expect to pay from R 4 752 to R 43 837 for a train ticket from Winter Haven to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at R 6 964, which is on 2025-12-15.
