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 |
Last refresh of the prices: Today at 2:55 PM EDT.
Compare 2 ways to go 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, 11 hours and with fares starting at just CLP 97,511, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5824 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 CLP 259,364
Frequently asked questions about traveling from Winter Haven to Chicago by train
Please note that schedules, routes, or operator details shown here may be updated or vary 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 CLP 259,364. The average price for this train route is around CLP 389,923. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Winter Haven to Chicago?
The average train ride duration from Winter Haven to Chicago is 1d 22h, covering a distance of 1013 miles (1634 km). The quickest train can get you there in 1d 18h and is operated by Amtrak.
Which train operators service the Winter Haven to Chicago route?
Several major train operators operate on this route with 3 trains available per day.
What is the earliest and latest departure time for the train from Winter Haven to Chicago?
The earliest train departs from Winter Haven to Chicago at 11:08am. And the latest train departs at 2:56pm.
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 Jun 12, 2026 with a price of CLP 375,648To 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 CLP 375,648 to CLP 2,922,632 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 CLP 375,648 which is on 2026-06-17.
