Previously seen trips
| 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 | 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 | ||||
| Train | Winter Haven Station | Chicago (Union Station), IL | No tags |
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, 9 hours 20 minutes, and with fares starting at just $152, it presents an excellent value for a comfortable ride.
Train companies
Based on 5754 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 $189
Frequently asked questions about travelling 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 at $189. The average price for this train route is around $545. Busbud recommends booking your tickets in advance to increase your chances of getting the lowest possible price.
How long is the train ride from Winter Haven to Chicago?
The average train trip from Winter Haven to Chicago takes 1d 22h and covers 1634 km. The quickest train gets you there in 1d 18h and is operated by Amtrak.
Which train operators serve the Winter Haven to Chicago route?
Several major train operators serve 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 11:08am. 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 Jan 31, 2026 with a price of $547To 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.
