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 | Cheapest | |||||
| Chicago (Union Station), IL | Winter Haven Station | Fastest | |||||
| 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: Last Tuesday at 6:31 PM CST.
Compare 2 ways to go from Chicago to Winter Haven
Among the sustainable travel choices, the bus stands out as the good way to reach Winter Haven. The journey takes about 1 day, 14 hours 20 minutes and with fares starting at just $141, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5694 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 $239
Frequently asked questions about traveling from Chicago to Winter Haven 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 Chicago to Winter Haven?
The cheapest train tickets from Chicago to Winter Haven start from $239. The average price for this train route is around $452. 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 Chicago to Winter Haven?
The average train ride duration from Chicago to Winter Haven is 1d 17h, covering a distance of 1013 miles (1634 km). The quickest train can get you there in 1d 17h and is operated by Amtrak.
Which train operators service the Chicago to Winter Haven route?
Several major train operators operate on this route with 1 trains available per day.
What is the earliest and latest departure time for the train from Chicago to Winter Haven?
The earliest train departs from Chicago to Winter Haven at 6:40pm. And the latest train departs at 6:40pm.
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 Jan 3, 2026 with a price of $464To 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 $464 to $2,153 for a train ticket from Chicago to Winter Haven based on the last 1 days. You can expect to find the cheapest price for the trip at $464 which is on 2026-01-03.
