Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Price and booking link |
|---|---|---|---|---|---|---|---|
 | Train
| Winter Haven Station | Chicago (Union Station), IL | ||||
| Train
| Winter Haven Station | Chicago (Union Station), IL | ||||
| Train
| Winter Haven Station | Chicago (Union Station), IL | ||||
| Train
| Winter Haven Station | Chicago (Union Station), IL | ||||
| Train
| Winter Haven Station | Chicago (Union Station), IL |
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, 17 hours 45 minutes, and with fares starting at just MX$2,160, it presents an excellent value for a comfortable ride.
Train companies
Based on 6484 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 MX$4,342
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 MX$4,342. The average price for this train route is around MX$9,364. 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 Sep 14, 2026 with a price of MX$4,609To 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 MX$4,609 to MX$38,141 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 MX$4,609 which is on 2026-09-14.
