How much is the train ticket from Winter Haven to Chicago?

The cheapest train tickets from Winter Haven to Chicago start from $162. The average price for this train route is around $419. 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 21h, 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 12:08pm. And the latest train departs at 2:56pm.

Train Winter Haven to Chicago from $155 | Refundable Tickets

Next train departures

Next departures for Winter Haven to Chicago on December 15
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	2:56pm	Winter Haven Station	1d 18h	8:45am	Chicago (Union Station), IL	CheapestFastest
Train	2:56pm	Winter Haven Station	1d 18h	8:45am	Chicago (Union Station), IL	No tags
Train	12:08pm	Winter Haven Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	12:08pm	Winter Haven Station	1d 21h	8:45am	Chicago (Union Station), IL	No tags
Train	12:08pm	Winter Haven Station	1d 23h	10:12am	Chicago (Union Station), IL	No tags

Last refresh of the prices: Today at 9:44 AM EST.

Compare 2 ways to go from Winter Haven to Chicago

We recommend taking the bus

Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 7 hours and with fares starting at just $137, it presents an excellent value for a comfortable ride.

8bus per day

1d 7hAverage Duration

1011 milesDistance

41kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$137 - $510	Average Duration1d 7h	CO₂ emissions 41kg CO₂e
Train	Average Price$162 - $3,265	Average Duration1d 21h	CO₂ emissions 149kg CO₂e

Train Companies

Amtrak

4/55,645 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5645 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 $162

Train and bus companies in US:Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

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 $162. The average price for this train route is around $419. 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 21h, 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 12:08pm. 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.

Best price found

12/12

No data

12/13

$275

Today

$403

12/15

$403

12/16

No data

12/17

No data

12/18

No data

12/19

No data

The cheapest trip from Winter Haven to Chicago was searched and found on Dec 13, 2025 with a price of $275

To 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 $275 to $2,537 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 $403 which is on 2025-12-15.