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

The cheapest bus tickets from Winter Haven to Chicago start from $137. The average price for this route is around $274. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.

How long is the bus ride from Winter Haven to Chicago?

The average bus trip duration from Winter Haven to Chicago is 1d 7h, covering a distance of 1011 miles (1631 km). The quickest bus can get you there in 1d 17h and is operated by Greyhound .

Which bus companies service the Winter Haven to Chicago route?

Several major train operators operate on this route with 8 trains available per day.

What is the earliest and latest departure time for the bus from Winter Haven to Chicago?

The earliest bus departs from Winter Haven to Chicago at 8:35am. And the latest bus departs at 3:20pm.

What are the CO₂ emissions for the bus trip from Winter Haven to Chicago?

A bus trip from Winter Haven to Chicago generates an estimated 41 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.

Bus Winter Haven to Chicago from $146 | Refundable Tickets

Next bus departures

Next departures for Winter Haven to Chicago on December 17
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Greyhound Lines, Inc. + FlixBus	Bus	8:35am	Winter Haven Transportation Center	1d 6h	1:40pm	Chicago 95Th & Dan Ryan	Cheapest
Greyhound Lines, Inc. + FlixBus	Bus	3:15pm	Winter Haven Transportation Center	1d 5h	8:10pm	Downtown Greyhound Station	Fastest
Greyhound Lines, Inc. + FlixBus	Bus	8:35am	Winter Haven Transportation Center	1d 7h	2:35pm	Downtown Greyhound Station	No tags
	Bus	3:20pm	Winter Haven Transportation Center	1d 18h	8:25am	Downtown Greyhound Station	No tags
Greyhound Lines, Inc. + FlixBus	Bus	8:35am	Winter Haven Transportation Center	1d 6h	2:10pm	537-517 W. Jackson Blvd	No tags

Last refresh of the prices: Today at 12:11 PM 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

Compare bus companies

Greyhound

3.5/587,434 reviews

Staff3.6

Timeliness2.9

Cleanliness3.3

Wifi2.4

Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.

US bus companies: FlixBus, BlaBlaCar Bus, ALSA, Greyhound, Intercape, Trenitalia, Big Sky

Frequently asked questions about traveling from Winter Haven to Chicago by bus

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 bus ticket from Winter Haven to Chicago?
The cheapest bus tickets from Winter Haven to Chicago start from $137. The average price for this route is around $274. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Winter Haven to Chicago?
The average bus trip duration from Winter Haven to Chicago is 1d 7h, covering a distance of 1011 miles (1631 km). The quickest bus can get you there in 1d 17h and is operated by Greyhound.
Which bus companies service the Winter Haven to Chicago route?
Several major train operators operate on this route with 8 trains available per day.
What is the earliest and latest departure time for the bus from Winter Haven to Chicago?
The earliest bus departs from Winter Haven to Chicago at 8:35am. And the latest bus departs at 3:20pm.
What are the CO₂ emissions for the bus trip from Winter Haven to Chicago?
A bus trip from Winter Haven to Chicago generates an estimated 41 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.

Find cheapest prices for buses

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

12/14

$269

12/15

$333

Today

$265

12/17

$337

12/18

No data

12/19

No data

12/20

No data

12/21

No data

The cheapest trip from Winter Haven to Chicago was searched and found on Dec 16, 2025 with a price of $265

To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Winter Haven to Chicago, as early as possible.

You can expect to pay from $265 to $337 for a bus ticket from Winter Haven to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $337 which is on 2025-12-17.