Previously seen trips
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
Greyhound + FlixBus | Bus | Winter Haven Transportation Center | Chicago 95Th & Dan Ryan | No tags | ||||
FlixBus + Greyhound | Bus | Winter Haven Transportation Center | 537-517 W. Jackson Blvd | No tags | ||||
FlixBus + Greyhound | Bus | Winter Haven Transportation Center | Chicago 95Th & Dan Ryan | No tags | ||||
Greyhound + FlixBus | Bus | Winter Haven Transportation Center | 537-517 W. Jackson Blvd | No tags | ||||
FlixBus + Greyhound | Bus | Winter Haven Transportation Center | Downtown Greyhound Station | 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 $151, it presents an excellent value for a comfortable ride.
Compare bus companies
Based on 87519 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the temperature but often complained with the Wi‑Fi. Greyhound ticket prices on this trip start at $152
Frequently asked questions about travelling 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 $151. The average price for this route is around $334. 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 travel time from Winter Haven to Chicago is 1d 9h, covering a distance of 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 bus companies operate on this route with 8 buses available per day.
What are the earliest and latest departure times 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 a mode of travel recommended by Busbud.
Find cheapest prices for buses
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 30, 2026 with a price of $453To 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.
What's the cheapest way to go from Winter Haven to Chicago?
The Bus is the cheapest travel choice for this destination
