Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
Greyhound Lines, Inc. + FlixBus | Bus | Winter Haven Transportation Center | Chicago 95Th & Dan Ryan | Cheapest | ||||
Greyhound Lines, Inc. + FlixBus | Bus | Winter Haven Transportation Center | Downtown Greyhound Station | Fastest | ||||
Greyhound Lines, Inc. + FlixBus | Bus | Winter Haven Transportation Center | Downtown Greyhound Station | No tags | ||||
 | Bus | Winter Haven Transportation Center | Downtown Greyhound Station | No tags | ||||
Greyhound Lines, Inc. + FlixBus | Bus | Winter Haven Transportation Center | 537-517 W. Jackson Blvd | No tags |
Last refresh of the prices: Today at 10:00 AM EST.
Compare 2 ways to travel 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, 7 hours and with fares starting at just R 2 344, it presents an excellent value for a comfortable ride.
Compare bus companies
Based on 87433 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 R 2 628
Frequently asked questions about travelling from Winter Haven to Chicago by bus
Please note that timetables, routes, or operator details shown here may be updated or differ 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 at R 2 344. The average price for this route is around R 4 392. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the bus journey from Winter Haven to Chicago?
The average bus journey time from Winter Haven to Chicago is 1d 7h, covering a distance of 1631 km. The fastest bus gets 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 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 08:35. And the latest bus departs at 15:20.
What are the CO₂ emissions for the bus trip from Winter Haven to Chicago?
A bus trip from Winter Haven to Chicago produces an estimated 41 kg of CO₂, making it a highly eco-friendly travel option and Busbud’s recommended way to travel.
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 16 Dec 2025 with a price of R 4 562To 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 R 4 562 to R 5 732 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 R 4 562, which is on 2025-12-16.
What's the cheapest way to go from Winter Haven to Chicago?
The bus is the cheapest travel choice for this destination
