Next departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
Greyhound Lines, Inc. + FlixBus | Winter Haven Transportation Center | Downtown Greyhound Station | Cheapest | |||||
Greyhound Lines, Inc. + FlixBus | Winter Haven Transportation Center | Chicago 95Th & Dan Ryan | Fastest | |||||
Greyhound Lines, Inc. + FlixBus | Winter Haven Transportation Center | Downtown Greyhound Station | No tags | |||||
 | Winter Haven Transportation Center | Downtown Greyhound Station | No tags | |||||
Greyhound Lines, Inc. + FlixBus | Winter Haven Transportation Center | 537-517 W. Jackson Blvd | No tags |
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Compare 2 ways to go from Winter Haven to Chicago
Busbud recommends taking the bus from Winter Haven to ChicagoAmong 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 US$162, it presents an excellent value for a comfortable ride.
Bus Winter Haven to Chicago: Trip Overview
Compare bus companies
Based on 87204 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 WiFi. Greyhound ticket prices on this trip start at US$231
Winter Haven to Chicago Bus
Busbud helps you find a bus from Winter Haven to Chicago. Get the best fare and schedule, book a round trip ticket or find buses with WiFi and electrical outlets.
Bus service from Winter Haven to Chicago will be provided by the most trusted bus companies.
Discover how much the bus trip from Winter Haven to Chicago will cost you. Use our filters and sorting features to find the cheapest bus tickets or luxury buses.
Frequently asked questions on the trip Winter Haven - Chicago
What is the distance between Winter Haven and Chicago?
It's about 1630 km (1011 miles) from Winter Haven to Chicago.
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 Aug 25, 2025 with a price of US$227To 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 US$227 to US$265 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 US$229 which is on 2025-08-26.
About Bus Travel
Bus Travel Tips
Make friends with the driver. They usually know a lot about your destination and may even recommend which side of the bus to sit on to get the best views on the road between Winter Haven and Chicago!
Much more than a mere vehicle taking you from Winter Haven to Chicago, riding the bus will expose you to some of the most stunning panoramas while enroute to your final bus stop.
Buses have one of the smallest carbon footprints of motorized transport modes. A bus going from Winter Haven to Chicago will emit less CO2 than a car or an airplane.
Make a music playlist for your bus ride from Winter Haven to Chicago, and enjoy the scenery to tunes from your own personal soundtrack.
Did you know?
Did you know there are on average 4,400 intercity bus departures every day in the US only? This number has been growing for 9 years in a row, yay!
The average number of passengers on a coach bus is 32 meaning that a bus could replace a minimum of at least 30 cars!
It takes 27 hours to go by bus from Lima to Cusco, one of the craziest bus trips on the world. This route is used daily by locals and backpackers.
What's the cheapest way to go from Winter Haven to Chicago?
The bus is the cheapest travel choice for this destinationTop travelled bus routes
Why choose Busbud?
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Busbud helps you easily search, compare and book intercity bus tickets on a worlwide scale with our comprehensive list of bus routes and schedules. With Busbud, wherever you go, you have a worldwide bus station within reach and available in your own language and currency. With Busbud, you can buy tickets with confidence. We ensure that you make the most out of your bus trip by partnering up with reliable bus companies from all around the world such as Greyhound, Eurolines, ALSA, OUIBUS (BlaBlaBus), National Express and many others.
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