Find coaches from Winter Haven to Chicago

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Today2 Sept
Tomorrow3 Sept
Thu4 Sept
Fri5 Sept
from US$166
Sat6 Sept
Sun7 Sept
from US$166
Mon8 Sept
Tue9 Sept
from US$166

Cheap buses leaving Friday

One passenger / one way

  • This trip is recommended because it is the: Cheapest
    Departure time: 5 September at
    Departure city: Winter Haven
    Departure location: Winter Haven Transportation Center
    Arrival time: 6 September at
    Destination city: Chicago
    Destination location: Chicago 95Th & Dan Ryan
    Operated by: Greyhound Lines, Inc. + FlixBus
    Greyhound Lines, Inc. + FlixBus
    Vehicle: BusDuration:
  • This trip is recommended because it is the: Fastest
    Departure time: 5 September at
    Departure city: Winter Haven
    Departure location: Winter Haven Transportation Center
    Arrival time: 6 September at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: Greyhound Lines, Inc. + FlixBus
    Greyhound Lines, Inc. + FlixBus
    Vehicle: BusDuration:
  • Departure time: 5 September at
    Departure city: Winter Haven
    Departure location: Winter Haven Transportation Center
    Arrival time: 6 September at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: Greyhound Lines, Inc. + FlixBus
    Greyhound Lines, Inc. + FlixBus
    Vehicle: BusDuration:
  • Departure time: 5 September at
    Departure city: Winter Haven
    Departure location: Winter Haven Transportation Center
    Arrival time: 7 September at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: Greyhound Lines, Inc.Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • Departure time: 5 September at
    Departure city: Winter Haven
    Departure location: Winter Haven Transportation Center
    Arrival time: 6 September at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: Greyhound Lines, Inc. + FlixBus
    Greyhound Lines, Inc. + FlixBus
    Vehicle: BusDuration:

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Compare 2 ways to travel from Winter Haven to Chicago

Bus
Average priceUS$162 - US$281Average duration1d 7h
40kg CO₂e5 out of 5 stars
FastestMost eco-friendly
Train
Average priceUS$135 - US$622Average duration1d 21h
149kg CO₂e1 out of 5 stars
Cheapest
busbud logoBusbud recommends taking the bus 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 US$162, it presents an excellent value for a comfortable ride.

8bus per day
1d 7hAverage duration
US$162Cheapest ticket
40kgCO₂ emissions

Bus Winter Haven to Chicago: Trip Overview

Average ticket priceUS$179
Average bus trip duration1d 7h
Number of daily buses8
Earliest bus departure08:35
Distance1001 miles
Latest bus departure15:20

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

  1. How far is Chicago from Winter Haven by coach?

    The distance between Winter Haven and Chicago by coach is approximately 1011 miles (1630 km).

  2. What is the best way to go from Winter Haven to Chicago without flying?

    You can choose the coach to travel this route. Choosing the coach guarantees a comfortable and sustainable travel experience, allowing you to admire the views on your way to your destination. You might also find carpooling options to travel between the two cities.

Find cheapest prices for buses

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

Best price found
31/08
US$234
01/09
No data
Today
No data
03/09
No data
04/09
No data
05/09
US$233
06/09
No data
07/09
US$233
busbud logoThe cheapest trip from Winter Haven to Chicago was searched and found on 5 Sept 2025 with a price of US$233

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 US$233 to US$234 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$233, which is on 2025-09-05.

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 the smallest carbon footprint of all motorized transport modes. A bus going from Winter Haven to Chicago will emit half the CO2 emitted by a train, and radically less 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?

busbud logoThe bus is the cheapest travel choice for this destination

Will you be returning to Winter Haven by bus?

Bus from Chicago to Winter Haven

You can also go to Chicago by train

Train from Winter Haven to Chicago

Why choose Busbud?

The Best Way To Book Bus and Train Tickets

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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