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The cheapest and fastest buses from Winter Haven, FL to Chicago, IL
Showing times and prices for Feb 06
Cheapest price
$475
Average price
$529
Fastest journey
1 d 5 h 10 m
Average duration
1 d 5 h 45 m
Buses per day
2
Distance
1628 km
Cheap tickets
The best way to find a cheap bus ticket from Winter Haven, FL to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Winter Haven, FL to Chicago, IL will cost around $529 if you buy it on the day, but the cheapest tickets can be found for only $475.
Fast buses
It's difficult to get from Winter Haven, FL to Chicago, IL without transferring at least 2 times.
08:35AM30h20
Winter Haven, FL02:55PMChicago, IL
$4751One-way
2 transfers
03:15PM29h10
Winter Haven, FL08:25PMChicago, IL
$5841One-way
3 transfers
03:15PM29h10
Winter Haven, FL08:25PMChicago, IL
$5841One-way
3 transfers
08:35AM30h20
Winter Haven, FL02:55PMChicago, IL
$4751One-way
2 transfers
Live departures
Winter Haven, FL to Chicago, IL bus times
The table below shows live departures for Winter Haven, FL to Chicago, IL buses for tomorrow, Friday, February 6. You can also manually refresh the results below to see updated bus journeys.
Last updated at 4:15 PM
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 8:35 AM Winter Haven, FL | 30h20 | 2:55 PM Chicago, IL | 2 transfers | |
| 3:15 PM Winter Haven, FL | 29h10 | 8:25 PM Chicago, IL | 3 transfers | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Winter Haven, FL to Chicago, IL by bus, train, or flight
Compare bus, train, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Why should you book Winter Haven, FL to Chicago, IL buses with Omio?
Greyhound operates all buses services from Winter Haven, FL to Chicago, IL.
Omio is an official ticket reseller for all your travel options from Winter Haven, FL to Chicago, IL.
Why book with Omio vs Greyhound?
- Compare with other providers: On Omio, you can not only buy tickets for Greyhound, but also compare tickets for the likes of to find the best option for your trip from Winter Haven, FL to Chicago, IL.
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare Greyhound with all available travel options, which are bus, train and flight to ensure you get the best deal for traveling from Winter Haven, FL to Chicago, IL.
Why book with Omio over Wanderu?
- Multiple modes of transport: Omio allows you to compare travel options including bus, train and flight to find the ideal travel option from Winter Haven, FL to Chicago, IL.
Journey information
Overview: Bus from Winter Haven, FL to Chicago, IL
USAUSA
Buses from Winter Haven, FL to Chicago, IL run on average 5 times per day, taking around 29h 45m. Cheap bus tickets for this journey start at $471 (€375) if you book in advance.
The earliest bus runs at 06:10, the last at 23:15. The fastest bus covers the 1011 miles (1628 km) distance in 29h 10m.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Distance 1011 miles (1628 km) |
Average bus duration 29h 45m |
Cheapest ticket price $471 (€375) |
Buses per day 5 |
Fastest bus 29h 10m |
First bus 06:10 |
Last bus 23:15 |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Bus providers: Greyhound from Winter Haven, FL to Chicago, ILYou can travel by bus between Winter Haven, FL to Chicago, IL with Greyhound for as low as $471 (€375). When you search for schedules and tickets, Omio will show you the best journey
Greyhound
About
Greyhound Lines, Inc. is a prominent American intercity bus transportation provider, established in 1914. It operates the largest intercity bus network in the United States, also extending services to Canada and Mexico. Greyhound is known for offering affordable and reliable long-distance travel, connecting major cities and rural communities across North America. The company's buses are equipped with amenities such as free Wi-Fi, power outlets, and extra legroom to enhance passenger comfort. Greyhound is a subsidiary of Flix SE, which also owns FlixBus, and together they offer an extensive network of over 1,600 destinations.
Luggage & cancellation policy
Average Duration
30h 55m
Cheapest Price
$186 (€148)
Greyhound frequency
2 a day
Luggage included
One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
Additional luggage
$15 per additional bag.
Cancellation Policy
You can cancel your ticket for a refund or exchange up to 24 hours before departure, for a cancellation fee applied.
Amenities on board the bus
Wifi
Food sold onboard
Seat reservation
Toilets
USB plugs
Accessibility
Assistance; Priority seating; Wheelchair-accessible buses.
Bikes
Bikes are allowed.
FAQs: Bus from Winter Haven, FL to Chicago, IL
Find answers to the most common questions about traveling from Winter Haven, FL to Chicago, IL by bus. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest bus, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.
Cheap bus tickets from Winter Haven, FL to Chicago, IL can start from as little as $471 (€375) when you book in advance. The average bus ticket price for Winter Haven, FL to Chicago, IL is $525 (€419) ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by bus from Winter Haven, FL to Chicago, IL is 29h 10m to travel the 1011 miles (1628 km) long journey. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
The earliest bus from Winter Haven, FL to Chicago, IL leaves at 6:10 AM. Plan your trip with the Journey Planner from Omio.
The latest bus from Winter Haven, FL to Chicago, IL leaves at 11:15 PM.
There are 5 buses a day from Winter Haven, FL to Chicago, IL which require at least one change with Greyhound. Schedules can vary on holidays or weekends with fewer buses.
When taking a bus from Winter Haven, FL to Chicago, IL, you can count on Greyhound for the best way to get you to Chicago, IL. You can also check all possible bus companies who offer a service between Winter Haven, FL and Chicago, IL and compare the amenities they offer before buying a bus ticket.
A trip to Chicago, IL from Winter Haven, FL is worth doing but not as a day trip with a journey time of 29h 10m each way. Check with Omio app the best way to travel.
The cheapest month for a bus from Winter Haven, FL to Chicago, IL is August.
It's helpful to compare your options as there are 3 ways to travel between Winter Haven, FL and Chicago, IL including taking a bus, train, and flight.
Yes, there are bathrooms on board the bus from Winter Haven, FL to Chicago, IL for bus company Greyhound.
Yes, the following accessibility options are available when taking the bus from Winter Haven, FL to Chicago, IL:
- Greyhound
- Assistance
- Priority seating
- Wheelchair-accessible buses.
Some of the most interesting sights to explore in Chicago, IL are:
- Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
- Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
- Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
- Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
- Field Museum, a natural history museum with vast exhibits including the famous T. rex skeleton, Sue.
The best things to do in Chicago, IL include:
- Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
- Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
- Take a river cruise to see the city's iconic architecture from a different perspective
- Attend a live performance at the historic Chicago Theatre
- Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U.S., offering free admission.
Whether you can cancel your bus ticket from Winter Haven, FL to Chicago, IL depends on the bus companies:
- Greyhound
- You can cancel your ticket for a refund or exchange up to 24 hours before departure, for a cancellation fee applied.
Yes, bikes are allowed on board the bus with bus company Greyhound.
Tickets are often cheaper when booked early. Traveling during off-peak hours or on weekdays can help you save money. Sort results by price to quickly identify the most affordable options. Check for promotions or discounts available on our website and app.
Yes, there is food available to purchase on board the bus from Winter Haven, FL to Chicago, IL.
Yes, the following luggage options are included when booking a bus ticket from Winter Haven, FL to Chicago, IL:
- Greyhound
- One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
Yes, the following additional luggage options are available when booking a bus ticket from Winter Haven, FL to Chicago, IL:
- Greyhound
- $15 per additional bag.
Unfortunately, pets are not allowed on the bus from Winter Haven, FL to Chicago, IL.
You can reserve your seat on the bus from Winter Haven, FL to Chicago, IL with the following bus company: Greyhound
Yes, there are USB plugs on board the bus from Winter Haven, FL to Chicago, IL with the following bus company: Greyhound.
Yes, there is Wifi on board the bus from Winter Haven, FL to Chicago, IL with the following bus company: Greyhound.
popular bus stations
Popular bus stations from Winter Haven, FL to Chicago, IL
Winter Haven
Chicago
The major bus station for departures in Winter Haven is Winter Haven, Terminal (Ave E NW / 5th St NW). Find all the information you need to know about services, amenities and connections at Winter Haven, Terminal (Ave E NW / 5th St NW) for your trip from Winter Haven to Chicago.
Winter Haven, Terminal (Ave E NW / 5th St NW)
information
The major bus station for arrivals in Chicago is Chicago, Greyhound Bus Station. Find all the information you need to know about services, amenities and connections at Chicago, Greyhound Bus Station for your trip to Chicago from Winter Haven.
Chicago, Greyhound Bus Station
information
Chicago, Union Station (Amtrak)
information
Most popular bus connections from Winter Haven, FL
More options for your journey from Winter Haven, FL to Chicago, IL
Here are some other resources that might have the information you need
Most popular buses to and from Chicago, IL and Winter Haven, FL
Most popular bus connections to Chicago, IL
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