- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
2,000+ travel companies
2,000+ travel companies
Scan to get our free app
Use our app to get live travel updates and book mobile tickets for trains, buses, flights, and ferries.
App Store
4.942K ratings
Google Play
4.6136K reviews
The cheapest and fastest buses from Winter Haven, FL to Chicago, IL
Showing times, prices and bookable tickets for Nov 04
- Cheapest price on Nov 04
- €230
- Average ticket price on Nov 04
- €230
- Fastest journey on Nov 04
- 1 d 6 h 40 m
- Average journey duration on Nov 04
- 1 d 6 h 40 m
- Buses on Nov 04
- 1
- 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 €230 if you buy it on the day, but the cheapest tickets can be found for only €230.
Fast buses
It's difficult to get from Winter Haven, FL to Chicago, IL without transferring at least 2 times.
8:35 AM 30h40 Winter Haven, FL 3:15 PM Chicago, IL €230 1 One-way 2 transfers
8:35 AM 30h40 Winter Haven, FL 3:15 PM Chicago, IL €230 1 One-way 2 transfers
Journey information
Overview: Bus from Winter Haven, FL to Chicago, IL
USAUSA
Take a bus from Winter Haven, FL to Chicago, IL and enjoy the approximately 1011 miles (1628 km) long journey. Find schedules and pricing options for a convenient and affordable trip.
The earliest bus runs at 06:10, the last at 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
Plan this route
Journey facts
- Distance1011 miles (1628 km)
- First bus6:10 AM
- Last bus11:15 PM
- Cheapest MonthFeb
- Cheapest DayThu
- High SeasonJan - Mar
- Low SeasonJul - Sep
Understand & plan this route
Book with confidence
- Why book with Omio?Compare options, payment & support
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
Frequently asked questions about your Winter Haven, FL to Chicago, IL trip
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Winter Haven, FL to Chicago, IL.
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.
Winter Haven, FL to Chicago, IL Bus Timetables
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Greyhound USA | Departure Time 08:35AM | Arrival Time 03:15PM | Duration 30h40 | Departure days Tue, Wed, Fri, Sat, Sun | Cheapest price €230 |
Operator Greyhound | Departure Time 01:35PM | Arrival Time 09:15PM | Duration 31h40 | Departure days Thu | Cheapest price €307 |
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, Wednesday, November 4. You can also manually refresh the results below to see updated bus journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 8:35 AM Winter Haven, FL | 30h40 | 3:15 PM Chicago, IL | 2 transfers | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Bus companies
Bus companies from Winter Haven, FL to Chicago, IL
Buses from Winter Haven, FL to Chicago, IL with Greyhound. Use the details below to compare onboard facilities.
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 Greyhound Duration
30h 40m
Cheapest Greyhound Price
€230
Greyhound frequency
3 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.
Companies, tickets, and onboard amenities between Winter Haven, FL and Chicago, IL
Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.
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.
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.
Yes, bikes are allowed on board the bus with bus company {providersWithBike}.
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, 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.
Complete guide to Chicago, IL
Things to do in Chicago, IL
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
- Must visit
Field Museum
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
- Must visit
Museum of Science and Industry
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
- Must visit
Millennium Park
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
- Must visit
Magnificent Mile
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
- Must visit
Chicago Riverwalk
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-Dish Pizza
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
Chicago-Style Hot Dog
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian Beef Sandwich
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Johnnie's Beef
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Superdawg Drive-In
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
Alinea
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
US dollar ($)
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Average meal costs
- Budget
- $10-18 for fast food or casual takeout.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $75+ per person for upscale restaurants.
- Coffee
- $3-6 for coffee or cappuccino.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
Plan your visit to Chicago, IL
Get destination-focused answers for the end of your trip, including what to do, when to go, practical entry details, and tips for making the most of your time in Chicago, IL.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
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.
Yes, you can take a bus between Winter Haven, FL and Chicago, IL.
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.
popular bus stations
Popular bus stations from Winter Haven, FL to Chicago, IL
Most Winter Haven, FL to Chicago, IL buses use the Winter Haven, Terminal (Ave E NW / 5th St NW) to Chicago, Greyhound Bus Station station pair, with some services arriving at Chicago, Union Station (Amtrak). Use this guide to compare Winter Haven, FL and Chicago, IL bus stations on this route, check city-centre transport, alongside checking practicalities like bus station facilities and services.
Departure bus stations in Winter Haven
Arrival bus stations in Chicago
Which Winter Haven, FL station do buses to Chicago, IL leave from?
Buses from Winter Haven, FL to Chicago, IL leave from Winter Haven, Terminal (Ave E NW / 5th St NW). The station is 0 miles (1 km) from Winter Haven, FL city centre at Winter Haven (E), 555 Ave E NW, Winter Haven, FL 33881, USA.
Winter Haven, Terminal (Ave E NW / 5th St NW)Winter Haven (E), 555 Ave E NW, Winter Haven, FL 33881, USA
City-centre transport
Getting to Winter Haven, Terminal (Ave E NW / 5th St NW) from Winter Haven city centre
Bus4044 · 4m · €1
Winter Haven, Terminal (Ave E NW / 5th St NW) bus station facilities and services
Winter Haven, Terminal (Ave E NW / 5th St NW) has practical services for this route, including Wifi, Parking, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Wi-Fi and ATMs
Wi-Fi is available at Winter Haven, Terminal (Ave E NW / 5th St NW). ATMs are available at Winter Haven, Terminal (Ave E NW / 5th St NW).
Tickets and information
Ticket office support is available at Winter Haven, Terminal (Ave E NW / 5th St NW).
Parking, taxis and toilets
Available at Winter Haven, Terminal (Ave E NW / 5th St NW): Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Winter Haven, Terminal (Ave E NW / 5th St NW): Basic accessibility features present.
Which Chicago, IL station do buses from Winter Haven, FL arrive at?
Buses from Winter Haven, FL to Chicago, IL most often arrive at Chicago, Greyhound Bus Station. Some services arrive at Chicago, Union Station (Amtrak), so check your ticket before travel to confirm your Chicago, IL arrival station.
Chicago, Greyhound Bus Station630 W Harrison St, Chicago, IL 60607, USA
City-centre transport
Getting to Chicago, Greyhound Bus Station from Chicago city centre
Chicago, Greyhound Bus Station is 2 km from Chicago city centre. Public transport options include:
Bus7 · 8m · €3 · every ~6 min
Chicago, Greyhound Bus Station bus station facilities and services
Chicago, Greyhound Bus Station has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food and drink
Food options include: Snack shop and vending machines available
Wi-Fi and ATMs
Free Wi-Fi in waiting area. ATMs are located near entrance.
Tickets and information
Ticket office support is available at Chicago, Greyhound Bus Station.
Parking, taxis and toilets
Available at Chicago, Greyhound Bus Station: Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Chicago, Greyhound Bus Station: Wheelchair accessible entrances and seating.
Chicago, Union Station (Amtrak)Chicago Union Station, 225 S Canal St, Chicago, IL 60606, USA
City-centre transport
Getting to Chicago, Union Station (Amtrak) from Chicago city centre
Chicago, Union Station (Amtrak) is 3 km from Chicago city centre. Public transport options include:
Bus28, 151 · 7m · €3 · every ~13 min
Chicago, Union Station (Amtrak) bus station facilities and services
Chicago, Union Station (Amtrak) has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food and drink
Food options include: Multiple dining options are available inside the station.
Wi-Fi and ATMs
Free Wi-Fi is available in waiting areas. ATMs are aTMs are located near the main entrance.
Tickets and information
Ticket office support is available at Chicago, Union Station (Amtrak).
Parking, taxis and toilets
Available at Chicago, Union Station (Amtrak): Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Chicago, Union Station (Amtrak): Station is accessible with elevators and ramps.
Bus stations for Winter Haven, FL to Chicago, IL
Check bus stations information for Winter Haven, FL and Chicago, IL, including where buses depart and arrive on this route.
When departing from Winter Haven, FL , you have various bus station options to start your journey from including Winter Haven, Terminal (Ave E NW / 5th St NW) . When arriving in Chicago, IL , you can end your journey in bus stations like Chicago, Greyhound Bus Station, Chicago, Union Station (Amtrak) .Passengers board the bus most frequently from Winter Haven, Terminal (Ave E NW / 5th St NW), which is located around 0 miles (1 km) away from the city centre, and they get off the bus at Chicago, Greyhound Bus Station, located 3 away from the city centre.
Most popular buses to and from Chicago, IL and Winter Haven, FL
Most popular bus connections to Chicago, IL
The Omio App Makes Travel Planning Easy
We’ll get you where you want to go. From live train updates to mobile tickets, our innovative app is the ideal way to plan and keep track of your travel.
