- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
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The cheapest and fastest buses from Winter Haven, FL to Chicago, IL
Showing times and prices for Aug 06
Cheapest price
$376
Average price
$376
Fastest journey
1 d 7 h 40 m
Average duration
1 d 7 h 40 m
Buses per day
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 $376 if you buy it on the day, but the cheapest tickets can be found for only $376.
Fast buses
Of the 1 buses that leave Winter Haven, FL for Chicago, IL on Thu, Aug 06, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Thu, Aug 06 the direct buses cover the 1628 km distance in an average of 1 d 7 h 40 m but if you time it right, some buses will get you there in just 1 d 7 h 40 m .
On Thu, Aug 06 the slowest buses will take 1 d 7 h 40 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
1:35 PM31h40Winter Haven, FL9:15 PMChicago, IL$3761One-way0 transfers
- 1:35 PM31h40Winter Haven, FL9:15 PMChicago, IL$3761One-way0 transfers
Travel Information
Compare bus, train, and flight for Winter Haven, FL to Chicago, IL
Omio recommends booking the flight as it is the most popular option from Winter Haven, FL to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from $135. For those with little time consider booking a flight which can get you there in 3h 5m. The ticket price range depends on the travel mode: a flight costs an average of $135, and a bus costs an average of $376.
Distance: 1011 miles (1628 km)
Compare bus with
| Bus | Most popular Flight | Train | Driving |
|---|---|---|---|
$376 Average price | $135 Average price Cheapest | $311 Average price | $229 Average price (fuel + tolls) |
32h 10m Average total duration 31h 40m Onboard + 30m Additional time* | 6h 5m Average total duration Fastest 3h 5m Onboard + 3h 0m Additional time* | 46h 4m Average total duration 45h 34m Onboard + 30m Additional time* | 17h 25m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Winter Haven, FL to Chicago, IL is a flight with an average price of $135.
This is compared to other travel options from Winter Haven, FL to Chicago, IL:
A flight is $176 less than a train for this route with tickets for a train from Winter Haven, FL to Chicago, IL costing on average $311.
A flight is $241 less than a bus for this route with tickets for a bus from Winter Haven, FL to Chicago, IL costing on average $376.
The fastest way to travel from Winter Haven, FL to Chicago, IL is by flight with an average journey time of 3h 5m.
Other travel options to Chicago, IL take longer:
Bus takes on average 31h 40m.
Train takes on average 45h 34m.
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.
We recommend using the flight as it is the most popular way to get from Winter Haven, FL to Chicago, IL among Omio's users.
Take the bus. On this route, it's both cheaper and quicker than driving.
You'll arrive about {timeSavings} sooner ({durationInMinutes} by bus vs {drivingDurationInMinutes} by car) and save roughly {savingsAmount} compared to fuel and tolls ({cheapestPrice} vs {drivingPriceInCents}). You also skip the drive itself — no traffic stress, no parking, and you can use the time to work, nap, or catch up on a series with the onboard Wi-Fi.
Direct coaches are operated by {directProviders}.
Driving is still worth considering if you're travelling with bulky luggage, need flexibility on departure times, or plan to stop along the way.
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 $283 |
Operator Greyhound | Departure Time 01:35PM | Arrival Time 09:15PM | Duration 31h40 | Departure days Thu | Cheapest price $376 |
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?
- 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 4 times per day, taking around 31h 40m. Cheap bus tickets for this journey start at $376 but you can travel from only $135 by flight.
The earliest bus runs at 06:10, the last at 23:15. The fastest bus covers the 1011 miles (1628 km) distance in 31h 40m.
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
Cheapest alternative travel mode
Flight from $135
Distance 1011 miles (1628 km) |
Average bus duration 31h 40m |
Cheapest ticket price $376 |
Buses per day 4 |
Fastest bus 31h 40m |
First bus 6:10 AM |
Last bus 11:15 PM |
Cheapest Month Aug |
Cheapest Day Wed |
High Season Jan - Mar |
Low Season Jul - Sep |
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
Cheapest alternative travel mode
Flight from $135
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 $135. 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
31h 40m
Cheapest Price
$376
Greyhound frequency
4 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.
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.
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 $376 when you book in advance. The average bus ticket price for Winter Haven, FL to Chicago, IL is $376 ; 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 31h 40m 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 4 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.
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), Bartow, Polk County Courthouse (Garage), FL, Lake Wales, US-27 (Citgo), FL . When arriving in Chicago, IL , you can end your journey in bus stations like Chicago, Greyhound Bus Station, Chicago, Union Station (Amtrak), IL .Passengers board the bus most frequently from Winter Haven, Terminal (Ave E NW / 5th St NW), which is located around away from the city centre, and they get off the bus at Chicago, Greyhound Bus Station, located 2 away from the city centre.
A trip to Chicago, IL from Winter Haven, FL is worth doing but not as a day trip with a journey time of 31h 40m 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, 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, there are bathrooms on board the bus from Winter Haven, FL to Chicago, IL for bus company Greyhound.
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.
Since neither Winter Haven, FL nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
We recommend using the flight as it is the most popular way to get from Winter Haven, FL to Chicago, IL among Omio's users.
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.
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 · $4 · 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 · $4 · 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.
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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