- Must visit
Art Institute Of Chicago
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
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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 $134. 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 $134, and a bus costs an average of $374.
Distance: 1011 miles (1628 km)
Compare bus with
| Bus | Most popular Flight | Train | Driving |
|---|---|---|---|
$374 Average price | $134 Average price Cheapest | $309 Average price | $228 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 $134 (€110).
This is compared to other travel options from Winter Haven, FL to Chicago, IL:
A flight is $175 (€143) less than a train for this route with tickets for a train from Winter Haven, FL to Chicago, IL costing on average $309 (€253).
A flight is $240 (€197) less than a bus for this route with tickets for a bus from Winter Haven, FL to Chicago, IL costing on average $374 (€306).
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 $281 |
Operator Greyhound | Departure Time 01:35PM | Arrival Time 09:15PM | Duration 31h40 | Departure days Thu | Cheapest price $374 |
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 $374 (€306) but you can travel from only $134 (€110) 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 $134 (€110)
Distance 1011 miles (1628 km) |
Average bus duration 31h 40m |
Cheapest ticket price $374 (€306) |
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 $134 (€110)
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 $134 (€110). 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
$374 (€306)
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
Things to do in Chicago
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
- Must visit
Field Museum
Major natural history museum famous for Sue the T. rex, ancient cultures, and extensive science collections that appeal to both adults and children.
- Must visit
Museum Of Science And Industry
Large hands-on science museum in Hyde Park featuring a submarine, space exhibits, engineering displays, and immersive family-friendly experiences.
- Must visit
Millennium Park
The city’s signature public space, home to Cloud Gate, gardens, events, and major skyline views that define modern Chicago.
- Must visit
The Magnificent Mile
Famous stretch of Michigan Avenue lined with historic buildings, shops, hotels, and frequent first-time visitor photo stops.
- Must visit
Chicago Riverwalk
Highly popular waterfront promenade with architecture views, bridges, and one of the best urban walks in the city.
Deep-Dish Pizza
Chicago’s iconic thick-crust pizza baked in a deep pan, layered with cheese, toppings, and chunky tomato sauce. It is one of the city’s most famous comfort foods.
Chicago-Style Hot Dog
An all-beef hot dog on a poppy seed bun topped with mustard, onions, neon relish, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food.
Italian Beef Sandwich
Thinly sliced roast beef piled onto an Italian roll, often dipped in seasoned jus and topped with sweet peppers or giardiniera. It is a defining Chicago sandwich.
Gene & Georgetti
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Alinea
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
Lou Malnati's Pizzeria
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
United States Dollar
Moderate for a major U.S. city: casual food is manageable, but hotels, attractions, and downtown dining can be pricey.
Average meal costs
- Budget
- USD 10-18 for fast food or casual takeout.
- Mid-range
- USD 20-40 per person at a mid-range restaurant.
- Fine dining
- USD 75+ per person before drinks and tax.
- Coffee
- USD 4-7 for a regular café coffee.
Tipping culture
Tip 18-20% in restaurants; 20%+ for great service. Tip bartenders USD 1-2 per drink, taxis about 10-15%, and hotel staff a few dollars.
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 $374 (€306) when you book in advance. The average bus ticket price for Winter Haven, FL to Chicago, IL is $374 (€306) ; 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.
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
Winter Haven, Terminal (Ave E NW / 5th St NW)
City-centre transport
Getting to Winter Haven, Terminal (Ave E NW / 5th St NW) from Winter Haven city centre
Bus4044 · 4m · $1
Chicago, Greyhound Bus Station
City-centre transport
Getting to Chicago, Greyhound Bus Station from Chicago city centre
Bus7 · 8m · $4 · every ~6 min
Chicago, Union Station (Amtrak)
City-centre transport
Getting to Chicago, Union Station (Amtrak) from Chicago city centre
Bus28, 151 · 7m · $4 · every ~13 min
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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