- 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, prices and bookable tickets for Sep 20
Cheapest price on Sep 20
$281
Average ticket price on Sep 20
$281
Fastest journey on Sep 20
1 d 6 h 40 m
Average journey duration on Sep 20
1 d 6 h 40 m
Buses on Sep 20
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 $281 if you buy it on the day, but the cheapest tickets can be found for only $281.
Fast buses
It's difficult to get from Winter Haven, FL to Chicago, IL without transferring at least 2 times.
8:35 AM30h40Winter Haven, FL3:15 PMChicago, IL$2811One-way2 transfers
- 8:35 AM30h40Winter Haven, FL3:15 PMChicago, IL$2811One-way2 transfers
Travel Information
Compare bus for Winter Haven, FL to Chicago, IL
Omio recommends booking the bus as it is the most popular option from Winter Haven, FL to Chicago, IL among Omio's users.
Distance: 1011 miles (1628 km)
Compare bus with
Most popular Bus | Driving |
|---|---|
$232 Average price (fuel + tolls) | |
17h 25m Average total duration (door-to-door) | |
Direct Options | Direct Options |
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 |
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, Sunday, September 20. 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
Compare prices and tickets Winter Haven, FL to Chicago, IL by bus
Compare bus 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.
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
Distance 1011 miles (1628 km) |
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
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.
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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