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The cheapest and fastest buses from Chicago, IL to Winter Park, FL
Showing times and prices for Apr 05
Cheapest price
$299
Average price
$337
Fastest journey
1 d 40 m
Average duration
1 d 2 h 54 m
Buses per day
9
Distance
1580 km
Cheap tickets
The best way to find a cheap bus ticket from Chicago, IL to Winter Park, FL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Winter Park, FL will cost around $337 if you buy it on the day, but the cheapest tickets can be found for only $299.
Fast buses
It's difficult to get from Chicago, IL to Winter Park, FL without transferring at least once.
undefined · undefined10:15 AM29h05Chicago, Union Station (Amtrak), IL4:20 PMOrlando, N John Young Pkwy (Greyhound Bus Station)$2991One-way1 transfer- undefined · undefined+
FlixBus · FlixBus10:15 AM36h44Chicago, Union Station (Amtrak), IL11:59 PMOrlando, The Florida Mall, FL$3001One-way3 transfers - FlixBus · FlixBus6:00 PM28h59Chicago, Greyhound Bus Station11:59 PMOrlando, The Florida Mall, FL$3101One-way1 transfer
- FlixBus · FlixBus6:00 PM25h25Chicago, Greyhound Bus Station8:25 PMOrlando, N John Young Pkwy (Greyhound Bus Station)$3201One-way1 transfer
- +FlixBus10:50 PM30h00Chicago, Greyhound Bus Station5:50 AMOrlando, N John Young Pkwy (Greyhound Bus Station)$3241One-way1 transfer
- +FlixBus6:10 AM24h40Chicago, Greyhound Bus Station7:50 AMOrlando, N John Young Pkwy (Greyhound Bus Station)$3971One-way1 transfer
- FlixBus · FlixBus6:00 PM25h25Chicago, Greyhound Bus Station8:25 PMOrlando, N John Young Pkwy (Greyhound Bus Station)$3201One-way1 transfer
- FlixBus+1:00 PM26h20Chicago, Greyhound Bus Station4:20 PMOrlando, N John Young Pkwy (Greyhound Bus Station)$3911One-way1 transfer
- FlixBus · FlixBus6:00 PM28h59Chicago, Greyhound Bus Station11:59 PMOrlando, The Florida Mall, FL$3101One-way1 transfer
- undefined · undefined10:15 AM29h05Chicago, Union Station (Amtrak), IL4:20 PMOrlando, N John Young Pkwy (Greyhound Bus Station)$2991One-way1 transfer
Travel Information
Compare train and bus for Chicago, IL to Winter Park, FL
Omio recommends booking the bus as it is the most popular option from Chicago, IL to Winter Park, FL among Omio's users. If you are prioritising price take the train with prices starting from $321. For those with little time consider booking a bus which can get you there in 30h 4m. The ticket price range depends on the travel mode: a train costs an average of $321, and a bus costs an average of $366.
Distance: 981 miles (1580 km)
Compare bus with
Most popular Bus | Train |
|---|---|
$411 Average price | $321 Average price Cheapest |
30h 34m Average total duration Fastest 30h 4m Onboard + 30m Additional time* | 39h 29m Average total duration 38h 59m Onboard + 30m Additional time* |
Direct Options | Direct Options |
Chicago, IL to Winter Park, FL Bus Timetables
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Greyhound | Departure Time 06:10AM | Arrival Time 02:55PM | Duration 31h45 | Departure days Sun | Cheapest price $365 |
Operator Greyhound | Departure Time 10:15AM | Arrival Time 04:20PM | Duration 29h05 | Departure days Sun | Cheapest price $299 |
Operator FlixBus | Departure Time 01:00PM | Arrival Time 04:20PM | Duration 26h20 | Departure days Sun | Cheapest price $391 |
Operator FlixBus | Departure Time 06:00PM | Arrival Time 11:59PM | Duration 28h59 | Departure days Sun | Cheapest price $310 |
Operator Greyhound | Departure Time 10:50PM | Arrival Time 05:50AM | Duration 30h00 | Departure days Sun | Cheapest price $324 |
Operator Greyhound | Departure Time 11:10PM | Arrival Time 05:50AM | Duration 29h40 | Departure days Sun | Cheapest price $324 |
Live departures
Chicago, IL to Winter Park, FL bus times
The table below shows live departures for Chicago, IL to Winter Park, FL buses for today, Saturday, April 4. You can also manually refresh the results below to see updated bus journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 10:50 PM Chicago, IL | 31h11 | 6:01 AM Winter Park, FL | 3 transfers | |
| Sunday, April 5 | |||||
| +FlixBus | 11:10 AM Chicago, Greyhound Bus Station | 24h40 | 11:50 AM Orlando, N John Young Pkwy (Greyhound Bus Station) | 1 transfer | |
| +FlixBus · FlixBus | 11:10 AM Chicago, Greyhound Bus Station | 31h45 | 6:55 PM Orlando, The Florida Mall, FL | 2 transfers | |
| undefined · undefined | 3:15 PM Chicago, Union Station (Amtrak), IL | 29h05 | 8:20 PM Orlando, N John Young Pkwy (Greyhound Bus Station) | 1 transfer | |
| undefined · undefined+FlixBus · FlixBus | 3:15 PM Chicago, Union Station (Amtrak), IL | 36h44 | 3:59 AM Orlando, The Florida Mall, FL | 3 transfers | |
| FlixBus+ | 6:00 PM Chicago, Greyhound Bus Station | 26h20 | 8:20 PM Orlando, N John Young Pkwy (Greyhound Bus Station) | 1 transfer | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Chicago, IL to Winter Park, FL by train or bus
Compare train and 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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Apr 05
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Apr 11
Apr 11
Why should you book Chicago, IL to Winter Park, FL buses with Omio?
Greyhound as well as FlixBus offer buses services from Chicago, IL to Winter Park, FL.
Omio is an official ticket reseller for all your travel options from Chicago, IL to Winter Park, FL.
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 FlixBus to find the best option for your trip from Chicago, IL to Winter Park, FL.
- 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 train and bus to ensure you get the best deal for traveling from Chicago, IL to Winter Park, FL.
Why book with Omio over Wanderu or Trainline?
- Compare with other providers: On Omio, you can also compare tickets for the likes of FlixBus to find the best option for your trip from Chicago, IL to Winter Park, FL.
- Multiple modes of transport: Omio allows you to compare travel options including train and bus to find the ideal travel option from Chicago, IL to Winter Park, FL.
Journey information
Overview: Bus from Chicago, IL to Winter Park, FL
USAUSA
Buses from Chicago, IL to Winter Park, FL run on average 9 times per day, taking around 30h 4m. Cheap bus tickets for this journey start at $366 (€298) but you can travel from only $321 (€262) by train.
The earliest bus runs at 05:15, the last at 23:10. The fastest bus covers the 981 miles (1580 km) distance in 27h 34m.
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
Train from $321 (€262)
Distance 981 miles (1580 km) |
Average bus duration 30h 4m |
Cheapest ticket price $366 (€298) |
Buses per day 9 |
Fastest bus 27h 34m |
First bus 5:15 AM |
Last bus 11:10 PM |
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
Train from $321 (€262)
Bus providers: Greyhound, FlixBus from Chicago, IL to Winter Park, FLYou can travel by bus between Chicago, IL to Winter Park, FL with Greyhound, FlixBus for as low as $321 (€262). When you search for schedules and tickets, Omio will show you the best journey
FlixBus
About
FlixBus is one of Europe’s leading low-cost bus companies, founded in Germany and now offering long-distance services across Europe and the United States. In addition to its extensive daytime network, FlixBus also operates overnight buses on select European routes. Standard amenities include free Wi-Fi, power outlets to charge devices, extra legroom, luggage space, and onboard toilets, with snacks and drinks available for purchase. FlixBus offers a single Standard ticket type for all routes, which includes one carry-on bag and one checked bag per passenger. Additional fees apply for extra luggage and for reserving specific seats, such as Extra Seats, Table Seats, or Panorama Seats. This combination of affordability, comfort, and wide coverage makes FlixBus a popular choice for budget-conscious travelers.
Luggage & cancellation policy
Average Duration
28h 26m
Cheapest Price
$366 (€298)
FlixBus frequency
3 a day
Luggage included
One carry-on bag up to 7kg (42x30x18 cm) and one checked bag up to 20kg (80x50x30 cm).
Additional luggage
Additional luggage can be purchased for a fee.
Cancellation Policy
You can cancel your ticket up to 15 minutes before departure and receive a voucher for future travel. Refund requests for delays over 120 minutes are possible.
Amenities on board the bus
Wifi
Food sold onboard
Seat reservation
Toilets
USB plugs
Accessibility
Assistance; Priority boarding; Wheelchair-accessible buses.
Bikes
Bikes are allowed for a fee; must be booked.
Pets
Small pets in carriers allowed; guide dogs travel for free.
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
27h 34m
Cheapest Price
$404 (€329)
Greyhound frequency
6 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 Chicago, IL to Winter Park, FL
Find answers to the most common questions about traveling from Chicago, IL to Winter Park, FL 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 Winter Park, FL, this guide helps you travel smarter and with confidence.
Cheap bus tickets from Chicago, IL to Winter Park, FL can start from as little as $366 (€298) when you book in advance. The average bus ticket price for Chicago, IL to Winter Park, FL is $411 (€335) ; 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 Chicago, IL to Winter Park, FL is 27h 34m to travel the 981 miles (1580 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 Chicago, IL to Winter Park, FL leaves at 5:15 AM. Plan your trip with the Journey Planner from Omio.
The latest bus from Chicago, IL to Winter Park, FL leaves at 11:10 PM.
There are 9 buses a day from Chicago, IL to Winter Park, FL which require at least one change with Greyhound, FlixBus. Schedules can vary on holidays or weekends with fewer buses.
When taking a bus from Chicago, IL to Winter Park, FL, you can count on Greyhound, FlixBus for the best way to get you to Winter Park, FL. You can also check all possible bus companies who offer a service between Chicago, IL and Winter Park, FL and compare the amenities they offer before buying a bus ticket.
A trip to Winter Park, FL from Chicago, IL is worth doing but not as a day trip with a journey time of 27h 34m each way. Check with Omio app the best way to travel.
The cheapest month for a bus from Chicago, IL to Winter Park, FL is March.
It's helpful to compare your options as there are 2 ways to travel between Chicago, IL and Winter Park, FL including taking a train and bus.
Yes, the following accessibility options are available when taking the bus from Chicago, IL to Winter Park, FL:
- Greyhound
- Assistance
- Priority seating
- Wheelchair-accessible buses.
- FlixBus
- Assistance
- Priority boarding
- Wheelchair-accessible buses.
Yes, there are bathrooms on board the bus from Chicago, IL to Winter Park, FL for bus company Greyhound, FlixBus.
Whether you can cancel your bus ticket from Chicago, IL to Winter Park, FL 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.
- FlixBus
- You can cancel your ticket up to 15 minutes before departure and receive a voucher for future travel. Refund requests for delays over 120 minutes are possible.
Yes, bikes are allowed on board the bus with bus company Greyhound, FlixBus.
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 Chicago, IL to Winter Park, FL.
Yes, the following luggage options are included when booking a bus ticket from Chicago, IL to Winter Park, FL:
- Greyhound
- One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
- FlixBus
- One carry-on bag up to 7kg (42x30x18 cm) and one checked bag up to 20kg (80x50x30 cm).
Yes, the following additional luggage options are available when booking a bus ticket from Chicago, IL to Winter Park, FL:
- Greyhound
- $15 per additional bag.
- FlixBus
- Additional luggage can be purchased for a fee.
Yes, you can bring your pet on the bus from Chicago, IL to Winter Park, FL. The following conditions apply:
- FlixBus
- Small pets in carriers allowed
- guide dogs travel for free.
You can reserve your seat on the bus from Chicago, IL to Winter Park, FL with the following bus company: Greyhound, FlixBus
Yes, there are USB plugs on board the bus from Chicago, IL to Winter Park, FL with the following bus company: Greyhound, FlixBus.
Yes, there is Wifi on board the bus from Chicago, IL to Winter Park, FL with the following bus company: Greyhound, FlixBus.
Since neither Chicago, IL nor Winter Park, FL 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 bus as it is the most popular way to get from Chicago, IL to Winter Park, FL 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 Winter Park, FL, travelers should be cautious of petty theft, especially in crowded areas and parking lots. Common scams include overpriced parking and unauthorized tour operators offering boat rides or carriage tours. It's advisable to use official services, keep valuables secure, and stay aware of surroundings to ensure a safe visit.
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 Chicago, IL to Winter Park, FL
Chicago
Winter Park
Chicago, Greyhound Bus Station
information
Chicago, Union Station (Amtrak)
information
Most popular bus connections from Chicago, IL
More options for your journey from Chicago, IL to Winter Park, FL
Here are some other resources that might have the information you need
Most popular buses to and from Winter Park, FL and Chicago, IL
Most popular bus connections to Winter Park, FL
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