4.9
4.6The cheapest and fastest buses from Chicago, IL to Winter Park, FL
Cheapest price
$366
Average price
$414
Fastest journey
1 d 3 h 54 m
Average duration
1 d 5 h 44 m
Buses per day
4
Distance
1580 km
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 $414 if you buy it on the day, but the cheapest tickets can be found for only $366.
It's difficult to get from Chicago, IL to Winter Park, FL without transferring at least 3 times.
Travel Information
Compare train and bus for Chicago, IL to Winter Park, FL
Omio recommends booking the train 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 €266. 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 €266, and a bus costs an average of €302.
Distance: 981 miles (1580 km)
Compare bus with
| Bus | Most popular Train |
|---|---|
€339 Average price | €266 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 |
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, Thursday, November 6. You can also manually refresh the results below to see updated bus journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 1:00 PM Chicago, IL | 28h26 | 5:26 PM Winter Park, FL | 3 transfers | |
| 2:45 PM Chicago, IL | 30h16 | 9:01 PM Winter Park, FL | 3 transfers | |
| 9:45 PM Chicago, IL | 32h43 | 6:28 AM Winter Park, FL | 3 transfers | |
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.
Nov 07
Nov 08
Nov 09
Nov 10
Nov 11
Nov 12
Nov 13
Journey information
Overview: Bus from Chicago, IL to Winter Park, FL
USAUSA
Distance 981 miles (1580 km) |
Average bus duration 30h 4m |
Cheapest ticket price $370 (€302) |
Buses per day 9 |
Fastest bus 27h 34m |
First bus 05:15 |
Last bus 22:55 |
Key Takeaways
Train Ticket Prices
- Budget Options: Train tickets from Chicago, IL to Winter Park, FL start from as low as $370 (€302) if booked well in advance.
- Standard Fares: Typically, trains cost $416 (€339) depending on the train type and class.
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 $326 (€266). When you search for schedules and tickets, Omio will show you the best journey
FlixBus
Greyhound
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.
- FlixBus
- Assistance
- Priority boarding
- Wheelchair-accessible buses.
- Greyhound
- Assistance
- Priority seating
- Wheelchair-accessible buses.
- 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.
- Greyhound
- You can cancel your ticket for a refund or exchange up to 24 hours before departure, for a cancellation fee applied.
To find the cheapest bus tickets for your trip from Chicago, IL to Winter Park, FL, follow these tips:
Start your search now and compare ticket prices to find the best deal!
- FlixBus
- One carry-on bag up to 7kg (42x30x18 cm) and one checked bag up to 20kg (80x50x30 cm).
- Greyhound
- One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
- FlixBus
- Additional luggage can be purchased for a fee.
- Greyhound
- $15 per additional bag.
- FlixBus
- Small pets in carriers allowed
- Guide dogs travel for free.
popular bus stations
Popular bus stations from Chicago, IL to Winter Park, FL
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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