What is the cheapest way to get from Chicago to Winter Park?

The cheapest way to get from Chicago to Winter Park is to fly which costs $75 - $650 and takes 6h 6m.

What is the fastest way to get from Chicago to Winter Park?

The fastest way to get from Chicago to Winter Park is to fly which takes 5h 45m and costs $200 - $490.

Is there a direct bus between Chicago and Winter Park?

No, there is no direct bus from Chicago station to Winter Park. However, there are services departing from Chicago Bus Station and arriving at New York Ave & Welbourne Ave via Atlanta Bus Station, John Young Pkwy & Amelia St and N Garland Ave & W Amelia St. The journey, including transfers, takes approximately 26h 2m.

Is there a direct train between Chicago and Winter Park?

Yes, there is a direct train departing from Chicago Union Station station and arriving at Winter Park Amtrak Station station. Services depart once daily, and operate every day. The journey takes approximately 37h 59m.

How far is it from Chicago to Winter Park?

The distance between Chicago and Winter Park is 1026 miles. The road distance is 1116.2 miles.

How do I travel from Chicago to Winter Park without a car?

The best way to get from Chicago to Winter Park without a car is to bus which takes 26h 2m and costs $180 - $350.

How long does it take to get from Chicago to Winter Park?

It takes approximately 5h 45m to get from Chicago to Winter Park, including transfers.

Where do I catch the Chicago to Winter Park bus from?

Chicago to Winter Park bus services, operated by Greyhound USA, depart from Chicago Bus Station.

Where do I catch the Chicago to Winter Park train from?

Chicago to Winter Park train services, operated by Amtrak, depart from Chicago Union Station.

Train, bus or fly from Chicago to Winter Park?

The best way to get from Chicago to Winter Park is to fly which takes 5h 45m and costs $200 - $490. Alternatively, you can bus, which costs $180 - $350 and takes 26h 2m, you could also train, which costs $550 - $1,200 and takes 37h 59m.

Where does the Chicago to Winter Park bus arrive?

Chicago to Winter Park bus services, operated by Greyhound USA, arrive at Atlanta Bus Station.

What is the time difference between Chicago and Winter Park?

Winter Park is 1h ahead of Chicago. It is currently 3:09 AM in Chicago and 4:09 AM in Winter Park.

Where does the Chicago to Winter Park train arrive?

Chicago to Winter Park train services, operated by Amtrak, arrive at Winter Park Amtrak Station.

Can I drive from Chicago to Winter Park?

Yes, the driving distance between Chicago to Winter Park is 1116 miles. It takes approximately 19h 48m to drive from Chicago to Winter Park.

How do I get a train ticket from Chicago to Winter Park?

Book your Chicago to Winter Park train tickets online with Omio.

Where can I stay near Winter Park?

There are 1415+ hotels available in Winter Park.

Chicago to Winter Park - 9 ways to travel via train, plane, bus, and car

How to get fromChicago to Winter Park

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There are 9 ways to get from Chicago to Winter Park by plane, bus (Greyhound, Flixbus), train (Amtrak), car, or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

Fly Chicago Midway International Airport to Orlando
best
1. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane MDW - MCO
5h 45m
$206–490
Fly Chicago O'Hare International Airport to Orlando
cheapest
1. Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane ORD - MCO
6h 6m
$76–610
Bus
1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus Greyhound US0100
2. Take the bus from Atlanta Bus Station to Orlando Bus Stationbus FlixBus N2401 / ...
26h 2m
$180–345
Train (Amtrak)
1. Take the train from Chicago Union Station to Winter Park Amtrak Stationtrain Floridian
37h 59m
$550–1,200
Drive 1,109.7 mi
1. Drive from Chicago to Winter Parkcar 1,109.7 mi
19h 48m
$203–293
Train to South Bend, fly to Orlando Sanford
1. Take the train from Van Buren St. to South Bend Airporttrain
2. Fly from South Bend (SBN) to Orlando Sanford (SFB)plane SBN - SFB
6h
$183–674
Train to General Mitchell International Airport, fly to Orlando
1. Take the train from Chicago Union Station to Milwaukeetrain
2. Fly from General Mitchell International Airport (MKE) to Orlando (MCO)plane MKE - MCO
7h 24m
$204–675
Fly Chicago Midway International Airport to Tampa, train
1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane MDW - TPA
2. Take the train from Tampa to Winter Park Amtrak Stationtrain
8h 43m
$158–676
Fly Chicago O'Hare International Airport to Tampa, train
1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane ORD - TPA
2. Take the train from Tampa to Winter Park Amtrak Stationtrain
9h 11m
$188–626

Chicago to Winter Park by bus

40Weekly Buses

26h 2mAverage Duration

$180Cheapest Price

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Questions & Answers

Map of how to get from Chicago to Winter Park.

Launch map view

Distance: 1,019.6 mi
Duration: 5h 45m

What companies run services between Chicago, IL, USA and Winter Park, FL, USA?

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Orlando (MCO) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to New York Ave & Welbourne Ave via Atlanta Bus Station, Orlando Bus Station, John Young Pkwy & Amelia St, and N Garland Ave & W Amelia St in around 26h 2m.

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