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

The cheapest way to get from Chicago to Winter Springs is to fly which costs $90 - $650 and takes 5h 54m.

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

The fastest way to get from Chicago to Winter Springs is to subway and fly which takes 5h 32m and costs $220 - $550.

Is there a direct bus between Chicago and Winter Springs?

No, there is no direct bus from Chicago station to Winter Springs station. However, there are services departing from Chicago Bus Station and arriving at Orlando Bus Station via Atlanta Bus Station. The journey, including transfers, takes approximately 25h 14m.

Is there a direct train between Chicago and Winter Springs?

No, there is no direct train from Chicago station to Winter Springs station. However, there are services departing from Chicago Union Station and arriving at Winter Park Amtrak Station via . The journey, including transfers, takes approximately 38h 14m.

How far is it from Chicago to Winter Springs?

The distance between Chicago and Winter Springs is 1030 miles. The road distance is 1110.8 miles.

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

The best way to get from Chicago to Winter Springs without a car is to bus which takes 25h 14m and costs $210 - $390.

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

It takes approximately 5h 32m to get from Chicago to Winter Springs, including transfers.

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

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

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

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

Train, bus or fly from Chicago to Winter Springs?

The best way to get from Chicago to Winter Springs is to bus which takes 25h 14m and costs $210 - $390. Alternatively, you can train, which costs $550 - $1,200 and takes 38h 14m, you could also fly, which costs $90 - $650 and takes 5h 54m.

Where does the Chicago to Winter Springs bus arrive?

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

What is the time difference between Chicago and Winter Springs?

Winter Springs is 1h ahead of Chicago. It is currently 9:44 AM in Chicago and 10:44 AM in Winter Springs.

Where does the Chicago to Winter Springs train arrive?

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

Can I drive from Chicago to Winter Springs?

Yes, the driving distance between Chicago to Winter Springs is 1111 miles. It takes approximately 20h 15m to drive from Chicago to Winter Springs.

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

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

Where can I stay near Winter Springs?

There are 469+ hotels available in Winter Springs.

Chicago to Winter Springs - 7 ways to travel via train, subway, plane, and bus

How to get fromChicago to Winter Springs

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There are 7 ways to get from Chicago to Winter Springs by subway, 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.

Subway to Chicago Midway International Airport, fly to Orlando
best
1. Take the subway from Adams/Wabash to Midwaysubway
2. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane MDW - MCO
5h 32m
$220–507
Fly Chicago O'Hare International Airport to Orlando
cheapest
1. Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane ORD - MCO
5h 54m
$90–627
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 / ...
25h 14m
$216–387
Train (Amtrak)
1. Take the train from Chicago Union Station to Winter Park Amtrak Stationtrain Floridian
38h 14m
$589–1,140
Drive 1,104.3 mi
1. Drive from Chicago to Winter Springscar 1,104.3 mi
20h 15m
$202–292
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 11m
$218–691
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
5h 45m
$160–647

Chicago Midway International Airport (MDW) to Orlando (MCO) flights

45Weekly Planes

2h 55mAverage Duration

$114Cheapest Price

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Questions & Answers

Map of how to get from Chicago to Winter Springs.

Launch map view

Distance: 1,023.8 mi
Duration: 5h 32m

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

You can take a bus from Chicago Bus Station to Winter Springs via Atlanta Bus Station and Orlando Bus Station in around 25h 14m. Alternatively, Amtrak operates a train from Chicago Union Station to Winter Park Amtrak Station once daily. Tickets cost $550–1,200 and the journey takes 37h 59m.

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