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

The cheapest way to get from Chicago to Winter Haven is to fly and bus which costs $110 - $430 and takes 7h 37m.

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

The fastest way to get from Chicago to Winter Haven is to fly and bus which takes 7h 37m and costs $110 - $430.

Is there a direct bus between Chicago and Winter Haven?

No, there is no direct bus from Chicago station to Winter Haven. However, there are services departing from Chicago Bus Station and arriving at Winter Haven Transportation Center via Atlanta Bus Station and Orlando Bus Station. The journey, including transfers, takes approximately 27h.

Is there a direct train between Chicago and Winter Haven?

No, there is no direct train from Chicago station to Winter Haven station. However, there are services departing from Chicago Union Station and arriving at Lakeland Amtrak Station via . The journey, including transfers, takes approximately 41h 41m.

How far is it from Chicago to Winter Haven?

The distance between Chicago and Winter Haven is 1077 miles. The road distance is 1128.7 miles.

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

The best way to get from Chicago to Winter Haven without a car is to bus which takes 27h and costs $160 - $330.

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

It takes approximately 7h 37m to get from Chicago to Winter Haven, including transfers.

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

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

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

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

Train or bus from Chicago to Winter Haven?

The best way to get from Chicago to Winter Haven is to bus which takes 27h and costs $160 - $330. Alternatively, you can train, which costs $470 - $1,100 and takes 41h 41m.

Where does the Chicago to Winter Haven bus arrive?

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

What is the time difference between Chicago and Winter Haven?

Winter Haven is 1h ahead of Chicago. It is currently 9:51 AM in Chicago and 10:51 AM in Winter Haven.

Where does the Chicago to Winter Haven train arrive?

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

Can I drive from Chicago to Winter Haven?

Yes, the driving distance between Chicago to Winter Haven is 1129 miles. It takes approximately 20h 12m to drive from Chicago to Winter Haven.

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

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

How do I get a bus ticket from Chicago to Winter Haven?

Book your Chicago to Winter Haven bus tickets online with Omio and FlixBus.

Where can I stay near Winter Haven?

There are 629+ hotels available in Winter Haven.

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

How to get fromChicago to Winter Haven

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

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 Tampa, bus
best
1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane MDW - TPA
2. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus
7h 37m
$112–421
Fly Chicago O'Hare International Airport to Orlando, bus
cheapest
1. Fly from Chicago O'Hare International Airport (ORD) to Orlando (MCO)plane ORD - MCO
2. Take the bus from Orlando Bus Station to Winter Haven Transportation Centerbus
8h 20m
$82–431
Bus
1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus
2. Take the bus from Atlanta Bus Station to Orlando Bus Stationbus
3. Take the bus from Orlando Bus Station to Winter Haven Transportation Centerbus
27h
$166–322
Train (Amtrak)
1. Take the train from Chicago Union Station to Lakeland Amtrak Stationtrain Floridian
41h 41m
$479–1,049
Drive 1,122.2 mi
1. Drive from Chicago to Winter Havencar 1,122.2 mi
20h 12m
$205–296
Fly Chicago Midway International Airport to Orlando, bus
1. Fly from Chicago Midway International Airport (MDW) to Orlando (MCO)plane MDW - MCO
2. Take the bus from Orlando Bus Station to Winter Haven Transportation Centerbus
7h 50m
$202–501
Fly Chicago O'Hare International Airport to Tampa, bus
1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane ORD - TPA
2. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus
8h 6m
$162–571
Fly Chicago Midway International Airport to Sarasota–Bradenton International Airport, bus
1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane MDW - SRQ
2. Take the bus from Sarasota Cattlemen Transfer Center to Tampa Bus Stationbus
3. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus
10h 23m
$200–938
Fly Chicago O'Hare International Airport to Sarasota–Bradenton International Airport, bus
1. Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)plane ORD - SRQ
2. Take the bus from Sarasota Cattlemen Transfer Center to Tampa Bus Stationbus
3. Take the bus from Tampa Bus Station to Winter Haven Transportation Centerbus
10h 57m
$150–688

Chicago to Winter Haven by bus

7Weekly Buses

27hAverage Duration

$166Cheapest Price

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Questions & Answers

Map of how to get from Chicago to Winter Haven.

Launch map view

Distance: 1,070.5 mi
Duration: 7h 37m

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

You can take a bus from Chicago Bus Station to Winter Haven Transportation Center via Atlanta Bus Station and Orlando Bus Station in around 27h. Alternatively, Amtrak operates a train from Chicago Union Station to Lakeland Amtrak Station once daily. Tickets cost $470–1,100 and the journey takes 39h 58m.

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