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

The cheapest way to get from Winter Haven to Chicago is to bus and fly which costs $80 - $650 and takes 7h 36m.

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

The fastest way to get from Winter Haven to Chicago is to bus and fly which takes 6h 47m and costs $100 - $480.

Is there a direct bus between Winter Haven and Chicago?

No, there is no direct bus from Winter Haven to Chicago station. However, there are services departing from Winter Haven Transportation Center and arriving at Chicago Bus Station via Orlando Bus Station and Atlanta Bus Station. The journey, including transfers, takes approximately 26h 25m.

Is there a direct train between Winter Haven and Chicago?

No, there is no direct train from Winter Haven station to Chicago station. However, there are services departing from Lakeland Amtrak Station and arriving at Chicago Union Station via . The journey, including transfers, takes approximately 42h 5m.

How far is it from Winter Haven to Chicago?

The distance between Winter Haven and Chicago is 1077 miles. The road distance is 1131.5 miles.

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

The best way to get from Winter Haven to Chicago without a car is to bus which takes 26h 25m and costs $180 - $370.

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

It takes approximately 6h 47m to get from Winter Haven to Chicago, including transfers.

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

Winter Haven to Chicago bus services, operated by Greyhound USA, depart from Winter Haven Transportation Center station.

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

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

Train or bus from Winter Haven to Chicago?

The best way to get from Winter Haven to Chicago is to bus which takes 26h 25m and costs $180 - $370. Alternatively, you can train, which costs $550 - $1,200 and takes 42h 5m.

Where does the Winter Haven to Chicago bus arrive?

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

What is the time difference between Winter Haven and Chicago?

Chicago is 1h behind Winter Haven. It is currently 11:48 AM in Winter Haven and 10:48 AM in Chicago.

Where does the Winter Haven to Chicago train arrive?

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

Can I drive from Winter Haven to Chicago?

Yes, the driving distance between Winter Haven to Chicago is 1132 miles. It takes approximately 20h 12m to drive from Winter Haven to Chicago.

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

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

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

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

Where can I stay near Chicago?

There are 1125+ hotels available in Chicago.

Winter Haven to Chicago - 7 ways to travel via train, bus, plane, and car

How to get fromWinter Haven to Chicago

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There are 7 ways to get from Winter Haven to Chicago by bus, plane, 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.

Bus to Tampa, fly to Chicago Midway International Airport
best
1. Take the bus from Winter Haven Transportation Center to Tampa Bus Stationbus
2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane TPA - MDW
6h 47m
$107–474
Bus to Orlando, fly to Chicago O'Hare International Airport
cheapest
1. Take the bus from Winter Haven Transportation Center to Orlando Bus Stationbus
2. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane MCO - ORD
7h 36m
$83–623
Bus
1. Take the bus from Winter Haven Transportation Center to Orlando Bus Stationbus
2. Take the bus from Orlando Bus Station to Atlanta Bus Stationbus
3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus
26h 25m
$182–364
Train (Amtrak)
1. Take the train from Lakeland Amtrak Station to Chicago Union Stationtrain Floridian
42h 5m
$552–1,202
Drive 1,125 mi
1. Drive from Winter Haven to Chicagocar 1,125 mi
20h 12m
$206–297
Bus to Tampa, fly to Chicago O'Hare International Airport
1. Take the bus from Winter Haven Transportation Center to Tampa Bus Stationbus
2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane TPA - ORD
7h 19m
$172–574
Bus to Orlando, fly to Chicago Midway International Airport
1. Take the bus from Winter Haven Transportation Center to Orlando Bus Stationbus
2. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane MCO - MDW
7h 13m
$213–513

Winter Haven to Chicago by bus

7Weekly Buses

26h 25mAverage Duration

$182Cheapest Price

See schedules

Questions & Answers

Map of how to get from Winter Haven to Chicago.

Launch map view

Distance: 1,071.1 mi
Duration: 6h 47m

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

You can take a bus from Winter Haven Transportation Center to Chicago Bus Station via Orlando Bus Station and Atlanta Bus Station in around 26h 25m. Alternatively, Amtrak operates a train from Lakeland Amtrak Station to Chicago Union Station once daily. Tickets cost $550–1,200 and the journey takes 40h 20m.

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