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How to Travel from

Chicago to Winter Haven

by Plane, Rideshare, Route or Car

Chicago
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Winter Haven
Transport search to Winter Haven
Chicago
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Winter Haven
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Eleven ways to Travel from Chicago to Winter Haven

Select an Option Below to Start Your Journey
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Transport providers

Airlines

Spirit Airlines

Website:
spirit.com
Plane from Chicago O'Hare International Airport to Orlando
Ave. Duration:
2h 46m
Frequency:
Every day
Estimated price:
$45.86–$369.42
Plane from Chicago O'Hare International Airport to Tampa
Ave. Duration:
2h 51m
Frequency:
Every day
Estimated price:
$38.22–$522.28

American Airlines

Website:
aa.com/
Plane from Chicago O'Hare International Airport to Orlando
Ave. Duration:
2h 41m
Frequency:
Every day
Estimated price:
$108.28–$764.32
Plane from Chicago O'Hare International Airport to Tampa
Ave. Duration:
2h 42m
Frequency:
Every day
Estimated price:
$121.02–$891.70
Plane from Chicago O'Hare International Airport to Sarasota–Bradenton
Ave. Duration:
2h 41m
Frequency:
Every day
Estimated price:
$203.82–$891.70

Delta

Website:
delta.com/
Plane from Midway International Airport to Tampa
Ave. Duration:
4h 30m
Frequency:
Every day
Estimated price:
$152.86–$356.68
Plane from Chicago O'Hare International Airport to Tampa
Ave. Duration:
4h 32m
Frequency:
Every day
Estimated price:
$140.12–$318.46
Plane from Midway International Airport to Sarasota–Bradenton
Ave. Duration:
4h 56m
Frequency:
Every day
Estimated price:
$242.03–$547.76

United Airlines

Website:
united.com/
Plane from Chicago O'Hare International Airport to Orlando
Ave. Duration:
2h 49m
Frequency:
Every day
Estimated price:
$121.02–$458.59
Plane from Chicago O'Hare International Airport to Tampa
Ave. Duration:
2h 48m
Frequency:
Every day
Estimated price:
$152.86–$828.01
Plane from Chicago O'Hare International Airport to Sarasota–Bradenton
Ave. Duration:
2h 58m
Frequency:
Every day
Estimated price:
$267.51–$891.70

Frontier Airlines

Website:
flyfrontier.com/
Plane from Midway International Airport to Tampa
Ave. Duration:
2h 41m
Frequency:
Monday, Wednesday, Friday, and Saturday
Estimated price:
$62.42–$203.82
Plane from Midway International Airport to Orlando
Ave. Duration:
2h 46m
Frequency:
Monday, Thursday, Friday, Saturday, and Sunday
Estimated price:
$48.41–$305.73
Plane from Chicago O'Hare International Airport to Orlando
Ave. Duration:
2h 53m
Frequency:
Tuesday to Sunday
Estimated price:
$47.13–$203.82
Plane from Chicago O'Hare International Airport to Tampa
Ave. Duration:
2h 48m
Frequency:
Every day
Estimated price:
$54.78–$624.19
Plane from Chicago O'Hare International Airport to Sarasota–Bradenton
Ave. Duration:
2h 53m
Frequency:
Monday, Wednesday, and Friday
Estimated price:
$70.06–$382.16

Southwest Airlines

Website:
southwest.com/
Plane from Midway International Airport to Tampa
Ave. Duration:
2h 34m
Frequency:
Every day
Estimated price:
$152.86–$458.59
Plane from Midway International Airport to Orlando
Ave. Duration:
2h 37m
Frequency:
Every day
Estimated price:
$152.86–$484.07
Plane from Chicago O'Hare International Airport to Orlando
Ave. Duration:
2h 40m
Frequency:
Tuesday and Wednesday
Estimated price:
$140.12–$445.85
Plane from Midway International Airport to Sarasota–Bradenton
Ave. Duration:
2h 36m
Frequency:
Every day
Estimated price:
$242.03–$700.62

Allegiant Air

Website:
allegiantair.com/
Plane from South Bend to Orlando
Ave. Duration:
2h 28m
Frequency:
Every day
Estimated price:
$152.86–$509.54

Train operators

Amtrak

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Chicago Union Station to Winter
Ave. Duration:
41h 59m
Frequency:
Once daily
Estimated price:
$178.34–$573.24

South Shore Line

Phone:
+1 219-926-5744
Website:
mysouthshoreline.com/
Train from Van Buren St. to South
Ave. Duration:
1h 58m
Frequency:
Every 2 hours
Estimated price:
$7.01–$16.56

Bus operators

Greyhound USA

Phone:
+1 214-849-8100
Website:
greyhound.com/
Bus from Tampa Bus Station to Winter
Ave. Duration:
1h 35m
Frequency:
Twice daily
Estimated price:
$4.08–$76.43
Bus from Chicago Bus Station to Atlanta
Ave. Duration:
16h 30m
Frequency:
4 times a day
Estimated price:
$57.32–$343.94
Bus from Atlanta Bus Station to Orlando
Ave. Duration:
7h 55m
Frequency:
3 times a day
Estimated price:
$34.39–$229.29
Bus from Orlando Bus Station to Winter
Ave. Duration:
50 min
Frequency:
Once daily
Estimated price:
$3.57–$70.06

Flixbus USA

Phone:
+1 (855) 626-8585
Website:
flixbus.com
Bus from Chicago Bus Station to Atlanta
Ave. Duration:
15h 45m
Frequency:
Once daily
Estimated price:
$63.69–$203.82
Bus from Atlanta Bus Station to Orlando
Ave. Duration:
7h 55m
Frequency:
4 times a day
Estimated price:
$42.04–$140.12
Bus from Sarasota Cattlemen Transfer Center to Tampa
Ave. Duration:
1h 10m
Frequency:
4 times a day
Estimated price:
$8.28–$44.59

Questions and Answers

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 $43.48 - $347.83 and takes 7h 44m.

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

The fastest way to get from Chicago to Winter Haven is to train and fly and drive which takes 6h 50m and costs $141.30 - $478.26 .

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 15m.

How far is it from Chicago to Winter Haven?

The distance between Chicago and Winter Haven is 1722 km. The road distance is 1886.2 km.

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 15m and costs $81.52 - $597.83 .

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

It takes approximately 7h 44m 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.

Train or bus from Chicago to Winter Haven?

The best way to get from Chicago to Winter Haven is to bus which takes 27h 15m and costs $81.52 - $597.83 . Alternatively, you can train, which costs $184.78 - $532.61 and takes 42h 1m.

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 05:29 in Chicago and 06:29 in Winter Haven.

Can I drive from Chicago to Winter Haven?

Yes, the driving distance between Chicago to Winter Haven is 1886 km. It takes approximately 19h 32m to drive from Chicago to Winter Haven.

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 626+ hotels available in Winter Haven. Prices start at $53.04 per night.
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