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How to Travel from

Winter Haven to Chicago

by Plane, Rideshare, Route or Car

Winter Haven
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Chicago
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Winter Haven
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Chicago
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Twelve ways to Travel from Winter Haven to Chicago

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Transport providers

Airlines

Spirit Airlines

Website:
spirit.com
Plane from Orlando to Chicago
Ave. Duration:
3h 9m
Frequency:
Every day
Estimated price:
$46.04–$370.86
Plane from Tampa to Chicago
Ave. Duration:
3h 7m
Frequency:
Monday, Tuesday, and Sunday
Estimated price:
$38.37–$524.32
Plane from Orlando to General
Ave. Duration:
3h 4m
Frequency:
Every day
Estimated price:
$44.76–$242.98

American Airlines

Website:
aa.com/
Plane from Orlando to Chicago
Ave. Duration:
3h 7m
Frequency:
Every day
Estimated price:
$108.70–$767.30
Plane from Tampa to Chicago
Ave. Duration:
3h 4m
Frequency:
Every day
Estimated price:
$121.49–$895.19
Plane from Sarasota–Bradenton International Airport to Chicago
Ave. Duration:
3h 13m
Frequency:
Every day
Estimated price:
$121.49–$524.32

Delta

Website:
delta.com/
Plane from Orlando to General
Ave. Duration:
4h 44m
Frequency:
Every day
Estimated price:
$127.88–$294.13

United Airlines

Website:
united.com/
Plane from Orlando to Chicago
Ave. Duration:
3h 11m
Frequency:
Every day
Estimated price:
$121.49–$460.38
Plane from Tampa to Chicago
Ave. Duration:
3h 7m
Frequency:
Every day
Estimated price:
$153.46–$831.25
Plane from Sarasota–Bradenton International Airport to Chicago
Ave. Duration:
3h 13m
Frequency:
Every day
Estimated price:
$153.46–$524.32

Frontier Airlines

Website:
flyfrontier.com/
Plane from Tampa to Midway
Ave. Duration:
2h 56m
Frequency:
Monday, Wednesday, Friday, and Saturday
Estimated price:
$62.66–$204.61
Plane from Orlando to Midway
Ave. Duration:
3h 3m
Frequency:
Monday, Thursday, Friday, Saturday, and Sunday
Estimated price:
$48.60–$306.92
Plane from Orlando to Chicago
Ave. Duration:
3h 25m
Frequency:
Tuesday to Sunday
Estimated price:
$47.32–$204.61
Plane from Tampa to Chicago
Ave. Duration:
3h 7m
Frequency:
Every day
Estimated price:
$54.99–$626.63
Plane from Sarasota–Bradenton International Airport to Chicago
Ave. Duration:
3h 13m
Frequency:
Monday, Wednesday, and Friday
Estimated price:
$42.20–$230.19
Plane from Orlando to General
Ave. Duration:
3h 17m
Frequency:
Every day
Estimated price:
$42.20–$217.40

Southwest Airlines

Website:
southwest.com/
Plane from Tampa to Midway
Ave. Duration:
2h 50m
Frequency:
Every day
Estimated price:
$166.25–$498.75
Plane from Orlando to Midway
Ave. Duration:
2h 55m
Frequency:
Every day
Estimated price:
$127.88–$409.23
Plane from Orlando to Chicago
Ave. Duration:
3h 5m
Frequency:
Tuesday, Wednesday, Saturday, and Sunday
Estimated price:
$108.70–$319.71
Plane from Tampa to Chicago
Ave. Duration:
4h 50m
Frequency:
Monday to Friday
Estimated price:
$127.88–$383.65
Plane from Sarasota–Bradenton International Airport to Midway
Ave. Duration:
2h 55m
Frequency:
Every day
Estimated price:
$166.25–$485.96
Plane from Orlando to General
Ave. Duration:
2h 58m
Frequency:
Every day
Estimated price:
$127.88–$383.65

Sun Country Airlines

Website:
suncountry.com/
Plane from Orlando to General
Ave. Duration:
3h 4m
Frequency:
Thursday, Saturday, and Sunday
Estimated price:
$95.91–$294.13

Allegiant Air

Website:
allegiantair.com/
Plane from Orlando Sanford to South
Ave. Duration:
2h 35m
Frequency:
Every day
Estimated price:
$140.67–$460.38

Train operators

Amtrak

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Winter Haven to Chicago
Ave. Duration:
42h 49m
Frequency:
Once daily
Estimated price:
$179.04–$575.48
Train from Milwaukee to Chicago
Ave. Duration:
1h 29m
Frequency:
Every 4 hours
Estimated price:
$12.79–$89.52

South Shore Line

Phone:
+1 219-926-5744
Website:
mysouthshoreline.com/
Train from South Bend Airport to Van
Ave. Duration:
2h 1m
Frequency:
Every 2 hours
Estimated price:
$7.03–$16.62

Bus operators

Greyhound USA

Phone:
+1 214-849-8100
Website:
greyhound.com/
Bus from Winter Haven Transportation Center to Tampa
Ave. Duration:
1h 40m
Frequency:
Twice daily
Estimated price:
$4.09–$70.34
Bus from Winter Haven Transportation Center to Orlando
Ave. Duration:
1h 30m
Frequency:
Once daily
Estimated price:
$3.58–$70.34
Bus from Orlando Bus Station to Atlanta
Ave. Duration:
7h 15m
Frequency:
3 times a day
Estimated price:
$34.53–$230.19
Bus from Atlanta Bus Station to Chicago
Ave. Duration:
16h 10m
Frequency:
4 times a day
Estimated price:
$57.55–$345.29

Flixbus USA

Phone:
+1 (855) 626-8585
Website:
flixbus.com
Bus from Orlando Bus Station to Atlanta
Ave. Duration:
8h 15m
Frequency:
4 times a day
Estimated price:
$42.20–$140.67
Bus from Atlanta Bus Station to Chicago
Ave. Duration:
14h 40m
Frequency:
Twice daily
Estimated price:
$63.94–$204.61
Bus from Tampa Bus Station to Sarasota
Ave. Duration:
1h 20m
Frequency:
4 times a day
Estimated price:
$8.31–$44.76

Questions and Answers

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 $43.48 - $347.83 and takes 7h 11m.

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

The fastest way to get from Winter Haven to Chicago is to drive and fly and train which takes 6h 59m and costs $130.43 - $423.91 .

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 55m.

How far is it from Winter Haven to Chicago?

The distance between Winter Haven and Chicago is 1723 km. The road distance is 1885.5 km.

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 55m and costs $81.52 - $597.83 .

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

It takes approximately 7h 11m 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.

Train or bus from Winter Haven to Chicago?

The best way to get from Winter Haven to Chicago is to bus which takes 26h 55m and costs $81.52 - $597.83 . Alternatively, you can train, which costs $184.78 - $532.61 and takes 42h 51m.

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 06:41 in Winter Haven and 05:41 in Chicago.

Can I drive from Winter Haven to Chicago?

Yes, the driving distance between Winter Haven to Chicago is 1886 km. It takes approximately 19h 34m to drive from Winter Haven to Chicago.

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 1249+ hotels available in Chicago. Prices start at $65.98 per night.
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