How to Travel from

Chicago to Windsor

by Plane, Rideshare, Route or Car

United States of America Chicago Windsor

How to Get from Chicago to Windsor

Plane

2 h 6 min

Select a Ticket

Car

15 h

from $79

Rideshare

15 h

from $18.84

Cheapest

By car (1 444 km)

15 h

1444 km.

from $79

Fastest

Other

Rideshare

15 h

1444 km.

from $18.83

Bus

24 h 46 min

1238 km.

from $225.91

Airlines

American Airlines

Website:

aa.com/

Plane from Chicago O'Hare International Airport to Bradley

Ave. Duration:

2h 10m

Frequency:

Every day

Estimated price:

$119.57–$532.61

Delta

Website:

delta.com/

Plane from Midway International Airport to Bradley

Ave. Duration:

4h 58m

Frequency:

Every day

Estimated price:

$119.57–$326.09

United Airlines

Website:

united.com/

Plane from Chicago O'Hare International Airport to Bradley

Ave. Duration:

2h 12m

Frequency:

Every day

Estimated price:

$152.17–$532.61

Southwest Airlines

Website:

southwest.com/

Plane from Chicago O'Hare International Airport to Bradley

Ave. Duration:

4h 55m

Frequency:

Tuesday and Wednesday

Estimated price:

$130.43–$402.17

Plane from Midway International Airport to Bradley

Ave. Duration:

2h 1m

Frequency:

Every day

Estimated price:

$130.43–$423.91

Train operators

Amtrak

Phone:

+1 800-872-7245

Website:

amtrak.com/home.html

Train from Chicago Union Station to Springfield

Ave. Duration:

19h 19m

Frequency:

Once daily

Estimated price:

$81.52–$271.74

Bus operators

Flixbus USA

Phone:

+1 (855) 626-8585

Website:

flixbus.com

Bus from Chicago Bus Station to New

Ave. Duration:

20h 20m

Frequency:

Once daily

Estimated price:

$70.65–$228.26

Bus from New York Midtown to Hartford

Ave. Duration:

2h 30m

Frequency:

3 times a day

Estimated price:

$10.87–$50.00

What is the cheapest way to get from Chicago to Windsor?

The cheapest way to get from Chicago to Windsor is to bus which costs $86.96 - $282.61 and takes 24h 46m.

What is the fastest way to get from Chicago to Windsor?

The fastest way to get from Chicago to Windsor is to fly which takes 4h 35m and costs $108.70 - $336.96 .

Is there a direct bus between Chicago and Windsor?

No, there is no direct bus from Chicago station to Windsor. However, there are services departing from Chicago Bus Station and arriving at Central St @ Broad St via New York Midtown, Union Pl @ Union Stn Transit Center and Central Row South Side @ Travelers. The journey, including transfers, takes approximately 24h 46m.

Is there a direct train between Chicago and Windsor?

No, there is no direct train from Chicago station to Windsor. However, there are services departing from Chicago Union Station and arriving at Windsor via Springfield. The journey, including transfers, takes approximately 20h 43m.

How far is it from Chicago to Windsor?

The distance between Chicago and Windsor is 1298 km. The road distance is 1444.9 km.

How do I travel from Chicago to Windsor without a car?

The best way to get from Chicago to Windsor without a car is to train which takes 20h 43m and costs $86.96 - $467.39 .

How long does it take to get from Chicago to Windsor?

It takes approximately 4h 55m to get from Chicago to Windsor, including transfers.

Where do I catch the Chicago to Windsor bus from?

Chicago to Windsor bus services, operated by Flixbus USA, depart from Chicago Bus Station.

Where do I catch the Chicago to Windsor train from?

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

Train, bus or fly from Chicago to Windsor?

The best way to get from Chicago to Windsor is to fly which takes 4h 55m and costs $130.43 - $413.04 . Alternatively, you can train, which costs $86.96 - $467.39 and takes 20h 43m, you could also bus, which costs $86.96 - $282.61 and takes 24h 46m.

Where does the Chicago to Windsor bus arrive?

Chicago to Windsor bus services, operated by Flixbus USA, arrive at New York Midtown station.

What is the time difference between Chicago and Windsor?

Windsor is 1h ahead of Chicago. It is currently 05:29 in Chicago and 06:29 in Windsor.

Where does the Chicago to Windsor train arrive?

Chicago to Windsor train services, operated by Amtrak, arrive at Springfield station.

Can I drive from Chicago to Windsor?

Yes, the driving distance between Chicago to Windsor is 1445 km. It takes approximately 14h 57m to drive from Chicago to Windsor.

Which airlines fly from Chicago O'Hare International Airport Airport to Bradley International Airport Airport?

Southwest Airlines, United Airlines and American Airlines offer flights from Chicago O'Hare International Airport Airport to Bradley International Airport Airport.

How do I get a train ticket from Chicago to Windsor?

Book your Chicago to Windsor train tickets online with Omio.

Where can I stay near Windsor?

There are 136+ hotels available in Windsor. Prices start at $47.60 per night.

Book in Windsor

HYATT house Hartford North/Windsor

200 Corporate Dr, Windsor

Fine

8.9

Courtyard By Marriott Hartford/Windsor Airport

1 Day Hill Rd, Windsor

Fine

8.7

Marriott Hartford/Windsor Airport

28 Day Hill Rd, Windsor

Fine

8.5

All accommodation options in WindsorAll hotels

New England Air Museum

Mark Twain House

Wadsworth Atheneum

Windsor

Windsor is a town in Hartford County, Connecticut, United States, and was the first English settlement in the state. It lies on the northern border of Connecticut's capital, Hartford. The town is part of the Capitol Planning Region. The population of Windsor was 29,492 at the 2020 census.

Read in Wikipedia

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Four ways to Travel from Chicago to Windsor

Transport providers

Airlines

American Airlines

Delta

United Airlines

Southwest Airlines

Train operators

Amtrak

Bus operators

Flixbus USA

Questions and Answers

What is the cheapest way to get from Chicago to Windsor?

What is the fastest way to get from Chicago to Windsor?

Is there a direct bus between Chicago and Windsor?

Is there a direct train between Chicago and Windsor?

How far is it from Chicago to Windsor?

How do I travel from Chicago to Windsor without a car?

How long does it take to get from Chicago to Windsor?

Where do I catch the Chicago to Windsor bus from?

Where do I catch the Chicago to Windsor train from?

Train, bus or fly from Chicago to Windsor?

Where does the Chicago to Windsor bus arrive?

What is the time difference between Chicago and Windsor?

Where does the Chicago to Windsor train arrive?

Can I drive from Chicago to Windsor?

Which airlines fly from Chicago O'Hare International Airport Airport to Bradley International Airport Airport?

How do I get a train ticket from Chicago to Windsor?

Where can I stay near Windsor?