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How to get from Chicago to Windsor, ON

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What is the best way to travel from Chicago to Windsor, ON?

Looking for a trip? Compare all the available Flights and Buses for the journey to Windsor, ON from Chicago. Check between different modes of transportation, look for the cheapest tickets, fastest rides and most popular stations, and see all 2 available companies to find your perfect trip!
Bus is the cheapest, while Flight is the fastest way on this route
Transport type
Travel time
Cheapest price
Average price
Daily departures
Flight
1h 21m
$131
$211
19
Bus
6h 55m
$45
$51
10

What is the cheapest way to reach Windsor, ON from Chicago?

You can get to Windsor, ON with just $45 by taking a Bus from Greyhound US, but you can find many more cheap offers: we have selected the best ones for next few days here for you.

today
tomorrow
from $248
Monday
from $63
Tuesday
Wednesday
from $46
Thursday
from $45
Friday
from $51

    Cheapest Flights tomorrow

  • Skyscanner
    1h 24m
    0
    7:45 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:09 AM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $248
  • Skyscanner
    1h 28m
    0
    5:50 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    8:18 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $248
  • Skyscanner
    1h 35m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:10 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $248
  • United Airlines
    1h 21m
    0
    2:56 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:17 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $248

    Cheapest Buses Monday

  • Greyhound US
    9h 35m
    0
    6:20 AM
    Chicago
    Greyhound Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $63
  • Greyhound US
    8h 0m
    0
    10:10 PM
    Chicago
    Greyhound Bus Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $63
  • Cheapest Flights Monday

  • Skyscanner
    1h 24m
    0
    7:45 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:09 AM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $250
  • Skyscanner
    1h 35m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:10 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $250
  • Skyscanner
    1h 24m
    0
    9:05 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    11:29 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $250
  • United Airlines
    1h 21m
    0
    2:56 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:17 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $250

    Cheapest Buses Wednesday

  • Greyhound US
    9h 55m
    0
    1:45 AM
    Chicago
    Union Station
    12:40 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46
  • Greyhound US
    9h 10m
    0
    6:45 AM
    Chicago
    Union Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46
  • Greyhound US
    7h 35m
    0
    10:35 PM
    Chicago
    Union Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46
  • Greyhound US
    7h 20m
    0
    10:50 PM
    Chicago
    Union Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46
  • Greyhound US
    9h 35m
    0
    6:20 AM
    Chicago
    Greyhound Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $50
  • Cheapest Flights Wednesday

  • Skyscanner
    1h 28m
    0
    5:50 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    8:18 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $249
  • Skyscanner
    1h 35m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:10 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $249
  • United Airlines
    1h 21m
    0
    2:56 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:17 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $249
  • United Airlines
    1h 21m
    0
    9:10 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    11:31 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $249
  • Skyscanner
    1h 24m
    0
    7:45 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:09 AM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $324

    Cheapest Buses Thursday

  • Greyhound US
    9h 10m
    0
    6:45 AM
    Chicago
    Union Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $45
  • Greyhound US
    7h 35m
    0
    10:35 PM
    Chicago
    Union Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $45
  • Greyhound US
    7h 20m
    0
    10:50 PM
    Chicago
    Union Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $45
  • Greyhound US
    9h 55m
    0
    1:45 AM
    Chicago
    Union Station
    12:40 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46
  • Greyhound US
    9h 35m
    0
    6:20 AM
    Chicago
    Greyhound Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $61
  • Cheapest Flights Thursday

  • Skyscanner
    1h 33m
    0
    7:45 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:18 AM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $164
  • Skyscanner
    1h 35m
    0
    10:55 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    1:30 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $164
  • Skyscanner
    1h 34m
    0
    5:50 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    8:24 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $164
  • United Airlines
    1h 25m
    0
    2:59 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:24 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $164

    Cheapest Buses Friday

  • Greyhound US
    9h 55m
    0
    1:45 AM
    Chicago
    Union Station
    12:40 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $51
  • Greyhound US
    9h 10m
    0
    6:45 AM
    Chicago
    Union Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $51
  • Greyhound US
    6h 55m
    0
    4:00 PM
    Chicago
    Union Station
    11:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $51
  • FlixBus
    12h 5m
    0
    11:35 PM
    Chicago
    95th Red Line Station
    12:40 PM
    Windsor, ON
    International Transit Terminal
    0
    FlixBus
    Economy
    $67
  • Cheapest Flights Friday

  • United Airlines
    1h 25m
    0
    2:59 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:24 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $131
  • United Airlines
    1h 34m
    0
    5:50 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    8:24 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $131
  • United Airlines
    1h 33m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:08 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $131
  • United Airlines
    1h 32m
    0
    9:12 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    11:44 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $131
  • Skyscanner
    1h 33m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:08 PM
    Windsor, ON
    0
    Skyscanner
    Economy
    from $147
  • Skyscanner
    1h 32m
    0
    9:13 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    11:45 PM
    Windsor, ON
    0
    Skyscanner
    Economy
    from $147

What are the fastest trips from Chicago to Windsor, ON?

You can get to Windsor, ON from Chicago in just 1h 21m with a Flight from United Airlines. This is not the only option, and you can click on any of the offers below to compare it with the other modes of transportations.

today
tomorrow
from 1h 21m
Monday
from 1h 21m
Tuesday
Wednesday
from 1h 21m
Thursday
from 1h 25m
Friday
from 1h 25m

    Fastest Flights tomorrow

  • United Airlines
    1h 21m
    0
    2:56 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:17 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $248
  • Skyscanner
    1h 24m
    0
    7:45 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:09 AM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $248
  • Skyscanner
    1h 28m
    0
    5:50 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    8:18 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $248
  • Skyscanner
    1h 35m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:10 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $248

    Fastest Flights Monday

  • United Airlines
    1h 21m
    0
    2:56 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:17 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $250
  • Skyscanner
    1h 24m
    0
    7:45 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:09 AM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $250
  • Skyscanner
    1h 24m
    0
    9:05 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    11:29 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $250
  • Skyscanner
    1h 35m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:10 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $250
  • Fastest Buses Monday

  • Greyhound US
    8h 0m
    0
    10:10 PM
    Chicago
    Greyhound Bus Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $63
  • Greyhound US
    9h 35m
    0
    6:20 AM
    Chicago
    Greyhound Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $63

    Fastest Flights Wednesday

  • United Airlines
    1h 21m
    0
    2:56 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:17 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $249
  • United Airlines
    1h 21m
    0
    9:10 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    11:31 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $249
  • Skyscanner
    1h 24m
    0
    7:45 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:09 AM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $324
  • Skyscanner
    1h 28m
    0
    5:50 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    8:18 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $249
  • Skyscanner
    1h 35m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:10 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $249
  • Fastest Buses Wednesday

  • Greyhound US
    7h 20m
    0
    10:50 PM
    Chicago
    Union Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46
  • Greyhound US
    7h 35m
    0
    10:35 PM
    Chicago
    Union Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46
  • Greyhound US
    9h 10m
    0
    6:45 AM
    Chicago
    Union Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46
  • Greyhound US
    9h 35m
    0
    6:20 AM
    Chicago
    Greyhound Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $50
  • Greyhound US
    9h 55m
    0
    1:45 AM
    Chicago
    Union Station
    12:40 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46

    Fastest Flights Thursday

  • United Airlines
    1h 25m
    0
    2:59 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:24 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $164
  • Skyscanner
    1h 33m
    0
    7:45 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:18 AM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $164
  • Skyscanner
    1h 34m
    0
    5:50 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    8:24 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $164
  • Skyscanner
    1h 35m
    0
    10:55 AM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    1:30 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    Skyscanner
    Economy
    from $164
  • Fastest Buses Thursday

  • Greyhound US
    7h 20m
    0
    10:50 PM
    Chicago
    Union Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $45
  • Greyhound US
    7h 35m
    0
    10:35 PM
    Chicago
    Union Station
    7:10 AM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $45
  • Greyhound US
    9h 10m
    0
    6:45 AM
    Chicago
    Union Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $45
  • Greyhound US
    9h 35m
    0
    6:20 AM
    Chicago
    Greyhound Bus Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $61
  • Greyhound US
    9h 55m
    0
    1:45 AM
    Chicago
    Union Station
    12:40 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $46

    Fastest Flights Friday

  • United Airlines
    1h 25m
    0
    2:59 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:24 PM
    Windsor, ON
    0
    United Airlines
    Economy
    from $147
  • United Airlines
    1h 25m
    0
    2:59 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    5:24 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $131
  • Skyscanner
    1h 32m
    0
    9:13 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    11:45 PM
    Windsor, ON
    0
    Skyscanner
    Economy
    from $147
  • United Airlines
    1h 32m
    0
    9:12 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    11:44 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $131
  • Skyscanner
    1h 33m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:08 PM
    Windsor, ON
    0
    Skyscanner
    Economy
    from $147
  • United Airlines
    1h 33m
    0
    7:35 PM
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    10:08 PM
    Detroit Metropolitan Wayne County Airport
    Detroit Metropolitan Wayne County Airport
    0
    United Airlines
    Economy
    from $131
  • Fastest Buses Friday

  • Greyhound US
    6h 55m
    0
    4:00 PM
    Chicago
    Union Station
    11:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $51
  • Greyhound US
    9h 10m
    0
    6:45 AM
    Chicago
    Union Station
    4:55 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $51
  • Greyhound US
    9h 55m
    0
    1:45 AM
    Chicago
    Union Station
    12:40 PM
    Windsor, ON
    International Transit Terminal
    0
    Greyhound US
    Economy
    $51
  • FlixBus
    12h 5m
    0
    11:35 PM
    Chicago
    95th Red Line Station
    12:40 PM
    Windsor, ON
    International Transit Terminal
    0
    FlixBus
    Economy
    $67
Here you will find all operators and timetables for a Bus from Chicago to Windsor, ON

What are the most popular stations in Chicago and Windsor, ON?

In Chicago, you will usually depart from Union Station, 95th Red Line Station or Cumberland CTA, while in Windsor, ON you will be arriving at International Transit Terminal, Windsor Train Station or University, but there are many more stops to explore in both locations.

How do I decide? Some tips and tricks from our experience

Are you having trouble deciding on how to get to Windsor, ON from Chicago? With 8 connections between 2 Flight and Bus operators, it can be difficult to find the one ride that will make you happy. But we have some tips that can help you make the best informed decision. First of all, the best trip is always the one that meets all your needs, so make a list of all the things that you want from this journey and look for something that will satisfy all of them. Here we will go through some of the factors mostly commonly taken into consideration.

Look for the lowest price

Ticket price is usually the main concern: even if you can afford to pay more, why do it if there are cheaper options? Saving on the trip means that you can spend more on the vacation itself! Between Chicago and Windsor, ON, you can pay as low as $45 with a Bus from Greyhound US.

Travel duration

Time is also an important factor. An earlier departure may allow you to see a beautiful sunset or relax before an important event. And remember, time is money, so paying more for a shorter trip may be well worth it. For longer distances, flights are without doubt the best options, but be mindful of airport times and possible delays: a high-speed train may end up cheaper and faster! Here the quicker option is definitely the Flight from United Airlines: you will get to Windsor, ON in just 1h 21m.

Comfort makes all the difference

You should always take into account what your personal travelling preferences are. Is one hand luggage enough, or are you trasporting more? Would you like to have a snack during the journey? Can you relax in a busy compartment, or do you need space for yourself? Even among the same mode of transportation, different companies will offer you varying levels of comfort and amenities. The main operators connecting Chicago and Windsor, ON are Greyhound US, Skyscanner and United Airlines, but be sure to check what they have to offer!

Save money with deals, and always compare

One last tip? Even if you live in Chicago and Windsor, ON is your only destination, it may be wise to check the offers from and to nearby cities or, if you are flyng, nearby airports. Check the trips from Cicero, IL or to Detroit, and look at flights from Chicago Midway Airport, and landing at Detroit Metropolitan Wayne County Airport. Comparing different routes may allow you to find deals or promotions you were not aware of. Consider also signing up to CheckMyBus to see even more exclusive promotions!

Which companies offer a trip from Chicago to Windsor, ON?

The most popular companies between Chicago and Windsor, ON, are Greyhound US, Skyscanner and United Airlines. Be sure to check their seat class offers and the amenities that they provide.

Bus companies: Greyhound US and FlixBus

Airlines: Skyscanner, United Airlines and Air Canada

All you need to know when you travel from Chicago to Windsor, ON

Check all information on comfort and services on all modes of transports from Chicago to Windsor, ON. See which seat classes are available, and what amenities are other advantages offered by the operators on your journey.

FAQs about the trip from Chicago to Windsor, ON

How can I reach Windsor, ON from Chicago?

Every day, there are on average 8 connections between Flight and Bus, with which you can get to Windsor, ON from Chicago.

How far is Windsor, ON from Chicago?

The distance between Chicago and Windsor, ON is 237.9 miles.

What is the most ecofriendly mode of transport between Chicago and Windsor, ON?

Trains and buses are by far the greenest options, with trains surpassing buses on longer routes. Planes will always be the worst polluters, especially in shorter flights, were the emissions from the takeoff and landing are less offset by the distance. On this particular route, a bus will emit, per person, a total of 10 kgs of CO2, a train 13 kgs, a car 65 kgs, and a flight 94 kgs.

What is the cheapest mode of transport from Chicago to Windsor, ON?

You can get to Windsor, ON with just $45 by taking a Bus from Greyhound US.

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

While a plane is travelling fastest boarding and transfer to airport consumes a lot of time. Usually, high speed trains are better than flights if pure train travel time is below 4 hours. For this particular route, you can get to Windsor, ON in just 1h 21m with a Flight from United Airlines.

More routes to Chicago and to Windsor, ON

Looking for more options? Here you can see the most popular routes to Chicago and to Windsor, ON. Simply click on a connection, and you’ll find all the details about the route!

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