C$605 Cheap Flights from Windsor (YQG) to Chicago (CHIA)

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Flight deals from Windsor to Chicago

Looking for a cheap last-minute deal or the best return flight from Windsor Airport to Chicago? If you want to travel next month, return fares start from C$616. Find the lowest prices on one-way and return tickets right here.

Chicago.C$311 per passenger.Departing Mon., Sep. 28.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Windsor on Mon., Sep. 28, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$311, select.

Chicago.C$345 per passenger.Departing Sun., Nov. 1.One-way flight with Air Canada.Outbound indirect flight with Air Canada, departs from Windsor on Sun., Nov. 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$345, select.

Chicago.C$350 per passenger.Departing Sun., Oct. 11.One-way flight with Air Canada.Outbound indirect flight with Air Canada, departs from Windsor on Sun., Oct. 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$350, select.

Chicago.C$392 per passenger.Departing Fri., Aug. 21.One-way flight with WestJet.Outbound indirect flight with WestJet, departs from Windsor on Fri., Aug. 21, arriving in Chicago Midway.Price includes taxes and charges.From C$392, select.

Find the cheapest month to fly from Windsor to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Windsor to Chicago flights are currently cheapest in September.

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Alternative Windsor to Chicago routes

Looking for the cheapest, fastest or easiest route from Windsor to Chicago? You could fly into the following airports instead.

Windsor to Chicago: Flight information

The things to know before you go.

Cheapest flight found	C$311
Cheapest month to fly	September

Finding cheap flights from Windsor to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are return flights from Windsor to Chicago?

The best price we found for a return flight from Windsor to Chicago is C$605. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Windsor to Chicago?

Currently, there are no airlines that fly direct from Windsor to Chicago. But we found flights with one or more stops from C$605.

How many flights are there a week from Windsor to Chicago?

As of August 2026, there are no flights flying from Windsor to Chicago.

When is the cheapest time to fly from Windsor to Chicago?

The cheapest month to fly from Windsor to Chicago is usually October.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Windsor Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from C$605.

Which upcoming date is cheapest to fly from Windsor Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Windsor Airport to Chicago on Sunday, October 4, 2026.

Can I get a direct flight from Windsor Airport to Chicago?

No airlines currently offer direct flights between Windsor Airport and Chicago. Most routes have one or more stops.

How can I get the best flight deal from Windsor Airport to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In August, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Windsor Airport to Chicago with?

Currently, Air Canada offers the cheapest flight tickets to Chicago.

Flying from Windsor International Airport (YQG) to Chicago: what you need to know

Chicago is 1 hour behind Windsor, where Windsor International Airport is located. Chicago operates on the UTC-5 timezone.
For stress-free travel, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This will give you enough time to catch your flight from YQG to Chicago.
You'll likely experience longer queues during popular months such as August and other peak seasons. Arriving up to fours hours ahead of international flights and two hours for domestic departures will help ensure a smooth travel experience.
If you hold a passport from Canada and are travelling to United States for tourism purposes, you won't need a visa. However, visa and entry requirements may differ based on the reason for your trip and are subject to change. For the latest rules, contact your destination's nearest consulate or embassy before reserving a cheap ticket from Windsor International Airport to Chicago.
Located around 11 kilometres from the centre of Windsor, YQG can be reached in about 20 minutes by car, depending on traffic. The same journey on public transport is roughly 1 hour and 7 minutes.
After a hassle-free start to your travels? Stay near YQG. Whether you have an early flight from Windsor International Airport to Chicago or just don't like being rushed, these hotels are perfect:

How to find the cheapest flights from Windsor International Airport (YQG) to Chicago

The lowest price we've found for a one-way ticket from Windsor International Airport to Chicago is C$311. The cheapest price for a return flight is C$605. Remember fares may change due to demand at the time of booking.
It's often best to book early if you want to find cheap tickets from YQG to Chicago. That's because airlines adjust prices based on demand, which tends to rise closer to the departure date.
If you're flexible with your travel dates, make the most of the 'Whole month' tool. It'll find the cheapest price across every month when searching for your ticket from Windsor International Airport to Chicago.
Getting a cheap ticket from YQG to Chicago is easy with Price Alerts. Simply create one of these automatic alerts and we'll notify you when the price has fallen.
Tailor your trip with filters. Select your departure and arrival times, total journey duration and airlines. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest' flights from Windsor International Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

O'Hare International Airport (ORD) to central Chicago is around 35 minutes by car. It's approximately 40 kilometres away.
Travelling by public transport takes around 54 minutes.
The last thing you want is a lengthy journey to your hotel if you're arriving on a late flight from Windsor International Airport to Chicago. Book one of these accommodation options near ORD instead:

Chicago Midway International Airport (MDW)

The centre of Chicago is about 19 kilometres from Chicago Midway International Airport (MDW). Once your flight from Windsor International Airport to Chicago has hit the runway and you've made your way to arrivals, the drive should be around 21 minutes.
You can also opt for public transport, which will take roughly 46 minutes.
Hang up the 'Do not disturb' sign and rest at a hotel near MDW. Here are a few options where you can put your feet up after your flight from YQG to Chicago:

Best time to go to Chicago

August is the most popular month for flights from Windsor International Airport to Chicago. To avoid the crowds, visit Chicago in February when it's quieter.
Before locking in your flight from Windsor International Airport to Chicago, think about the type of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.
Search for cheap flights from YQG to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

When it comes to looking for somewhere to rest your head, you'll find the best stays in Chicago right here. Browse these options once you've locked in your flight from Windsor International Airport to Chicago:
There are so many things to explore in this city it can be hard to figure out where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are popular attractions which should be on any well-planned Chicago itinerary.

Complete your Chicago trip with a car rental

We use the same magic that helped you find your cheap flight from Windsor International Airport to Chicago to track down incredible deals on car rentals. Search for your ride in seconds and easily compare your options. Plus we give you all the info you need to know about car rentals in Chicago, from the most popular car type to the best time to book.