C$288 Cheap Flights from Windsor (YQG) to Chicago O'Hare International (ORD)

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Flight deals from Windsor to Chicago O'Hare International

Looking for a cheap last-minute deal or the best return flight from Windsor Airport to Chicago O'Hare International Airport? If you want to travel next month, return fares start from C$611. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Windsor to Chicago O'Hare International

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

Windsor to Chicago O'Hare International: Alternative routes

Compare routes from Windsor to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago O'Hare International.

Windsor to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$288
Cheapest month to flyJuly

Finding cheap flights from Windsor to Chicago O'Hare International: Frequently asked questions

The best price we found for a return flight from Windsor to Chicago O'Hare International is C$611. 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.
Currently, there are no airlines that fly direct from Windsor to Chicago O'Hare International. But we found flights with one or more stops from C$611.
As of June 2026, there are no flights flying from Windsor to Chicago O'Hare International.
The cheapest month to fly from Windsor to Chicago O'Hare International is usually July.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Windsor Airport to Chicago O'Hare International Airport on Wednesday, July 1, 2026.
No airlines currently offer direct flights between Windsor Airport and Chicago O'Hare International Airport. Most routes have one or more stops.
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 O'Hare International 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.
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.
Currently, Air Canada offers the cheapest flight tickets to Chicago O'Hare International.

How to find the cheapest flights from Windsor International Airport (YQG) to O'Hare International Airport (ORD)

  • C$288 is currently the best price for a one-way ticket from Windsor International Airport to O'Hare International Airport. A return flight starts at C$611. These fares can change based on availability and demand.

  • Don't leave everything to the last minute. You're more likely to find cheap flight tickets from YQG to ORD if you book ahead. Airlines often have some fantastic early bird discounts.

  • If you're flexible with your travel plans, try using the 'Whole month' tool. It'll show you the lowest price across each month when searching for your ticket from Windsor International Airport to O'Hare International Airport.

  • Set up a Price Alert for cheap flight tickets from YQG to ORD. There's no need to search every day to find out if airfares have dropped. We'll let you know as soon as there's a change in price.

  • Tailor your trip using filters. Pick your ideal arrival and departure times, airlines and total journey duration. You can also sort results by 'Best,' 'Cheapest' or 'Fastest' flights from Windsor International Airport to O'Hare International Airport.

Handy information about Windsor International Airport (YQG)

  • Located around 11 kilometres from central Windsor, Windsor International Airport can be reached in approximately 20 minutes by car (depending on traffic). The same journey on public transport will take roughly 1 hour and 7 minutes.

  • Want a hassle-free start to your break? Stay near YQG. Whether you're boarding an early flight from Windsor International Airport to O'Hare International Airport or want to avoid feeling rushed, these hotels are ideal:

Arriving at O'Hare International Airport (ORD)

Getting from O'Hare International Airport (ORD) to central Chicago

  • O'Hare International Airport is approximately 40 kilometres from the center of Chicago. With your own car rental or in a cab, the drive is around 35 minutes.

  • It'll take around 54 minutes if you're traveling by public transport.

When to fly to O'Hare International Airport (ORD)

  • August is the most popular month for flights from Windsor International Airport to O'Hare International Airport. To escape the crowds, go to Chicago in February.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Lock in your flights from Windsor International Airport to O'Hare International Airport in this month if this is the kind of weather you like.

  • January sees average temperatures of between -12ºC and 3ºC. Search for cheap flight tickets from YQG to ORD around that time if you want to travel when it's cooler.

More about Chicago

Complete your Chicago trip with hotels and a car rental

  • After you've secured your cheap ticket to O'Hare International Airport, discover the lowest prices and exclusive offers on hotels. You can also compare a range of car rental companies in one place to get the best car rental price for your Chicago getaway.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.