Find Cheap Flights from Waterloo to Chicago (YTO - CHI)

Flights overview

Useful information for finding cheap flights from Waterloo to Chicago and booking your next trip

Cheapest round-trip flights	$288	Air Canada 1 stop 15 hr Thu, Jun 4 — Wed, Jun 10	The cheapest round-trip flight from Waterloo to Chicago is currently $288
Cheapest one-way flight	$166	Air Canada 1 stop 15 hr Wed, Jun 3	The cheapest one-way flight from Waterloo to Chicago is currently $166
Last-minute weekend getaway	$692	Air Canada, United 2 stops 11 hr Sat, May 9 — Sun, May 10	The cheapest last-minute weekend getaway from Waterloo to Chicago is currently $692
Cheapest business class flights	$646	Air Canada, United 1 stop 5 hr Thu, Jul 9 — Wed, Jul 15	The cheapest business class round-trip flight from Waterloo to Chicago is currently $646

Fastest flight	4 hr 15 min	The fastest flight with stops from Waterloo to Chicago takes 4 hr 15 min
Nonstop flights	None	There are no direct flights on this route.

When is the cheapest time to fly?

The cheapest month to fly from Waterloo to Chicago is typically October. The most expensive month to fly is typically December.

October Cheapest	Typical prices: $200–485
December Most expensive	Typical prices: $280–490

Popular airlines from Waterloo to Chicago

Air Canada

from $288

Typical price: $225–450

251 weekly connecting flights

YKF - ORD Every day
WestJet

from $1,062

Typical price: $970–1,950

2 weekly connecting flights

YKF - ORD Every Wed, Sun

Popular airports near Waterloo

Toronto Pearson International Airport (YYZ)

Toronto Canada 1 hr 47 mi
Region of Waterloo International Airport (YKF)

Waterloo Canada 21 min 7 mi
Billy Bishop Toronto City Airport (YTZ)

Toronto Canada 1 hr 35 min 57 mi
John C. Munro Hamilton International Airport (YHM)

Hamilton Canada 1 hr 3 min 36 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Waterloo to Chicago

The cheapest flights from Waterloo to Chicago are usually in October. Typical ticket prices in October range from $200 to $485.

The cheapest round-trip flight from Waterloo to Chicago recently found on Google Flights was with Air Canada from $288. The cheapest one-way flight was with Air Canada from $166.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Air Canada flight from Waterloo to Chicago is $288, flying from Jun 4 to Jun 10.
The cheapest WestJet flight from Waterloo to Chicago is $1,062, flying from May 31 to Jun 9.

The cheapest round-trip flight from Waterloo to Chicago starts at $288 from Thu, Jun 4 to Wed, Jun 10. The cheapest one-way flight starts at $166 and departs on Wed, Jun 3.

4 hr 15 min is the shortest flight time from Waterloo to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Waterloo to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Waterloo to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Waterloo to Chicago.

In terms of flights, Air Canada is the most popular. Air Canada offers 251 connecting flights per week. Air Canada flies from Region of Waterloo International Airport (YKF) to Chicago O'Hare International Airport (ORD) .

Another popular airline flying from Waterloo to Chicago is:

WestJet offers 2 connecting flights per week. WestJet flies from Region of Waterloo International Airport (YKF) to Chicago O'Hare International Airport (ORD) .

The number of connecting flights refers to distinct flights with at least one stop between Waterloo and Chicago.

The cheapest round-trip flight from Waterloo to Chicago recently found on Google Flights was with Air Canada from $288. The cheapest one-way flight was with Air Canada from $166.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Air Canada flight from Waterloo to Chicago is $288, flying from Jun 4 to Jun 10.
The cheapest WestJet flight from Waterloo to Chicago is $1,062, flying from May 31 to Jun 9.

No airline flies direct from Waterloo to Chicago.

There are 251 Air Canada connecting flights from Waterloo to Chicago per week. Flights are available every day.
There are 2 WestJet connecting flights from Waterloo to Chicago per week. Flights are available on Wednesday and Sunday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Waterloo and Chicago at price $692 is offered by Air Canada, United from Sat, May 9 to Sun, May 10.

No airline flies direct from Waterloo to Chicago.

There are 251 Air Canada connecting flights from Waterloo to Chicago per week. Flights are available every day.
There are 2 WestJet connecting flights from Waterloo to Chicago per week. Flights are available on Wednesday and Sunday.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are no direct flights from Waterloo to Chicago.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Waterloo to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Waterloo and Chicago start at $646 from Thu, Jul 9 to Wed, Jul 15 with Air Canada, United.

The cheapest economy class round-trip flights between Waterloo and Chicago start at $288 from Thu, Jun 4 to Wed, Jun 10.

To book business class trips from Waterloo to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Waterloo and Chicago starts at $692 from Sat, May 9 to Sun, May 10 with Air Canada, United.

The cheapest last-minute deal between Waterloo and Chicago at price $692 is offered by Air Canada, United from Sat, May 9 to Sun, May 10.

To find last-minute flight deals from Waterloo to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.