Find Cheap Flights from Calgary to Chicago (YYC - CHI)

Flights overview

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

Cheapest round-trip flights	$219	WestJet Nonstop 4 hr Thu, May 21 — Wed, May 27	The cheapest round-trip flight from Calgary to Chicago is currently $219
Cheapest one-way flight	$135	United Nonstop 4 hr Wed, May 20	The cheapest one-way flight from Calgary to Chicago is currently $135
Last-minute weekend getaway	$310	American Nonstop 4 hr Thu, May 7 — Sun, May 10	The cheapest last-minute weekend getaway from Calgary to Chicago is currently $310
Cheapest business class flights	$728	American Nonstop 4 hr Thu, May 21 — Wed, May 27	The cheapest business class round-trip flight from Calgary to Chicago is currently $728

Fastest flight	3 hr 27 min	The fastest nonstop flight from Calgary to Chicago takes 3 hr 27 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Calgary to Chicago is typically October. The most expensive month to fly is typically July.

October Cheapest	Typical prices: $180–290
July Most expensive	Typical prices: $240–365

Popular airlines from Calgary to Chicago

United

Nonstop

from $296

Typical price: $320–660

7 weekly nonstop flights

YYC - ORD Every day

112 weekly connecting flights

YYC - ORD Every day
American

Nonstop

from $271

Typical price: $305–660

7 weekly nonstop flights

YYC - ORD Every day

59 weekly connecting flights

YYC - ORD Every day
WestJet

Nonstop

from $219

Typical price: $405–810

4 weekly nonstop flights

YYC - ORD Every Mon, Thu, Fri, Sun
Delta

from $231

Typical price: $250–520

152 weekly connecting flights

YYC - MDW, ORD Every day
Air Canada

from $295

Typical price: $260–590

106 weekly connecting flights

YYC - ORD Every day
Alaska

from $508

Typical price: $540–1,100

21 weekly connecting flights

YYC - ORD Every day

Popular airports near Calgary

Calgary International Airport (YYC)

Calgary Canada 16 min 5 mi
Edmonton International Airport (YEG)

Edmonton Canada 2 hr 38 min 157 mi
Lethbridge Airport (YQL)

Lethbridge Canada 2 hr 24 min 112 mi
Medicine Hat Regional Airport (YXH)

Medicine Hat Canada 2 hr 59 min 163 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 Calgary to Chicago

The cheapest flights from Calgary to Chicago are usually in October. Typical ticket prices in October range from $180 to $290.

The cheapest round-trip flight from Calgary to Chicago recently found on Google Flights was with WestJet from $219. The cheapest one-way flight was with United from $135.

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

The cheapest United flight from Calgary to Chicago is $296, flying from May 22 to May 29.
The cheapest American flight from Calgary to Chicago is $271, flying from May 23 to Jun 1.
The cheapest WestJet flight from Calgary to Chicago is $219, flying from May 21 to May 27.
The cheapest Delta flight from Calgary to Chicago is $231, flying from May 21 to May 27.
The cheapest Air Canada flight from Calgary to Chicago is $295, flying from Jul 20 to Jul 27.
The cheapest Alaska flight from Calgary to Chicago is $508, flying from May 24 to Jun 2.

The cheapest round-trip flight from Calgary to Chicago starts at $219 from Thu, May 21 to Wed, May 27. The cheapest one-way flight starts at $135 and departs on Wed, May 20.

3 hr 27 min is the shortest flight time from Calgary 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 Calgary 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 Calgary 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 Calgary to Chicago.

In terms of nonstop flights, United is the most popular. United offers 7 nonstop flights and 112 connecting flights per week. United flies from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Delta is the most popular. Delta offers 152 connecting flights per week. Delta flies from Calgary International Airport (YYC) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Calgary to Chicago are:

American offers 7 nonstop flights and 59 connecting flights per week. American flies from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) .
WestJet offers 4 nonstop flights per week. WestJet flies from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) .
Air Canada offers 106 connecting flights per week. Air Canada flies from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) .
Alaska offers 21 connecting flights per week. Alaska flies from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) .

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

The cheapest round-trip flight from Calgary to Chicago recently found on Google Flights was with WestJet from $219. The cheapest one-way flight was with United from $135.

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

The cheapest United flight from Calgary to Chicago is $296, flying from May 22 to May 29.
The cheapest American flight from Calgary to Chicago is $271, flying from May 23 to Jun 1.
The cheapest WestJet flight from Calgary to Chicago is $219, flying from May 21 to May 27.
The cheapest Delta flight from Calgary to Chicago is $231, flying from May 21 to May 27.
The cheapest Air Canada flight from Calgary to Chicago is $295, flying from Jul 20 to Jul 27.
The cheapest Alaska flight from Calgary to Chicago is $508, flying from May 24 to Jun 2.

American, United and WestJet fly direct from Calgary to Chicago.

There are 7 United direct flights from Calgary to Chicago per week. Flights are available every day.
There are 7 American direct flights from Calgary to Chicago per week. Flights are available every day.
There are 4 WestJet direct flights from Calgary to Chicago per week. Flights are available on Monday, Thursday, Friday and Sunday.

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

The cheapest last-minute deal between Calgary and Chicago at price $310 is offered by American from Thu, May 7 to Sun, May 10.

American, United and WestJet fly direct from Calgary to Chicago.

There are 7 United direct flights from Calgary to Chicago per week. Flights are available every day.
There are 7 American direct flights from Calgary to Chicago per week. Flights are available every day.
There are 4 WestJet direct flights from Calgary to Chicago per week. Flights are available on Monday, Thursday, Friday and Sunday.

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

There are direct flights from Calgary to Chicago on a daily basis.

The cheapest direct (nonstop) round-trip flights between Calgary and Chicago start at $219 from Thu, May 21 to Wed, May 27 with WestJet.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Calgary 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 Calgary and Chicago start at $728 from Thu, May 21 to Wed, May 27 with American.

The cheapest economy class round-trip flights between Calgary and Chicago start at $219 from Thu, May 21 to Wed, May 27.

To book business class trips from Calgary 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 Calgary and Chicago starts at $310 from Thu, May 7 to Sun, May 10 with American.

The cheapest last-minute deal between Calgary and Chicago at price $310 is offered by American from Thu, May 7 to Sun, May 10.

To find last-minute flight deals from Calgary 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.