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	$210	American Nonstop 4 hr Thu, Jan 15 — Wed, Jan 21	The cheapest round-trip flight from Calgary to Chicago is currently $210
Cheapest one-way flight	$129	American Nonstop 4 hr Wed, Oct 22	The cheapest one-way flight from Calgary to Chicago is currently $129
Cheapest nonstop flights	$210	American Nonstop 4 hr Thu, Oct 23 — Wed, Oct 29	The cheapest nonstop round-trip flight from Calgary to Chicago is currently $210
Last-minute weekend getaway	$164	Air Canada 1 stop 8 hr Sat, Oct 25 — Sun, Oct 26	The cheapest last-minute weekend getaway from Calgary to Chicago is currently $164
Cheapest business class flights	$619	Delta 1 stop 6 hr Thu, Jan 15 — Wed, Jan 21	The cheapest business class round-trip flight from Calgary to Chicago is currently $619

Fastest flight	3 hr 25 min	The fastest nonstop flight from Calgary to Chicago takes 3 hr 25 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 May. The most expensive month to fly is typically December.

May Cheapest	Typical prices: $180–255
December Most expensive	Typical prices: $250–620

Popular airlines from Calgary to Chicago

United

Nonstop

from $210

Typical price: $300–680

7 weekly nonstop flights

YYC - ORD Every day

111 weekly connecting flights

YYC - ORD Every day
American

Nonstop

from $210

Typical price: $305–660

7 weekly nonstop flights

YYC - ORD Every day

54 weekly connecting flights

YYC - ORD Every day
WestJet

Nonstop

from $233

Typical price: $365–720

5 weekly nonstop flights

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

from $222

Typical price: $230–540

167 weekly connecting flights

YYC - MDW, ORD Every day
Air Canada

from $217

Typical price: $225–550

119 weekly connecting flights

YYC - ORD Every day
Alaska

from $408

Typical price: $500–960

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 37 min 157 mi
Lethbridge Airport (YQL)

Lethbridge Canada 2 hr 23 min 112 mi
Medicine Hat Regional Airport (YXH)

Medicine Hat Canada 2 hr 56 min 163 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 39 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 37 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 57 min 165 mi

Frequently asked questions about flying from Calgary to Chicago

When are the cheapest days to fly from Calgary to Chicago?

The cheapest flights from Calgary to Chicago are usually in May. Typical ticket prices in May range from $180 to $255.

Which airlines provide the cheapest flights from Calgary to Chicago?

The cheapest round-trip flight from Calgary to Chicago recently found on Google Flights was with American from $210. The cheapest one-way flight was with American from $129.

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

The cheapest United flight from Calgary to Chicago is $210, flying from Jan 17 to Jan 23.
The cheapest American flight from Calgary to Chicago is $210, flying from Oct 23 to Oct 29.
The cheapest WestJet flight from Calgary to Chicago is $233, flying from Dec 5 to Dec 12.
The cheapest Delta flight from Calgary to Chicago is $222, flying from Nov 13 to Nov 19.
The cheapest Air Canada flight from Calgary to Chicago is $217, flying from Jan 12 to Jan 20.
The cheapest Alaska flight from Calgary to Chicago is $408, flying from Jan 15 to Jan 21.

What are the cheapest flights from Calgary to Chicago?

The cheapest round-trip flight from Calgary to Chicago starts at $210 from Thu, Jan 15 to Wed, Jan 21. The cheapest one-way flight starts at $129 and departs on Wed, Oct 22.

How long does it take to fly from Calgary to Chicago?

3 hr 25 min is the shortest flight time from Calgary to Chicago.

When should you fly to Chicago, United States?

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.

How do I find cheap dates to fly from Calgary to Chicago?

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 is the best airline to fly from Calgary to Chicago?

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 111 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 167 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 54 connecting flights per week. American flies from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) .
WestJet offers 5 nonstop flights per week. WestJet flies from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) .
Air Canada offers 119 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.

Which airlines provide the cheapest flights from Calgary to Chicago?

The cheapest round-trip flight from Calgary to Chicago recently found on Google Flights was with American from $210. The cheapest one-way flight was with American from $129.

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

The cheapest United flight from Calgary to Chicago is $210, flying from Jan 17 to Jan 23.
The cheapest American flight from Calgary to Chicago is $210, flying from Oct 23 to Oct 29.
The cheapest WestJet flight from Calgary to Chicago is $233, flying from Dec 5 to Dec 12.
The cheapest Delta flight from Calgary to Chicago is $222, flying from Nov 13 to Nov 19.
The cheapest Air Canada flight from Calgary to Chicago is $217, flying from Jan 12 to Jan 20.
The cheapest Alaska flight from Calgary to Chicago is $408, flying from Jan 15 to Jan 21.

Which airlines have direct flights from Calgary to Chicago?

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 5 WestJet direct flights from Calgary to Chicago per week. Flights are available on Monday, Thursday, Friday, Saturday and Sunday.

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

Which airline provides the cheapest last-minute getaway flight from Calgary to Chicago?

The cheapest last-minute deal between Calgary and Chicago at price $164 is offered by Air Canada from Sat, Oct 25 to Sun, Oct 26.

Which airlines have direct flights from Calgary to Chicago?

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 5 WestJet direct flights from Calgary to Chicago per week. Flights are available on Monday, Thursday, Friday, Saturday and Sunday.

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

When are direct flights from Calgary to Chicago available?

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

What are the cheapest direct flights from Calgary to Chicago?

The cheapest direct (nonstop) round-trip flights between Calgary and Chicago start at $210 from Thu, Oct 23 to Wed, Oct 29 with American.

How can I find nonstop flights from Calgary to Chicago?

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.

What are the cheapest business class flights from Calgary to Chicago?

The cheapest business class round-trip flights between Calgary and Chicago start at $619 from Thu, Jan 15 to Wed, Jan 21 with Delta.

What are the cheapest economy class flights from Calgary to Chicago?

The cheapest economy class round-trip flights between Calgary and Chicago start at $210 from Thu, Jan 15 to Wed, Jan 21.

How can I book business class trips from Calgary to Chicago?

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.

Are there any last-minute deals from Calgary to Chicago next weekend?

The best last-minute getaway deal for the next weekend between Calgary and Chicago starts at $164 from Sat, Oct 25 to Sun, Oct 26 with Air Canada.

Which airline provides the cheapest last-minute getaway flight from Calgary to Chicago?

The cheapest last-minute deal between Calgary and Chicago at price $164 is offered by Air Canada from Sat, Oct 25 to Sun, Oct 26.

How can I find last-minute flight deals from Calgary to Chicago?

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.