$113 Cheap flight deals from Calgary (YYC) to Chicago (CHI)

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This Weekend's Flight Deals from Calgary to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Nov 15 - Mon, Nov 24
YYC
Calgary Intl.
ORD
O'Hare Intl.
$553 Roundtrip, found 2 days ago
$553
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Sat, Nov 15 from Calgary Intl. to O'Hare Intl., returning Mon, Nov 24, priced at $553 found 2 days ago

Airfares from $113 One Way, $162 Round Trip from Calgary to Chicago

Prices starting at $162 for return flights and $113 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Dec 26 - Mon, Jan 5
YYC
Calgary
ORD
Chicago
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Dec 26 from Calgary to Chicago, returning Mon, Jan 5, priced at $162 found 3 days ago
Mon, Dec 22 - Fri, Jan 9
YYC
Calgary
ORD
Chicago
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select WestJet flight, departing Mon, Dec 22 from Calgary to Chicago, returning Fri, Jan 9, priced at $169 found 2 days ago
Thu, Dec 25 - Wed, Jan 7
YYC
Calgary
ORD
Chicago
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, Dec 25 from Calgary to Chicago, returning Wed, Jan 7, priced at $185 found 2 days ago
Mon, Jan 12 - Sun, Feb 1
YYC
Calgary
ORD
Chicago
$245 Roundtrip, found 6 days ago
$245
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Jan 12 from Calgary to Chicago, returning Sun, Feb 1, priced at $245 found 6 days ago
Fri, Nov 14 - Fri, Nov 21
YYC
Calgary
ORD
Chicago
$321 Roundtrip, found 1 day ago
$321
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, Nov 14 from Calgary to Chicago, returning Fri, Nov 21, priced at $321 found 1 day ago

More About Flying To Chicago from Calgary

Route Information for Flights from Calgary to Chicago

Origin Airport IATA Code
YYC
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Travel from Calgary to Chicago

When you’re ready to book your getaway, find huge discounts and savings on flights from Calgary to Chicago on Orbitz.com. Chicago will seem a million miles away from the prairies and foothills of Alberta. Take in a play at the famous Goodman Theater or enjoy some Chicago-style stuffed pizza at one of the city’s many restaurants.

Flying out of Calgary, Alberta

Travelers leaving Calgary, Alberta will fly from Calgary International Airport (YYC), which is located approximately six miles from downtown. The airport offers parking spaces that start at under ten dollars per week. Many travelers choose to use one of several bus routes that serve the airport. This costs eight dollars, and you must have exact change. Alternatively, a taxi from downtown will cost about forty-five dollars. A wide range of bars, shops, and restaurants offer pre-flight drinks, meals, and snacks.

Visiting Chicago, Illinois

Visitors flying into Chicago will arrive at one of two airports: Chicago O’Hare International Airport (eighteen miles from downtown) or Chicago Midway International Airport (twelve miles from downtown). Both airports are served by a variety of affordable public transport options and taxis. Many travelers decide to rent a car from one of several car rental companies. While in Chicago, many visitors are amazed by the variety and quality of the cuisine. With twenty-three Michelin-starred restaurants, the city truly is a culinary destination. A bit of retail therapy on the Magnificent Mile and State Street is also a must. Chicago has a humid continental climate, reaching average high temperatures of 85°F in July, and average low temperatures of 16°F in January. June is the wettest month to visit with just over four inches of precipitation.

Flying to Chicago

Visit Orbitz.com for amazing deals on flights from Calgary to Chicago. You can also find great savings on hotels, car rentals, and more. Booking in advance is a great way to save money, so you’ll have more to spend when visiting the third most populous city in the United States.

Frequently asked questions

What is the shortest flight from Calgary to Chicago?
From Calgary, the thrilling sights and sounds of Chicago are at least 3 hours and 48 minutes away. Choose your favorite seat, or maybe even one with a bit more legroom, and travel to your destination in comfort.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.