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Fares from $179 One Way, $311 Round Trip from Calgary to Chicago

Prices starting at $311 for return flights and $179 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.

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More About Flying To Chicago from Calgary

Route Information for Flights from Calgary to Chicago

Origin Airport IATA CodeYYC
Destination Airport IATA CodeCHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Flights Review

Oct 30, 2019

Very pleased

Jul 29, 2019

Not enough room cuz seats are too close

Oct 19, 2018

Medical problem with a passenger that was handled professionally.

Oct 18, 2018

Keep it up

Sep 6, 2018

long lines at Calgary airport

Jul 20, 2018

Arrived 20 minutes early

Jun 24, 2018

Didn't like the automated boarding announcements and disorganized lineup process. Always frustrating to the rule followers.

Flying from Calgary to Chicago

Calgary International Airport

Finding deals on flights from Calgary, Alberta, doesn't have to be hard. Orbitz.com makes it easy to find fares from several different carriers. Calgary International Airport is the airport that provides international and domestic flight service to Calgary and the surrounding regions. The airport is 11 miles northeast of the center of town. Airlines including Air Canada, British Airways and United Airlines provide service to cities all over the globe, including London, Zurich and Amsterdam. The airport handles more than 12 million passengers a year.

Transportation to Calgary International Airport

Calgary's public transportation system provides service to and from the airport. One of the routes is the Route 300 BRT Airport/City Centre Route. This bus makes limited stops from downtown by way of Centre Street. It operates from 5 a.m. until midnight seven days a week. You can pay with an $8 Calgary Transit boarding pass, or you can pay $8 cash on the bus. If you pay with cash, you need to have exact change. If you take a taxi, you can expect to pay from $40 to $45 if you start from the city center.

Parking Options at the Airport

Short-term parking at the airport is free for the first 30 minutes. After that, it's $6 for every 30 minutes for a daily maximum of $35. There are two long-term parking lots. The daily rates range from $59 to $99 per week depending on the lot you choose.

Dining at the Airport

There are dozens of dining options available at the airport, and they're available day or night. The Great Canadian Bagel in Concourse B is the place to go for fresh coffee and a hearty breakfast. The restaurant is open from first to last flight every day, so it's perfect for an early morning flight. Booking your air ticket through Orbitz.com is a good way to ensure that you're getting great deals on flights from Calgary.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Flights from Calgary to Chicago - Frequently Asked Questions

Are there non-stop flights from Calgary to Chicago?

Two airlines offer direct flights from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.) — United Airlines and American Airlines. They'll get you where you need to go quickly and comfortably.

What is the shortest flight from Calgary to Chicago?

Getting from Calgary, AB (YYC-Calgary Intl.) to Chicago, IL (ORD-O'Hare Intl.) will take you at least 3 hours and 19 minutes. Savor a wine and watch a flick or two — this is your chance to sit back and relax.

What airlines fly from Calgary (and vicinity) to Chicago (and vicinity) most frequently?

There are two airlines offering frequent flights from Calgary, AB Airport (YYC-Calgary Intl.) to Chicago, IL Airport (ORD-OHare Intl.), including United Airlines (UA). Popular with travelers, it operates 68 flights on this route each month. Alternatively, lock in your favorite window (or aisle) seat with American Airlines (AA). You'll have 20 monthly flights between Calgary (and vicinity) and Chicago (and vicinity) to select from with this airline.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

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 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. 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 the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.