One Way

Popular Filters

+ 1 more

One Way Price

CAD 241 CAD 800

Duration

3 h 27 m 16 h 0 m

Stops From Calgary

Departure From Calgary

6 AM - 12 PM

CAD 249

12 PM - 6 PM

CAD 241

After 6 PM

CAD 263

Arrival at Chicago

6 AM - 12 PM

CAD 263

12 PM - 6 PM

CAD 241

After 6 PM

CAD 249

Alliances & Airlines

Oneworld

(2)

SkyTeam

(3)

Star Alliance

(8)

Layover Airports

+ 2 more

Layover Duration

42 m 11 h 0 m

Flights From India to Canada

Calgary To Chicago Flights

Book Calgary to Chicago flight tickets at lowest price. Get best deals on your upcoming Calgary to Chicago flights only on MakeMyTrip. Also Book Chicago to Calgary Flights. Currently 16 flights flying from Calgary to Chicago. To save maximum on flight booking click on below Fare Calendar button and choose your dates.Avail Zero Cancellation for flight bookings.


Sorted By:
Departure
Duration
Arrival
Price
United Airlines

CAD 241

Calgary to Chicago , 7 May

United Airlines UA | 1655

12:34

Thu, 7 May 26

Calgary, Canada

03 h 27 m

17:01

Thu, 7 May 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

United Airlines

More Timing Options

CAD 249

Calgary to Chicago , 7 May

United Airlines UA | 1953

13:27

Thu, 7 May 26

Calgary, Canada

02 h 36 m

16:03

Thu, 7 May 26

Denver, United States

BAGGAGE : CHECK INCABIN

Information not available

United Airlines UA | 675

16:45

Thu, 7 May 26

Denver, United States

02 h 39 m

20:24

Thu, 7 May 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

CAD 260

Calgary to Chicago-Midway , 7 May

Delta Air Lines DL | 2492

06:45

Thu, 7 May 26

Terminal I

Calgary, Canada

02 h 45 m

10:30

Thu, 7 May 26

Terminal T1

Minneapolis, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 4750

11:40

Thu, 7 May 26

Terminal T1

Minneapolis, United States

01 h 39 m

13:19

Thu, 7 May 26

Chicago-Midway, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines

CAD 262

Calgary to Chicago , 7 May

American Airlines AA | 4161

13:40

Thu, 7 May 26

Calgary, Canada

03 h 35 m

18:15

Thu, 7 May 26

Terminal T3

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

CAD 263

Calgary to Chicago , 7 May

Air Canada AC | 8144

20:30

Thu, 7 May 26

Calgary, Canada

53 m

21:23

Thu, 7 May 26

Edmonton, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC | 332

01:00

Fri, 8 May 26

Edmonton, Canada

04 h 10 m

07:10

Fri, 8 May 26

Terminal T1

Montreal, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC | 8477

08:40

Fri, 8 May 26

Montreal, Canada

02 h 38 m

10:18

Fri, 8 May 26

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines

CAD 270

Calgary to Chicago , 7 May

American Airlines AA | 2521

06:45

Thu, 7 May 26

Terminal I

Calgary, Canada

03 h 49 m

11:34

Thu, 7 May 26

Dallas/Fort Worth, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines AA | 3287

19:49

Thu, 7 May 26

Terminal 0

Dallas/Fort Worth, United States

02 h 31 m

22:20

Thu, 7 May 26

Terminal T3

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

CAD 286

Calgary to Chicago , 7 May

Air Canada AC | 4412 | Operated By United Airlines

13:27

Thu, 7 May 26

Calgary, Canada

02 h 36 m

16:03

Thu, 7 May 26

Denver, United States

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC | 4509 | Operated By United Airlines

16:45

Thu, 7 May 26

Denver, United States

02 h 39 m

20:24

Thu, 7 May 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Air Canada

CAD 290

Calgary to Chicago , 7 May

Air Canada AC | 4026 | Operated By United Airlines

12:34

Thu, 7 May 26

Calgary, Canada

03 h 27 m

17:01

Thu, 7 May 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

WestJet

CAD 618

Calgary to Chicago , 7 May

WestJet WS | 1610

12:00

Thu, 7 May 26

Calgary, Canada

03 h 40 m

16:40

Thu, 7 May 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

CAD 693

Calgary to Chicago , 7 May

Delta Air Lines DL | 7063 | Operated By WestJet

12:00

Thu, 7 May 26

Calgary, Canada

03 h 40 m

16:40

Thu, 7 May 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Chicago Address

Calgary Address

Calgary International Airport
2000 Airport Rd. N.E.
Calgary
Alberta
Canada
Tel: +1-403-735-1200

Calgary to Chicago Flights Information:-

Looking for Calgary to Chicago Flight? Here’s all you need to know! For convenience and to save time, pick the airport that is closest to your destination. The nearest airport to Chicago is Chicago Midway Intl and the IATA code for the same is CHI.
Currently, there are 5 airlines operating flights between the two destinations and approximately 16 flights take off from Calgary to Chicago every week.

Need information on Calgary to Chicago airfare?

The minimum airfare for a Calgary to Chicago flight would be 241, which may go up to 700 depending on the route, booking time and availability.
It is recommended that you book a round-trip, since it always works out to be more economical.

Flight Details for Calgary to Chicago

If you are looking for Calgary to Chicago flights, there is no dearth of options to choose from. Several reputed airlines currently offer both direct and indirect flights between the two destinations. Some of these are Air Canada, American Airlines, Delta Air Lines, United Airlines, WestJet. Out of these, only 5 airlines operate direct flights. Indirect flights may involve more travel time, but they usually cost lesser than direct flights.

The number of flights operated by each airline is as follows:Air Canada : 3, American Airlines : 3, Delta Air Lines : 3, United Airlines : 3, WestJet : 3

To board the first Calgary to Chicago flight, choose United Airlines, which departs at 06:00 The last flight for this route is Air Canada, departing at 20:30

Chicago Airport Information

Chicago Midway Intl

About Calgary (YYC)

Calgary is one of the liveliest cities of Canada and proves to be a great holiday destinations for those who want to experience something a little different from the typical. This is a city of absolute extremes, because if there is a Heritage Park Historical Village, there is also a TELUS Spark. From the top of the Calgary Tower, tourists can enjoy stunning views of the city and at the Calgary Zoo, they can enjoy being close to animals. Besides, there several festivals held in the city from time to time and also there are numerous museums. Some of the best museums include the Glenbow Museum, Military Museum and Grain Academy Museum. For those who prefer spending their time outdoors, there are opportunities to indulge in fly fishing or skating at the Olympic Oval. Calgary is also the city for food connoisseurs as there are several award winning restaurants here. Nightlife is also remarkable and travellers will never need to hunt for a pub or club as these are present everywhere. Calgary holidays promise to leave one with wonderful memories, and travellers can seek help of MakeMyTrip to book their tickets and accommodation in this beautiful city.

About Chicago (CHI)

Chicago is a dazzling city that captivates visitors with its vibrant atmosphere and stunning architecture. For travelers from Canada, Chicago offers an array of experiences, from world-class museums to picturesque waterfront parks. The city's rich cultural heritage and dynamic arts scene make it a must-visit destination.

Best Time to Visit

The ideal time to visit Chicago is during the spring (April to June) and fall (September to November) when the weather is pleasant, and the city is alive with festivals. Summers can be warm and bustling, while winters are cold and snowy, perfect for those who enjoy winter sports.

Getting There

Chicago is served by two major airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). There are numerous flights to Chicago from Canada, including direct flights from Toronto, Vancouver, and Montreal. Ensure you have a valid passport and check visa requirements before booking your flight. Airlines such as Air Canada and United Airlines offer cheap flights to Chicago, making it accessible for Canadian travelers.

Where to Stay

Chicago boasts a wide range of accommodation options to suit all budgets. For luxury, consider staying in the Magnificent Mile area, home to upscale hotels and designer boutiques. Budget travelers can find affordable options in neighborhoods like Lincoln Park and Wicker Park. The Loop, Chicago's downtown area, is ideal for tourists wanting to be close to major attractions.

Must-See Places & Experiences

Chicago is renowned for its iconic landmarks and cultural institutions. Don't miss:
• The Art Institute of Chicago
• Millennium Park and the famous Cloud Gate sculpture
• Navy Pier, offering entertainment and stunning lake views
• Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium
• The Magnificent Mile for shopping
• Willis Tower Skydeck for breathtaking city views

Local Transportation

Chicago's public transportation system is efficient and easy to navigate. The Chicago Transit Authority (CTA) operates buses and trains that connect the city and suburbs. Taxis and ride-sharing services like Uber and Lyft are readily available. For a scenic option, consider renting a bike and exploring the city's extensive bike paths.

Food & Dining

Chicago's culinary scene is diverse and delicious. Be sure to try local specialties such as deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. The city offers a variety of dining options, from Michelin-starred restaurants to casual eateries. Recommended spots include:
• Lou Malnati's Pizzeria for deep-dish pizza
• Portillo's for Chicago-style hot dogs
• Alinea for an upscale dining experience

Practical Travel Tips

• Currency: The US Dollar (USD)
• Language: English
• Safety: Chicago is generally safe, but be aware of your surroundings and avoid less populated areas at night
• Useful Apps: Download the CTA Transit app for public transport information and OpenTable for restaurant reservations

Start planning your trip and book your Chicago flight today. With so much to offer, Chicago is a city that promises unforgettable experiences for Canadian travelers.

Frequently Asked Questions - Calgary to Chicago Flights

What is the best time to book cheap flight tickets from Calgary to Chicago?

To get cheap flight tickets from Calgary to Chicago, the best time would be to plan your trip during the off season. At that time the flight tickets are usually cheaper than the peak season and the accommodation booking is also available at the affordable price. The other way of booking cheap flight tickets from Calgary (YYC) to Chicago (CHI) is to book atleast 4 weeks in advance before your departure date to get competitive pricing on your tickets even during the peak season.

Is there a way to make flexible departure date bookings for your Calgary to Chicago flight tickets?

Some travel portals like MakeMyTrip offer flexible departure and arrival booking option with certain air carrier when booking from Calgary to Chicago. You can check the flexible booking flight options once you get the results filters based on your search and make the booking accordingly. Please note, some airlines make charge extra for flexible travel dates.

Is passport mandatory to travel from Calgary to Chicago?

When making an international trip, passport is mandatory as it defines your identity to the other nation officials. The VISA norms may differ from country to country, which means some would allow Visa on arrival and others may require you to obtain visa in advance. But the availability of passport is mandatory at the time of departure and arrival as well.

Can I cancel my ticket from Calgary to Chicago without cancellation charges?

To avoid cancellation charges on your air tickets, you need to make a selection at the time of booking for ZERO cancellation. Please note, the zero cancellation facility is chargeable with minimum amount and can help you save a lot at the time sudden cancellations.

Which airlines offer cheapest airfare from Calgary to Chicago?

There is no set pricing for airlines to offer cheap flight fare from Calgary to Chicago. These fares are mostly decided on the basis of algorithms followed by air carriers to final the prizing based on demand. However, some multiple route flights with stop-overs offer cheap flights as compared to direct flight departing from Calgary to Chicago.

How do MakeMyTrip finds the lowest available dare for flights from Calgary to Chicago?

MakeMyTrip is a popular travel portal that also works as a travel search engine that allows you to see best available results for your flight search. Every time you make search for flights to any destination, the MMT algorithm picks all the available air carriers for the route and filter rates basis on the cheapest fare available in their system. At MMT, you can not only search flights on the basis of the fare, but you can also see which flight offers direct route, which has multiple stop-overs, baggage allowance, in-flight meal options, cancellation policy, etc. You can also check available discounts offered by payments partners and air carriers when booking the flight.

Can I find cheap accommodation near to airport when travelling from Calgary to Chicago?

There are several accommodation options available near the Chicago Midway Intl. You can check for both budget friendly and well as five star accommodation near the airport depending on your requirement and budget. These hotels are mostly suitable for business travellers.