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Flight Deals from Chicago to Calgary from $101

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Stops

  • Up to nonstop
    $253
  • Up to 2 stops
    $266
  • Up to 1 stop
    $263

Airlines

  • Air Canada
    $328
  • American Airlines
    $339
  • Delta Air Lines
    $319
  • Porter Airlines
    $589
  • United Airlines
    $253
  • WestJet
    $255

Cabin Class

  • Economy
    $253

Departure Airports

  • Chicago Metropolitan Area
    $253

Arrival Airports

  • Calgary International Airport
    $253

Layover Airports

  • Dallas Fort Worth International Airport
    $386
  • Denver International Airport
    $263
  • Edmonton Airport
    $266
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $319
  • Montreal Trudeau Airport
    $500
  • Ottawa Macdonald-Cartier International Airport
    $366
  • Salt Lake City International Airport
    $359
  • Toronto Pearson Airport
    $266
  • Winnipeg / James Armstrong Richardson International Airport
    $362

Best Price. GUARANTEED.

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EXPRESS DEAL

BUDGET FRIENDLY

You’re guaranteed to get one of these airlines:

DeltaDelta
AlaskaAlaska
UnitedUnited
AmericanAmerican
ORD YYC
Aug 06 - Aug 12 ‧ Economy
$351

Round-trip

United Airlines Logo
United Airlines

05/25/26

CHI
2h 55m
Direct

05/25/26

YYC
United Airlines Logo
United Airlines

06/01/26

YYC
4h 37m
Direct

06/01/26

CHI
$253
WestJet Logo
WestJet

05/27/26

CHI
2h 55m
Direct

05/27/26

YYC
WestJet Logo
WestJet

05/29/26

YYC
4h 40m
Direct

05/29/26

CHI
$255
United Airlines Logo
United Airlines

06/06/26

CHI
15h 48m
DEN

06/06/26

YYC
United Airlines Logo
United Airlines

06/08/26

YYC
4h 37m
Direct

06/08/26

CHI
$263
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
United Airlines Logo
United Airlines

05/25/26

CHI
15h 48m
DEN

05/25/26

YYC
United Airlines Logo
United Airlines

06/02/26

YYC
4h 37m
Direct

06/02/26

CHI
$263
United Airlines Logo
United Airlines

05/25/26

CHI
2h 55m
Direct

05/25/26

YYC
United Airlines Logo
United Airlines

06/01/26

YYC
12h 35m
YEG
YYZ

06/02/26

CHI
$266
United Airlines Logo
United Airlines

06/02/26

CHI
15h 48m
DEN

06/02/26

YYC
United Airlines Logo
United Airlines

06/06/26

YYC
14h 30m
DEN

06/06/26

CHI
$278
Delta Air Lines Logo
Delta Air Lines

06/11/26

CHI
8h 11m
MSP

06/11/26

YYC
Delta Air Lines Logo
Delta Air Lines

06/16/26

YYC
6h 24m
MSP

06/16/26

CHI
$319
Air Canada Logo
Air Canada

05/25/26

CHI
2h 55m
Direct

05/25/26

YYC
Air Canada Logo
Air Canada

05/30/26

YYC
7h 31m
YEG

05/30/26

CHI
$328
Air Canada Logo
Air Canada

05/25/26

CHI
2h 55m
Direct

05/25/26

YYC
Air Canada Logo
Air Canada

05/27/26

YYC
4h 37m
Direct

05/27/26

CHI
$328
Air Canada Logo
Air Canada

06/03/26

CHI
5h 51m
YEG

06/03/26

YYC
Air Canada Logo
Air Canada

06/08/26

YYC
4h 37m
Direct

06/08/26

CHI
$333
American Airlines Logo
American Airlines

05/26/26

CHI
2h 48m
Direct

05/26/26

YYC
American Airlines Logo
American Airlines

06/01/26

YYC
4h 30m
Direct

06/01/26

CHI
$339
American Airlines Logo
American Airlines

06/01/26

CHI
2h 48m
Direct

06/01/26

YYC
American Airlines Logo
American Airlines

06/03/26

YYC
4h 45m
Direct

06/03/26

CHI
$339
American Airlines Logo
American Airlines

05/25/26

CHI
2h 48m
Direct

05/25/26

YYC
American Airlines Logo
American Airlines

06/01/26

YYC
4h 30m
Direct

06/01/26

CHI
$339
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Air Canada Logo
Air Canada

05/25/26

CHI
2h 55m
Direct

05/25/26

YYC
Air Canada Logo
Air Canada

05/30/26

YYC
14h 51m
YEG
YYZ

05/31/26

CHI
$341
Air Canada Logo
Air Canada

05/27/26

CHI
5h 51m
YEG

05/27/26

YYC
Air Canada Logo
Air Canada

06/01/26

YYC
13h 20m
YEG
YYZ

06/02/26

CHI
$347
Delta Air Lines Logo
Delta Air Lines

06/01/26

CHI
8h
MSP

06/01/26

YYC
Delta Air Lines Logo
Delta Air Lines

06/03/26

YYC
11h 5m
SLC

06/03/26

CHI
$359
Air Canada Logo
Air Canada

06/05/26

CHI
12h 33m
YWG

06/06/26

YYC
Air Canada Logo
Air Canada

06/10/26

YYC
7h 31m
YEG

06/10/26

CHI
$362
Air Canada Logo
Air Canada

05/29/26

CHI
10h 10m
YOW

05/29/26

YYC
Air Canada Logo
Air Canada

06/08/26

YYC
4h 37m
Direct

06/08/26

CHI
$366
Air Canada Logo
Air Canada

05/30/26

CHI
10h 10m
YOW

05/30/26

YYC
Air Canada Logo
Air Canada

06/06/26

YYC
7h 31m
YEG

06/06/26

CHI
$366
Air Canada Logo
Air Canada

05/30/26

CHI
10h 10m
YOW

05/30/26

YYC
Air Canada Logo
Air Canada

06/03/26

YYC
4h 37m
Direct

06/03/26

CHI
$366
WestJet Logo
WestJet

05/29/26

CHI
2h 55m
Direct

05/29/26

YYC
WestJet Logo
WestJet

06/02/26

YYC
4h 40m
Direct

06/02/26

CHI
$369
Delta Air Lines Logo
Delta Air Lines

06/08/26

CHI
8h 11m
MSP

06/08/26

YYC
Delta Air Lines Logo
Delta Air Lines

06/16/26

YYC
6h 24m
MSP

06/16/26

CHI
$379
Delta Air Lines Logo
Delta Air Lines

05/27/26

CHI
8h
MSP

05/27/26

YYC
Delta Air Lines Logo
Delta Air Lines

05/29/26

YYC
11h 5m
SLC

05/29/26

CHI
$380
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
American Airlines Logo
American Airlines

06/06/26

CHI
15h 43m
DFW

06/06/26

YYC
American Airlines Logo
American Airlines

06/11/26

YYC
4h 30m
Direct

06/11/26

CHI
$386
Delta Air Lines Logo
Delta Air Lines

05/27/26

CHI
2h 55m
Direct

05/27/26

YYC
Delta Air Lines Logo
Delta Air Lines

05/29/26

YYC
11h 5m
SLC

05/29/26

CHI
$414
WestJet Logo
WestJet

05/25/26

CHI
2h 55m
Direct

05/25/26

YYC
WestJet Logo
WestJet

05/29/26

YYC
4h 40m
Direct

05/29/26

CHI
$416
American Airlines Logo
American Airlines

05/29/26

CHI
2h 48m
Direct

05/29/26

YYC
American Airlines Logo
American Airlines

06/06/26

YYC
11h 26m
DFW

06/06/26

CHI
$429
American Airlines Logo
American Airlines

05/27/26

CHI
2h 48m
Direct

05/27/26

YYC
American Airlines Logo
American Airlines

05/29/26

YYC
10h 47m
DFW

05/29/26

CHI
$429
Air Canada Logo
Air Canada

05/29/26

CHI
7h 14m
YUL

05/29/26

YYC
Air Canada Logo
Air Canada

06/06/26

YYC
12h 35m
YEG
YYZ

06/07/26

CHI
$500
Porter Airlines Logo
Porter Airlines

06/04/26

CHI
7h 36m
YYZ

06/04/26

YYC
Porter Airlines Logo
Porter Airlines

06/09/26

YYC
9h 15m
YYZ

06/09/26

CHI
$589

Top Deals on flights from Chicago to Calgary

Chicago, US (CHI) - Calgary, CA (YYC)

United Airlines Logo
United Airlines

May 25

CHI
2h 55m
Direct

May 25

YYC

as low as

$101

Chicago, US (CHI) - Calgary, CA (YYC)

WestJet Logo
WestJet

May 27

CHI
2h 55m
Direct

May 27

YYC

as low as

$102

Chicago, US (CHI) - Calgary, CA (YYC)

Air Canada Logo
Air Canada

May 12

CHI
7h 14m
YUL

May 12

YYC

as low as

$110

Chicago, US (CHI) - Calgary, CA (YYC)

United Airlines Logo
United Airlines

Jun 6

CHI
15h 48m
DEN

Jun 6

YYC

as low as

$111

Chicago, US (CHI) - Calgary, CA (YYC)

American Airlines Logo
American Airlines

Jun 8

CHI
2h 48m
Direct

Jun 8

YYC

as low as

$144

Chicago, US (CHI) - Calgary, CA (YYC)

Air Canada Logo
Air Canada

Jun 6

CHI
5h 51m
YEG

Jun 6

YYC

as low as

$144

Chicago, US (CHI) - Calgary, CA (YYC)

American Airlines Logo
American Airlines

Jun 6

CHI
15h 43m
DFW

Jun 6

YYC

as low as

$154

Chicago, US (CHI) - Calgary, CA (YYC)

Air Canada Logo
Air Canada

Jun 5

CHI
12h 33m
YWG

Jun 6

YYC

as low as

$173

Chicago, US (CHI) - Calgary, CA (YYC)

Air Canada Logo
Air Canada

May 25

CHI
12h 53m
YYZ

May 26

YYC

as low as

$176

Chicago, US (CHI) - Calgary, CA (YYC)

Delta Air Lines Logo
Delta Air Lines

Jun 4

CHI
8h
MSP

Jun 4

YYC

as low as

$213

Chicago, US (CHI) - Calgary, CA (YYC)

Delta Air Lines Logo
Delta Air Lines

Jun 4

CHI
7h 10m
MSP
YEG

Jun 4

YYC

as low as

$219

Chicago, US (CHI) - Calgary, CA (YYC)

Alaska Airlines Logo
Alaska Airlines

May 12

CHI
13h 53m
SEA

May 13

YYC

as low as

$268

Good to Know

Essential information to help you plan your flight from Chicago to Calgary

Cheapest Flight

$101

The lowest price we found in the last two weeks, departing May 25 and returning May 25

Airline UA2h 55m ‧ economy

Fastest Flights

$339

The fastest flight that we found in the last two weeks, departing May 26 and returning Jun 1

Airline AA2h 48m ‧ economy

Cheapest Flight Round-trip

$253

Cheapest price found in the last 14 days, departing May 25 and returning Jun 1

Airline UA2h 55m ‧ economy

Cheapest Flight One-way

$101

Cheapest price found in the last 14 days, departing May 25

Airline UA2h 55m ‧ economy

Cheapest Layover airport

$176

The cheapest layover airport to Calgary is currently $176

Airline AC1 stop ‧ 12h 53m ‧ economy

Best Arrival airport

$101

The best arrival airport to Calgary is currently $101

Airline UA2h 55m ‧ economy

Best Departure airport

$101

The best departure airport to Calgary is currently $101

Airline UA2h 55m ‧ economy

Cheapest Airline

$101

The cheapest airline to Calgary is currently $101

Airline UA2h 55m ‧ economy

Fly from Chicago to Calgary when prices are lower in late October and avoid peak costs from late February to early April.

When planning your flight from Chicago to Calgary, you'll find that the highest prices typically occur from late February to early April, peaking around mid-March with costs reaching over $600. The low price period is mainly in late October, where prices can drop to around $250. Overall, the high season extends from late February to early June, while the low season spans late September to early November. Expect a significant price difference of nearly $400 between these seasons, making it crucial to book during the leaner months for savings.

Book your flight to Calgary at least 54 days before departure for the best prices; avoid waiting until 10 days prior to departure as prices increase sharply.

To ensure you secure the best deal for your flight from Chicago to Calgary, it's advisable to book approximately 54 days prior to your departure, when prices are typically around $339. Prices remain affordable if you purchase between 163-153 and 110-78 days out, but be wary if you wait until closer to your departure date, especially within 10 days, as prices can surge from $421 to $514. Waiting much longer can result in significantly higher costs, making it imperative to buy early to avoid overpaying.

Frequently Asked Questions

What is the typical flight duration from Chicago to Calgary?

A direct flight from Chicago to Calgary typically lasts between 3 to 4 hours, although flight times may vary depending on weather conditions and the specific route taken. Travelers can expect a relatively short journey with minimal layovers when booking direct flights. It’s advisable to check with your airline for updates as departures can sometimes include slight delays. Planning ahead and arriving early at CHI can help secure a smooth transition once you reach YYC.

Are there any direct flights from Chicago to Calgary?

Yes, there are direct flights available from Chicago to Calgary. Airlines such as Air Canada and WestJet often offer non-stop services that shorten travel time considerably compared to connecting flights. Although schedules may vary seasonally, these direct options typically provide a quicker and more convenient travel experience. It is recommended to check multiple booking platforms and compare fares, as prices can range from moderate to premium depending on the time of year and how far in advance your ticket is purchased.

What are the best transportation options from Calgary airport to downtown?

Travelers arriving at Calgary’s international airport have several efficient transportation options to reach downtown. A popular choice is the airport shuttle service, which typically costs between $15 to $30 per person and takes about 20 to 30 minutes, depending on traffic. Taxis and rideshare services are also available, often costing between $35 to $60 for a trip. For an eco-friendly option, consider the C-Train where connections serve several downtown stops, offering convenience and affordability.

What are the must-see attractions in Calgary for travelers arriving from Chicago?

Visitors should not miss iconic attractions such as the Calgary Tower for panoramic city views and the historic Heritage Park for a taste of the region’s past. Additionally, the Glenbow Museum offers extensive exhibits on art and local history. For a unique cultural experience, consider exploring the vibrant Stephen Avenue Walk. Each site provides rich insights into Calgary’s history and dynamic modern culture, ensuring travelers from Chicago enjoy a memorable blend of sightseeing and learning about a city known for its Western charm.

Which local dishes should travelers from Chicago try when visiting Calgary?

Travelers are encouraged to savor local specialties such as Alberta beef steaks, bison burgers, and regional seafood dishes that highlight the freshest ingredients. Local restaurants also offer innovative takes on comfort food, blending international influences with Canadian flavors. In addition, consider sampling artisanal cheeses and craft beers from nearby microbreweries. For a true taste of the local culinary scene, seek out establishments that emphasize farm-to-table practices, ensuring a meal that’s not only delicious but also reflective of Calgary’s vibrant food culture.

What are the best family-friendly activities in Calgary for visitors from Chicago?

Families will find plenty to do in Calgary, including a visit to the Calgary Zoo, which offers interactive exhibits and educational programs. The TELUS Spark Science Centre provides hands-on learning experiences for children of all ages. Additionally, outdoor activities in parks and along the Bow River pathway can be both fun and educational. Seasonal attractions, such as local fairs and festivals, provide special family events. Each activity is designed to engage all ages, ensuring a diverse array of experiences that cater specifically to families looking for enjoyable daytime and evening entertainment.

Are there any seasonal events in Calgary that travelers from Chicago should not miss?

Yes, Calgary hosts several seasonal events that are a must-see. The Calgary Stampede in July is the most famous, offering rodeos, exhibitions, and live music that capture the spirit of the West. Winter festivals and holiday markets add a festive charm during colder months, while spring and summer bring a variety of outdoor food and cultural festivals. Check the event calendars ahead of time as ticket prices range from free entry to moderate fees, ensuring travelers can plan to enjoy dynamic, season-specific experiences that showcase local traditions.

What are the most affordable dining options in Calgary for travelers from Chicago?

Calgary offers a range of affordable dining options that include casual diners, local bakeries, and food trucks serving quick yet delicious meals. Prices typically range from $10 to $20 per meal, making it accessible for diverse budgets. Neighborhood cafes and ethnic eateries also provide hearty portions and unique flavors. Additionally, many fast-casual restaurants offer combo deals and lunch specials that are both tasty and economical. Exploring local districts like Inglewood or Beltline might unveil some hidden gems where you can enjoy authentic dishes without the high price tag.

What are the best car rental options in Calgary for travelers from Chicago?

Car rental services at Calgary International Airport include well-known agencies such as Enterprise, Budget, and Avis, making it convenient for visitors. Daily rates typically range from $50 to $100, depending on the vehicle type and rental duration. Online bookings often provide discounts and special deals. Renting a car offers flexibility for exploring neighboring attractions and scenic routes beyond the city center. Before renting, compare options, check for any additional fees, and review insurance requirements to ensure a seamless and cost-effective travel experience.

What are the customs requirements for travelers flying from Chicago to Calgary?

Travelers flying from Chicago to Calgary must comply with Canadian customs and immigration procedures. A valid passport is required, and some travelers might need a visa or an Electronic Travel Authorization (eTA) depending on their nationality. It is advisable to complete any customs declaration forms provided during the flight. Additionally, be aware of restrictions on food, alcohol, and other items. To streamline your process upon arrival, ensure that all documentation is organized and comply with Canadian customs regulations, which can help prevent delays at border control.

Is there a specific time of year when Calgary is best visited by travelers from Chicago?

While Calgary boasts attractions year-round, many travelers prefer visiting during late spring to early summer for comfortable weather and vibrant outdoor events. The warm season, particularly around July during the Calgary Stampede, offers a dynamic blend of cultural festivities and outdoor activities. Alternatively, visiting in the fall when the scenery is picturesque and festivals continue can be equally enjoyable. Assessing your interests, such as festivals, outdoor adventures, or milder weather, will help narrow down the ideal window, ensuring an immersive and enjoyable experience during your trip.

What unique cultural attractions in Calgary should travelers from Chicago explore?

Unique cultural attractions include the Glenbow Museum, which highlights art and historical artifacts, and Studio Bell, home of the National Music Centre, providing interactive exhibits on Canadian music history. Additionally, local Indigenous cultural centers offer rich storytelling and art displays that showcase the region’s heritage. These venues provide depth to your travel experience, offering insights into local traditions and creative expressions. Booking guided tours or interactive workshops at these sites can further enhance your understanding of Calgary’s diverse cultural landscape and provide memorable, hands-on experiences.

Are there any pet-friendly services available at Calgary airport for travelers from Chicago?

Yes, Calgary International Airport offers pet-friendly services that cater to travelers with animals. The facility features designated pet relief areas and, in some cases, pet lounges to ensure comfort during layovers. It is recommended to inform your airline about traveling with a pet, as there are specific guidelines and fees that may range from $50 to $100 depending on size and carrier type. Planning ahead by reviewing the airport’s pet policies and packing essentials like a pet carrier and food will ensure a smoother experience when traveling with your furry companion.

What are the top outdoor activities in Calgary for travelers arriving from Chicago?

Outdoor enthusiasts will enjoy activities such as biking along the Bow River Pathway, hiking in nearby areas like the Canada Olympic Park, and exploring scenic parks throughout the city. These activities generally cater to various fitness levels and can range from short walks to multi-hour hikes. Additionally, kayaking, bird watching, and even winter sports during colder months provide a diverse set of experiences. Rental equipment is available at local shops with fees typically ranging from $20 to $50 per hour, ensuring you can fully enjoy Calgary’s vibrant outdoor lifestyle.

What are the unique airport amenities in Calgary for travelers arriving from Chicago?

Calgary International Airport offers several unique amenities designed to enhance the traveler experience. These include comfortable lounges, free Wi-Fi throughout the terminal, and an array of dining and retail options that cater to diverse tastes. There are dedicated pet relief areas and even quiet zones for relaxation before your onward journey. For business travelers, meeting rooms and charging stations are available, typically at no extra charge. These amenities ensure a pleasant and productive transit experience, making the time spent at YYC both convenient and comfortable upon arrival.

Flights to Calgary