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Flight Deals from Calgary to Chicago O Hare Airport from $116

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Stops

  • Nonstop
    from $206
  • Up to 1 stop
    $214
  • Up to 2 stops
    $495

Airlines

  • Aeromexico
    $470
  • Air Canada
    $216
  • Alaska Airlines
    $448
  • American Airlines
    $206
  • Delta Air Lines
    $214
  • United Airlines
    $240
  • WestJet
    $215

Cabin Class

  • Economy
    $206

Departure Airports

  • Calgary International Airport
    $206

Arrival Airports

  • Chicago O Hare Airport
    $206

Layover Airports

  • Dallas Fort Worth International Airport
    $300
  • Denver International Airport
    $240
  • Edmonton Airport
    $379
  • Licenciado Benito Juarez International Airport
    $470
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $270
  • Montreal Trudeau Airport
    $233
  • Salt Lake City International Airport
    $214
  • Seattle Tacoma International Airport
    $448
  • Toronto Pearson Airport
    $216

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On average save $240 per traveler
American Airlines Logo
American Airlines

08/06/25

YYC
4h 25m
Direct

08/06/25

ORD
American Airlines Logo
American Airlines

08/20/25

ORD
2h 55m
Direct

08/20/25

YYC
$206
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

08/12/25

YYC
10h 50m
SLC

08/12/25

ORD
Delta Air Lines Logo
Delta Air Lines

08/26/25

ORD
9h 8m
SLC

08/26/25

YYC
$214
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

08/12/25

YYC
4h 29m
Direct

08/12/25

ORD
WestJet Logo
WestJet

09/03/25

ORD
2h 49m
Direct

09/03/25

YYC
$215
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

08/12/25

YYC
9h 4m
YYZ

08/12/25

ORD
Air Canada Logo
Air Canada

09/03/25

ORD
7h 27m
YYZ

09/03/25

YYC
$216
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

08/12/25

YYC
4h 25m
Direct

08/12/25

ORD
American Airlines Logo
American Airlines

08/26/25

ORD
2h 55m
Direct

08/26/25

YYC
$217
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

07/24/25

YYC
4h 25m
Direct

07/24/25

ORD
American Airlines Logo
American Airlines

08/07/25

ORD
2h 55m
Direct

08/07/25

YYC
$222
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

08/19/25

YYC
10h 18m
YUL

08/19/25

ORD
Air Canada Logo
Air Canada

09/02/25

ORD
9h 17m
YYZ

09/02/25

YYC
$233
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

08/20/25

YYC
10h 18m
YUL

08/20/25

ORD
Air Canada Logo
Air Canada

09/03/25

ORD
7h 31m
YUL

09/03/25

YYC
$236
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

08/19/25

YYC
6h 54m
DEN

08/19/25

ORD
United Airlines Logo
United Airlines

09/02/25

ORD
9h 17m
YYZ

09/02/25

YYC
$240
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

08/20/25

YYC
4h 29m
Direct

08/20/25

ORD
WestJet Logo
WestJet

09/03/25

ORD
2h 49m
Direct

09/03/25

YYC
$248
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

07/22/25

YYC
4h 29m
Direct

07/22/25

ORD
WestJet Logo
WestJet

08/13/25

ORD
2h 49m
Direct

08/13/25

YYC
$263
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

08/19/25

YYC
10h 15m
MSP

08/19/25

ORD
Delta Air Lines Logo
Delta Air Lines

09/02/25

ORD
8h 28m
MSP

09/02/25

YYC
$270
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

08/12/25

YYC
8h 2m
DFW

08/12/25

ORD
American Airlines Logo
American Airlines

08/26/25

ORD
2h 55m
Direct

08/26/25

YYC
$300
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

08/06/25

YYC
8h 2m
DFW

08/06/25

ORD
American Airlines Logo
American Airlines

08/20/25

ORD
2h 55m
Direct

08/20/25

YYC
$307
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

08/19/25

YYC
4h 25m
Direct

08/19/25

ORD
American Airlines Logo
American Airlines

09/02/25

ORD
8h 32m
DFW

09/02/25

YYC
$309
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

08/12/25

YYC
4h 29m
Direct

08/12/25

ORD
Delta Air Lines Logo
Delta Air Lines

08/26/25

ORD
9h 8m
SLC

08/26/25

YYC
$310
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

08/06/25

YYC
9h 35m
SLC

08/06/25

ORD
Delta Air Lines Logo
Delta Air Lines

08/20/25

ORD
8h 28m
MSP

08/20/25

YYC
$312
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

08/19/25

YYC
6h 54m
DEN

08/19/25

ORD
United Airlines Logo
United Airlines

09/02/25

ORD
2h 45m
Direct

09/02/25

YYC
$375
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

08/12/25

YYC
4h 29m
Direct

08/12/25

ORD
WestJet Logo
WestJet

09/03/25

ORD
5h
YEG

09/03/25

YYC
$379
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

08/07/25

YYC
4h 31m
Direct

08/07/25

ORD
United Airlines Logo
United Airlines

08/21/25

ORD
7h 28m
YUL

08/21/25

YYC
$387
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

08/11/25

YYC
4h 29m
Direct

08/11/25

ORD
WestJet Logo
WestJet

09/03/25

ORD
5h
YEG

09/03/25

YYC
$396
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

08/20/25

YYC
4h 29m
Direct

08/20/25

ORD
WestJet Logo
WestJet

09/03/25

ORD
5h
YEG

09/03/25

YYC
$396
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

08/06/25

YYC
8h 50m
DEN

08/06/25

ORD
United Airlines Logo
United Airlines

08/20/25

ORD
6h 35m
YYZ

08/21/25

YYC
$409
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

08/12/25

YYC
10h 40m
SEA

08/13/25

ORD
Alaska Airlines Logo
Alaska Airlines

09/03/25

ORD
2h 49m
Direct

09/03/25

YYC
$448
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

08/11/25

YYC
10h 40m
SEA

08/12/25

ORD
Alaska Airlines Logo
Alaska Airlines

08/16/25

ORD
8h 41m
SEA

08/16/25

YYC
$457
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

08/11/25

YYC
10h 40m
SEA

08/12/25

ORD
Alaska Airlines Logo
Alaska Airlines

09/03/25

ORD
2h 49m
Direct

09/03/25

YYC
$464
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

08/08/25

YYC
15h 9m
YEG

08/09/25

ORD
Aeromexico Logo
Aeromexico

09/03/25

ORD
13h 31m
MEX

09/04/25

YYC
$470
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

08/10/25

YYC
4h 29m
Direct

08/10/25

ORD
Aeromexico Logo
Aeromexico

09/03/25

ORD
13h 31m
MEX

09/04/25

YYC
$470
Free cancellation within 83 hours of booking
Aeromexico Logo
Aeromexico

08/11/25

YYC
18h 35m
MEX

08/12/25

ORD
Aeromexico Logo
Aeromexico

09/03/25

ORD
2h 49m
Direct

09/03/25

YYC
$470
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

07/29/25

YYC
13h 59m
YUL
YYZ

07/29/25

ORD
Air Canada Logo
Air Canada

08/20/25

ORD
6h 35m
YYZ

08/21/25

YYC
$495
Free cancellation within 83 hours of booking

Top Deals on flights from Calgary to Chicago O Hare Airport

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

Air Canada Logo
Air Canada

Jun 11

YYC
4h 33m
Direct

Jun 11

ORD

as low as

$116

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

American Airlines Logo
American Airlines

Jun 11

YYC
4h 25m
Direct

Jun 11

ORD

as low as

$116

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

United Airlines Logo
United Airlines

May 28

YYC
4h 33m
Direct

May 28

ORD

as low as

$116

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

Air Canada Logo
Air Canada

May 15

YYC
8h 38m
YWG

May 15

ORD

as low as

$122

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

Air Canada Logo
Air Canada

Jun 3

YYC
8h 57m
YUL

Jun 3

ORD

as low as

$122

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

WestJet Logo
WestJet

Jun 11

YYC
4h 29m
Direct

Jun 11

ORD

as low as

$127

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

Air Canada Logo
Air Canada

May 18

YYC
9h 5m
YYZ

May 18

ORD

as low as

$128

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

United Airlines Logo
United Airlines

May 23

YYC
14h 11m
DEN

May 24

ORD

as low as

$132

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

Delta Air Lines Logo
Delta Air Lines

Jun 11

YYC
4h 29m
Direct

Jun 11

ORD

as low as

$172

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

Delta Air Lines Logo
Delta Air Lines

May 28

YYC
11h 54m
SEA

May 28

ORD

as low as

$187

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

Alaska Airlines Logo
Alaska Airlines

Jun 4

YYC
11h 18m
SEA

Jun 5

ORD

as low as

$215

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

American Airlines Logo
American Airlines

May 19

YYC
11h 11m
DFW

May 19

ORD

as low as

$222

Frequently Asked Questions

What is the typical flight duration from Calgary to Chicago O Hare Airport?
The flight from Calgary to Chicago O’Hare generally takes between 3 to 4 hours. This duration can vary slightly based on the specific route and weather conditions. Direct flights usually adhere closely to this timeframe, whereas flights with connections might extend your overall travel time. It’s advisable to check with your airline for real-time updates before departure. Both Calgary and Chicago O’Hare are well-equipped for efficient travel, ensuring that even minor delays are communicated promptly to keep you informed.
Are there any direct flights from Calgary to Chicago O Hare Airport?
Yes, direct flights are available from Calgary to Chicago O’Hare. Airlines like Air Canada and United Airlines have schedules that often include nonstop routes between these hubs. It’s important to check current flight schedules as availability can fluctuate based on the season and day of the week. Direct flights typically offer a simpler travel experience along with a consistent flight duration, helping to minimize transit times and potential delays. Booking in advance can also secure competitive pricing and preferred departure times.
What are the best transportation options from Chicago O Hare Airport to downtown Chicago?
Chicago O’Hare offers several convenient transportation options to downtown Chicago. The CTA Blue Line train provides a cost-effective journey for around $5 to $10, taking approximately 35 to 45 minutes. Alternately, taxis and rideshare services like Uber or Lyft are available and typically cost between $30 to $50, depending on traffic. For those seeking comfort and speed, a private shuttle service is also an option. Each mode of transport has its benefits depending on your budget and time constraints when traveling from Calgary.
What are the must-see attractions in Chicago for travelers arriving from Calgary?
Visitors arriving from Calgary should not miss iconic attractions in Chicago. A visit to Millennium Park to see Cloud Gate and enjoy outdoor art is essential, while the Art Institute of Chicago offers a deep dive into world-class art. The Willis Tower Skydeck provides breathtaking views, and Navy Pier is great for shopping, dining, and family-friendly entertainment. Exploring historic neighborhoods and riverwalks also enhances your cultural experience. Each destination provides unique insights into Chicago’s vibrant atmosphere and diverse cultural tapestry.
Which local dishes should travelers from Calgary try when visiting Chicago?
When visiting Chicago, travelers from Calgary should certainly sample the city’s renowned cuisine. Chicago deep-dish pizza stands out as a hearty and flavorful option, while the Italian beef sandwich provides a unique, savory experience. Additionally, trying a classic Chicago-style hot dog, topped with sport peppers and a pickle, offers an authentic twist on local flavors. For an extra treat, explore gourmet food trucks, especially in downtown areas, where the cost may range from $10 to $25 for a full meal. Each bite reflects the city’s culinary creativity.
What are the best family-friendly activities in Chicago for visitors from Calgary?
Chicago offers an array of family-friendly activities ideal for visitors from Calgary. The Shedd Aquarium and Field Museum provide educational and interactive experiences for kids, while the Lincoln Park Zoo offers free admission and engaging wildlife exhibits. Navy Pier also features rides, interactive exhibits, and seasonal events suitable for all ages. City parks and public spaces, complete with play areas and picnic spots, enrich the family day out. These attractions combine learning with leisure, ensuring that families can enjoy a well-rounded, culturally immersive experience throughout Chicago.
Are there any seasonal events in Chicago that travelers from Calgary should not miss?
Yes, Chicago hosts a wide range of seasonal events that visitors from Calgary will appreciate. During the summer months, festivals such as Lollapalooza and Taste of Chicago dominate the scene, offering diverse food and music experiences. In the winter, the Christkindlmarket brings a distinctive European flair with artisanal crafts and holiday meals, while outdoor ice skating at Millennium Park creates a festive atmosphere. Each season brings its unique celebrations, so planning your trip around these events can maximize your enjoyment and offer an authentic taste of Chicago’s cultural vibrancy.
What are the most affordable dining options in Chicago for travelers from Calgary?
Affordable dining in Chicago is plentiful for visitors arriving from Calgary. Neighborhoods like Chinatown, Pilsen, and the West Loop host casual eateries and family-run diners offering meals ranging from $10 to $25. Local food trucks and small bistros serve authentic ethnic dishes, including Mexican, Italian, and Middle Eastern flavors, at wallet-friendly prices. Additionally, many downtown cafes provide set menus and lunch specials that cater to budget-conscious travelers. These options allow you to explore Chicago’s culinary scene without overspending, making each meal both economical and memorable.
What are the best shopping areas in Chicago for souvenirs for visitors from Calgary?
The Magnificent Mile is one of Chicago’s prime shopping destinations, offering a mix of high-end retailers and unique boutiques perfect for picking up souvenirs. Historic State Street and neighborhoods such as Wicker Park also feature specialty shops with locally crafted items and vintage finds. For travelers from Calgary, these areas provide a diverse range of shopping experiences where you can find authentic Chicago memorabilia. Prices and selections vary considerably, so taking your time to explore multiple areas can help you secure meaningful souvenirs that capture the spirit of your visit.
What health precautions should travelers from Calgary take before flying to Chicago?
Travelers from Calgary should take a few health precautions before flying to Chicago. It is advisable to ensure that routine vaccinations are up-to-date; checking for any seasonal flu shots or travel-specific vaccines can be beneficial. Bring a sufficient supply of any prescribed medications, and consider purchasing travel insurance that covers medical emergencies. Additionally, wearing loose and comfortable clothing can help alleviate fatigue during the flight. Staying hydrated and practicing good hygiene during your journey is also recommended to maintain your overall well-being upon arrival.
Is there a specific time of year when Chicago is best visited by travelers from Calgary?
Chicago is particularly inviting during the late spring and early fall months, making them ideal times for travelers from Calgary. During these periods, mild temperatures and lower crowds allow you to enjoy outdoor festivals, lakefront walks, and cultural events without the extremes of summer heat or winter cold. However, if you risk winter weather, you can still experience unique attractions such as holiday markets and indoor museums. Each season offers distinct charms, so plan according to your preferred activities and tolerance for seasonal temperatures to maximize your experience.
What are the customs requirements for travelers flying from Calgary to Chicago O Hare Airport?
Traveling from Calgary to Chicago requires preparedness for U.S. customs and immigration processes. Ensure you carry a valid passport, and if applicable, the necessary visa or Electronic System for Travel Authorization (ESTA) approval. It is recommended to complete necessary documentation before boarding to streamline the process on arrival at Chicago O’Hare. Declare any items as required by U.S. Customs regulations, and be aware of duty-free allowances. Being well-versed in these requirements can help avoid delays and facilitate a smoother transition between the two cities.
What unique airport amenities can travelers expect at Chicago O Hare Airport?
Chicago O’Hare offers a range of unique amenities designed to enhance the transit experience for visitors from Calgary. Travelers can enjoy a variety of dining options that span quick service to sit-down restaurants, many of which feature local flavors and seasonal menus. In addition, the airport provides free Wi-Fi, comfortable lounges, and diverse retail outlets for last-minute shopping. Modern art installations and interactive information kiosks add a cultural flair to the terminal. These amenities ensure that whether you’re waiting for a connecting flight or just arriving, your time at the airport is both productive and comfortable.
What are the best seating options for families traveling from Calgary to Chicago?
For families traveling from Calgary to Chicago, selecting the right seating arrangements on your flight can significantly enhance comfort. Opting for bulkhead seats or seats with extra legroom can provide additional space for children, allowing for easier movement and storage for family essentials. If possible, booking seats together can facilitate smoother boarding and in-flight activities. Some airlines also offer family seating policies, so inquire during booking. These options not only cater to comfort but also ensure that both parents and children have a stress-free and enjoyable flying experience.
What are the top cultural experiences in Chicago for travelers arriving from Calgary?
Travelers arriving from Calgary should consider immersing themselves in Chicago’s rich cultural scene. Start by exploring notable museums such as the Art Institute of Chicago and the Field Museum, both renowned for their impressive collections. Architectural tours, particularly by boat along the Chicago River, offer insightful perspectives on the city’s history and modern design. In addition, attending live theater performances or an outdoor concert in Millennium Park can further enrich your visit. Each cultural experience is designed to provide a deep understanding of Chicago’s heritage and vibrant contemporary arts scene.