Flight Ticket and Schedule From Calgary (YYC) to Chicago (ORD) start from

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Calgary to Chicago

Flight Schedule from Calgary to Chicago

The following are all scheduled flights from Calgary to Chicago, with the shortest duration being 0 hours and 0 minutes.
Thu, 16 Oct 2025 (Today)
Fri, 17 Oct 2025
Sat, 18 Oct 2025
Airline
Departure Time
Arrival Time
Origin airport
Destination airport
WestJet
WestJet
12:15
16:43
Calgary (YYC)
Chicago (ORD)
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Delta Airlines
Delta Airlines
12:15
16:43
Calgary (YYC)
Chicago (ORD)
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United Airlines
United Airlines
12:38
17:10
Calgary (YYC)
Chicago (ORD)
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Air Canada
Air Canada
12:38
17:10
Calgary (YYC)
Chicago (ORD)
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American Airlines
American Airlines
13:29
17:54
Calgary (YYC)
Chicago (ORD)
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Direct Airline from Calgary to Chicago

Available Airline that flying directly from Calgary to Chicago start from
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United Airlines
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About Chicago

Complete Guide to Flights from Calgary (YYC) to Chicago (ORD)

Planning a trip from Calgary to Chicago? This comprehensive guide covers everything you need to know, from finding the best flight deals to exploring the Windy City's vibrant culture. We'll help you navigate the flight options, transportation within Chicago, and even suggest some money-saving tips.

Chicago offers a diverse range of experiences, from its iconic architecture and world-class museums to its thriving food scene and lively nightlife. Understanding the local culture and weather conditions will enhance your trip significantly. Remember to check the current weather forecast before you go!

Flight Routes and Travel Information from Calgary (YYC) to Chicago (ORD)

Direct Flights

Several airlines offer direct flights from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD), significantly reducing travel time. The flight duration is typically around 2.5 to 3 hours. Check Traveloka for the most up-to-date schedules and availability.

Connecting Flights

Connecting flights often involve layovers in major hubs like Denver (DEN) or Minneapolis (MSP). While potentially longer, connecting flights can sometimes offer more affordable options. Consider the total travel time versus cost when comparing options. Again, checking Traveloka for flight comparisons is recommended.

Flight Frequency

The frequency of flights from YYC to ORD varies depending on the season and airline. Generally, you'll find more frequent flights during peak travel seasons. To find the most current flight schedules, it's best to check directly with airlines or use a flight comparison website like Traveloka.

Popular Airlines for the YYC to ORD Route

Major airlines serving this route include Air Canada, United Airlines, and WestJet. Each airline offers different classes of service and amenities. Comparing prices and services across these airlines is crucial for finding the best fit for your travel style and budget. Remember to check Traveloka for the latest deals.

Main Airports in Chicago and Their Facilities

Chicago's primary airport is O'Hare (ORD), a massive international airport with extensive facilities, including numerous restaurants, shops, and lounges. Chicago also has Midway International Airport (MDW), which is smaller but still well-equipped. Knowing which airport your flight arrives at is essential for planning your onward journey.

Transport Options from Chicago (ORD) Airport to the City Centre

Several options exist for getting from ORD to downtown Chicago: the 'L' train (CTA Blue Line), taxis, ride-sharing services (Uber/Lyft), and airport shuttle buses. The 'L' train is a cost-effective choice, while taxis and ride-sharing offer convenience. Consider your budget and time constraints when choosing.

Best Time to Visit Chicago: Experiences & Events

Chicago's weather is quite variable. Summer offers warm temperatures and numerous outdoor events, while winter brings snow and festive celebrations. Spring and autumn provide pleasant weather and fewer crowds. Consider the events and activities you're interested in when choosing your travel dates.

Recommended Areas to Stay in Chicago for Different Travel Styles

Chicago offers diverse neighborhoods, each with its own character. From the luxurious Gold Coast to the trendy Wicker Park, choosing the right area depends on your preferences and budget. Research different neighborhoods to find the best fit for your trip.

Essential Preparations Before Travelling to Chicago

Before your trip, ensure you have a valid passport or ID, travel insurance, and any necessary visas. Confirm your flight details, accommodation bookings, and any planned activities. Packing appropriate clothing for the expected weather is also crucial.

Iconic Landmarks & Must-Try Activities in Chicago

Chicago boasts iconic landmarks like the Willis Tower, Cloud Gate ("The Bean"), and Navy Pier. Don't miss exploring Millennium Park, taking an architectural boat tour, or catching a show in the Theater District. Researching activities in advance will help you plan your itinerary effectively.

Alternative Travel Options from Calgary to Chicago Besides Flying

While flying is the most common option, driving or taking a train (though less practical) are alternatives. Driving offers flexibility but requires significant travel time. Train travel is scenic but may not be the most efficient option for this route.

Budget Guide: Money-Saving Tips for Trips to Chicago

To save money, consider traveling during the off-season, utilizing public transportation, taking advantage of free activities, and seeking out affordable dining options. Planning your trip in advance and booking flights and accommodation early can also help secure better deals. Check Traveloka for flight deals.

Visa Information & Entry Requirements for Travellers from Calgary

Canadian citizens generally do not require a visa for tourist visits to the United States, but it's crucial to check the latest visa requirements and entry regulations well in advance of your trip. Ensure your passport is valid for at least six months beyond your intended stay.

Local Cuisine Recommendations in Chicago

Chicago is renowned for its deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. Exploring the city's diverse culinary scene, from fine dining to casual eateries, is a must. Research restaurants and make reservations in advance, especially for popular spots.

Souvenir Shopping Guide in Chicago

From unique artwork to Chicago-themed apparel, the city offers a variety of souvenir options. Explore local shops and markets to find one-of-a-kind mementos of your trip. Consider your budget and what type of souvenirs you're looking for.

Maximise the Best Flight Deals to Chicago via Traveloka

For the best flight deals from Calgary (YYC) to Chicago (ORD), we highly recommend checking Traveloka. They offer a wide selection of flights from various airlines, allowing you to compare prices and find the perfect option for your needs.

Key benefits of using Traveloka:

  • Simple and user-friendly booking process.
  • Flexibility to change or cancel bookings (Reschedule/Refund feature).
  • 24/7 customer support that’s responsive and helpful.

Flight Information to Chicago

Flight Duration

0 hr(s) 0 mins

Airport in Calgary

Airport in Chicago

Frequently Asked Questions

How early should I get to the airport for a domestic & international flight?
For domestic flights, we recommend arriving at the airport at least 2 hours before your scheduled departure time. For international flights, aim to be at the airport at least 3 hours prior to ensure smooth check-in, security checks, and to account for any unexpected delays. It’s better to be early and relaxed than rushing at the last minute right?
When is the best time to buy airline tickets?
Timing is everything when it comes to grabbing airline tickets. Typically, it’s best to book around 4-6 weeks in advance for domestic flights and 2-3 months for international routes. But the prices also depend on the travel demand, seasonality, and major events. You can always monitor the fare trends on Traveloka and set alerts to catch the best deals or promotions!
What is the cheapest day to fly to Chicago?
Looking for the best deals to Chicago? Historically, midweek flights (particularly on Tuesdays and Wednesdays), tend to be cheaper due to lower demand. However, airfares can fluctuate so we recommend keeping an eye on flight prices and being flexible with your travel dates. Booking in advance can be one the hacks to travel to Chicago without breaking the bank!
What information do I need to know when booking a flight?
When booking a flight, every choice sets the tone for your trip. From the preferred flight route – be it direct or with layovers – to the in-flight experience – whether you opt for a standard economy seat or a luxurious first-class journey – and understanding baggage limits, there's a lot to weigh. Other considerations include travel insurance and the airline's booking policies.
How far in advance should I book an international flight?
For international flights, it’s wise to start your search about 5-6 months ahead with the optimal booking window being around 3-4 months before departure. This period often provides a balance between good fares and a reasonable choice of flight times and routes. But please note that several factors such as destination popularity, peak travel season, and regional major events can influence the timeline.
Do I need a passport and visa to fly between Calgary to Chicago?
Traveling from Calgary to Chicago typically requires specific documents. For international flights, a passport is almost always necessary. However, for domestic flights, neither a passport nor a visa is usually required, but an official ID will be needed. The necessity of a visa depends on the traveler's citizenship and Chicago's entry regulations. It's crucial to verify visa requirements, as rules can differ between countries.
Why should I book my flight with Traveloka?
Booking flight tickets with Traveloka can feel like diving into an ocean of options! Our platform provides the most comprehensive choices to ensure you find the perfect flight for your adventure. With our smooth booking process, you'll also be provided with a variety of payment methods. Anxious about transacting online? We've got you covered with our top-tier security for each transaction! With Traveloka, your flight booking journey becomes hassle-free!
How long does it take to fly from Calgary to Chicago?
0 hours and 0 minutes is the shortest flight time from Calgary to Chicago.

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