Best airline to fly to Canada from Chicago

Best airline to fly to Canada from Chicago

When it comes to planning a trip to Canada from Chicago, one of the most critical decisions you’ll have to make is choosing the best airline to fly with. The right airline can make your journey comfortable and hassle-free, while the wrong choice might lead to a less-than-enjoyable experience. In this blog post, I’ll take you through the factors to consider when selecting the best airline to fly to Canada from Chicago, discuss the available airline options, and share some valuable tips for making the right choice.

Factors to Consider

Before diving into the specific airline options, let’s explore the essential factors you should consider when deciding which airline to choose for your journey to Canada.

Destination in Canada: Firstly, it’s important to determine your exact destination in Canada. Different airlines may have better routes and schedules to various cities within the country, so this will be a crucial factor in your decision-making process.

Travel Budget: Your budget plays a significant role in your choice of airline. You’ll want to find the right balance between your budget and the benefits of the airline. A more expensive ticket might offer better services, but it’s essential to ensure it’s worth the extra cost.

Travel Dates and Flexibility: The flexibility of your travel dates can impact your choice. If you have flexible travel dates, you might be able to find better deals. Consider whether you can adjust your plans to get the most value for your money.

Flight Duration and Layovers: Some travelers prioritize non-stop flights for their convenience, while others may not mind layovers if it means a lower fare. The duration of the flight and the number of layovers are critical considerations.

Baggage Allowance: If you’re planning to bring a lot of luggage or specialized equipment, be sure to check the airline’s baggage allowance and any associated fees. This is especially important for sports enthusiasts who may need to transport equipment.

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In-Flight Amenities: Depending on the airline, you’ll have different in-flight amenities at your disposal. Some airlines offer Wi-Fi, entertainment systems, and better meal options than others.

Frequent Flyer Programs: If you’re a frequent traveler, it might be worth considering which airlines have the best loyalty programs and rewards.

Safety and Reliability: Safety should always be a priority. Check the airline’s safety record and reliability to ensure a worry-free journey.

Reviews and Recommendations: Reading reviews and seeking recommendations from friends or family who have traveled to Canada can provide valuable insights into the quality of the airlines.

Accessibility to Airports: Consider the convenience of the departure and arrival airports. How accessible are they from your starting point in Chicago and your final destination in Canada?

Now that we’ve covered the essential factors, let’s explore the airline options for flying to Canada from Chicago.

Airline Options

Chicago offers a variety of airline options for your journey to Canada, each with its own set of benefits and advantages. Let’s take a closer look at some of the top choices.

United Airlines

United Airlines is a well-established carrier that offers multiple daily flights from Chicago O’Hare International Airport (ORD) to several major Canadian cities. Their extensive network and partnership with Air Canada make them a popular choice for travelers heading to Canada.

Air Canada

Air Canada, the flagship carrier of Canada, is known for its excellent service and extensive route network. Flying with Air Canada is often a seamless experience, with numerous daily flights connecting Chicago to various Canadian destinations. The benefit of choosing Air Canada is that you’ll be in the hands of a reputable and reliable airline with an in-depth knowledge of Canadian travel.

American Airlines

American Airlines is another major player in the aviation industry with a significant presence in Chicago. While American Airlines primarily serves domestic routes, they also offer connections to Canadian cities, including Toronto and Montreal. If you’re a member of the American Airlines AAdvantage loyalty program, you might be able to take advantage of miles and rewards for your journey to Canada.

Features of American Airlines:

  • Extensive domestic network in the United States.
  • Possibility of using frequent flyer miles for Canadian flights.
  • Multiple daily flights to Canadian cities from Chicago.
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Delta Air Lines

Delta Air Lines provides a robust network of routes from Chicago to Canada, offering options to reach destinations like Vancouver, Toronto, and more. Delta is known for its commitment to passenger comfort and convenience, and you can expect a pleasant flying experience when choosing this airline.

Porter Airlines

If you’re looking for a regional option with a focus on Eastern Canada, Porter Airlines is worth considering. This Toronto-based airline connects Chicago to cities like Toronto and Ottawa. Porter Airlines is known for its exceptional customer service and the convenience of flying from Billy Bishop Toronto City Airport, which is closer to downtown Toronto.

Alaska Airlines

Alaska Airlines may not be the first airline that comes to mind when thinking about flying from Chicago to Canada, but they offer connections to several Canadian destinations, including Vancouver. If you’re already a loyal customer of Alaska Airlines, this could be a convenient choice for your journey.


WestJet is a Canadian-based airline known for its friendly service and competitive fares. They offer flights from Chicago to several Canadian cities, making them a great choice for travelers who appreciate affordability without sacrificing quality.


Choosing the best airline to fly to Canada from Chicago is a decision that should be made after careful consideration of your specific needs and preferences. Whether you prioritize cost, convenience, or amenities, you’ll find an airline that suits your travel style. To make the right choice, weigh the factors mentioned earlier and consider the airline options available.

Tips for Choosing the Best Airline

Before we wrap up, here are a few tips to help you make an informed decision:

  • Book in Advance: To secure the best deals and options, try to book your tickets well in advance of your travel date.
  • Compare Prices: Don’t forget to compare prices from various airlines to find the best value for your budget.
  • Check for Deals: Keep an eye out for promotions, discounts, and special offers that airlines may have for flights to Canada.
  • Consider Loyalty Programs: If you’re a frequent traveler, enrolling in an airline’s loyalty program can lead to substantial benefits and rewards.
  • Read Reviews: Look for reviews and recommendations from other travelers who have made the same journey.
  • Pack Light: Consider packing only what you need to avoid excess baggage fees.
  • Stay Informed: Keep up with travel advisories, rules, and regulations for your destination.
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Now you’re well-equipped to choose the best airline for your journey to Canada from Chicago. Safe travels!

Key Takeaways

  • When selecting the best airline to fly to Canada from Chicago, consider factors such as your destination, budget, travel dates, baggage needs, and in-flight amenities.
  • United Airlines, Air Canada, American Airlines, Delta Air Lines, Porter Airlines, Alaska Airlines, and WestJet are some of the top airline options for flying to Canada from Chicago, each with its own advantages.
  • American Airlines offers domestic routes to Canada and the option to use frequent flyer miles for Canadian flights.
  • Porter Airlines is a regional option focusing on Eastern Canada with exceptional customer service.
  • Consider loyalty programs, deals, and reviews when making your decision.


Q: What is the benefit of flying to Canada from Chicago with United Airlines? A: United Airlines provides an extensive network and partnership with Air Canada, offering multiple daily flights to major Canadian cities.

Q: Is Air Canada a reliable choice for traveling to Canada from Chicago? A: Yes, Air Canada is the flagship carrier of Canada and is known for its excellent service and extensive route network, making it a reliable choice for Canadian travel.

Q: Can I use American Airlines’ frequent flyer miles for flights to Canada? A: Yes, American Airlines allows you to use frequent flyer miles for Canadian flights, making it a convenient option for loyal customers.

Q: What destinations does Porter Airlines connect to from Chicago? A: Porter Airlines primarily connects to Eastern Canadian cities like Toronto and Ottawa, providing exceptional customer service.

Q: Is Alaska Airlines a viable option for traveling from Chicago to Canada? A: Yes, Alaska Airlines offers connections to several Canadian destinations, including Vancouver, making it a viable choice for your journey.

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