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Best Time to Book Montreal to Chicago Flights for the Lowest Fare

Best Time to Book Montreal to Chicago Flights for the Lowest Fare

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June 26, 2025 11:34:13

Best Time to Book Montreal to Chicago Flights for the Lowest Fare

Best Time to Book Montreal to Chicago Flights for the Lowest Fare

Both business and pleasure travelers enjoy traveling between Montreal and Chicago. Booking your Montreal-Chicago flights in advance can save you a lot of money, whether you are planning a weekend trip or attending a conference.

This post will reveal the best times to book, compare airline options and give you real-world tips on how to get the cheapest YUL ORD flights.


Why Montreal to Chicago is a Popular Route


The Montreal-Chicago flight connects these two North American icons. Montreal has an old-world charm while Chicago is known for its skyscrapers and deep-dish pie.

The flight duration between Montreal and Chicago is usually two hours and thirty minutes. This makes it a quick and easy journey for travelers.

It is also convenient to fly back from Chicago to Montreal, with the availability of multiple direct flights and connecting options.


When is the best time to book?


It is best to book your Montreal-Chicago flights between 3 and 6 weeks before the flight. This window, according to travel data offers the best combination between availability and low prices.

Here is a guide to the general season:

  1. January to March: Cold, but Cheap (Low Demand)
  2. April to June: mild weather and moderate prices
  3. July to August: High prices due to summer demand
  4. From September to November: Amazing deals, especially during midweek
  5. December: Expensive due holidays

Avoid booking on long weekends and major U.S./Canadian Holidays like Canada Day or Thanksgiving.


Pro Tips for Finding Cheap Flights from Montreal to Chicago


1. Fly Midweek

The fares are usually lower on Tuesdays and Wednesdays than they are at weekends. If you want to save money, avoid flying on Sundays and Fridays.

2. Set Fare Alerts

Set up alerts using tools such as Google Flights or Skyscanner. These notifications will help you grab deals before they are gone.

3. Use Incognito Mode

Search for flights using the incognito/private mode of your browser to avoid dynamic pricing.

4. Book in the morning

Prices for flights are often reset over night. Early morning is the best time to catch new deals.

Airlines offering flights between Montreal and Chicago

Major carriers offer multiple direct and one stop Chicago to Montreal flights. Here are the top airlines that serve the YUL-ORD route.

Airline

Service

Highlights

Air Canada

Direct

Aeroplan Rewards: Good timing

United Airlines

Direct

Hub at ORD, multiple departures

American Airlines

1-stop via JFK

Enjoy smooth connections with loyalty points

Delta

One-stop shopping

SkyMiles offers friendly service

Porter Airlines

1-stop via YYZ

Boutique experience, downtown access

What is the average airfare from Chicago to Montreal?

  1. One way: CAD $290 - $180
  2. Roundtrip : CAD $350 to $540
  3. Budget fares: starting at $150 CAD

Remember that airfares from Chicago to Montreal can vary depending on season, day of the week, and demand. You can save up to $100 by flying during off-peak hours.

Tips on Packing and Saving Fees

Baggage restrictions are often a part of low-cost fares. How to avoid extra charges:

  1. Only carry-on luggage is allowed and you can use a soft bag with an overhead bin that fits the size.
  2. Pay for your bags in advance online instead of at the airport
  3. If you want to select your seat and carry a large bag, avoid basic economy.

Check your airline's luggage policy, especially if you are flying Montreal flights via Chicago with a different airline.

Round-Trip vs One-Way: Which Offers Better Deals?

Booking round-trips can be more economical. Using Montreal-Chicago flights with Chicago-Montreal flights can save you money and improve flight times.

Example:

  1. Outbound: Air Canada - Morning nonstop
  2. Return: United Airlines Evening Nonstop
    Result? Schedule flexibility and $70 off compared to the round-trip price on a single carrier.

Why Kapido Travel should be your go-to booking platform

Reliability and ease of booking Montreal-Chicago flights are important. Kapido Travel is the only travel website that offers this level of service. Kapido is a travel search engine that offers personalized service, transparency in pricing and the latest deals, all in one place.

With Kapido,you can:

  1. Compare prices instantly on YUL-ORD flights
  2. No hidden charges or last-minute fees.
  3. When you need assistance, you can get human support by real travel experts - not bots - when you need it.
  4. Track changes in airfare to take advantage of limited time deals

Kapido Travel offers the best fares, a smooth booking process, and reliable support at every stage.

Book your flight on Kapido Travel now and fly smarter.

Frequently Answered Questions (FAQs).

1. How long does it take to fly from Montreal to Chicago

The average direct flight takes 2 and 30 minutes. Check-in, security and possible delays at peak times will require extra time.

2. Which airlines fly directly from Montreal to Chicago the most?

Air Canada, and United Airlines offer the best nonstop flights from YUL to ORD .

3. What is the best time to fly between Chicago and Montreal?

The lowest fares are usually found in January, February and early March. Fly midweek and avoid holiday weekends to get the best prices.

4. What airport is the best to fly into for Chicago?

The majority of Montreal-Chicago flights land in O'Hare International Airport. This is Chicago's main hub, with excellent airline coverage and public transportation.

Final Thoughts - Timing is the Key for Smart Travel

If you plan well, flying between Montreal and Chicago is both affordable and fun. The key to saving money is timing your booking . You can also save by being flexible with travel dates and comparing prices on different platforms. There's no need to pay more than necessary when there are YUL-ORD flights available daily, as well as seasonal promotions and multiple airlines. Book midweek and pay attention to seasonal trends. You'll find low-cost flights from Montreal, Illinois quickly.

Are you ready to save money on your next flight? Take advantage of Kapido Travel’s best flight deals to save on your next trip.