Toronto is a big, vibrant city and a long weekend there is a perfect amount of time to explore everything it has to offer. Are you a foodie? Check! Bringing kids with you? Check! Want to experience arts and culture and see a play? Check! And you can easily fit in a day trip to one of North America’s most iconic sights – Niagara Falls.

There’s no shortage of hotels in Toronto for all tastes and budgets and getting there from almost anywhere in the U.S. is easy. In this article, we’ll explore how to do a long weekend in Toronto with points and miles. At the end of this article, we’ll look at a few ways to earn the points and miles you’ll need for your long weekend jaunt to Toronto.

How to Book Flights to Toronto With Points and Miles

Because there are so many flights to Toronto from all major U.S. airports, the first step in finding the best awards would be Google flights. You can plug in your home airport to see the most optimal routes and airlines and then search the frequent flyer programs where you have miles.

Consider the programs that are transfer partners of all major transferrable currencies, such as Chase Ultimate Rewards points, Citi ThankYou points, American Express Membership Rewards points and Capital One miles.

Award Hacker is a great starting point to see which program offers the best value and which airline miles and credit card currencies can be used for the specific program. Keep in mind that Award Hacker doesn’t show available award space. It’s just a research tool that tells us which programs/miles/points are best for our specific situation. You still need to search each program to find available awards.

There are times when Award Hacker doesn’t have accurate rates so it’s important to confirm how many miles you’ll need before transferring points.

Air Canada Aeroplan

To check for the best award rates for our trip to Toronto, I plugged in Atlanta to Toronto flights into the Awardhacker tool and the winner is clearly Air Canada’s frequent flyer program Aeroplan. You can fly from Atlanta to Toronto for just 15,000 miles round-trip.

I then went to Aeroplan to search for the actual award flights.

Aeroplan has a special rate for short-haul Fixed Mileage Flight Rewards in North America for flights to the province of Ontario. The flights from the following states have to be operated by Air Canada, Air Canada Express and the Canadian domestic partners:­

As you can see in the example above, the short-haul rate is 7,500 miles one-way in economy. Business class is 15,000 miles one-way, but most likely, these flights are operated by small regional aircraft, so splurging on a business class ticket won’t be worth the extra miles.

If you don’t live in any of the states with reduced short-haul rates, then you’ll need 12,500 miles one-way in economy and 25,000 one-way in business class.

Note that Aeroplan passes on surcharges, but for travel between the U.S. and Canada, the surcharges are very reasonable, about $55.

Aeroplan is a transfer partner of American Express and Membership Rewards points transfer 1:1 to Aeroplan. Capital One miles also transfer to Aeroplan at 2:1.5.

American Airlines

American Airlines operates a few non-stop routes from the U.S. to Toronto, and of course you can connect from most airports in the U.S. To search for AA award flights, you don’t even need to create an account. Just plug in your dates and the destination on the home screen and click search.

AA still has an award chart and the saver level redemption should be 15,000 miles one-way in economy and 25,000 one-way in business class. But with the introduction of AA’s web specials, we can expect award prices to be a bit all over the place.

As you can see, you can find fares as low as 10,000 miles one-way in economy. Web specials are more restrictive than regular award tickets, so check the terms and conditions carefully before you book.

Delta Air Lines

Delta also operates a few non-stop flights to Toronto, and of course you can connect from a number of smaller airports and get to Toronto with just one layover.

You don’t need an account to search for available award space on Delta, just plug in your dates and your departure/destination and make sure Shop with Miles is checked.

Delta doesn’t have an award chart anymore, so the best way to see the lowest award rates is to click on the Price Calendar on the top left.

The price calendar will show you five weeks of availability. Calendar view is the best way to find the lowest rates, especially during Delta’s award sales.

If you don’t have any Delta miles, Delta is a transfer partner of American Express Membership Rewards points. The points transfer 1:1 and the transfer is instant. Amex charges “excise tax” on points transfer to domestic airlines, but it’s minimal.

Chase Travel Portal for Flights

Don’t forget to check the prices in the portal. If you come across a good fare sale and find a good cash price, check if it’ll be cheaper to book with Ultimate Rewards instead of transferring points to a partner airline by using Chase’s Ultimate Rewards travel portal.

Flights booked through the portal earn miles, so that’s another reason to book cheap fares with Ultimate Rewards points rather than transferring them to partner airlines.


Where to Stay in Toronto With Points

There are so many chain and independent hotels in the city for every taste and budget. To help you narrow down the choices, let’s look at what you can book with Hilton, Marriott, Hyatt and Ultimate Rewards points.

Use Hilton Points to Book Your Stay in Toronto

Hilton doesn’t have an award chart, so the price in points will depend on the location and the demand for any particular property. When you book four nights with points, you can get a fifth night free. This is a great way to extend your weekend trip!

There are three Hilton Properties right in downtown Toronto and many other cheaper options on the outskirts of the city. Cash rates at Toronto hotels are quite high, especially during the warmer months. When I was writing this, I saw that all the three downtown properties hovered around 60,000 points a night.

If you want to save points, it might be worth looking at one of the suburban hotels near a subway station. Homewood Suites properties will offer more room for families and will help you save on food costs as well.

DoubleTree by Hilton Hotel Toronto Downtown is conveniently located close to all the major attractions. It’s just a 10 minute walk to the Art Gallery of Ontario or a 15 minute walk to the Hockey Hall of Fame. The rooms look modern and there’s even an indoor swimming pool which is perfect for the kids to let off some steam after a long day of sightseeing.

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Hilton Toronto has an executive lounge for Hilton Honors Diamond members where Diamond elites can grab breakfast and snacks and drinks in the evening. It’s located close to Chinatown and is within walking distance to a lot of Toronto’s most popular attractions.

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Hilton Garden Inn Toronto Downtown is a modern hotel located between Toronto’s entertainment district and downtown and about 1000 feet from the nearest subway station, making it a perfect location if you want to explore downtown Toronto and also be connected to other areas of the city.

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Use Marriott Points to Book Your Stay in Toronto

There are quite a few Marriott properties in Toronto. Here we’ll highlight a family-friendly option, a luxury option and an upscale waterfront option.

If you book a four night stay with Bonvoy points, you get fifth night free, so if time allows, you can stay five nights in the city for the price of four nights. There are also a few category 5 hotels where you can use the annual free night certificate that comes with a number of Marriott personal and business credit cards, such as Chase Marriott Bonvoy Boundless card.

The Residence Inn Toronto Downtown/Entertainment District is a great option for families. The rooms are actually mini suites that come with a kitchenette and a dining table and a free breakfast is included for all guests. You’ll have room to spread out and will save on food costs – perfect for families!

The standard rate at this property is 35,000 Bonvoy points, 30,000 off-peak and the peak rate is 40,000 points.

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The St. Regis Toronto is located in the heart of Old Toronto neighborhood and as a category 7 is definitely a splurge. To save points, look for PointSavers or off-peak rates (50,000 points). The standard rate is 60,00 and the peak rate is 70,000 points.

The glam factor is amplified by the gorgeous Art Deco decor throughout the property.

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The Westin Harbour Castle is located on Toronto’s waterfront and has spectacular lake views. Toronto has a beautiful lakefront and the hotel is located close to the entertainment district, making it a perfect place to stay for catching a show or a play.

The hotel is also just a 20 minute walk (most of it along the lakefront) from Toronto’s charming Distillery Historic District that has a lot of good eateries, breweries, art galleries and one of a kind shops.

This is a category 5 hotel and the standard rate at this property is 35,000 Bonvoy points, off-peak is 30,000 and peak rate is 40,000 points.

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Use World of Hyatt Points to Book Your Stay in Toronto

Hyatt Regency Toronto is a category 3 hotel located near the entertainment district and close to Toronto’s lakefront and all the major attractions. The standard room is just 12,000 World of Hyatt points.

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If you don’t have enough Hyatt points, you can easily transfer Chase Ultimate Rewards points to your World of Hyatt account. The transfer is instant and the points transfer 1:1.

Use Chase Portal to Book Toronto Hotels

If you have a good stash of Chase Ultimate Rewards points, you can use the Chase travel portal to book many non-chain and condo-style properties in Toronto.

If you have Chase Sapphire Reserve®, the points are worth 1.5c each. If you have the Chase Sapphire Preferred® Card or the Ink Business Preferred® Credit Card, then the points are worth 1.25c each.

To search for hotels on the portal, login to your Ultimate Rewards account and plug in your dates and destination.

The biggest advantage of booking a hotel through the portal is the ability to pick the exact location and the room type you want. You can also book rooms that can accommodate more than two people in the room.

Note that you likely won’t earn any hotel loyalty points and won’t receive elite benefits with a portal booking.

Here’s a pro-tip – if you book a refundable rate, check the price often to see if the price dropped. If you can find the same hotel for less, just cancel and rebook.

3 Things You Should Do In Toronto

In a city of this size, it’s hard to pick just three must-do things. There are great restaurants, breweries, museums and galleries and sporting events. Toronto’s CN tower is a must see for a bird’s eye view of the city.

A Day Trip to Niagara Falls

Niagara Falls

Niagara Falls is just 90-100 minutes from Toronto by car. So if you’ve had your feel of the city, rent a car for a day or book a bus tour to see the remarkable natural beauty of Niagara Falls.

Niagara Falls is beautiful any time of the year, but it’s especially beautiful in the fall, when the leaves are changing colors. Don’t worry, we have lots of great warm and sunny days in the fall in the Northeast!

A must do in Niagara Falls is a Maid of the Mist boat tour. The boat brings you really close to the waterfall and in spite of the provided rain poncho, you will get wet, so wear something that’ll dry quickly. Your kids will also get a kick of being so close to the massive wall of water, it’s great fun for the entire family!

The area around Niagara Falls is also known for its many wineries.

A Foodie Paradise


Toronto, Ontario, Canada: Toronto's Distillery District is a historically significant area of the downtown core. In the past, as its name suggests, the area was devoted largely to distilling spirits. Years ago, with the distillery business in sharp decline, the area was redeveloped into shops, restaurants, bars, theatres, galleries etc. It brought together residential condos/apartments, and commercial enterprises into high end developments. The area is now a tourist destination.

Toronto is a city of immigrants and is one of the most diverse cities in North America. So if you like international cuisine, this is THE place to be. I am crazy about Vietnamese and Turkish food, so everywhere I go, I seek out those restaurants.

Whatever you are in the mood for – Moroccan, Hungarian, Portugese, Ethioian or Laotian, the city has got you covered. And don’t forget to sample Toronto’s many excellent craft breweries!

For the Art and Museum Lover

Toronto, Ontario, Canada: The Royal Ontario Museum (ROM) in Toronto, houses numerous historic collections, notably dinosaur bones, artifacts from ancient Europe, Africa, Asia, a discovery centre for youth, and hosts many special collections and special events. It is one of Canada's most famous museums and cultural facilities.

Toronto has no shortage of world-class museums. There’s Royal Ontario Museum with its futuristic looking modern addition and the Art Gallery of Ontario.

For more quirky fun, head to the Bata Shoe Museum. This museum has a collection of over 13,000 shoes from ancient times to the present day. It might sound strange that there’s an entire museum dedicated to shoes, but we can learn a lot about different societies through everyday objects like shoes and clothes.

The Textile Museum of Canada is also one of a kind. If you have a fashion lover in your party, these are a nice break from the more traditional museums.

How to Earn Points for Your Weekend Trip to Toronto

If you are going to book your flight and hotel through the portal, then collecting a good amount of Ultimate Rewards points should be a priority. There are a few excellent Chase personal and business cards that come with generous welcome bonuses and great spending categories, such as Chase Sapphire Reserve® and Chase Ink Preferred.

You can earn even more Ultimate Rewards points and airline miles by using shopping portals, especially if you are just a few thousand miles short.

The World of Hyatt Credit Card comes with a great welcome bonus and awards an annual free night certificate that can be used at any Category 1-4 Hyatt property on the credit card anniversary.

Chase and American Express offer a few personal and business Marriott Bonvoy credit cards. They all come with generous welcome bonuses and annual free night certificates every year after account anniversary.

You have to be under 5/24 with Chase to be approved for any of these cards.

American Express has a number of personal and business co-branded Hilton credit cards. They all come with very generous welcome bonuses. Hilton Honors American Express Aspire cardmembers get top tier Hilton Honors Diamond status. Diamond members get access to the executive lounge and get free breakfast.

Some of the best Membership Rewards earning cards include The Blue Business® Plus Credit Card from American Express and the American Express® Gold Card. The Blue Business Plus Card earns 2X on everything up to $50,000 a year and then 1X thereafter. The Amex Gold card has generous spending categories, such as 4X at restaurants and at U.S. supermarkets (on up to $25,000 per calendar year, then 1X thereafter).

American Airlines has a couple of consumer and business credit cards issued by Citi and Barclays. Barclays AAdvantage Aviator Red World Elite MasterCard comes with a generous welcome offer of 60,000 miles after making one purchase in the first 90 days.

Delta Air Lines has quite a few personal and business credit cards issued by American Express. The Delta SkyMiles® Gold American Express Card is a great option because it comes with a nice welcome bonus and has low minimum spending requirements and a free checked bag benefit.

Final Thoughts

Toronto can be a great weekend getaway for solo travelers, couples or families. There are so many things to do, from the Hockey Hall of Fame, to world class museums, to performing arts and major sporting events.

And let’s not forget about the food! It is a great foodie destination and offers a chance to sample a variety of international cuisines without leaving North America.

Travel well,