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Cheap Weekend Flights from Toronto

Spend your next long weekend exploring a new city! We’ve got a bunch of cheap weekend flights from Toronto for you right here. Whether it’s to another Canadian city or a long weekend to a popular spot in the U.S., affordable getaways are right here for you below.

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There are plenty of opportunities for long weekend getaways from Toronto throughout the year. Fly to Quebec City for the Civic Holiday weekend or spend Victoria Day weekend wandering the streets of New York City before the tourist crowds flock in for the summer. Here are the holidays that fall on a Friday or Monday in Canada, making for a perfect long weekend holiday.

Long Weekends in Canada

Ontario’s Statutory holidays

  • Victoria Day: Monday, May 20th
  • Canada Day: Monday, July 1st
  • Civic Holiday: Monday, August 5th
  • Labour Day: Monday, September 2nd
  • Thanksgiving Day: Monday, October 14th
  • Remembrance Day: Monday, November 11th

So for your next long weekend getaway, you just need to decide whether you want to be surrounded by city lights or sandy beaches. Here are some popular destinations with cheap weekend flights from Toronto, so you can pack your overnight bag and get ready for your next mini adventure.

busy New York City streets at dusk.
Spend a long weekend in a new city

1. New York City

Experience New York’s museums, parks, shopping, and food for a long weekend

Why visit: World-class shopping, sights, architecture and food, New York City is consistently an excellent destination for a long weekend getaway from Toronto. Beat the intense summer heat and explore New York City during Victoria Day weekend. Note that Columbus Day is a national holiday in the U.S. and it falls on the same day as our Thanksgiving Day this year, so tourist places will be particularly busy at this time.

What to do: New York City’s many parks are inspiring and easy to explore, especially during the fall and spring months. Central Park, Battery Park, and Brooklyn Bridge Park are some of the most popular choices for a New York City trip. Splurge on your long weekend getaway and go shopping (or just window shop) at the many boutiques along Fifth Avenue. With some of the best museums in the world, no trip to New York City is complete without a visit to at least one of New York’s museums. Check out our guide on free things to do in New York City for information on free museum days and the best spots to check out in New York.

Places to eat: If you want some of the best food that New York has to offer, head downtown to Katz’s Deli for some classic deli food in this New York establishment. For a splurge, there’s Gramercy Tavern, which is consistently one of New York City’s top-rated restaurants. Or you can head completely Uptown to Harlem and experience the Red Rooster for classic American fare, live music, and inventive cocktails (they have a signature cocktail called the Obamatini!). What can’t you do in New York?!

Getting around: The five New York City boroughs are accessible by public transport: from the MTA and the Staten Island Ferry. You can purchase a 7-Day Unlimited MetroCard for easy access to the New York City subway system and discounts on numerous New York City attractions. New York City’s three major airports; JFK, Newark, and LaGuardia, all have shuttle services that take passengers from the airport into Manhattan. Buy a round-trip ticket at your destination airport to save some money.

Find Cheap Weekend Flights from Toronto to New York

2. Boston

Boston offers so many kid-friendly activities, historical walks, and architecture to fill a weekend getaway

Why visit: Often overlooked by other cities along the east coast, this U.S. city is just waiting to be explored. Fill your time on your Boston long weekend with historic walks, visits to outdoor markets, picturesque neighbourhoods, and indulge in some excellent food. There’s also plenty of kid-friendly activities in Boston if you’re planning a family vacation. Boston is an ideal weekend getaway in the warmer months, as it’s a very walkable city and a lot of the sights are outdoors. Try planning a long weekend in Boston for Victoria Day or Canada Day.

What to do: A Boston attraction (or a series of attractions, really) that will take you the entire day is the Freedom Trail. Stretching 4 kilometres, this outdoor history museum experience passes through Boston’s oldest neighbourhoods. The Boston Public Garden is a beautiful place to explore, especially during the spring months when the tulips are in bloom. Take the kids to the Boston Children’s Museum, complete with a toddler play area, a science playground and an art studio. The hands-on exhibits are sure to keep everyone entertained (and educated!) for at least a few hours.

Places to eat: The popular Boston restaurant Fire and Ice takes an interactive concept to the dining experience, where you can pick your ingredients (noodles, veggies, meat) buffet-style and the chefs grill your food in front of your eyes on a large circular grill area! The Boston Public Market on Hanover St. has a huge selection of local food including produce, meats, fish, cheese and some gourmet snacks.

Getting around: The neighbourhoods and main sights in Boston are very walkable, so book a hotel in the city to be close to your favourite Boston attractions. The MBTA or “the T” is Boston’s public transportation system which connects the city and metro area by subway, train, bus and ferry. Rent a car and explore the surrounding area of Boston and some of the country’s top universities: Harvard and MIT are just a short drive away from Boston’s city centre.

Find Cheap Weekend Flights from Toronto to Boston

3. Miami

Miami is home to beautiful beaches, art, and culture and makes for a great long weekend getaway

Why visit: With stylish sandy beaches along its shores to booming and beautiful art scenes scattered around its vibrant neighbourhoods, Miami is the closest you can get to paradise on a long weekend getaway from Toronto. When things start to cool down in Toronto, head to Miami over the Remembrance Day long weekend this year or take a longer beach getaway over winter break.

What to do: The Wynwood Art District in the north of Miami features the Wynwood Walls, an outdoor museum home to the works of some of the world’s top graffiti and street artists. Wander and admire the art all day, and all for free! For some outdoor experiences, the Miami Beach Botanical Garden offers free admission and is a beautiful space to explore for a few hours. Take the kids on this Miami vacation to the Miami Children’s Museum, where you can spend the day enjoying interactive exhibits like Pet Central, Sketch Aquarium, and the Construction Zone. Of course, you should leave space in the itinerary for Miami’s many beaches. Head to Miami Beach and head south until the infamous South Beach.

Places to eat: A top-rated Miami restaurant is the Yardbird Southern Table & Bar, which serves some of the best soul food in the city. For some excellent Cuban cuisine in a classy setting, try the Versailles Restaurant along the popular Calle 8. And if you just can’t get enough, the real Havana is less than an hour away.

Getting around: The Miami Trolley is free and an easy way to get around major attractions and tourist areas like Miami Beach, Wynwood, Downtown and Little Havana. Rideshare apps like Uber and Lyft are also very popular ways to get around Miami.

Find Cheap Weekend Flights from Toronto to Miami

4. Washington D.C.

Fill your vacation time in D.C. with visits to free museums, walkable outdoor sights and excellent food

Why visit: From alternative neighbourhoods to world-class museums, the U.S. capital might surprise you! This city is filled to the brim with sights that can easily fill a long weekend vacation with friends or the family. Washington D.C.’s weather is comfortable throughout the year, but the most popular time to visit is in the spring to see the cherry blossoms.

What to do: There are 11 Smithsonian Museums located in the National Mall area of D.C., most notably the National Museum of African American History and Culture, the National Museum of American History with exhibits of the best of American pop culture and politics, and the Air and Space Museum. There’s an IMAX theatre closeby if you want to keep the kids extra entertained. The National Mall from the U.S. Capitol Building to the memorial lawns of the Vietnam and Korean wars to the Lincoln Memorial were designed to be walked and wandered through day or night. The Lincoln Memorial is particularly picturesque at nighttime. Plus, all of the museums and sights in Washington D.C. are free!

Places to eat: For excellent food options and atmosphere, head to the neighbourhood of Georgetown. Along Wisconsin Avenue, you can choose between establishments like Martin’s Tavern or head south to Chaia Tacos Georgetown for some tasty vegetarian and vegan tacos made with homemade corn tortillas.

Getting around: The main areas and attractions of Washington D.C. are easily accessible by the city’s metro system. The National Mall is one of the most walkable sights in the country, so bring comfortable shoes and get exploring.

Find Cheap Weekend Flights from Toronto to Washington

5. Quebec City

Spend the long weekend enjoying Quebec’s unique history, culture, and food

Why visit: The quaint capital city of the province of Quebec has so much to see and do for a weekend trip. Boasting some noteworthy natural sights and plenty of historical landmarks, a quick getaway to Quebec City can easily fill more than a few days of exploring. Spend your Canada Day weekend or Civic Holiday in Quebec City, when the weather is warm and sunny and you can dine on a restaurant patio on the cobblestone streets of Old Quebec.

What to do: From the Citadel to the Plains of Abraham, the world-class Museum of Civilization and the UNESCO World Heritage Site of the Fortifications; the only preserved walled city of its kind in all of Canada and the U.S., French colonial history of North America tells its story here in Quebec City. Be sure to spend a few hours wandering the Quartier Petit Champlain in Old Quebec. Just a short drive north of downtown is the nearby Montmorency Falls, one of the top natural sights in Quebec City. Towering at 83 metres, these falls are higher than the ones in Niagara Falls!

Places to eat: Check out the Marche du Vieux-Port and get some of the freshest produce, meats and cheese from local farmers. For a top-notch farm-to-table dining experience, the chef at Légende par la Tanière shows his guests the best food that this Boreal region has to offer. If you’re looking for some authentic French Canadian fare, try the Buffet de L’Antiquaire, which serves classic Québécois dishes.

Getting around: The Old Town is very walkable and a lot of the major sights in Quebec City are within close proximity to each other. The RTC is Quebec’s public transportation system which connects the main neighbourhoods and main attractions. You can get a day pass for $8.25 and single fares are $3.50.

Find Cheap Weekend Flights from Toronto to Quebec City

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