Weekend in Toronto: Two-Day Travel Guide

Weekend in Toronto: Two-Day Travel Guide by Chicago-based travel blogger Bows & Sequins

Thinking about spending a weekend in Toronto? Here’s everything I wish I had known before our trip!

Toronto was the first leg of our Canadian road trip between Christmas and New Year’s Eve. We spent a mere two days in Toronto, but packed a ton into those 48 hours!

Toronto gave me Chicago vibes… World-class city on a big body of water, great skyline, distinct neighborhoods, incredible restaurants, and bustling food scene, and nice people, too.

On the flip side, it felt like a very international city, which was great! I always enjoy walking around and hearing a bunch of other languages being spoken in conversations you pass. I think I was kind of surprised by it, though, since it’s just across the lake from the United States. (If you think about it, Wisconsin is just across Lake Michigan from the state of Michigan, and the people and places are quite similar, you know?)

How to Get to Toronto

Getting to Toronto

Toronto is in Canada’s Ontario province, just across Lake Ontario from Niagara Falls and Buffalo, New York. Since we were road-tripping to Quebec, we made the eight-hour drive from Chicago to Toronto. Surprisingly, it’s not a bad drive at all! From Detroit, you cross into Canada through Windsor and then Toronto is another four hours from there.

Just remember to bring your passport! No matter if you’re driving or flying, you’ll have a customs check when you get there.

If you’re planning just a weekend in Toronto, driving probably doesn’t make sense. But there are a few flying options to choose from!

Flying into Toronto

Flying into Toronto seems pretty straightforward, it’s roughly a ~1.5-hour flight from Chicago.

Toronto’s Pearson International Airport: YYZ

Located in Mississauga, Pearson is the main international airport serving the Toronto region. Lots of daily non-stop flights from Chicago on American, United, and Air Canada. Without traffic, it’s a ~30-minute drive from the airport to downtown Toronto.

Billy Bishop Toronto City Airport: YTZ

When you’re looking at flights, you might come across airport code YTZ. Located on the Toronto Islands, YTZ is referred to as the Toronto City Airport. Porter Airlines seems to be the main airline operating out of the island airport, but Air Canada has a few flights as well.

If you’re getting to and from Billy Bishop Airport to the mainland, there’s a free ferry (~3 minutes) every 20 minutes, a pedestrian tunnel (~10-minute walk), as well as a complementary shuttle bus (~15 minutes depending on traffic). The shuttle buses are located on the mainland in front of the Main Terminal/Passenger Tunnel Access Building and downtown on the west side of Fairmont Royal York Hotel (across from Union Station).

You can also get to/from the island airport by car/taxi/Uber/Lyft, but will have to pay the ($15) ferry fee and any applicable parking fees should you take a car across on the ferry.

Flying Porter Airlines

If you’re anything like me, you might be unfamiliar with Porter Airlines. (Admittedly an ORD girlie over here!) Porter Airlines is a low-cost Canadian airline actually headquartered at Billy Bishop Toronto City Airport on Toronto Island. They seem to have daily direct flights from YTZ to many Canadian destinations, as well as Newark, Boston, DC, and Chicago’s Midway airport.

CN Tower at Night with Red & Green Christmas Lights

Where to Stay for a Toronto Weekend Trip

We stayed at the Hilton in Downtown Toronto. The lobby was under construction, which normally wouldn’t be a big deal at all, but since we had Marley with us, it was a colossal cluster. From the lobby, you had to take an escalator down to the basement to access the elevator banks to get to the rooms. Even if Marley did know how to ride on an escalator, it’s extremely dangerous for dog paws. The only elevator access was through a kitchen, which obviously dogs cannot go through for health reasons. So each and every time we had to take her outside, we had to lift all 65lbs of her and hold her on each way of the escalator ride. Especially since it was raining a lot of the time we were there, it was just uncomfortable for all of us.

They notified us two days before the trip to let us know and I honestly wish we would have just booked a different hotel. Dave is not the type for a last-minute change of plans, so we stuck with the original reservation.

We didn’t mind the hotel, though! We had a very spacious room and bathroom, which was actually bigger than the suite we had in Quebec City. Plus, it seems like the lobby will be nice once the renovations are done. The Hilton is downtown near the CN Tower, which was a very central location that allowed us to walk to most of the areas we were going to on my first trip to Toronto. Nathan Phillips Square (with the iconic Toronto sign) was just a few blocks away, as was Dundas Square (that’s sort of like Shibuya Crossing meets Times Square, on a much smaller scale).

To be honest with you, I’d probably choose a different area to stay in next time. For my Chicago gals, our hotel location was kind of like staying in the Loop for a weekend trip to Chicago. Very centrally located to most touristy attractions, but not necessarily the vibe I want for a quick weekend trip.

Where I’d Stay in Toronto Next Time

If you only have a weekend in Toronto, my favorite neighborhood that we visited was the Yorkville area. It’s one of the bougier parts of town with fancy hotels like the Four Seasons and the Park Hyatt, but there are some seemingly great and more affordable options nearby, as well. From some quick research, I’d look into the Kimpton Saint George, Canopy by Hilton, The Anndor House, or Royal Sonesta.

Where to Eat + Drink in Toronto

If you’re anything like me, planning your meals is the first thing you do after booking your flight! There’s nothing better than eating and drinking your way through a city. In my opinion, the best (and most valuable) part of any itinerary is the restaurant list!

Chinatown in Toronto

I mentioned this in this blog post, but since we were getting to Toronto on Christmas night, we knew a restaurant in Chinatown was going to be our best option for dinner.

Swatow was at the top of my list, but it was absolutely mobbed and we were too tired to wait. Dumpling House and Hong Kong Bistro Cafe are also highly rated, but there was too long of a line. We ended up eating at Yin Ji Chang Fen and it was fine, but I wouldn’t necessarily add it to your list. Dave did re-discover his love of congee, though, which was a win. And I discovered a beer I like: Kronenbourg 1664 Blanc! It’s like a lighter, lemony version of a Blue Moon. Highly recommend.

Restaurant Recommendations (open on Boxing Day)

On Boxing Day, we ate lunch at d|Bar (by Daniel Boulud) at the Four Seasons. I had the burger, which was absolutely DELISH, as well as a ‘Coffee & Tonic’ mocktail that was made up of espresso and Fever Tree Indian Tonic Water.

We ended up talking to the hotel’s concierge for restaurant recommendations since all of the restaurants on my list were closed for the day. Here’s what he recommended:

  • Adrak
  • Trattoria Nervosa
  • Dimmi Bar & Trattoria
  • Barberian’s Steak House
  • Amal Toronto
  • Blu Ristorante
Weekend in Toronto: Must-Visit Restaurant: Adrak

Must-Visit Restaurant: Adrak

We had the BEST experience at Adrak! It’s an (elevated) Indian restaurant serving delicious food in the coziest venue with chic decor. We sat at the bar and the service was absolutely outstanding. The food and drinks were out of this world, too. We can’t say enough good things about it!

I was thrilled we got there early to snap a few photos of the empty restaurant, as it filled up quickly!

Bar Seating at Adrak in Yorkville Toronto

What to Order at Adrak

To start with cocktails, I had the Magadha and Dave tried the Himalayan. Later, Dave also tried the Maritime Silk Road. We loved them all!

For food, we ordered Prawn Tandoori, Tandoori Gobi Chaat, Thecha Paneer Tikka, Murg Tikka Masala, Garlic Naan, and Pulao Rice.

For dessert, we had the Falooda and two Masala Chais.

Other Restaurants on My List for Next Time

  • Prime Seafood Palace
  • MIMI Chinese
  • Sunny’s Chinese
  • Le Select Bistro in the Fashion District
Nathan Phillips Square in Toronto at Night with Ice Skaters and Iconic Toronto Sign

What to Do in Toronto: Fun Ways to Spend a Weekend in Toronto

If you’re ever planning to be in Canada over the holidays, take note of Boxing Day on the 26th of December. In the US, most things return to regularly scheduled programming on the day after Christmas, but we found that a lot of businesses and restaurants were still closed on Boxing Day. Thankfully, not everything, but it’s something to remember if you’re visiting over the holidays!

Distillery District in Old Toronto with Christian Dior Christmas Tree Decorations

Distillery District

The Distillery District was very cute! It was festively decorated for the holidays and actually had a ton of outdoor vendors. Not realizing that it was primarily outside and dog-friendly, we regrettably left Marley at the hotel for this morning’s activity.

Dave’s been to Toronto for work a few times and has had dinner and drinks outside in the Distillery District, so it’s a great place to explore no matter the time of year.

Dior Christmas Tree in Distillery District Toronto

Shopping in the Distillery District

Not all of the shops were open when we were there first thing in the morning, but we did find the cutest dog store called Sniffany & Co. We grabbed some treats and bully sticks for Marley, as well as a Canadian-themed toy ‘Pawson Canadian.’

Shopping in Distillery District Toronto: Sniffany & Co Pet Store

Coffee in the Distillery District

We got coffee at Balzac’s in the Distillery District, which had the coolest interior with a giant old bar and upstairs seating area. The hot maple latte I got (half sweet) was also excellent, so be sure to add Balzac’s to your list… I’m pretty sure there are locations all over Toronto.

St. Lawrence Market

I saw online that St. Lawrence Market was going to be open on the 26th so we tried to get the notorious Peameal Bacon Sandwich on our walk over to the Distillery District. Sadly, the market was closed on Boxing Day so we went right when they opened on the 27th.

St Lawrence Indoor Market in Toronto

Peameal Bacon Sandwich

Two destinations are serving Peameal Bacon Sandwiches inside St. Lawrence Market. You can see Paddington’s from outside of the market and might be tempted to stop there, but Carousel Bakery is where you want to go! It’s inside on the east side of the market.

Toronto Itinerary Ideas

Since we had such a short time to visit, that felt cut even shorter because of Christmas and Boxing Day, there’s still so much I want to see and do in Toronto. Here are a bunch of things that are on my list for next time!

Graffiti Alley in Toronto

Toronto has a legal street art scene and Graffiti Alley (just off Queen Street near the Ace Hotel) is a great place to see a few blocks worth of outdoor murals.

Royal Ontario Museum

The Royal Ontario Museum is Canada’s largest and most comprehensive museum that showcases art, culture, and nature from around the world and across the ages.

Casa Loma

Located in Midtown Toronto, Casa Loma is a Gothic Revival castle-style mansion and garden that is now a National historic site.

Art Gallery of Toronto

The Art Gallery of Ontario is the the Grange Park neighborhood on Dundas Street West. With a collection of more than 90,000 works of art, it’s among the most distinguished museums in North America.

Kensington Market in Toronto

Located in the heart of Toronto, Kensington Market is one of the most vibrant and diverse neighborhoods in the city. Chinatown is actually within Kensington Market. It’s a multicultural mix of vintage stores, hipster cafes, and affordable hole-in-the-wall restaurants.

On my list for next time is Pancho’s Bakery! They have soft-serve ice cream that’s served in a warm churro cone — YUM!

The Perfect Day: Weekend in Toronto Itinerary

If I was planning out the perfect day, I would start with Carousel Bakery at St. Lawrence Market for peameal bacon sandwiches for breakfast. From there, I’d walk over to the Distillery District for coffee at Balzac’s and some shopping. Wildly Delicious came highly recommended for lunch and they have lots of local syrups and cheeses to buy, as well.

I’d spend the afternoon shopping in Yorkville, followed by dinner at Adrak in the neighborhood. If you’re going out in the Kensington Market area after dinner, I’d swing by Swatow for late-night eats.

Summertime Attractions in Toronto

If you’re visiting in the summer, catching a Toronto Blue Jays game would be fun! (As I mentioned in this post, that was sort of the seed that started this trip!)

The Beaches is a relaxed neighborhood in Toronto with a small-town vibe is a top summer destination, drawing families and tourists to its sandy beaches and quaint boardwalk. Vibrant Queen Street East features indie boutiques, intimate bistros, and bars, along with bakeries and ice cream shops.


1. Is Toronto worth visiting?

We joked that we could have skipped Toronto, but that’s not to say that it’s not worth visiting. We just loved the vibe of Quebec, as it felt more European and that’s what we were after on this trip. I can’t wait to go back sometime and spend a weekend eating and drinking my way through Toronto when everything is open!

2. Is Toronto a good weekend trip?

I think it’s the perfect weekend trip, as it’s a quick flight from both Chicago and New York.

3. Is a weekend enough in Toronto?

Just like spending a weekend in Chicago or New York City, a weekend will put a very small dent in your very long list of places to go. But it’s definitely worth it!

More to Explore

Have you been to Toronto? If so, let me know some of your favorite spots in the comments below.

You can check out this post for all of the outfits I wore on our trip to Canada!

If you’re looking for more city guides, you can find them all here.

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  1. 1.17.24
    instapro said:

    Kudos for the incredible Toronto weekend guide! Your detailed insights on travel, stay, and must-visit spots are pure gold. I am your great Insta follower. Your personal touch makes it feel like we’re exploring Toronto together.

  2. 1.19.24
    Clare said:

    Hey! Toronto local here! So happy you had a great time in a city I have grown up in! There is actually a Balzacs right by the St Lawrence Market (if you didn’t want to walk to Distillery) on the west side (Market st) outside the market!!

    In terms of food recommendations, Trattoria Nervosa is one of my fav Italian spots in the city, and a classic! Super reasonable too.

    A restaurant not mentioned, and you can have both dinner, or snacks and drinks here (perfect for after a show) is Coffee Oysters Champagne (if they ask to take you on a Champagne tour, GO! You are in for a surprise!). Highly recommend seeing the National Ballet of Canada when in the city!

    I could go on and on, but there is also fun things in the West end, along Queen street, including Trinity Bellwoods Park (so fun in the summer), tons of restaurants (far west in Parkdale is a tiki inspired restaurant called Miss Things) and small shops, etc.