Last Updated On: October 15, 2017

Girl’s Guide Chicago goes to Toronto!

My husband and I just got back from a whirlwind, last minute road trip. We had been wanting to do a road trip for awhile and we just couldn’t decide where to go. My husband loves the Bulls so we decided to first go to Cleveland since the Bulls were playing the Cavs. Hang out in Cleveland for a night (because we had both never been). Then the next day, head up to Niagara Falls (I had never been), and then continue on to Toronto (we had both never been). We don’t like super long days in the car so the driving was broken up perfectly. Obviously, we started in Chicago and it was about 3 to 5 hours to each destination. We were really excited to go to another country and to explore another city that we had heard so much about.

You can read about what we did on our road trip below and use this Girl’s Guide to plan your own couple or girlfriend road trip. The whole road trip was five days and I really recommend planning a similar trip. You can also download my 48 Hours in Toronto checklist below to help you plan.

Niagara Falls (Canadian Side)

NiagaraFalls(Canadian Side)

Niagara Falls (Canadian Side)3

NiagaraFalls(Canadian Side)2

After seeing the Bulls game and spending the night in Cleveland. We left mid-morning to drive to Niagara Falls. If you decide to follow along and do the same or similar route we did, head to the Canadian side of the Falls. It’s so cheesy, fun, and beautiful all at the same time. We spent just a couple hours there which was plenty of time for us but you can also spend the night, go to the casinos, or relax at the resorts and enjoy some spa services.

Toronto, Canada

Next stop Toronto! We got into Toronto, late evening so we just hung around the hotel and had dinner. We stayed a the Omni King Edward Hotel which, was really beautiful and ended up being in the perfect location for us. We ended up walking or taking the TTC (Toronto’s transit system) to almost everything we did. If you used the transit system in Chicago, you will find it easy to use in Toronto. It’s basically the same but way nicer than ours!

Day 1

On the first full day in Toronto, we did a lot of walking! I think my husband said 14 miles! However, since we are from Chicago and we do a lot of walking all over the city, we really enjoyed walking and thought it was a great way to see as much as we could.

St. Lawrence Market

From our hotel, we walked just a few short blocks over to St. Lawrence Market. St. Lawerence Market is over on Front Street which is a really cute area with some great bars and restaurants. We didn’t spend long at the market because that’s what it truly was. The market is a great place to try and shop for all different meats and a huge variety of seafood and cheeses. It was interesting to see so definitely stop by.


Eaton Centre Mall

Next, we walked passed and stopped into Eaton Centre Mall. If you love shopping this is a great place to go! This mall is huge and it has stores that are both American and Canadian so you could really spend all day here. It’s perfect for a rainy or cold day in Toronto.


Kensington Market

From the mall, we walked over to Kensington Market. We weren’t sure what to expect but this ended up being one of our favorite areas in Toronto. It’s not a market but a few streets full of brightly colored and funky and fun bohemian stores, bars, and restaurants. We had so much fun shopping in the trendy and vintage stores and just walking around to people watch. We stop for lunch at a place called Rasta Pasta which was AMAZING! If you go, you have to go eat here. Get the gnocchi pasta with the red sauce and the jerk chicken. It’s a different kind of combo but so, so good!





Queen West Shopping District (Queen West at Spadina)

After a 15-minute walk from Kensington and we arrived at our next destination, Queen West Shopping District. Start at Queen and Spadina and explore dozens of trendy boutiques and cool restaurants. For us Chicagoans, it’s definitely the Wicker Park of Toronto.

CC Whiskey Lounge

Before dinner, we walked over a few blocks from our hotel to CC Whiskey Lounge on Front Street. It had great reviews and since my husband is a huge whiskey lover I thought he would enjoy it. They actually had a great happy hour and so much whiskey that my husband was so overwhelmed by all the choices, so he loved it.


The Distillery District

Later that evening, we headed to the Distillery District for dinner. The Distillery District is one of the oldest parts of Toronto. It’s only a few small streets but the streets are cobblestone streets and no cars are allowed. We ate at Cluny’s which was an amazing French restaurant and then we had hot chocolate for dessert at Cacao 70. I LOVE hot chocolate and it did not disappoint! I snapped a photo of this LOVE lock wall. You can purchase a lock, write a message on the lock, and then hang it on the LOVE lock wall.



Day 2

I also have to say there are coffee shops everywhere in Toronto, too many to even mention! We did try a few that were close to our hotel each morning. One was Rooster Coffee, and the other was Neo Coffee.

Front Street and the Gooderham Building

I took this photo of the Gooderham Building during our morning walk with our dog Bella. This is Toronto’s version of the Flat Iron Building in NYC. I thought the area on Front Street, right by our hotel was so cute. It’s part of Old Town Toronto and Downtown.


Castle Loma

I was really excited to go to a castle that is pretty much right in the middle of a city! We took the TTC almost right to Castle Loma. I thought the castle was really beautiful but we saw almost everything in under an hour. It was $27 per person and although I’m glad I went, if you don’t want to spend the money, I would say it’s ok to skip the castle.


Bloor Street and Yorkville

After Castle Loma, we took the TTC back south and got off a the Museum stop to check out Bloor Street and Yorkville. This is the upscale part of Toronto. As soon as we got off the train and walked to Bloor Street, we saw Louis Vuitton right away. Bloor Street is basically Michigan Avenue and Yorkville, which is a few streets over is basically the Gold Coast. I thought the area was really pretty and a perfect area to do some holiday shopping or if you are looking to really treat yourself. We had coffee a Nespresso Cafè. (It’s a tradition that my husband and I have coffee if a city has a Nespresso Cafè. We have been going to different ones, for years!) Then we had lunch at a casual pizza place. Everywhere was really busy because it was right in the middle of lunchtime and we were hungry and didn’t want to wait long for food.

Back to Queen West District

Early evening, we headed back to Queen West and had dinner at this restaurant we had spotted the day before called Peter Pan Bistro. It was really quaint and really delicious. It was the perfect way to end our trip. We enjoyed a slow walked back to our hotel and took a peek in a few stores before enjoying a nightcap in the hotel bar.


If you have any questions about our road trip or if we missed some places in Toronto that we should try on our next visit, please leave a comment below. And be sure to download the checklist below if you would like a little help in planning your trip to Toronto.

Free Download: Save a copy of this checklist I made:
A Girl’s Guide: 48 Hours in Toronto, Canada



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