Weekend Getaway in Chicago

Here are a few highlights from my weekend getaway to Chicago. Including food recommendations, activities and music.

By Anabelle LeblancJuly 13, 2018 Posted in:DestinationsNorth AmericaTravel Inspiration

My sister and I always use concerts or events as an “excuse” to visit a new city. So when the opportunity arose to see Taylor Swift’s reputation Tour in Chicago, we knew we had to take it. We called up our two best friends and next thing I knew – we were all off to Chicago for a weekend adventure.

This was my first time visiting The Windy City and I have to say, I’ve never had a city leave such a wonderful impression on me. Even as we were heading to the airport back home, my friends and I were already talking about when we could come back. It’s crazy how a place can make you feel so inspired!

Chicago is home to a vibrant food scene, a rich history and beautiful architecture. It feels like there is an endless list of things to see and do here, and if you’re like me – you’ll want to try to do as much as possible in your time away! If you’re thinking of heading to Chicago any time soon, here are some of my personal top-rated experiences you might want to check out:

Try Deep Dish Pizza

Chicago is home to the famous deep dish pizza, so obviously it was a must-try! After lots of researching and speaking with Chicago locals, we decided to have our deep dish experience at Pizzeria Uno. Fun fact: this restaurant is actually where deep dish pizza was invented. If you aren’t familiar with deep dish, it is a pizza with a thick crumbly crust, homemade sauce, fresh toppings and an alarming amount of cheese. Perfect for late night eats. So filling, but so tasty!

Architectural Boat Tour

The Architectural Boat Tour is a MUST for anyone visiting this city. The tour is a 75-minute boat ride along the Chicago River. The tour guide highlights key architectural pieces you can see from the waters and some quick history lessons along with it. I learned all about the different architects who built this city, key historical moments, different architectural eras and so much more. It was super informative, fun and it really makes you feel passionate about Chicago. You can feel the pride from all the staff who work this tour. Even if you think you don’t care about architecture, this tour will change your mind. Plus, the boat has tons of seating, snacks and drinks to keep you content on your ride.

Photo-Op with The Bean

Going to Chicago for your first time, you have to do the most classic tourist activity: visit The Bean. Or, Cloud Gate to be more accurate. This iconic sculpture is located in Millennium Park, a very cute area to walk around. We arrived to The Bean late morning. The area was crowded – but not as bad as I thought it was going to be! If you want less people around, I would suggest going early in the morning or late at night. We walked around and took some photos. After, we decided we wanted to get an elevated look so we headed across the street to Cindy’s Rooftop Bar. It’s a hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel. Their upper patio has incredible views of the Bean and downtown Chicago. We were able to grab a drink, relax and get our perfect photo-op.

Explore Navy Pier

Known as Chicago’s lakefront treasure, Navy Pier is a fun area that offers so many experiences and things to do. It’s filled with incredible shops, restaurants and activities. Plus, there’s even a ferris wheel offering all-encompassing views of the city. If you are travelling to Chicago with your family, this area is the perfect place to go. There is something for everyone – no matter your age!

See a Show or Sporting Event


As I have previously mentioned, our trip to Chicago was originally inspired by seeing Taylor Swift. She brought her highly-acclaimed reputation tour to Soldier Field, home to the Chicago Bears, and it was nothing short of incredible. I had never been to an outdoor stadium concert, or even a venue of this magnitude before. Walking through Soldier Field, you see so much history of the Chicago Bears. Even if Taylor Swift isn’t your cup of tea, there are so many great artists and events that come to Chicago. From the famous music festival Lollapalooza to famed baseball games – the entertainment here is amazing.

Eat, Eat and Eat Some More

As an extreme food lover, one of the most important parts of any trip I take is my meals.  The food scene in Chicago did not disappoint. There are so many different culinary options, from Michelin star dining to casual fast food. All the food was high quality and left me wanting more – no matter the price. I could go on and on about all the food I tried here, but I’ll just leave you with a list of some of my favourites:

Alinea: My first-ever 3 Michelin Star dining experience. An 18-course, multi sensory meal that was like no other meal I have had in my life.

Hampton Social: Cute, nautical themed restaurants where you can get seafood, dips and even rose-flavoured doughnuts. 

Shake Shack: Any time I head to a city with Shake Shack, I have to get it. The burgers, fries and shakes are to die for.

Magnificent Mile

Magnificent Mile- Chicago

Somehow in our jam-packed schedule of sightseeing and eating, we managed to fit in some shopping. Along Michigan Avenue, this vibrant, bustling area is home to shopping, cool restaurants, historic buildings and incredible city views. From upscale boutiques to large department stores and even souvenir shops, Magnificent Mile made for one great shopping experience.

The Windy City swept me away and left me inspired. I hope you found my suggestions helpful. Is there anything you think is missing? Let me know so I can plan my next trip!

Plan your perfect trip to Chicago today!

Cheap flight and hotel packages to Chicago.

Anabelle Leblanc