This past weekend my boyfriend, Colin and I took advantage of the Easter long weekend and visited Chicago. Only an 8 hour drive from our home in Toronto we opted to drive instead of fly (you can easily fly from most places) We drove Thursday and stopped in Ann Arbor, Michigan, an adorable University town. Although we didn’t see as much here because we were en route to Chicago we did stop for breakfast at a great spot called Fred’s.

Once we arrived in Chicago we headed straight to our hotel at The Talbott. We loved this hotel so much and we are super happy to have partnered with them to create a video coming soon. Read our full review (also coming soon).

The Talbott Hotel

The Talbott Hotel

Here is our full list of places we loved or places that were recommended to us by locals that we will have to try next time! 


  • Restoration Hardware 3 Arts Club Cafe - This beautiful spot is not only an interior design/furniture store but a stunning spot for food, most well known for their brunch. 

  • The Hampton Social River North  - We loved having our Easter brunch at this adorable restaurant. Featuring white and blue decor with greenery throughout this spot feels like it was made to blog about. The food and drinks were amazing - I would recommend the french toast and a frose! 

  • The Talbott East 20 - Located in the lobby of The Talbott hotel is the bar/lounge and restaurant. Saturday morning of our trip was rainy so we opted for breakfast in bed and honestly it was the best room service I've ever had - smoothie bowls, hash browns and full american-style breakfast it did not disappoint. 

Restoration Hardware Rooftop

Restoration Hardware Rooftop


  • True Food Kitchen - Large open concept restaurant serving fresh salads, bowls, 

  • The Little Beet Table - Healthy bowls and salads in a more business forward area made this spot seem like the perfect work lunch date or a good place to grab a bite while travelling to people watch. 

  • Bernie’s Lunch and Supper - This spot looks super cute and although we didn't get to try it we heard great things. They feature a ladies night, happy hour and a larger dinner menu too! 

  • Parlor Pizza Bar - Always ready for a pizza especially when you can eat in the sunshine on their beautiful patio! 

  • SweetGreen - Any of these locations are great but we stopped at the River North spot to grab a generous size salad for a healthy lunch for our road trip home. 

  • Deep Dish - I used Time Out’s Top Deep Dish Pizza in Chicago and chose Giordano’s and Lou Malnati’s both with many locations.

TIP for any deep dish pizza spot: if you can order in advance order in advance. These little cheese baby pizza’s are hand made to order at most spots and can take 45 mins, which if you’re hungry can seem like a lifetime.

True Food

True Food

True Food Kitchen (Honey Lemonade) 

True Food Kitchen (Honey Lemonade) 

SweetGreen River North

SweetGreen River North

Bernie's Lunch & Supper (courtesy of their website) 

Bernie's Lunch & Supper (courtesy of their website) 

Parlor Pizza Patio (courtesy of their website) 

Parlor Pizza Patio (courtesy of their website) 

Deep Dish Pizza at Lou Malnati's

Deep Dish Pizza at Lou Malnati's


Our first day in Chicago we wandered down to the world famous Magnificent Mile and walked in the tourist crowds towards the river. I generally like to get the touristy things out of the way first and then enjoy the rest of the city.


Here are a few of the top tourist attractions in Chicago. You can easily get a City Pass, which gives you access to most attractions.

  • The Bean - Unless you head here at sunrise you will most likely not get the perfect bean shot. 

  • 360 Chicago / The Skydeck - We opted not to do these attractions and instead made it our mission to find fun rooftops to still get a view without feeling like tourists. 

  • Millenium Park - Wander around this beautiful park with a great view of the city! We heard it's even more beautiful in the summer! 

  • The Wrigley Building - Enjoy the architecture of Chicago surrounding this building. 

The Bean in Millenium Park

The Bean in Millenium Park


Our Favorite Things to Do...

  • The Oak Street Shopping Luxury

  • Lakefront Trail to beach view of the city

  • South Pond Nature Walk in Lincoln Park

  • Bike to Navy Pier Ferris Wheel along the boardwalk - Stop at the beach in the summer! 

  • Architecture Boat Cruise - A great way to see the city and learn about the architecture

  • Shameless House - If you're a fan of the show you won't want to miss driving to the south side to see where they film! 



If you have a sweet tooth after lunch like I do then you should definitely check out these spots…

  • Magnolia Bakery (close to The Bean) Originally from NY this spot seems like a staple for Chicago locals. I suggest trying there salted caramel cupcakes, cookies and famous banana pudding

  • The Doughnut Vault - This spot is tiny and adorable and gathers a large crowd - they bake fresh and are open until they sell out, which can happen quickly we heard so maybe stop by here in the morning and save for your afternoon treat.

  • Stan's Donuts and Coffee - Had this line not been so long we definitely could have enjoyed the donuts! If you're willing to wait they are supposed to be pretty delicious! 



  • Cindy’s Rooftop in the Athletic Association Building for a drink. Note: Make a reservation in advance if you’d like to eat.

  • London House Chicago - Overlooks the river and has a beautiful view of some of the most beautiful buildings. Serving cocktails and apps in the summer. 

  • Apeego - Stop by for late night drinks with a beautiful view of the city. 

  • J Parker Hotel - Another hotel with a great rooftop. 

Cindy's Rooftop

Cindy's Rooftop

The London House Hotel

The London House Hotel

Restoration Hardware

Restoration Hardware



  • RPM Italian - I have mixed feelings about this spot because it was so hyped up to me by friends and family who had been. The atmosphere seemed a bit too touristy, though the food and drinks were tasty. Note: Also make a reservation in advance.

  • GILT Bar - We loved this spot so much. The main dining area feels like you’ve stepped into a movie set. With dark leather lounge areas and tables lining the walls this spot is perfect for a romantic candle light dinner. After dinner and dessert (the food was incredible) head downstairs to Gilt’s hidden speakeasy bar, which actually feels like you've transported in time to Paris. 

  • Cruz Blanca Winery & Tacos  - Although we didn't get to enjoy the tacos we heard they were amazing and served up in this cute spot with a patio in the summer. 

  • Girl and the Goat - We stopped by for drinks one night after dinner and regretted being so full because the food looked incredible. 

  • Pops for Champagne - A cute spot for a happy hour beverage or evening cocktail with live jazz. 

  • Federales Chicago - Serving up Mexican food by day and huge frozen margarita's by night this is a great spot for a night out. Wander around the West Loop and you will find a ton of bars in this area. 

Thanks so much for reading and I hope it inspires you to plan your next weekend getaway to Chicago!