Chicago is up there with Nashville for one of my favourite American cities. Chicago feels like a New York Lite to me…lots to do, lots to eat, easy to walk the downtown – all the things! I’ve stayed both at The Gwen and The Omni and both were perfect walking distance for everything we wanted to do. 


Walks & Exploring

  • We did a pedway tour (so random)…I actually don’t recommend doing that, but they have walking tours…would be a nice way to see the sights. Or just walk, walk, walk…so much to see!
  • Hop on a boat!
  • Go get a picture by the Cloud Gate and walk around Millennium Park, taking in the Crown Fountain and more
  • The Art Museum is worth seeing
  • Walk around Grant Park – a lovely spacious area which is one of the oldest parks in the city, and close to the water
  • Visit Navy Pier to eat, drink, and hop on some rides. It’s so beautifully set up around Christmas, and a gorgeous view any other time – it is a true highlight of mine!
  • Wander along the Chicago Riverwalk

Ticketed Events


Great for Kids

  • If you need a ride, Ride in Bliss is wonderful with kids – they have good rental car seats, snacks and music that are kid-friendly, and they are a really unique and wonderful driving option for families travelling in a big city!
  • BabyQuip is always an incredible option for rentals of any kind that you may need for kids while travelling
  • Maggie Daley Park has the coolest playground – you could be there for days! Plus, they have a fun set up in the Winter
  • Play at the Children’s Museum, if you need an indoor activity
  • If you’re a zoo-going family, there is Lincoln Park Zoo
  • And if you want to take in some aquatic life, there is Shedd Aquarium

Now to the Food…



  • Starbucks Reserve – you can decide if it’s overrated or not, but if you want something more upscale to the usual Starbucks, you have five levels to choose from!
  • Ralph’s Coffee – I was a fan of their matcha latte
  • Juice RX – juice or coffee, they have it all

Quick Lunch

  • Eataly – definitely go there!! It’s kind of like a Sunterra on steroids, but there are so many different restaurants in it. This has always been one of my top places in Chicago, in New York, and in Vegas!
  • Lou Malnati’s – a bunch of locals told us they have the best Chicago Deep Dish pizza, and they were right!
  • Pizzeria Due – another local-recommended, Chicago Deep Dish pizza spot
  • sweetgreen – always a fav healthy, quick lunch spot of mine
  • Joe & the Juice – if you want to get hit with some fruit and veggies fast, this is your place
  • Time Out Market – a food court option

Restaurants (Dinner)

I hope you see the best sights and eat the best food…deep-dish style!