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
- Get a bird’s eye view of the city from the John Hancock Center. Buy tickets ahead of time for this, because you save so much time not waiting in line
- Check out the Broadway in Chicago shows
- Get your laugh on at The Second City – such good improv comedy!
- See the Chicago Blackhawks take on your favourite hockey team
- Take in any of the other sport teams that Chicago has to offer
- Go skating on the ribbon-shaped rink in Maggie Daley Park (or any of the other outdoor rink options)
- Visit the Christmas Kindlemarket to eat some German-cuisine and get your Christmas shopping in
- Walk Michigan Ave (The Magnificent Mile) to take in the Christmas lights and decorations
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
- 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
- The Dearborn – you have to experience their breakfast
- The Purple Pig – delicious Mediterranean-cuisine and great for sharing
- Au Cheval – the best burger
- Maple and Ash – if you want to splurge, this is my husband’s fav spot
- True Food Kitchen – if there is ever a True Food spotting, you will find me there!!
- The Capital Grille – steakhouse option
- Alinea – I haven’t done this one, but if you’re searching for 3 Michelin Star spots, this is one!
I hope you see the best sights and eat the best food…deep-dish style!