Chicago, the Windy City! Like a mini NYC with an insane amount of delicious restaurants, local watering holes and sights to see. OH, and great shopping… let’s not forget that! Here we’ve got a list of must-do’s and must-see’s while you’re visiting this beautiful city.
Stay at the Peninsula Chicago. Their hotel literally just underwent a renovation (April 2016) and they did an amazingly beautiful job. The rooms are stunning and everything is controlled by a master iPad… the new age version of the clap on/clap off lights? Plus, its location is so central to everything and is just off the Magnificent Mile. If you don’t believe it’s one of the best places to stay in town just ask Justin Bieber… oh yes, he was there at the same time as us.
Do the architectural boat tour. Wendella is the original boat tour company however, every local said that no matter which of the companies are taking you out, the tour will be amazing. After the great fire of 1871, most of the buildings downtown Chicago were destroyed and numerous architects assisted in the rebuilding of the downtown core making it a fascinating tour with many original sights to see. If you have any interest in architecture or simply learning about a city’s history this is a must. You’ll probably even learn the true meaning of “The Windy City”!
Millennium Park should also be on your hit list. This is where you can find Cloud Gate/The Bean and play “Where’s Waldo”. It’s actually a very cool public sculpture that can provide ample entertainment. Crown Fountain, an interactive public art piece, and Jay Pritzker Pavilion, which is home to the last remaining free outdoor classical music series, are also located here. No one was performing at Jay Pritzker Pavilion when we went through but we can only imagine how fabulous it would be to watch a show there.
From Millennium Park, head across the street to The Gage for some specialty crafted cocktails in a cozy, classic Chicago bar.
Don’t miss The Sky Deck at Willis Tower. The glass floored ledge at 1,353 feet above ground is surreal as is the view looking out over Lake Michigan!
This part is the easy part for us… where to eat. Let’s start with dinner at RPM Italian. Owned, among many more, by Giuliana and Bill Rancic (something we found out later, we were too focused on the carbonara – not our favourite by the way but everything else was so delicious). The space is quite glamorous, which goes well with your potential to see a celeb dining here. The food, overall, was melt in your mouth delish and their wine and cocktail list are quite extensive with some great options.
Grab lunch on the patio at Nico Osteria, after a morning of shopping along Rush Street. Their burger is so insanely good. We were “roll me home” full after our lunch there… we even go the salad instead of fries. To walk off that burger, finish off your shopping day by walking along Michigan Ave/The Magnificent Mile.
Don’t miss Old Town. A Victorian picturesque side of Chicago that is lined with restaurants and bars. Oh, and don’t miss the comedy clubs here – this is where Second City theatre is!! Every great comic got their start here!!
Chicago is a very walkable city so pack those tennis shoes when you go. Keep your luggage light on the way there because there’s always excuses to hit up Chanel, YSL, Hermes, or Cartier on a weekend getaway… You know, to get a nice souvenir to remember your Chicago trip. When you’re done getting that special souvenir (or maybe still debating it) go grab a cocktail and a burrata plate from Cafe Spiaggia… be careful though, they might seat you right in front of a place you’re trying hard to justify… or forget about…
Michelle & Samantha