Chicago City Guide (Part I)

Chicago City Guide (Part I)

Chicago, Chicago. What a city! It’s huge, it’s beautiful, and it’s clean. Chicago has amazing architecture, top of the line shopping, award winning food, unlimited selection of museums, and legendary sports teams (just to name a few of the countless things the city has going for it). Chicago sports an incredible city skyline as you might expect, but is unmatched (as far as I’m concerned) as it also has a river running directly through the city and it has a “beach”!

I put together a fairly exhaustive list of what to do, where to eat, and a few recommendations of where to stay in Chicago. We are starting with what to do and where to stay (food comes later, and let me tell you it’s a great list).

Things to Do:


  • See The Bean! If you swing by The Bean also stop by Chicago Athletic Association’s Game Room/Cindy’s Rooftop for an amazing view of the city and a killer cocktail (in our opinion one of the best in the city).
  • Sky Deck: If you can’t leave Chicago without visiting the Sky Deck, I understand. My one recommendation however is to go right when it opens! This way you can avoid 2+ hour long waits.
    • Another option instead of the Sky Deck is to go to the Signature Lounge on the 96th Floor at the Hancock Building, buy a $15 cocktail and the views are very similar. Keep in mind for both of these activities you’ll want a clear visible day!
  • Chances are there is some sporting event in season while you visit! Check out the Cubs, the Blackhawks, the Bulls, the Bears, or the White Sox! Also get yourself a Chicago Dog (hotdog with onions, pickle, relish, celery salt, tomato, and mustard – sounds weird but I actually love it and look forward to it every sporting event).
  • Architecture Boat Tour: It sounds touristy and overall it probably is, but we’ve gone numerous times! Great views of the city from the river/lake and an awesome way to learn about the history and architecture.
    • If you’re going to bypass on the boat tour a great alternative is walking the Riverwalk and grabbing a carafe of wine at City Winery, soaking up the sun (assuming it’s nice out), and watching the yachts go by (and dreaming you had one).
  • Second City: Get tickets to see a hysterical comedy show. Second City is known for improv. Some of their alumni are Steve Carrell, Stephen Colbert, Tina Fey, and Amy Poehler just to name a few!
  • Cold Weather: Ice Skating by the Bean or the Christkindlmarket (be forewarned it gets CROWDED)
  • Warm/Warmish Weather: Rent Divvy Bikes and ride the Lake Front (my favorite skyline view is right behind the Shedd Aquarium), Go to the Beach, if you’re in the area run/walk the 606 Trail
  • Museums: I’m not a pro on this topic, but whatever suits your fancy will be great!
  • Shop/Walk the Magnificent Mile (Mag Mile): A huge Nordstrom with a bar inside, 5 levels of Nike, and some of your other high end shopping store fronts and department stores
  • Other shopping areas I enjoy: Gold Coast/Viagra Triangle (Madewell, Warby Parker, Urban Outfitters, Doc Martens, Rag & Bone, Lululemon, Athleta, Aritzia), and my favorite local boutique Alice & Wonder in Lincoln Park (next to one of my favorite pizza places Homeslice, mentioned in Part II)

If you Happen to be in Town:

  • Flowers for Dreams: Seasonally have some of the most fun floral arrangement workshops
  • Scratch Goods: DIY Face Mask Bar with food grade skin care products. Typically available Saturday and Sunday. Would be a great girls weekend activity!
  • Restaurant Week: Special menus and food discounts (typically a two week period in late January to early February)
  • Lollapalooza: 4 days of crazy music fun, normally the first weekend in August
  • Renegade Craft Fair: We always have the best time at the Renegade Craft Fair when they come to Chicago (typically once per quarter May, July, September, and December)! Even if you aren’t in Chicago when they come check out their calendar for other cities. Handmade ceramics, woodworking, jewelry, candles, and so many unique and beautifully made pieces!

Where to Stay:
We’ve never done a staycation in Chicago, but we’ve talked about it and these would be my top choices for hotels! There are also limitless cool and affordable Airbnbs.

  • Chicago Athletic Association: Located on Michigan Avenue right by the Bean. Home to Cindy’s Rooftop, a Game Room, also has Shake Shack and Limitless Coffee in the lobby.
  • The Robey Hotel: We love having brunch here, and enjoying the tiny pool on the rooftop with a fun creative drink on a nice day!
  • Ace Hotel: Great rooftop bar, also home to City Mouse (another great restaurant spot). Hot location in the West Loop/Fulton Market District area.
  • Soho House (splurge): Hot hot spot! Celebs like Harry Styles stay here. It’s…exclusive. But anyone can enjoy a meal downstairs at The Allis. It’s beautiful and highly Instagrammable.

Part two will be all about food & drink, so GET READY!!



  1. Heather Brewington
    April 14, 2019 / 9:19 am

    This made me think…I’m overdue for a visit!

    • ekanicka
      April 14, 2019 / 11:06 am

      You’re always overdue for a visit! Xoxo

  2. Debs
    April 22, 2019 / 7:54 am

    Great ideas to do in such a fun and scenic city!! Loved the restaurant tour in the West Loop!!

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