The Ultimate Girl’s Weekend in Chicago

Chicago is one of those iconic cities in America with such a rich history yet still feels so young and new thanks to its vast modern skyscrapers surrounding the Windy City. I am very fortunate to have family in Chicago so I got a personal tour of all the fun things to do while visiting! Of course, I had the deep dish pizza, I got to visit Wrigley Field, and The Bean, and more!

(For a quick list, copy and paste this into your notes )



  • Sky Deck Willis tower
  • Chicago Skyline View
  • The Bean
  • Chicago Riverwalk
  • Lincoln Park Zoo
  • North Avenue Beach
  • The shops at North Bridge
  • Ohio Street Beach
  • Navy Pier
  • Magnificent Mile Shopping (Michigan Ave)
  • Grant Park
  • Buckingham Fountain


  • Machine Engineered


  • The Signature room at the 95th
  • TAO Chicago
  • Katana Chicago
  • Lou Malnati’s [PIZZA!!]
  • Beatnik on the River
  • Pierrot Gourmet
  • Sapori Trattoria
  • Ema
  • Wildberry Pancakes & Cafe
  • Cindy’s Rooftop [Lunch or Drinks]

Check out my Instagram story “Chicago” highlights | Follow me on Instagram” @kristinakayla


Brunch at 3 Arts Club Café at RH Chicago, a Restoration Hardware Restaurant

Address: 1300 N Dearborn St, Chicago, IL 60610

This Cafe inside the Restoration Hardware furniture store is one of the most picturesque places I’ve ever been to. The cafe feels like you are outdoors in a beautiful garden. The food itself wasn’t memorable but the ambiance absolutely makes this place worth the visit. Especially if you are a fan of the furniture store.

Maple and Ash

Address: 8 W Maple St, Chicago, IL 60610

This upscale steakhouse restaurant offers amazing means from Two-Michelin-star chef Danny Grant. The dinner was fabulous and we all got to try some of the best food I’ve ever had in my life! The ambiance was such a vibe with a mix of posh and modern aesthetics. I had the seafood tower and a beautiful steak with a Ketel One martini with a lemon twist! (my favorite!)

The Hampton Social

Address: 353 W Hubbard St, Chicago, IL 60654

If you want fun beach vibes in the city, head over for a frozen Rosê at the Hampton Social. This spot has great cocktails and a fun atmosphere. It’s one of the places we visited several times during our weekend trip!

Cocktail at the Purple Pig

The Purple Pig is an award-winning restaurant located on Michigan Ave.

Address: 444 Michigan Ave, Chicago, IL 60611

This restaurant is walk-in only and served some interesting dishes you don’t see often in such as,

  • Greek Tea Brined Chicken Wing
  • Milk Braised Berkshire Shoulder
  • Spanish Octopus
  • Crispy Pig’s Ear

Everything we had from the appetizers down to the dessert was phenomenal. We came by for lunch and they were packed. So look out for seats at the bar, or come by early before the lunch rush to grab a table!

Chicago River Boat Architecture Tours with

Address: 401 N Michigan Ave, Chicago, IL 60611

If you really want to look at Chicago’s history based on its spectacular buildings, you won’t want to skip out on the architecture tower.

The guides were extremely knowledgeable and friendly! I’m a History Nerd so this tour was the highlight of my trip to Chicago.

Skydeck Chicago at Willis Tower | Willis Tower Glass Ledge
Address: 233 S Wacker Dr, Chicago, IL 60606

You won’t experience Chicago until you get a birds-eye view of the city from the Skydeck.

Formally known as the Sears Tower, the Willis Tower is a 180 skyscraper. Not only did we get to visit during sunset but we were fortunate to visit this tower on the 4th of July. Just imagine, a hundred fireworks blasting off at the same time with this view! It was magical!

Sightseeing. Chicago has so much art and beauty in so many corners of the city. It’s also great because the city was pretty walkable. We were able to get from Magnificent Mile, the infamous shopping street to Millennium Park in under 20 minutes of walking.

Wrigley Field
Cloud Gate


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