Chicago Summer: Bucket List


This is my first summer that I am spending in Chicago and I am SO SO SO excited to to explore new places and be with my friends. This post is inspired by all the bloggers and articles I have read throughout the years. I have wanted to do so many things in the city since I have lived here, three years ago. My favorite thing about Chicago is that there is always something to do! Home of 7,000+ restaurants, the hottest rooftop bars, night life, amazing shopping, fun summer activities. The list goes ON, which is why this post is broken down into categories for all of you readers, looking for something to do this summer! I will be checking these off my list as the summer goes on as well. ENJOY ❤️


  • Rent out a boat to go on Lake Michigan
  • Go see a baseball game – go Cubbies!  💙🐻❤️⚾️ ✓
  • Stroll along the Chicago Riverwalk ✓
  • Kayaking on the river
  • Watch the Navy Pier fireworks ✓
  • Go on a run on Lake Shore Drive
  • Lay out at North Avenue Beach ✓
  • Bike around the city using Divvy Bikes ✓
  • Go to the Art Institute or Museum of Contemporary Art ✓
  • Lincoln Park Zoo (free!) ✓
  • Get tickets to Taste of Chicago
  • Attend the Food Truck Festival ✓
  • Movies in the Park in Millennium Park
  • Go to a concert: Lollapalooza + Spring Awakening + Pitchfork
  • See a Broadway Show (Just went to Hamilton and Dirty Dancing earlier this year!) ✓
  • Beach volleyball


  • Restoration Hardware ✓
  • Summer House Santa Monica
  • Soho House ✓
  • Mahalo ✓
  • Hampton Social ✓
  • Jeni’s Ice Cream ✓
  • Ema ✓
  • Park and Field
  • Broken English
  • Blue Door Farm Stand
  • Sweet Mandy B’s
  • FULTON DISTRICT: West Loop (Restaurant Row)
  • Big Star ✓
  • Parson’s
  • The Cabana Club
  • Home Slice
  • Tavern at the Park
  • The Shore Club
  • Cafe Robey ✓
  • Bombobar ✓


  • Joy District (rooftop) ✓
  • The London House (rooftop)
  • Deuce’s and the Diamond Club ✓
  • Sluggers ✓
  • Concrete Cowboy ✓
  • Cindy’s (rooftop) ✓
  • Paris Night Club ✓
  • Disco ✓
  • The Up Room (rooftop) ✓
  • Three Dots and a Dash
  • Punch Bowl Social
  • Bounce


  • Visit the street and farmers markets: Green City Market + Logan Square Farmers Market
  • Urban Outfitters Surplus (THE GOLD MINE) – 2352 N Clark St, Chicago, IL 60614 ✓
  • Michigan Avenue ✓
  • State Street ✓
  • Randolph Street (West Loop)
photo credits: Ashlee O’Neil

Enjoy your summer!

xoxo — Bree

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