Chicago Day Trip Guide

Summer-Time-Chi is in full swing and we can't get enough of it! As boats are making their way to the lake, others are enjoying rooftop views and sips of prosecco. The fun never stops when you're diving into the city for your summer adventures.

Speaking of, I've made a list of the go-to, talk-of-the-town hot spots for you to check out on your next day trip to the city! Shopping, food, site-seeing, and all of the Insta-worthy spots are covered to make it a day to remember.

Read on to find out where you should be headed to next...


  • Michigan Avenue
  • State Street
  • Oak Street
  • Water Tower Place
  • Randolph Street
  • Wicker Park (Thrifting!)
  1. Buffalo Exchange
  2. Crossroads Trading Co.
  3. Kokorokoko
  4. Ragstock


Insta-Worthy Spots

  • The Bean/Millennium Park
  • Lincoln Park Zoo
  • 3 Arts Club Cafe
  • Soho House
  • "Love" Wall (1873 N Damen Ave)
  • The Riverwalk
  • Garfield Conservatory
  • The Art Institute
  • Sprinkles
  • Bombobar
  • Grant Park

"Love" Wall


Garfield Conservatory


Soho House



  • Chicago Architecture Tour
  • Skydeck
  • Navy Pier (weekly fireworks are on Wednesday's and Saturday's)
  • John Hancock Building
  • Seadog Speed Boat Tour
  • Kayaking on the River
  • Divvy Bikes
  • Segway Tour
  • The Art Institute
  • The Shedd Aquarium
  • The Planetarium (and the view is amazing!)

Navy Pier Fireworks


John Hancock Building



Seadog Speed Boat Tour


  • Movie in the Park (every Tuesday night!)
  • Picnic in the Park
  • Oak Street/North Avenue Beach
  • The Buckingham Fountain
  • Wine on the Riverwalk

Buckingham Fountain


*All opinions are my own