The Best of Chicago for First Time Visitors

Chicago is a world class city filled with amazing restaurants, museums an activities. It’s always wonderful to host out of town guests. For the first time visitor, I’ve compiled my full list of activities and recommendations for you to make the most of your trip. I hope you come back to explore more off the beaten track activities!


  • Chicago is a foodie’s dream. Make reservations for the best restaurants weeks or months in advance for the best times, but if you don’t have reservations, arriving around 5 pm usually means you’ll get a seat.
  • Check out a roof top bar when the weather’s good, but get there early or be prepared to wait. They’re also pricey. 
  • The best place to take photos of the skyline (aside from being on a boat in Lake Michigan) is on the Adler Planetarium’s peninsula.  It’s easy to get to using the lake shore path.
  • Many of the boat cruises and kayak tours have sunset or firework options. You may want to consider doing that–booking in advance is recommended.
  • During the summer, the Shedd Aquarium has Jazzin’ at the Shedd Nights. There’s live music, cocktails and a great view of the fireworks. The Adler Plantarium has a similar program, called Adler After Dark.
  • A hidden gem is the Chicago Cultural Center. Upstairs is the largest Tiffany stained glass dome in the world. The center is free to explore (it used to be a public library) and is right across the street from Millennium Park.
  • Go to the Signature Room for a cocktail and an amazing view of Chicago.
  • Garrett’s Popcorn is a wonderful souvenir.

Must Do’s:

  • Eat Deep Dish Pizza (I recommend Lou Malnati’s, but Pizzeria Uno claims to have invented the style of pizza), Portillo’s and a nice steakhouse. 
  • Eat a nice steakhouse
  • Visit one of the many amazing museums
  • Take a river cruise
  • Enjoy the view from the Signature Lounge at the John Hancock building
  • See a show at Second City’s mainstage
  • Do a shot of  Malort!

Download the activities here.


Recommended reading: 

  • The Devil and the White City
  • The Third Coast: When Chicago Built the American Dream
  • Sin in the Second City: Madams, Ministers, Playboys and the Battle for America’s Soul
  • The Warmth of Other Suns

Fellow Chicagoans, did I miss anything?  Please comment below: