Chicago, Illinois-5-day-itinerary

Chicago Itinerary: 5 Days of Deep Dish & City Lights

This itinerary balances iconic attractions with hidden gems, catering to a variety of interests.

Where to Stay:

  • The Loop: (Luxury) The Langham, Chicago; (Mid-Range) Hotel Allegro Chicago; (Budget) Freehand Chicago
  • River North: (Luxury) The Godfrey Hotel Chicago; (Mid-Range) Hampton Inn & Suites Chicago Downtown
  • Wicker Park/Bucktown: (Boutique) The Robey; (Airbnb) Abundant options

Transportation:

  • Ventra Card: Essential for public transportation. Load it up for buses and trains.
  • Walking: Many attractions are within walking distance, especially in the Loop and River North.
  • Divvy Bikes: A fun and affordable way to explore.

Things to Know:

  • Chicago weather can be unpredictable. Pack layers!
  • Tipping is expected: 15-20% for restaurants and bars.
  • Reservations are recommended for popular restaurants, especially on weekends.

Day 1: Exploring the Loop & Magnificent Mile

  • Morning: Start with a stroll through Millennium Park, home to Cloud Gate (“The Bean”), Crown Fountain, and Lurie Garden.
  • Lunch: Grab a classic Chicago hot dog (hold the ketchup!) at Portillo’s Hot Dogs.
  • Afternoon: Ascend Willis Tower (formerly Sears Tower) for panoramic city views.
  • Evening: Stroll down Magnificent Mile, window-shop designer boutiques and department stores.

Dinner: Enjoy an upscale steak dinner at Gibson’s Bar & Steakhouse.

Day 2: Culture & History

  • Morning: Explore the Art Institute of Chicago, renowned for its Impressionist collection and American art.
  • Lunch: Savor a deep-dish pizza experience at Lou Malnati’s Pizzeria.
  • Afternoon: Delve into history at the Chicago History Museum or visit the Field Museum with its dinosaur exhibits and ancient artifacts.
  • Evening: Catch a Broadway show in the Theater District.

Dinner: Dine on authentic Italian fare at RPM Italian.

Day 3: Navy Pier & Lakeside Fun

  • Morning: Take a stroll along Navy Pier, enjoy street performers, and ride the Ferris wheel.

  • Lunch: Enjoy casual lakeside dining with stunning views at Riva Crab House.

  • Afternoon: Relax on the sandy shores of Oak Street Beach or rent a kayak and paddle around Lake Michigan.

  • Evening: Indulge in craft cocktails and live music at The Violet Hour, a speakeasy-style bar.

Dinner: Treat yourself to fresh seafood at Monteverde Restaurant & Bar.

Day 4: Neighborhood Exploration

  • Morning: Venture to Wicker Park/Bucktown for trendy boutiques, independent bookstores, and eclectic cafes.
  • Lunch: Grab a delicious brunch at Dove’s Luncheonette.
  • Afternoon: Visit the Lincoln Park Zoo (free entry) or explore the serene Japanese Garden within the park.

Evening: Enjoy live blues music at Kingston Mines, Chicago’s legendary blues club.

Dinner: Savor creative Mexican cuisine at Taqueria El Milagro.

Day 5: Farewell & Final Bites

  • Morning: Indulge in a leisurely brunch at Wildberry Pancakes & Cafe.
  • Afternoon: Visit Garfield Park Conservatory, a stunning indoor botanical garden.
  • Evening: Enjoy a final Chicago-style pizza dinner at Pequod’s Pizza (known for its caramelized crust).

Before departing, pick up some souvenirs at Garrett Popcorn Shops or the iconic Marshall Field’s department store.

Other Activities & Tips:

  • Architecture River Cruise: A unique way to see the city’s skyline and learn about its architectural history.
  • Museum of Science and Industry: Interactive exhibits for all ages.
  • Second City: Catch a hilarious improv comedy show.
  • Explore different neighborhoods: Pilsen (Mexican art & culture), Chinatown (authentic cuisine).
  • Use Yelp and TripAdvisor to research restaurants and activities.

Have an amazing time in Chicago!