Chicago 7 Day Itinerary

Chicago: A 7-Day Itinerary

This itinerary combines iconic landmarks with local favorites, offering a taste of everything Chicago has to offer.

Where to Stay:

  • Budget: Freehand Chicago (hostel vibes), HI Chicago (classic hostel)
  • Mid-Range: The Hoxton Chicago (trendy design), Hotel EMC2 (modern & artistic)
  • Luxury: The Peninsula Chicago (iconic luxury), Langham, Chicago (stunning views)

Transportation:

  • CTA “L” train: Efficient and affordable for getting around the city. Purchase a Ventra card for easy reloading.
  • Divvy bikes: Explore neighborhoods at your own pace.
  • Walking: Many attractions are within walking distance of each other, especially downtown.
  • Taxis & Ridesharing: Uber and Lyft are readily available.

Things to Know:

  • Weather: Chicago experiences all four seasons. Pack layers! Summers can be hot and humid, winters cold and snowy.
  • Deep Dish Pizza: A must-try Chicago delicacy. Lou Malnati’s, Pizzeria Uno, and Pequod’s are popular choices.

Day 1: Downtown Delights

  • Morning: Start with a walk along the Magnificent Mile, window shopping at iconic stores like Macy’s and Nordstrom.
  • Afternoon: Take an architecture boat tour on the Chicago River for stunning views of the city skyline.
  • Evening: Dine at RPM Steak (steakhouse), Girl & the Goat (creative American cuisine), or Au Cheval (burgers).

Day 2: Museum Hop & Millennium Park

  • Morning: Explore the Art Institute of Chicago, home to masterpieces by Monet, Picasso, and Warhol.
  • Afternoon: Stroll through Millennium Park, see Cloud Gate (“The Bean”), Crown Fountain, and enjoy free concerts in the summer.
  • Evening: Catch a Broadway show in the Theatre District or enjoy live blues music at Kingston Mines.

Day 3: Wicker Park & Lincoln Park Zoo

  • Morning: Explore the trendy boutiques, art galleries, and cafes of Wicker Park. Grab brunch at Dove’s Luncheonette (classic diner fare) or Big Star (tacos and tequila).
  • Afternoon: Visit the free Lincoln Park Zoo and see penguins, gorillas, and other animals.

Day 4: Navy Pier & Lake Michigan Cruise

  • Morning: Enjoy the rides, games, and street performers at Navy Pier. Ride the Ferris wheel for panoramic views of the city.
  • Afternoon: Take a scenic boat tour on Lake Michigan.
  • Evening: Indulge in seafood at Shaw’s Crab House or enjoy casual dining with lake views at Riva.

Day 5: History & Culture

  • Morning: Learn about Chicago’s history at the Chicago History Museum.
  • Afternoon: Visit the Field Museum, home to Sue the T-Rex and fascinating exhibits on ancient civilizations.
  • Evening: Enjoy a delicious meal in Chinatown followed by a traditional Chinese opera performance.

Day 6: Garfield Park Conservatory & West Loop Food Scene

  • Morning: Escape to the lush greenery of the Garfield Park Conservatory, one of the world’s largest indoor gardens.
  • Afternoon: Explore the trendy restaurants and bars of Chicago’s West Loop neighborhood. Enjoy brunch atAvec (Mediterranean), dinner at Monteverde (Italian), or drinks at The Aviary (craft cocktails).

Day 7: Farewell & Last-Minute Shopping

  • Morning: Stroll through the Green City Market for fresh produce, flowers, and artisan goods.
  • Afternoon: Do some last-minute souvenir shopping on State Street or in the Magnificent Mile shops.
  • Evening: Enjoy a final Chicago meal at one of your favorite spots before departing.

Tips:

  • Purchase a CityPASS for discounted admission to several attractions.
  • Check local event listings for festivals, concerts, and other happenings during your visit.
  • Take advantage of free activities like Millennium Park concerts, lakefront walks, and museum free days.
  • Be prepared for crowds during peak tourist season (summer).

Have a fantastic time exploring Chicago!