Chicago Illinois 7 Day Itinerary

7-Day Itinerary for Travelling in Chicago, Illinois

Day 1: Arrival and Exploring the Loop

  • Morning: Arrive in Chicago and check-in to your hotel. Recommended hotels include:
    • The Langham Chicago (luxury)
    • Hotel EMC2 (boutique)
    • Hyatt Centric The Loop Chicago (mid-range)
  • Afternoon: Start your day at Millennium Park, where you can take a stroll through the beautiful Lurie Garden and snap a photo in front of the famous “Cloud Gate” sculpture (also known as “The Bean”).
  • Evening: Head to State Street for dinner and shopping. Try:
    • The Berghoff Restaurant (German-American cuisine)
    • Lou Mitchell’s (classic American diner)
    • The Wit Hotel’s ROOF bar for a drink with a view
  • Tips:
    • Buy a Ventra Card or a Chicago Transit Authority (CTA) Visitor Pass for easy travel on public transportation.
    • Take advantage of the city’s many free museums and attractions on certain days of the week or month.

Day 2: Museums and Navy Pier

  • Morning: Spend the morning exploring one of Chicago’s world-class museums:
    • The Art Institute of Chicago (free admission on Thursday evenings)
    • Field Museum (home to Sue, the largest T. rex skeleton ever found)
    • Museum of Contemporary Art (free admission on Tuesdays)
  • Afternoon: Head to Navy Pier for lunch and entertainment options like boat cruises or an amusement park ride.
  • Evening: Enjoy dinner at:
    • Girl & the Goat (Mediterranean-inspired cuisine from Top Chef winner Stephanie Izard)
    • The Purple Pig (small plates and wine)
    • Black Dog Gelato (unique flavors and treats)
  • Tips:
    • Take a stroll along the Lakefront Trail for beautiful views of Lake Michigan.
    • Consider purchasing a Chicago CityPASS for discounted admission to several attractions.

Day 3: Wicker Park and Bucktown

  • Morning: Explore the trendy neighborhoods of Wicker Park and Bucktown, known for their vintage shops, independent coffee houses, and street art.
  • Afternoon: Visit the iconic Wrigley Field (even if you’re not a baseball fan) and take a stroll through the surrounding Lakeview neighborhood.
  • Evening: Enjoy dinner at:
    • Big Star (tacos and whiskey)
    • The Polo Café (American bistro fare)
    • Margie’s Candies (old-fashioned ice cream parlor)
  • Tips:
    • Take advantage of the free parking in Wicker Park and Bucktown.
    • Explore the many independent bookstores, record shops, and boutiques.

Day 4: Lincoln Park and Zoo

  • Morning: Spend the morning exploring Lincoln Park, including a visit to the Lincoln Park Zoo (free admission).
  • Afternoon: Take a stroll through the beautiful North Avenue Beach or rent a bike and ride along the Lakefront Trail.
  • Evening: Enjoy dinner at:
    • Alinea ( avant-garde, experimental cuisine)
    • The J. Parker ( rooftop bar with great city views)
    • Pequod’s Pizza (deep-dish pizza institution)
  • Tips:
    • Take a free yoga class in Lincoln Park during the summer months.
    • Visit the Peggy Notebaert Nature Museum for a unique look at Chicago’s natural history.

Day 5: Architecture and The 606

  • Morning: Take an architecture river cruise or walking tour to learn about Chicago’s rich architectural history.
  • Afternoon: Explore The 606, an elevated trail built on a former rail line, offering great city views and access to several parks.
  • Evening: Enjoy dinner at:
    • Girl & the Goat’s Little Goat Diner (breakfast and brunch options)
    • Au Cheval (trendy diner with a focus on eggs and burgers)
    • Blackbird (modern American cuisine with a focus on local ingredients)
  • Tips:
    • Take advantage of the many free outdoor concerts and movie screenings during the summer months.
    • Explore the many unique neighborhoods, each with its own character and charm.

Day 6: Hyde Park and The University of Chicago

  • Morning: Visit the Museum of Science and Industry (free admission on certain days) or take a stroll through the beautiful Hyde Park neighborhood.
  • Afternoon: Take a tour of the University of Chicago campus, including the stunning Rockefeller Chapel.
  • Evening: Enjoy dinner at:
    • A10 (American cuisine with a focus on local ingredients)
    • The Promontory ( upscale American bistro fare)
    • Valois Restaurant (Cajun and Creole cuisine)
  • Tips:
    • Take advantage of the free museum days or discounted admission with a Chicago CityPASS.
    • Explore the many unique shops and boutiques in Hyde Park.

Day 7: Departure

  • Morning: Spend the morning shopping for souvenirs or visiting any last-minute attractions.
  • Afternoon: Head to Midway International Airport (MDW) or O’Hare International Airport (ORD) for your departure flight.
  • Tips:
    • Consider purchasing a Chicago souvenir, such as a Deep-Dish Pizza-shaped keychain or a Cubs hat.
    • Leave some extra time in case of traffic or security delays at the airport.

Transportation

  • CTA ‘L’ Train: The easiest way to get around Chicago is by using the CTA ‘L’ train system. Purchase a Ventra Card or a Chicago Transit Authority (CTA) Visitor Pass for easy travel.
  • Ride-Sharing: Uber and Lyft are widely available in Chicago.
  • Taxi: Taxis are also an option, but be aware that they may not be as readily available as ride-sharing services.

Things to Know

  • Weather: Be prepared for unpredictable Midwestern weather. Pack layers and waterproof gear.
  • Tipping Culture: Tip 15-20% at restaurants and bars.
  • Safety: As with any city, take necessary precautions to stay safe. Avoid walking alone in dimly lit areas at night.

Other Things of Interest

  • Chicago Riverwalk: Take a stroll along the Chicago River and enjoy the beautiful views and public art installations.
  • Free Outdoor Concerts and Movie Screenings: During the summer months, many parks offer free outdoor concerts and movie screenings.
  • Farmers Markets: Visit one of the many farmers markets throughout the city to sample local produce and artisanal goods.

Enjoy your trip to Chicago!