Chicago, Illinois-6-day-itinerary
Day 1: Millennium Park and Downtown Chicago
- Morning: Start your day at Millenium Park (free admission) for a scenic walk through the beautiful Lurie Garden. Take a stroll around the famous “Cloud Gate” sculpture, also known as “The Bean.”
- Lunch: Grab a bite to eat at Lou Malnati’s Pizzeria (average price $15-$20 per entree), located near Millennium Park.
- Afternoon: Visit the Art Institute of Chicago ($20 admission), one of the top art museums in the country. Be sure to check out the famous American Gothic painting by Grant Wood and Claude Monet’s water lily paintings.
- Evening: Catch a show or concert at the Chicago Theatre (tickets vary in price) or grab dinner at Alinea, a Michelin-starred restaurant with a unique tasting menu experience (average price $250 per person).
- Accommodation: Stay at the Hotel Monaco Chicago (average price $200-$300 per night), located near Millennium Park.
- Things to Know:
- Be prepared for large crowds and long lines at popular attractions during peak season (June-August).
- Take advantage of the “Chicago Architecture River Cruise” tour, which offers a unique perspective on the city’s iconic buildings.
- Don’t forget to try some classic Chicago-style hot dogs or Italian beef sandwiches!
Day 2: Willis Tower and Navy Pier
- Morning: Visit the Skydeck at the Willis Tower ($22-$32 admission), which features stunning views of the city from the 103rd floor. Take a step out onto the glass balcony for a thrilling experience!
- Lunch: Head to Billy Goat Tavern (average price $15-$20 per entree) for some Chicago-style pizza and burgers.
- Afternoon: Explore Navy Pier, a popular destination with shops, restaurants, and entertainment options like boat cruises and a carousel. Be sure to check out the Crystal Gardens, an indoor botanical garden featuring tropical plants and waterfalls.
- Evening: Enjoy dinner at The Purple Pig (average price $30-$40 per entree), a Mediterranean-inspired restaurant with creative small plates.
- Transportation: Take the “L” train from Millennium Park to Willis Tower or Navy Pier.
- Tips:
- Book tickets for the Skydeck in advance to avoid long wait times.
- Don’t miss the stunning views of Lake Michigan and the Chicago skyline at sunset.
Day 3: Lincoln Park and the Magnificent Mile
- Morning: Visit the Lincoln Park Zoo (free admission), one of the oldest zoos in the country, featuring a beautiful botanical garden and a variety of animals.
- Lunch: Grab lunch at The Berghoff (average price $15-$20 per entree), a historic German restaurant with outdoor seating.
- Afternoon: Explore the Magnificent Mile (Michigan Avenue), lined with high-end shops, restaurants, and iconic landmarks like the Tribune Tower. Be sure to take a photo in front of the Chicago Theatre’s iconic sign!
- Evening: Enjoy dinner at Gibsons Italia Steakhouse (average price $30-$40 per entree), located on the Magnificent Mile.
- Accommodation: Stay at the Hotel InterContinental Chicago (average price $250-$350 per night), located near Lincoln Park.
- Things to Know:
- The Lincoln Park Zoo is home to a variety of animal species, including penguins and giraffes!
- Take advantage of the free “Chicago Walking Tours” app for guided tours of the city’s neighborhoods.
Day 4: Wrigleyville and Lakeview
- Morning: Visit Wrigley Field (free admission), one of the oldest baseball stadiums in the country, home to the Chicago Cubs.
- Lunch: Grab lunch at Pequod’s Pizza (average price $15-$20 per entree), a classic Chicago-style pizzeria with deep-dish pies.
- Afternoon: Explore the Wrigleyville neighborhood, known for its vibrant nightlife and sports bars. Take a stroll along Lake Shore Drive for stunning views of Lake Michigan and the city skyline.
- Evening: Enjoy dinner at The Gage (average price $30-$40 per entree), located near Millennium Park with upscale dining options.
- Transportation: Take the “L” train from Wrigleyville to downtown Chicago.
- Tips:
- Check out a Cubs game at Wrigley Field during baseball season!
- Don’t miss the stunning views of Lake Michigan and the city skyline from Lake Shore Drive.
Day 5: Museum Campus and Hyde Park
- Morning: Visit the Shedd Aquarium ($20-$30 admission) on the Museum Campus, featuring stunning aquatic exhibits and a variety of marine life.
- Lunch: Grab lunch at The Red Hot Chicken (average price $10-$15 per entree), a popular spot for fried chicken and Southern-style cuisine.
- Afternoon: Visit the Field Museum ($20-$30 admission) on the Museum Campus, featuring Sue, the largest T-Rex skeleton ever discovered. Be sure to check out the ancient Egyptian exhibit!
- Evening: Enjoy dinner at The Promontory (average price $25-$35 per entree), a restaurant and bar located in the Hyde Park neighborhood with creative small plates.
- Accommodation: Stay at the Hotel Blake Chicago (average price $150-$250 per night), located near Millennium Park.
- Things to Know:
- The Shedd Aquarium features stunning aquatic exhibits, including penguins and dolphins!
- Check out a University of Chicago sports game during baseball season!
Day 6: Jackson Park and the South Side
- Morning: Visit the Museum of Science and Industry ($20-$30 admission), featuring interactive exhibits on science and technology. Be sure to check out the Coal Mine exhibit!
- Lunch: Grab lunch at The Gino’s East (average price $15-$20 per entree), a classic Chicago pizzeria with deep-dish pies.
- Afternoon: Explore Jackson Park, a beautiful park featuring a Japanese garden and the historic Pullman Porters monument. Take a stroll along 53rd Street for unique shops and restaurants.
- Evening: Enjoy dinner at The Purple (average price $20-$30 per entree), a French-inspired restaurant with creative small plates.
- Transportation: Take the “L” train from Museum Campus to Jackson Park.
- Tips:
- Don’t miss the stunning views of Lake Michigan and the city skyline from Jackson Park!
- Explore the unique shops and restaurants along 53rd Street.
Other Tips and Reminders
- Always book tickets or reservations in advance for popular attractions to avoid long wait times.
- Be prepared for crowds and lines during peak season (June-August).
- Try some classic Chicago-style hot dogs, Italian beef sandwiches, or deep-dish pizza!
- Don’t miss the stunning views of Lake Michigan and the city skyline from various locations throughout the city.
- Take advantage of the “Chicago Walking Tours” app for guided tours of the city’s neighborhoods.