Chicago, USA-6-day-itinerary

Day 1: Monday

  • Morning: Start your day at Millennium Park (free admission), one of the city’s most iconic landmarks. Take a stroll through the Lurie Garden, and snap a photo in front of the “Cloud Gate” sculpture (also known as “The Bean”).
  • Lunch: Grab a bite to eat at Xoco (average price $10-$15 per person), Rick Bayless’ casual Mexican spot with delicious street food-style dishes.
  • Afternoon: Head over to The Art Institute of Chicago (tickets start at $20), one of the largest and most visited art museums in the country. Be sure to see famous works like “American Gothic” and “Nighthawks.”
  • Dinner: Enjoy dinner at Girl & the Goat (average price $30-$50 per person), a Mediterranean-inspired restaurant from Top Chef winner Stephanie Izard.
  • Where to Stay: Consider staying at The LondonHouse Chicago (average price $200-$300 per night), a luxury hotel located in the heart of the city, within walking distance to many top attractions.
  • Things to Know:
    • Millennium Park is free and open 365 days a year, from 6am to 11pm.
    • The Art Institute of Chicago offers free admission on Thursday evenings from 5pm to 8pm for Illinois residents.
    • Xoco and Girl & the Goat are both popular spots, so be prepared for potential wait times.

Day 2: Tuesday

  • Morning: Take a stroll along the Lake Michigan shoreline at North Avenue Beach (free admission), one of the city’s most popular beaches. You can also rent a bike or take a jog on the adjacent path.
  • Lunch: Grab lunch at Portillo’s (average price $10-$15 per person), a classic Chicago-style hot dog joint with multiple locations throughout the city.
  • Afternoon: Head over to The Field Museum (tickets start at $20), one of the largest natural history museums in the world. Be sure to see Sue, the largest T. rex skeleton ever found.
  • Dinner: Enjoy dinner at Au Cheval (average price $30-$50 per person), a trendy diner with some of the best burgers in the city.
  • Where to Stay: Consider staying at The Kimpton Hotel Allegro Chicago (average price $200-$300 per night), a stylish hotel located in the Loop, within walking distance to many top attractions.
  • Things to Know:
    • North Avenue Beach is free and open 365 days a year, from 6am to 11pm.
    • The Field Museum offers free admission on Thursday evenings from 5pm to 8pm for Illinois residents.
    • Portillo’s and Au Cheval are both popular spots, so be prepared for potential wait times.

Day 3: Wednesday

  • Morning: Take a tour of the historic Wrigley Building (tickets start at $10), one of the city’s most iconic landmarks. Be sure to see the stunning views from the rooftop observation deck.
  • Lunch: Grab lunch at The Purple Pig (average price $20-$30 per person), a Mediterranean-inspired restaurant with multiple locations throughout the city.
  • Afternoon: Head over to Lincoln Park Zoo (free admission, donations encouraged), one of the oldest zoos in the country. Be sure to see the historic carousel and take a stroll through the adjacent park.
  • Dinner: Enjoy dinner at Blackbird (average price $30-$50 per person), a contemporary American restaurant with a focus on seasonal ingredients.
  • Where to Stay: Consider staying at The Hotel Zachary (average price $200-$300 per night), a stylish hotel located in the heart of the city, within walking distance to many top attractions.
  • Things to Know:
    • Wrigley Building tours are available daily from 10am to 5pm.
    • Lincoln Park Zoo is free and open 365 days a year, from 9am to 4pm during the summer months.
    • The Purple Pig and Blackbird are both popular spots, so be prepared for potential wait times.

Day 4: Thursday

  • Morning: Take a stroll through the historic Pilsen neighborhood (free admission), one of the city’s most vibrant and eclectic neighborhoods. Be sure to see the stunning street art and take a photo in front of the iconic Mexican flag mural.
  • Lunch: Grab lunch at Big Star (average price $10-$15 per person), a classic Chicago-style hot dog joint with multiple locations throughout the city.
  • Afternoon: Head over to The Museum of Contemporary Art (tickets start at $20), one of the largest and most visited modern art museums in the country. Be sure to see famous works like “American Gothic” and “Nighthawks.”
  • Dinner: Enjoy dinner at Alinea (average price $50-$100 per person), a cutting-edge restaurant with a focus on avant-garde cuisine.
  • Where to Stay: Consider staying at The Langham Chicago (average price $250-$350 per night), a luxury hotel located in the heart of the city, within walking distance to many top attractions.
  • Things to Know:
    • Pilsen neighborhood is free and open 365 days a year, from 9am to 5pm during the summer months.
    • Big Star is a popular spot, so be prepared for potential wait times.
    • Alinea is one of the most expensive restaurants in the city, with prices starting at $50 per person.

Day 5: Friday

  • Morning: Take a stroll along the Lake Michigan shoreline at North Avenue Beach (free admission), one of the city’s most popular beaches. You can also rent a bike or take a jog on the adjacent path.
  • Lunch: Grab lunch at The Berghoff (average price $10-$15 per person), a classic German restaurant with multiple locations throughout the city.
  • Afternoon: Head over to Navy Pier (free admission, but attractions and activities may have separate fees), one of the city’s most iconic landmarks. Be sure to see the stunning views from the Ferris wheel and take a stroll along the adjacent lakefront path.
  • Dinner: Enjoy dinner at Gibsons Bar & Steakhouse (average price $30-$50 per person), a classic steakhouse with multiple locations throughout the city.
  • Where to Stay: Consider staying at The Sheraton Grand Chicago (average price $250-$350 per night), a luxury hotel located in the heart of the city, within walking distance to many top attractions.
  • Things to Know:
    • North Avenue Beach is free and open 365 days a year, from 6am to 11pm.
    • The Berghoff is a popular spot, so be prepared for potential wait times.
    • Navy Pier has separate fees for some attractions and activities.

Day 6: Saturday

  • Morning: Take a stroll through the historic Wicker Park neighborhood (free admission), one of the city’s most vibrant and eclectic neighborhoods. Be sure to see the stunning street art and take a photo in front of the iconic Mexican flag mural.
  • Lunch: Grab lunch at The Wildberry Cafe (average price $10-$15 per person), a classic American restaurant with multiple locations throughout the city.
  • Afternoon: Head over to The Peggy Notebaert Nature Museum (tickets start at $20), one of the largest and most visited natural history museums in the country. Be sure to see famous works like “American Gothic” and “Nighthawks.”
  • Dinner: Enjoy dinner at Black Dog Gelato (average price $10-$15 per person), a classic gelato shop with multiple locations throughout the city.
  • Where to Stay: Consider staying at The Hotel Julian (average price $200-$300 per night), a stylish hotel located in the heart of the city, within walking distance to many top attractions.
  • Things to Know:
    • Wicker Park neighborhood is free and open 365 days a year, from 9am to 5pm during the summer months.
    • The Wildberry Cafe is a popular spot, so be prepared for potential wait times.

Transportation:

  • Chicago has an excellent public transportation system, with buses and trains (the “L”) connecting many neighborhoods throughout the city.
  • You can also use ride-sharing services or taxis to get around.
  • Consider purchasing a Ventra card for convenient travel on public transportation.

Tips:

  • Be prepared for potential wait times at popular restaurants and attractions.
  • Take advantage of free admission days and discounts at museums and other attractions.
  • Don’t forget to try some of the city’s famous deep-dish pizza!
  • Be sure to tip your servers and bartenders, as they are an essential part of Chicago’s service industry.

I hope this itinerary helps you plan your trip to Chicago! Enjoy your travels!