New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Chicago Adventure 5 Days Itinerary
Last updated: 2024 Jun 14Welcome to Chicago
Morning
Start your day with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture, also known as 'The Bean.' Stroll through the park and enjoy its beautiful gardens and art installations.
Afternoon
Head over to Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend a few hours exploring its vast collection of artworks from around the world. For lunch, dine at The Purple Pig, known for its Mediterranean-inspired small plates.
Evening
In the evening, take a leisurely walk along Chicago Riverwalk. This scenic waterfront path offers stunning views of the city's architecture. End your day with dinner at Girl & the Goat, a highly-rated restaurant offering innovative dishes.
Bedtime
Find amazing hotels in Chicago.
4.69Millennium Park
Book Now
4.69Millennium Park
Book Now
4.61Art Institute of Chicago
Book Now
4.61Art Institute of Chicago
Book Now
Museum Marvels and City Views
Morning
Begin your day with a visit to Field Museum. This natural history museum boasts an extensive collection of artifacts, including Sue, the largest and most complete T. rex ever discovered.
Afternoon
Afterward, make your way to Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city from one of its tallest buildings. For lunch, enjoy classic deep-dish pizza at Lou Malnati's Pizzeria.
Evening
Spend your evening exploring Navy Pier, a popular destination for entertainment and dining. Enjoy dinner at Joe's Seafood, Prime Steak & Stone Crab, known for its delicious seafood and steaks.
Bedtime
Find amazing hotels in Chicago.
4.56Field Museum
Book Now
4.56Field Museum
Book Now
4.27Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
4.27Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
Architectural Wonders and Local Flavors
Morning
Kick off your day with a visit to Chicago Cultural Center, which hosts free art exhibits and performances in a stunning historic building.
Afternoon
Next, explore the architectural marvels along The Magnificent Mile, Chicago's premier commercial district. Stop for lunch at Portillo's Hot Dogs to try their famous Chicago-style hot dogs.
Evening
In the evening, catch a show at Chicago Theatre, an iconic venue known for its grand marquee and historic charm. Afterward, dine at Alinea, one of Chicago's most acclaimed restaurants offering an unforgettable dining experience.
Bedtime
Find amazing hotels in Chicago.
4.71Chicago Cultural Center
Book Now
4.71Chicago Cultural Center
Book Now
4.65The Magnificent Mile
Book Now
4.65The Magnificent Mile
Book Now
Parks and Planetarium Pleasures
Morning
Start your morning with a relaxing stroll through Grant Park, often referred to as 'Chicago's front yard.' Enjoy its beautiful landscapes and public art installations.
Afternoon
Visit the nearby Adler Planetarium in the afternoon. This planetarium offers fascinating exhibits on astronomy and space exploration. For lunch, head over to Frontera Grill for some delicious Mexican cuisine.
Evening
Conclude your day with an evening visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city skyline. Have dinner at Gibsons Bar & Steakhouse, renowned for its prime steaks and elegant atmosphere.
Bedtime
Find amazing hotels in Chicago.
4.70Grant Park
Book Now
4.70Grant Park
Book Now
4.61Adler Planetarium
Book Now
4.61Adler Planetarium
Book Now
Sports and Music Extravaganza
Morning
Begin your day with a visit to Wrigley Field, one of the oldest baseball stadiums in the country. Take a guided tour to learn about its rich history and maybe even catch a game if the Cubs are playing.
Afternoon
In the afternoon, head over to Lincoln Park & Zoo. This expansive park offers beautiful walking trails, gardens, and a free zoo that's perfect for all ages. For lunch, enjoy some mouth-watering BBQ at Smoque BBQ, known for its tender meats and flavorful sauces.
Evening
Wrap up your Chicago adventure with an evening at House of Blues. Enjoy live music performances in this iconic venue that celebrates blues culture. For dinner, savor some classic American fare at Au Cheval, famous for its burgers.
Bedtime
Find amazing hotels in Chicago.
4.86Wrigley Field
Book Now
4.86Wrigley Field
Book Now
4.29Lincoln Park & Zoo
Book Now
4.29Lincoln Park & Zoo
Book Now
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.