New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.Roam Around
5-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Exploring the Loop and Riverwalk
Morning
Start your day with a visit to Chicago Loop. The Loop is Chicago’s bustling business district, known for its iconic architecture and public art. Stroll around and take in the sights of the historic buildings and sculptures.
Afternoon
Head over to Chicago Riverwalk for a leisurely afternoon. The Riverwalk offers stunning views of the city’s skyline along with numerous dining options. For lunch, stop by Portillo's Hot Dogs to enjoy some classic Chicago-style hot dogs.
Evening
End your day with a visit to House of Blues. This legendary music venue offers live performances in an intimate setting. Enjoy dinner while listening to some great music.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.83Chicago Loop
Book Now
4.83
Chicago Loop
Book Now
4.72Chicago Riverwalk
Book Now
4.72
Chicago Riverwalk
Book Now
5.00House of Blues
Book Now
5.00
House of Blues
Book Now
Cultural Gems and Scenic Views
Morning
Begin your day at Art Institute of Chicago. This world-renowned museum houses an extensive collection of art from various periods and cultures. Spend a few hours exploring its galleries.
Afternoon
Afterwards, head to Millennium Park for a relaxing afternoon. The park is home to the famous Cloud Gate sculpture (also known as 'The Bean') and offers beautiful green spaces for a picnic or leisurely walk. Grab lunch at one of the nearby cafes.
Evening
In the evening, visit Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views of the city from one of its tallest buildings. For dinner, dine at Quartino Ristorante & Wine Bar, known for its delicious Italian cuisine.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.61Art Institute of Chicago
Book Now
4.61
Art Institute of Chicago
Book Now
4.69Millennium Park
Book Now
4.69
Millennium Park
Book Now
4.27Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
4.27
Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
Historic Sites and Modern Marvels
Morning
Start your day with a tour of Field Museum. This natural history museum features fascinating exhibits on everything from dinosaurs to ancient civilizations.
Afternoon
Next, make your way to Adler Planetarium for an afternoon under the stars. The planetarium offers engaging shows and exhibits about space exploration. Have lunch at their on-site cafe while enjoying views of Lake Michigan.
Evening
Conclude your day with a visit to Navy Pier. This popular attraction features rides, shops, restaurants, and entertainment options. Enjoy dinner at one of the pier’s many dining establishments.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.56Field Museum
Book Now
4.56
Field Museum
Book Now
4.61Adler Planetarium
Book Now
4.61
Adler Planetarium
Book Now
4.48Navy Pier
Book Now
4.48
Navy Pier
Book Now
Architectural Wonders and Lakeside Leisure
Morning
Kick off your morning with a visit to Wrigley Building, an architectural gem located near the Magnificent Mile. Take some time to admire its beautiful design.
Afternoon
Spend your afternoon exploring Museum of Science and Industry. This museum offers interactive exhibits that are fun for all ages. Have lunch at their on-site restaurant before continuing your exploration.
Evening
Wrap up your day with a stroll along The Magnificent Mile, Chicago’s premier shopping district. Browse through high-end stores or simply enjoy people-watching. For dinner, choose from one of the many upscale restaurants in the area.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.39Wrigley Building
Book Now
4.39
Wrigley Building
Book Now
4.31Museum of Science and Industry
Book Now
4.31
Museum of Science and Industry
Book Now
4.65The Magnificent Mile
Book Now
4.65
The Magnificent Mile
Book Now
Final Day in Chicago
Morning
Begin your last day with a visit to Lincoln Park & Zoo. This free zoo is one of the oldest in the country and offers a wonderful variety of animals and beautiful park grounds to explore. It's a perfect way to start your morning with some fresh air and nature.
Afternoon
In the afternoon, head over to Shedd Aquarium. Located on the Museum Campus, this aquarium is home to thousands of aquatic animals from around the world. Spend a few hours exploring its exhibits and enjoying interactive experiences. For lunch, stop by one of the nearby cafes or food trucks.
Evening
Conclude your trip with an evening at Chicago Theatre. This iconic venue hosts a variety of performances including concerts, comedy shows, and plays. Enjoy dinner at one of the nearby restaurants before catching a show.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.29Lincoln Park & Zoo
Book Now
4.29
Lincoln Park & Zoo
Book Now
4.75Shedd Aquarium
Book Now
4.75
Shedd Aquarium
Book Now
4.71Chicago Theatre
Book Now
4.71
Chicago Theatre
Book Now
Adjacent Cities
What others have been looking for
Find the right stay during your trip.
Got a question about your trip?