New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.Roam Around
4-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a visit to Millennium Park, one of Chicago's most iconic attractions. Here you can see the famous Cloud Gate sculpture (often referred to as 'The Bean') and enjoy the beautiful gardens and architecture.
Afternoon
Head over to Art Institute of Chicago, which is just a short walk from Millennium Park. This world-renowned museum houses an extensive collection of art from around the globe. For lunch, stop by The Purple Pig, known for its delicious Mediterranean-inspired small plates.
Evening
In the evening, take a stroll along Chicago Riverwalk. This scenic pathway offers stunning views of the city's architecture and is lined with bars and restaurants. For dinner, make a reservation at Alinea, one of Chicago's most celebrated fine dining establishments.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.69Millennium Park
Book Now
4.69
Millennium Park
Book Now
4.61Art Institute of Chicago
Book Now
4.61
Art Institute of Chicago
Book Now
4.72Chicago Riverwalk
Book Now
4.72
Chicago Riverwalk
Book Now
Exploring Chicago's Rich History
Morning
Begin your day with breakfast at Wildberry Pancakes and Cafe, famous for its delicious pancakes and hearty breakfast options. Afterward, visit Field Museum, where you can explore fascinating exhibits on natural history.
Afternoon
In the afternoon, head to Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city from one of its tallest buildings. For lunch, try some classic Chicago-style pizza at Lou Malnati's Pizzeria.
Evening
Spend your evening enjoying live music at House of Blues. This iconic venue hosts performances by top artists in various genres. Before the show, have dinner at Girl & The Goat, known for its innovative dishes and vibrant atmosphere.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.56Field Museum
Book Now
4.56
Field Museum
Book Now
4.27Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
4.27
Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
5.00House of Blues
Book Now
5.00
House of Blues
Book Now
Cultural Gems and Scenic Views
Morning
Start your day with a visit to the historic Museum of Science and Industry. This massive museum offers interactive exhibits that are fun for all ages. Grab a coffee at a nearby cafe before heading inside.
Afternoon
After exploring the museum, head over to Hyde Park to see the beautiful campus of the University of Chicago. Don't miss visiting the iconic Frederick C. Robie House, designed by Frank Lloyd Wright. For lunch, try some local favorites at Portillo's Hot Dogs.
Evening
In the evening, take in a show at the legendary comedy club Second City. Known for launching many famous comedians' careers, it's sure to be an entertaining night. Have dinner beforehand at Bavette's Bar & Boeuf, which offers an excellent selection of steaks and seafood.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.31Museum of Science and Industry
Book Now
4.31
Museum of Science and Industry
Book Now
3.51Frederick C. Robie House
Book Now
3.51
Frederick C. Robie House
Book Now
Second City
Book Now
Second City
Book Now
Architectural Wonders and Waterfront Fun
Morning
Begin your day with breakfast at another local favorite spot: Cafe Ba-Ba-Reeba! . Then head over to explore Chicago Loop , where you can admire some of Chicago’s most impressive skyscrapers.
Afternoon
Take an architectural boat tour along Chicago River , which provides unique perspectives on some iconic buildings while learning about their history from knowledgeable guides . Enjoy lunch afterward nearby at The Publican , known for its farm-to-table cuisine .
Evening
End your day exploring lively Navy Pier; ride Ferris wheel or catch fireworks show if available . Dine waterfront restaurant Joe's Seafood Prime Steak & Stone Crab ; savor fresh seafood & prime steaks
Bedtime
Find amazing hotels in Chicago, Illinois.
4.83Chicago Loop
Book Now
4.83
Chicago Loop
Book Now
4.61Chicago River
Book Now
4.61
Chicago River
Book Now
Final Day in Chicago
Morning
Start your final day with a visit to Adler Planetarium. This fascinating planetarium offers incredible exhibits on space and astronomy, perfect for a morning of exploration. For breakfast, head to Wildberry Pancakes and Cafe, known for its delicious pancakes and hearty breakfast options.
Afternoon
In the afternoon, explore the vibrant Chicago Cultural Center, which features stunning architecture and a variety of art exhibits. For lunch, enjoy some classic Chicago-style deep-dish pizza at Giordano's, a local favorite.
Evening
Conclude your trip with an evening at the iconic Chicago Theatre. This historic venue hosts a variety of performances, from concerts to plays. Before the show, have dinner at Avec Restaurant, known for its Mediterranean-inspired dishes and cozy atmosphere.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.61Adler Planetarium
Book Now
4.61
Adler Planetarium
Book Now
4.71Chicago Cultural Center
Book Now
4.71
Chicago Cultural Center
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?