New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
3-Day Chicago Exploration with Iconic Sights and Culinary Delights Itinerary
Last updated: 2024 Jun 14Architectural Marvels and Sky-High Thrills
Morning
Begin your Chicago adventure with a delightful breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. After fueling up, head to the iconic Chicago River 1.5-Hour Guided Architecture Cruise to witness the city's stunning skyline and learn about its renowned architectural history.
Afternoon
For lunch, enjoy the vibrant atmosphere and contemporary Italian cuisine at RPM Italian. Post-lunch, experience the breathtaking views from the Chicago Willis Tower Skydeck and The Ledge and test your courage by stepping out onto the glass-floored Ledge, offering a unique perspective of the city below.
Evening
As the sun sets, savor a sophisticated dinner at The Signature Room at the 95th, where you can enjoy a meal with panoramic views of the city. End your evening with a stroll at the Navy Pier, filled with entertainment options and the stunning Centennial Wheel offering dazzling views of the skyline.
Bedtime
Find amazing hotels in Chicago.
Cultural Wonders and Culinary Journeys
Morning
Kick off your day with a delightful breakfast at The Purple Pig, known for its inventive dishes. Afterward, immerse yourself in art at the world-renowned Art Institute of Chicago, home to a vast collection spanning centuries and continents.
Afternoon
For lunch, head to Eataly Chicago, a vibrant Italian marketplace offering a variety of dining options. Post-lunch, enjoy a leisurely walk at the Millennium Park, where you can't miss the famous "Bean" at the Cloud Gate sculpture.
Evening
Experience the vibrant dining scene of Chicago with dinner at Girl & the Goat, known for its bold flavors and creative dishes. Afterward, take a stroll along the Chicago Riverwalk and enjoy the beautiful riverside ambiance.
Bedtime
Find amazing hotels in Chicago.
Historical Tours and Gastro Pub Grub
Morning
Start your day with a classic Chicago breakfast at Portillo's Hot Dogs, offering a taste of the city's favorite fast foods. Afterward, embark on the Chicago Gangsters and Ghosts Guided Walking Tour to explore the city's notorious past and haunted sites.
Afternoon
For lunch, head to Big Star, a lively spot serving up delicious tacos and craft cocktails. Post-lunch, take a self-guided tour with the Chicago Go City Explorer Pass, allowing you to choose from a range of attractions including the 360 Chicago Observation Deck or the Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus.
Evening
Conclude your Chicago culinary journey with dinner at Kuma's Corner, a rock music-themed burger bar known for its unique, high-quality burgers. End your evening with a visit to The Magnificent Mile, Chicago's premier shopping destination, for a post-dinner stroll and some retail therapy.
Bedtime
Find amazing hotels in Chicago.
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.