New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Magnificent Mile Marvels: 3-Day Chicago Itinerary Itinerary
Last updated: 2024 Jun 14Iconic Sights and Skyline Splendor
Morning
Start your day with a delightful brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a leisurely stroll along the Magnificent Mile, where you can shop at high-end boutiques and admire the historic architecture.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria. Afterward, visit the Art Institute of Chicago with your fast-pass ticket to explore its world-class art collection.
Evening
In the evening, enjoy a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the city. End the night with a Chicago River Guided Sunset Cocktail & Architecture Tour to see the city lights come alive.
Bedtime
Find amazing hotels in Chicago.
Cultural Immersion and Culinary Delights
Morning
Start your day with a delicious breakfast at Au Cheval, known for its famous burger. Afterward, take a Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's renowned architecture.
Afternoon
For lunch, experience a variety of flavors at Eataly Chicago, a vibrant Italian marketplace. Afterward, visit the 360 Chicago Observation Deck with your skip-the-line ticket for panoramic views of the city.
Evening
Enjoy a unique dining experience at Alinea, a three-Michelin-star restaurant. After dinner, take a leisurely walk along the Chicago Riverwalk to admire the city's skyline.
Bedtime
Find amazing hotels in Chicago.
Museum Marvels and Lakefront Leisure
Morning
Indulge in a leisurely brunch at Lula Cafe, known for its farm-to-table cuisine. Afterward, visit the Field Museum of Natural History or opt for a VIP tour for a more in-depth experience.
Afternoon
For lunch, enjoy a casual meal at Portillo's Hot Dogs, a Chicago institution. Spend the afternoon at the Shedd Aquarium and the Adler Planetarium, both included in your CityPASS.
Evening
Conclude your trip with a dinner at Girl & The Goat, a popular spot for creative small plates. Afterward, take a relaxing Chicago Lake Michigan Skyline Cruise to see the city from a different perspective.
Bedtime
Find amazing hotels in Chicago.
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.