New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Ultimate 6-Day Chicago Exploration with a Culinary Twist Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and Deep Dish Delights
Morning
Start your Chicago adventure with a visit to the famous The Magnificent Mile, where you can do some shopping and enjoy the vibrant atmosphere of this renowned street.
Afternoon
For lunch, indulge in a classic Chicago deep-dish pizza at Lou Malnati's Pizzeria. Afterward, take a stroll to The Art Institute of Chicago and immerse yourself in world-class art.
Evening
In the evening, head to Millennium Park to see the iconic Cloud Gate sculpture, also known as "The Bean." For dinner, savor a meal at The Purple Pig, known for its Mediterranean-inspired cuisine.
Bedtime
Find amazing hotels in Chicago.
Lakefront Serenity and Sky-High Views
Morning
Enjoy a peaceful morning at Lake Michigan and take a leisurely walk along the Chicago Lakefront Trail.
Afternoon
For lunch, have a beachfront dining experience at Castaways Bar & Grill. Afterward, visit the 360 Chicago Observation Deck for stunning views of the city.
Evening
In the evening, take a Chicago River Guided Sunset Cocktail & Architecture Tour to see the city's skyline transform as the sun sets. Enjoy a delightful dinner at Shore Club, a restaurant with a beautiful view of Lake Michigan.
Bedtime
Find amazing hotels in Chicago.
Museum Day and Culinary Exploration
Morning
Spend your morning at the Field Museum exploring natural history and culture.
Afternoon
For a late lunch, experience the vibrant flavors of Mexico at Rick Bayless' Frontera Grill. Afterward, visit the Shedd Aquarium.
Evening
Enjoy a foodie adventure on the Chicago Gangsters and Food Tasting Walking Tour. Sample a variety of local dishes and learn about the city's history.
Bedtime
Find amazing hotels in Chicago.
Gangsters, Ghosts, and Gourmet Delights
Morning
Embark on the Chicago Mob and Crime Bus Tour to delve into the city's notorious past.
Afternoon
For a unique dining experience, have lunch at The SafeHouse, a spy-themed restaurant. Afterward, take a Chicago Discover the Gangsters & Ghosts of the City's Past walking tour.
Architectural Wonders and Culinary Delights
Morning
Begin your day with a Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's iconic buildings.
Afternoon
For lunch, savor the flavors of Spain at Mercat a la Planxa. Afterward, take a Chicago Riverwalk to enjoy the riverfront views.
Evening
Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse, and then take a Chicago River Guided Architecture Riverboat Tour to see the city's skyline illuminated at night.
Bedtime
Find amazing hotels in Chicago.
Culinary Farewell to the Windy City
Morning
Spend your last morning in Chicago at Navy Pier, enjoying the various attractions and lake views.
Afternoon
For a late lunch, indulge in a seafood feast at Joe's Seafood, Prime Steak & Stone Crab. Afterward, take a final stroll along the Chicago Riverwalk.
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.