New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14Magnificent Mile and Sky-High Views
Morning
Start your Chicago journey with a delightful breakfast at The Gage, known for its upscale American cuisine. Afterward, take a leisurely stroll along the prestigious Magnificent Mile, where you can explore a wide array of shops, boutiques, and luxury retailers.
Afternoon
For lunch, head to State and Lake Chicago Tavern and savor their modern takes on classic American dishes. Post-lunch, enjoy a skip-the-line visit to the 360 Chicago Observation Deck (formerly John Hancock Observatory) and witness breathtaking panoramic views of the city and Lake Michigan.
Evening
Dine at Cindy's Rooftop, located in the heart of Chicago's Loop with an unbeatable view of Millennium Park. After dinner, take a relaxing evening walk through the park and admire the famous Chicago Theatre before ending your night.
Bedtime
Find amazing hotels in Chicago.
4.65Magnificent Mile
Book Now
4.65Magnificent Mile
Book Now
4.17360 Chicago Observation Deck
Book Now
4.17360 Chicago Observation Deck
Book Now
Cultural Icons and River Cruising
Morning
Enjoy a hearty breakfast at Miller's Pub, a historic Chicago establishment. Post-breakfast, immerse yourself in the world of art at the renowned Art Institute of Chicago with a fast-pass ticket, allowing you to explore at your own pace.
Afternoon
Grab a quick bite at Billy Goat Tavern (Millennium Park) before embarking on a relaxing Chicago River 1.5-Hour Guided Architecture Cruise. Sail under the city's famous bridges and learn about the iconic skyscrapers that line the Chicago River.
Evening
Indulge in a sumptuous dinner at LUXBAR, offering a wide range of American fare. Afterward, take a leisurely walk along the Chicago Riverwalk and enjoy the vibrant nightlife and stunning views of the city's architecture.
Bedtime
Find amazing hotels in Chicago.
4.61Art Institute of Chicago
Book Now
4.61Art Institute of Chicago
Book Now
4.77Chicago River 1.5-Hour Guided Architecture Cruise
Book Now
4.77Chicago River 1.5-Hour Guided Architecture Cruise
Book Now
Lakeside Attractions and Navy Pier Fun
Morning
Start your day with breakfast at Doc B's Restaurant (River North), known for its fresh and flavorful dishes. Afterward, head to the picturesque Navy Pier and enjoy the morning exploring the various attractions and taking a ride on the Centennial Wheel with your express ticket.
Afternoon
For lunch, visit FireLake Grill House and Cocktail Bar and savor their farm-to-table cuisine. Post-lunch, continue your Navy Pier adventure or visit the nearby Chicago Children's Museum for a family-friendly experience.
Evening
Dine at Bar Mar by José Andrés, offering a unique and innovative dining experience. After dinner, catch a live performance at the Chicago Shakespeare Theater or simply enjoy the evening breeze by the lake.
Bedtime
Find amazing hotels in Chicago.
4.48Navy Pier
Book Now
4.48Navy Pier
Book Now
4.43Centennial Wheel
Book Now
4.43Centennial Wheel
Book Now
Museum Marvels and Evening Delights
Morning
Enjoy a delightful breakfast at The Dearborn, known for its contemporary American cuisine. Afterward, kick off your morning with a visit to the Field Museum or the Museum of Science and Industry, depending on your interest.
Afternoon
For lunch, head to Bar Louie - Printers Row and enjoy their casual and lively atmosphere. Post-lunch, take a guided walking tour to explore the city's Gangsters and Ghosts or opt for a more family-friendly Chicago 45-Minute Family-Friendly Architecture River Cruise.
Evening
Dine at Fadó Irish Pub for a cozy and welcoming atmosphere with a taste of Ireland. After dinner, take a stroll through the historic Wrigley Building and cap off your night with a visit to the iconic Wrigley Field if there's a game scheduled.
Bedtime
Find amazing hotels in Chicago.
4.56Field Museum
Book Now
4.56Field Museum
Book Now
4.31Museum of Science and Industry
Book Now
4.31Museum of Science and Industry
Book Now
Culinary Journey and Park Serenity
Morning
Enjoy a delicious breakfast at Plymouth Restaurant & Rooftop Bar, offering a great start to your day. After breakfast, take a morning walk through the serene Grant Park and visit the famous Buckingham Fountain.
Afternoon
For lunch, head to Sweetwater Tavern & Grille (Michigan Plaza - Chicago) and enjoy their wide selection of comfort food. Post-lunch, spend your afternoon at the Lincoln Park Zoo and the adjacent Lincoln Park Conservatory for a relaxing and nature-filled experience.
4.70Grant Park
Book Now
4.70Grant Park
Book Now
4.85Buckingham Fountain
Book Now
4.85Buckingham Fountain
Book Now
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.