New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.Roam Around
Chicago to Denver Road Trip: Architecture, Food & Nature Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks and Deep Dish Delight
Morning
Start your day with a visit to the iconic The Magnificent Mile, a prestigious section of Michigan Avenue known for its upscale shops. Afterward, take a stroll to the historic Wrigley Building and enjoy the architecture.
Afternoon
For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria, a Chicago classic. Afterward, explore the lively Navy Pier and take a ride on the Centennial Wheel for panoramic views of the city.
Evening
In the evening, head to The Signature Room at the 95th for a cocktail with a view from the John Hancock Center. Enjoy the city lights before calling it a night.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.65The Magnificent Mile
Book Now
4.65
The Magnificent Mile
Book Now
4.39Wrigley Building
Book Now
4.39
Wrigley Building
Book Now
Art, Science, and Sky-high Views
Morning
Begin your day with a visit to the world-renowned Art Institute of Chicago. Explore its vast collection of art and iconic masterpieces.
Afternoon
For lunch, experience the vibrant atmosphere of Xoco, known for its gourmet Mexican cuisine. Afterward, visit the Willis Tower Skydeck and step out onto The Ledge for a thrilling view of the city below.
Evening
Enjoy a leisurely dinner at Girl & The Goat, a top-rated restaurant known for its creative dishes. Afterward, take a night stroll along the Chicago Riverwalk to admire the city lights.
Bedtime
Find amazing hotels in Chicago, Illinois.
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
Gangsters, Ghosts, and Gourmet Delights
Morning
Embark on a Chicago Gangsters and Ghosts Guided Walking Tour to learn about the city's notorious past.
Afternoon
For a unique dining experience, have lunch at Alinea, a three-Michelin-star restaurant known for its innovative and avant-garde cuisine. Afterward, take a Chicago Architecture Boat Tour with Drinks to enjoy the city's skyline.
Evening
Conclude your day with a Chicago Gourmet Dinner River Cruise, where you can enjoy a delicious meal while cruising along the Chicago River.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.68Chicago Gangsters and Ghosts Guided Walking Tour
Book Now
4.68
Chicago Gangsters and Ghosts Guided Walking Tour
Book Now
4.85Chicago Architecture Boat Tour with Drinks
Book Now
4.85
Chicago Architecture Boat Tour with Drinks
Book Now
4.60Chicago Gourmet Dinner River Cruise
Book Now
4.60
Chicago Gourmet Dinner River Cruise
Book Now
Museums and Culinary Delights
Morning
Spend the morning at the Field Museum and the Shedd Aquarium in the Museum Campus.
Afternoon
For a late lunch, head to Gibsons Bar & Steakhouse for a classic Chicago steak experience. Afterward, visit the Adler Planetarium for a journey through the universe.
Evening
Enjoy a relaxed evening at The Purple Pig, known for its Mediterranean-inspired small plates and extensive wine selection.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.56Field Museum
Book Now
4.56
Field Museum
Book Now
4.75Shedd Aquarium
Book Now
4.75
Shedd Aquarium
Book Now
4.61Adler Planetarium
Book Now
4.61
Adler Planetarium
Book Now
Neighborhood Exploration and Local Eats
Morning
Explore the vibrant neighborhoods of Chicago, starting with a visit to the hipster haven of Wicker Park.
Afternoon
For lunch, try the famous burgers at Au Cheval. Afterward, take a walk in the artistic community of Pilsen and admire the colorful murals.
Evening
Have dinner at Little Goat Diner, a retro-chic diner with a creative menu. End the night with a drink at a local speakeasy.
Bedtime
Find amazing hotels in Chicago, Illinois.
Culinary Tour and Sunset Cocktails
Morning
Indulge in a food tour of Chicago, sampling a variety of local favorites from different neighborhoods.
Afternoon
Enjoy a leisurely afternoon at the Lincoln Park Zoo or take a bike ride along the Lakefront Trail.
Evening
Watch the sunset from the 360 Chicago Observation Deck with a Sip and View Ticket. Then, have a romantic dinner at Alinea.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.29Lincoln Park Zoo
Book Now
4.29
Lincoln Park Zoo
Book Now
4.39Sip and View Ticket
Book Now
4.39
Sip and View Ticket
Book Now
Farewell to Chicago: Brunch and Departure
Morning
Enjoy a leisurely brunch at The Publican, known for its farm-to-table fare and craft beer selection.
Afternoon
Spend your final hours in Chicago exploring the historic architecture of the city or doing any last-minute shopping.
Evening
Depart for your next destination with fond memories of your Chicago experience.
Bedtime
Find amazing hotels in Chicago, Illinois.
Adjacent Cities
What others have been looking for
Find the right stay during your trip.
Got a question about your trip?