New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights

Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and River Cruise

Morning
Start your Chicago adventure with a delightful breakfast at Lou Malnati's Pizzeria, known for its famous deep-dish pizza. After breakfast, take a stroll along the Chicago Riverwalk to admire the city's architecture and then head to the historic Wrigley Building.
Afternoon
For lunch, enjoy the vibrant atmosphere and gourmet tacos at Big Star in Wicker Park. Afterward, immerse yourself in the city's history with a visit to the Chicago History Museum or take a guided Chicago Gangsters and Ghosts Walking Tour to explore the city's darker past.
Evening
Dine at The Purple Pig, offering a menu of cheese, swine, and wine in the heart of the Magnificent Mile. Cap off the evening with a breathtaking view of the city from the 360 Chicago Observation Deck (Formerly John Hancock Observatory), where you can also enjoy a drink with your admission ticket.
Bedtime
Find amazing hotels in Chicago.

Art, Science, and Skyline Views

Morning
Enjoy a leisurely breakfast at Lula Cafe in Logan Square. Afterward, visit the world-renowned Art Institute of Chicago to explore its impressive collection, including the iconic "American Gothic" painting.
Afternoon
Have lunch at Eataly Chicago, an Italian marketplace with multiple dining options. Spend your afternoon at the Museum of Science and Industry, where you can interact with hands-on exhibits and learn about various scientific innovations.
Evening
Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. End your day with a serene evening walk at the Chicago River, enjoying the city lights and the cool breeze.
Bedtime
Find amazing hotels in Chicago.

Navy Pier, Lakefront, and Culinary Delights

Morning
Start your day with a breakfast at Little Goat Diner, known for its creative comfort food. After breakfast, head to the iconic Navy Pier to enjoy the attractions, lakefront views, and perhaps a ride on the Ferris wheel.
Afternoon
For lunch, savor the flavors of Mexico at Xoco, a Rick Bayless restaurant in River North. Afterward, take a relaxing walk or bike ride along the beautiful Lakefront Trail, with the shimmering Lake Michigan on one side and the city skyline on the other.
Evening
Indulge in a memorable dining experience at Au Cheval, famous for its mouthwatering burgers and upscale diner ambiance. After dinner, consider catching a live performance at the historic Chicago Theatre or exploring the nearby nightlife.
Bedtime
Find amazing hotels in Chicago.

Day of Museums and Culinary Exploration

Morning
Enjoy a hearty breakfast at Longman & Eagle in Logan Square, known for its farm-to-table cuisine. After breakfast, visit the Field Museum to immerse yourself in natural history and cultural exhibits.
Afternoon
Have a late lunch at Cafe Ba-Ba-Reeba!, where you can enjoy a variety of Spanish tapas. Spend your afternoon at the Shedd Aquarium, exploring the diverse marine life and attending animal presentations.
Evening
Dine at Girl & the Goat, an award-winning restaurant offering a bold menu with global influence. After dinner, take a leisurely walk through the charming neighborhood of Millennium Park, where you can admire the famous "Bean" (Cloud Gate) and the Crown Fountain.
Bedtime
Find amazing hotels in Chicago.

Breweries, Parks, and Skyline Panoramas

Morning
Start your day with a breakfast at Kuma's Corner, a rock music-themed restaurant known for its gourmet burgers. After breakfast, embark on a guided Chicago Craft Brewery Tour by Barrel Bus to sample some of the city's best craft beers.
Afternoon
Enjoy a picnic lunch at Lincoln Park, one of the city's most beloved green spaces. Afterward, visit the Lincoln Park Zoo to see a wide variety of animals from around the world.
Evening
Dine at Smoque BBQ for some of the best barbecue in the city. End your trip with a visit to the Skydeck Chicago at Willis Tower (Sears Tower), where you can step out onto The Ledge for a thrilling glass-bottomed view of the city below.
Bedtime
Find amazing hotels in Chicago.

Top Chicago Travel Videos

kayakFind the right stay during your trip.
Got a question about your trip?