New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Chicago Architectural Marvels and Culinary Delights

Chicago Architectural Marvels and Culinary Delights Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and Deep Dish Delights

Morning
Start your day with a classic Chicago experience by visiting The Magnificent Mile for some upscale shopping and iconic city views.
Afternoon
Enjoy a deep-dish pizza at Lou Malnati's Pizzeria, a local favorite. Afterward, take a leisurely walk to The Art Institute of Chicago to admire world-class art collections.
Evening
End your day with a visit to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning panoramic views of the city. Then, have a delightful dinner at The Signature Room at the 95th.
Bedtime
Find amazing hotels in Chicago.
Visit The Magnificent Mile in Chicago
star4.65

The Magnificent Mile

Book Now
Visit Art Institute of Chicago in Chicago
star4.61

The Art Institute of Chicago

Book Now
next arrow

Architectural Wonders and River Cruises

Morning
Start your day with a guided tour of the Chicago Riverwalk to learn about the city's architecture and history.
Afternoon
For lunch, savor the flavors of the city at Au Cheval, known for its delicious burgers. In the afternoon, take the Chicago Architecture River Cruise Skip-the-Ticket Line to see the city's iconic buildings from the water.
Evening
Enjoy a relaxing evening with a gourmet dinner cruise on Lake Michigan, experiencing the city's skyline at sunset.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Riverwalk in Chicago
star4.72

Chicago Riverwalk

Book Now
Visit Chicago Architecture River Cruise Skip-the-Ticket Line in Chicago
star4.83

Chicago Architecture River Cruise Skip-the-Ticket Line

Book Now

Museum Exploration and Culinary Journeys

Morning
Spend your morning at the Field Museum of Natural History exploring fascinating exhibits.
Afternoon
For a late lunch, head to Girl & the Goat, a renowned restaurant offering a unique dining experience. Afterward, visit the Shedd Aquarium to see a diverse range of marine life.
Evening
Conclude your day with a culinary adventure at Alinea, a three-Michelin-star restaurant known for its innovative and artistic dishes.
Bedtime
Find amazing hotels in Chicago.
Visit Field Museum in Chicago
star4.56

Field Museum of Natural History

Book Now
Visit Shedd Aquarium in Chicago
star4.75

Shedd Aquarium

Book Now

Gangsters, Ghosts, and Local Brews

Morning
Embark on a tour to Discover the Gangsters & Ghosts of the City's Past to uncover the darker side of Chicago's history.
Afternoon
Enjoy a late lunch at Pequod's Pizza, famous for its caramelized crust. Afterward, take a Craft Brewery Tour by Barrel Bus to sample a variety of local beers.
Evening
Have a casual dinner at Big Star, known for its tacos, and explore the vibrant nightlife of Wicker Park.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago
star4.68

Discover the Gangsters & Ghosts of the City's Past

Book Now
Visit Chicago Craft Brewery Tour by Barrel Bus in Chicago
star4.95

Craft Brewery Tour by Barrel Bus

Book Now

Neighborhood Charm and Culinary Delights

Morning
Explore the trendy neighborhood of Logan Square, known for its street art and unique shops.
Afternoon
For lunch, visit Lula Cafe, a neighborhood gem with a focus on seasonal and local ingredients. Afterward, take a leisurely walk in the nearby Humboldt Park.
Evening
Enjoy a delightful dinner at Longman & Eagle, a Michelin-starred gastropub, known for its creative and locally sourced menu.
Bedtime
Find amazing hotels in Chicago.

Relaxation and Cultural Immersion

Morning
Spend a relaxing morning at the Lincoln Park Zoo, one of the oldest zoos in the country.
Afternoon
Have a leisurely lunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, visit the Chicago History Museum to learn more about the city's past.
Evening
Enjoy a laid-back dinner at Xoco, a popular spot for Mexican street food, by renowned chef Rick Bayless.
Bedtime
Find amazing hotels in Chicago.

Top Chicago Travel Videos

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