New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Ultimate Chicago Architecture and Culinary Experience Itinerary

Last updated: 2024 Jun 14

Iconic Architecture and Deep Dish Delight

Morning

Start your day with a classic Chicago breakfast at Lou Malnati's Pizzeria, known for its deep-dish pizza. After breakfast, head to the Art Institute of Chicago to admire a world-class collection of art.

Afternoon

For lunch, savor the famous burgers at Au Cheval. Afterward, take a stroll down the Magnificent Mile for some shopping and architectural sightseeing, including the historic Wrigley Building.

Evening

In the evening, enjoy a sunset cocktail on a Chicago River Guided Sunset Cocktail & Architecture Tour. End the day with a dinner at Giordano's for another take on Chicago's deep-dish pizza.

Bedtime

Find amazing hotels in Chicago, Illinois.

4.61
Art Institute of Chicago
Book Now

4.65
Magnificent Mile
Book Now

Skyline Views and Gourmet Dining

Morning

Have a leisurely brunch on a Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise, enjoying the skyline views. After the cruise, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory).

Afternoon

For a late lunch, indulge in the Mediterranean small plates at The Purple Pig. Afterward, take a walk in Millennium Park and see the famous Cloud Gate sculpture.

Evening

Enjoy a fine dining experience at Alinea, a three-Michelin-star restaurant. After dinner, take a romantic Chicago 1.5-Hour Romantic Sunset Cruise on Lake Michigan.

Bedtime

Find amazing hotels in Chicago, Illinois.