New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
5-Day Chicago City Explorer and Culinary Delights Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and Skyline Views
Morning
Begin your Chicago adventure with a visit to the world-famous The Art Institute of Chicago. After immersing yourself in art, take a stroll in the lush Millennium Park. Don't miss the iconic Cloud Gate (The Bean) and the serene Lurie Garden.
Afternoon
For lunch, enjoy the vibrant atmosphere and diverse cuisines at Tong's Tiki Hut. Post-lunch, take an architectural cruise on the Chicago Architecture River Cruise to admire the city's skyline and learn about its renowned buildings.
Evening
Dine at Simon's Restaurant, known for its contemporary American cuisine. Afterward, experience the city from above at the 360 Chicago Observation Deck, where you can enjoy breathtaking panoramic views.
Bedtime
Find amazing hotels in Chicago.
4.42The Art Institute of Chicago
Book Now
4.42The Art Institute of Chicago
Book Now
4.56Cloud Gate (The Bean)
Book Now
4.56Cloud Gate (The Bean)
Book Now
History, Prohibition, and Speakeasies
Morning
Start with a hearty breakfast at More Brewing Company. Then, delve into Chicago's past with a visit to the Chicago History Museum.
Afternoon
Enjoy a guided Prohibition Speakeasies Bus Tour or Walking Tour and learn about the city's notorious history. For lunch, savor the flavors of Chicago on the Ultimate Food Walking Tour with Tastings.
Evening
Experience the unique atmosphere of a speakeasy at Park Boulevard Tavern, where you can enjoy crafted cocktails and a historic ambiance.
Bedtime
Find amazing hotels in Chicago.
4.77Chicago History Museum
Book Now
4.77Chicago History Museum
Book Now
4.90Prohibition Speakeasies Bus Tour or Walking Tour
Book Now
4.90Prohibition Speakeasies Bus Tour or Walking Tour
Book Now
Culinary Delights and Lake Michigan Cruise
Morning
Indulge in a delightful breakfast at Portillo's Villa Park, known for its Chicago-style hot dogs and Italian beef sandwiches. Then, take a leisurely morning walk along the Chicago Riverwalk.
Afternoon
Board the Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise for a luxurious dining experience with stunning views of the city's skyline. After the cruise, explore the Navy Pier's attractions and entertainment.
4.34Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
Book Now
4.34Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
Book Now
4.52Navy Pier
Book Now
4.52Navy Pier
Book Now
Neighborhood Explorations and Sports Excitement
Morning
Start your day with a breakfast at Cemitas Poblanas, offering a taste of authentic Mexican cuisine. Then, explore the vibrant neighborhood of Wrigleyville, home to the historic Wrigley Field.
Afternoon
Immerse yourself in the local craft beer scene with a visit to Chicago Craft Brewery Tour by Barrel Bus. For lunch, enjoy the brewpub experience at Manny's Ale House.
Evening
If it's baseball season, catch a thrilling game at Wrigley Field to witness the passion of Chicago sports. After the game, unwind at Caps Sports Bar & Grill with a drink and some sports talk.
Bedtime
Find amazing hotels in Chicago.
4.95Chicago Craft Brewery Tour by Barrel Bus
Book Now
4.95Chicago Craft Brewery Tour by Barrel Bus
Book Now
Family Fun and Culinary Exploration
Morning
Enjoy a family-friendly breakfast at Wendy's. Then, spend the morning at the LEGOLAND® Discovery Center Chicago, where both kids and adults can indulge in creative fun.
Afternoon
For lunch, visit Hi-View Restaurant, offering a casual dining experience with a variety of dishes. Afterward, explore the interactive exhibits at the Museum of Science and Industry.
Evening
Conclude your Chicago journey with a delightful dinner at Betty's Bistro, known for its warm ambiance and diverse menu. Reflect on your trip as you enjoy your meal.
Bedtime
Find amazing hotels in Chicago.
4.30LEGOLAND® Discovery Center Chicago
Book Now
4.30LEGOLAND® Discovery Center Chicago
Book Now
Top Chicago Travel Videos
Adjacent Cities
Find the right stay during your trip.