New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

5-Day Chicago Exploration with Unique Tours and Culinary Delights

5-Day Chicago Exploration with Unique Tours and Culinary Delights Itinerary

Last updated: 2024 Jun 14

Iconic Landmarks and River Cruises

Morning
Start your Chicago adventure with a skip-the-line visit to the 360 Chicago Observation Deck, where you'll enjoy breathtaking panoramic views of the city and Lake Michigan. After taking in the skyline, head to Millennium Park to see the famous Cloud Gate (The Bean) and the serene Lurie Garden.
Afternoon
Experience the city's architecture on a Chicago River 1.5-Hour Guided Architecture Cruise, learning about the history and design of the buildings along the river. After the cruise, enjoy a delightful lunch at Cindy's Rooftop, known for its stunning views and seasonal American cuisine.
Evening
Stroll down the Magnificent Mile for some upscale shopping and then have a relaxing dinner at The Gage, offering a menu with a focus on local, seasonal, and sustainable ingredients. End the evening with a visit to the historic Chicago Theatre to admire its grandeur.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago 360 Chicago Observation Deck General Admission in Chicago
star4.37

360 Chicago Observation Deck

Book Now
Visit Millennium Park in Chicago
star4.69

Cloud Gate (The Bean)

Book Now
next arrow

Museums and Cultural Delights

Morning
Begin your day with an early VIP tour of the Field Museum of Natural History, where you can explore the world of natural history and anthropology. After the tour, enjoy a hearty breakfast at Miller's Pub, a classic Chicago spot known for its comfort food and extensive beer selection.
Afternoon
Spend your afternoon at the Art Institute of Chicago, one of the oldest and largest art museums in the country. After immersing yourself in art, take a break with a guided Favorite Foods Walking Tour, sampling the diverse culinary offerings of the city.
Evening
For dinner, head to Gilt Bar, a trendy spot with a cozy atmosphere and a menu featuring upscale American fare. Afterward, take a leisurely walk along the Chicago Riverwalk to enjoy the city lights and the vibrant nightlife.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Field Museum of Natural History Ticket or VIP Tour in Chicago
star4.68

Field Museum of Natural History

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

Art Institute of Chicago

Book Now
next arrow

Gangsters, Ghosts, and Speakeasies

Morning
Embark on a unique journey through Chicago's dark past with a Chicago Mob and Crime Bus Tour, visiting famous crime scenes and learning about the city's notorious gangsters. After the tour, grab a quick breakfast at New Line Tavern to fuel up for the day.
Afternoon
Continue the theme with a Chicago Prohibition Speakeasies Walking Tour, discovering hidden bars and learning about the era of bootleggers and speakeasies. For lunch, enjoy the casual and laid-back atmosphere of Half Sour, known for its delicious sandwiches and craft beer selection.
Evening
As the sun sets, join a Chicago Gangsters and Ghosts Guided Walking Tour to explore the city's haunted history. After the tour, unwind with a sophisticated dinner at 676 Restaurant & Bar, offering a modern take on American cuisine in an elegant setting.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Mob and Crime Bus Tour in Chicago
star4.39

Chicago Mob and Crime Bus Tour

Book Now
Visit Chicago Prohibition Speakeasies Bus Tour or Walking Tour in Chicago
star4.90

Chicago Prohibition Speakeasies Walking Tour

Book Now
next arrow

Neighborhood Charm and Skyline Thrills

Morning
Venture to the vibrant neighborhood of Wrigleyville and visit the iconic Wrigley Field, home of the Chicago Cubs. After a tour of the stadium, enjoy a classic Chicago-style hot dog for breakfast at the nearby Timothy O'Toole's Pub Chicago.
Afternoon
Take a break from the city buzz and spend your afternoon at the serene Lincoln Park Zoo, one of the last free zoos in the country. Afterward, explore the boutiques and cafes in the surrounding Lincoln Park area and have a late lunch at Spectrum Bar & Grill.
Evening
For a thrilling end to the day, experience the city from new heights with a Private Helicopter Tour of Chicago Skyline. Afterward, enjoy a sophisticated dinner at State and Lake Chicago Tavern, where you can savor contemporary American cuisine in a stylish setting.
Bedtime
Find amazing hotels in Chicago.
Visit Wrigley Field in Chicago
star4.86

Wrigley Field

Book Now
Visit Lincoln Park & Zoo in Chicago
star4.29

Lincoln Park Zoo

Book Now
next arrow

Culinary Journey and Evening Delights

Morning
Start your day with a delightful breakfast at Sweetwater Tavern & Grille, known for its warm hospitality and classic American dishes. Afterward, take a leisurely walk along the Chicago Riverwalk to enjoy the morning serenity.
Afternoon
Immerse yourself in the vibrant flavors of Chicago's Chinatown with a Taste of Chinatown Food Walking Tour. Explore the cultural and culinary offerings of the neighborhood and enjoy a variety of authentic dishes. After the tour, take some time to explore the shops and attractions in the area.
Evening
Conclude your Chicago journey with a memorable dinner at Snickers Bar & Grill, where you can enjoy a mix of classic and innovative dishes in a lively atmosphere. After dinner, head to the Skydeck Chicago at Willis Tower (Sears Tower) to witness the city lights from the 103rd floor and perhaps step out onto the glass-floored Ledge for a thrilling experience.
Bedtime
Find amazing hotels in Chicago.
Visit Chicago Riverwalk in Chicago
star4.72

Chicago Riverwalk

Book Now
Visit Chicago Taste of Chinatown Food Walking Tour in Chicago
star4.79

Taste of Chinatown Food Walking Tour

Book Now
next arrow

Top Chicago Travel Videos

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