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5-Day Chicago and Beyond Adventure

5-Day Chicago and Beyond Adventure Itinerary

Published: 2024 Jan 09

City Icons and River Cruises

Morning
Start your Chicago adventure with a Chicago River 1.5-Hour Guided Architecture Cruise, immersing yourself in the city's stunning skyline. After the cruise, enjoy a delightful breakfast at Staytion Market & Bar, known for its fresh and locally sourced ingredients.
Afternoon
Post breakfast, continue with a visit to the iconic Navy Pier, where you can experience the Chicago 45-Minute Family-Friendly Architecture River Cruise for a different perspective. For lunch, head to 312 Chicago for a modern take on classic dishes in a stylish setting.
Evening
As the sun sets, elevate your view at the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with a Chicago 360 Chicago Observation Deck Sip and View Ticket, offering both a drink and a stunning panorama. Conclude the day with dinner at Cindy's Rooftop, enjoying their seasonal menu and one of the best rooftop views in the city.
Bedtime
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Museums and Millennium Park

Morning
Begin with a visit to the Art Institute of Chicago, utilizing your Chicago Art Institute of Chicago Fast-Pass Ticket to explore world-class art. For breakfast, indulge in the vibrant atmosphere and delectable dishes at The Gage, located just a short walk from the museum.
Afternoon
After the museum, take a leisurely stroll through Millennium Park, where you can't miss the famous "Bean" (Cloud Gate). For lunch, head to Miller's Pub, a historic spot offering a wide range of comfort food and a selection of beers.
Evening
Enjoy an evening performance at the Chicago Theatre with the The Chicago Theatre Tour Experience, gaining insights into the theater's rich history. For dinner, experience the elegant ambiance and innovative cuisine at Travelle at The Langham, Chicago.
Bedtime
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Parks, Zoos, and Evening Elegance

Morning
Spend your morning at Lincoln Park & Zoo, exploring the beautiful park and the diverse range of animals. For breakfast, visit South Branch Tavern & Grille (The Loop - Chicago) for a hearty meal in a relaxed setting.
Afternoon
Post-zoo, take a walk through the serene Grant Park, also known as Chicago's "front yard." For lunch, enjoy the riverside dining experience at The Franklin Room, offering a menu of American classics and a wide selection of spirits.
Evening
Dress up for an elegant evening and enjoy a fine dining experience at Gilt Bar, known for its intimate atmosphere and carefully crafted dishes. After dinner, take a leisurely stroll along the Chicago Riverwalk, admiring the city lights and the vibrant nightlife.
Bedtime
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Cultural Delights and Culinary Exploration

Morning
Start with a visit to the Field Museum, immersing yourself in natural history and world cultures. For breakfast, head to About Last Knife, a modern steakhouse offering a unique morning menu.
Afternoon
After the museum, take a short walk to the nearby Shedd Aquarium, where you can explore the wonders of the aquatic world. For lunch, enjoy the casual and friendly atmosphere of Billy Goat Tavern (Millennium Park), a Chicago classic known for its "Cheezborger."
Evening
Experience the vibrant flavors of the city with a Chicago Taste of Chinatown Food Walking Tour, where you'll sample a variety of dishes and learn about the culinary history of Chicago's Chinatown. Conclude the tour with a visit to Elephant & Castle for a relaxed dinner and a drink.
Bedtime
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Sports, Skyscrapers, and Spectacular Farewell

Morning
Explore the legendary Wrigley Field with a guided tour, getting an insider's look at the home of the Chicago Cubs. For breakfast, enjoy the classic American dishes at FireLake Grill House and Cocktail Bar.
Afternoon
After the tour, take a trip to the top of the city at the Skydeck Chicago at Willis Tower (Sears Tower), where you can step out onto The Ledge for a thrilling experience. For lunch, head to State and Lake Chicago Tavern for a relaxed meal in a stylish setting.
Evening
Conclude your Chicago journey with a delightful Chicago Gourmet Brunch, Lunch, or Dinner River Cruise, savoring the flavors of the city while enjoying the beautiful skyline. For a final dinner in Chicago, experience the historic and sophisticated ambiance of The Chicago Chop House, known for its prime steaks and extensive wine list.
Bedtime
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