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5-Day Chicago Highlights and Culinary Delights

5-Day Chicago Highlights and Culinary Delights Itinerary

Published: 2023 Dec 14

Iconic Landmarks and River Cruises

Morning
Begin your Chicago adventure with a delightful breakfast at Cindy's Rooftop, offering stunning views of the city skyline. Afterward, take a morning stroll along the Chicago Riverwalk to admire the architecture and the iconic Wrigley Building.
Afternoon
For lunch, head to The Gage, known for its upscale yet approachable cuisine. Post-lunch, enjoy a Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's famous buildings and history. After the cruise, visit the Art Institute of Chicago (skip-the-line ticket) to immerse yourself in world-class art.
Evening
Dine at Untitled Supper Club, an intriguing spot with live music and a speakeasy vibe. Afterward, experience the city from above at the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with a "Sip and View" ticket, savoring the panoramic views with a drink in hand.
Bedtime
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Science, History, and Navy Pier Fun

Morning
Enjoy a hearty breakfast at LG's Bar & Kitchen before starting your day at the Museum of Science and Industry (VIP tour). Spend the morning exploring the fascinating exhibits and interactive displays.
Afternoon
For lunch, head to South Branch Tavern & Grille (The Loop - Chicago) for a casual yet satisfying meal. Afterward, take a ride on the Chicago Navy Pier Centennial Wheel Regular & Express Ticket and explore the attractions at this iconic lakeside spot.
Evening
Dine at Lockwood Restaurant & Bar, offering a refined dining experience in the heart of the city. After dinner, if you're up for some entertainment, catch a show at the Chicago Theatre or enjoy the vibrant atmosphere of the nearby State Street.
Bedtime
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Culinary Delights and Evening River Cruise

Morning
Start your day with a classic Chicago breakfast at Miller's Pub, a historic establishment with a warm atmosphere. Post-breakfast, take a leisurely walk through the lush greenery of Grant Park and visit the serene Buckingham Fountain.
Afternoon
Indulge in a gourmet lunch cruise along Lake Michigan with Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise. Enjoy the skyline views and a delicious meal on the water. After the cruise, satisfy your sweet tooth with a visit to the Chicago Museum of Ice Cream (entry ticket).
Evening
For dinner, experience the vibrant atmosphere and diverse menu at Bar Siena. Cap off the evening with a relaxing Chicago River Architecture Cruise Skip-the-Ticket-Office, taking in the city's illuminated skyline from the water.
Bedtime
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Parks, Zoos, and Evening Elegance

Morning
Enjoy a breakfast with a view at Plymouth Restaurant & Rooftop Bar, overlooking the cityscape. Afterward, spend your morning at the Lincoln Park & Zoo, exploring the exhibits and the beautiful park surroundings.
Afternoon
For lunch, head to Sweetwater Tavern & Grille (Michigan Plaza - Chicago) for a casual and satisfying meal. Post-lunch, take a leisurely walk through the serene Lincoln Park, making your way to the historic Toboggan Slide and Statue for a unique photo opportunity.
Evening
Dine at Gilt Bar, known for its upscale American fare and stylish ambiance. After dinner, take a serene evening stroll through the enchanting Alfred Caldwell Lily Pool within Lincoln Park, a hidden gem of nature and design.
Bedtime
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Final Day of Exploration and Farewell Feasts

Morning
Enjoy a delightful breakfast at Five Star Bar, a local favorite with a laid-back atmosphere. After breakfast, take a morning walk along the famous Magnificent Mile, exploring the upscale shops and iconic landmarks.
Afternoon
For your final lunch in Chicago, savor the flavors at FireLake Grill House and Cocktail Bar, offering a menu inspired by the heartland. Afterward, visit the 360 Chicago Observation Deck Skip-the-Line Ticket to bid farewell to the city with one last panoramic view.
Evening
Conclude your Chicago journey with a memorable dinner at Exchequer Restaurant & Pub, a historic spot with a diverse menu. After dinner, if you're in the mood for some post-meal entertainment, consider visiting a nearby jazz club or lounge to enjoy live music and drinks.
Bedtime
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