Eat Your Way Through Chicago in 3 Days
Curated By
Claudia Cox
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Adventure Travel
City Travel
Arts & Culture
Food & Wine
Luxury Travel
Chicago
USA
Local Culture
Local Food
Entertainment
Curator’s statement
Get ready for a whirlwind of fancy and flavor with this three-day itinerary designed to satisfy your culinary cravings while providing a taste of Chicago's cultural and scenic offerings. Enjoy your time in the Windy City!
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Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
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Day 1: Culinary Exploration in the Windy City
Morning
Start your day with a luxurious brunch at the renowned Alinea. This three-Michelin-star restaurant offers an avant-garde dining experience that combines art and science. Indulge in their tasting menu for a gastronomic journey like no other.
Afternoon
Take a stroll down the iconic Magnificent Mile for some high-end shopping. Visit Eataly, a bustling Italian marketplace, for a delightful afternoon snack. Savor fresh pasta, artisanal cheeses and authentic gelato.
Evening
For dinner, immerse yourself in the city's vibrant food scene at Girl & the Goat. Chef Stephanie Izard's innovative menu showcases a variety of flavors and textures. Reservations are a must, as this restaurant is a local favorite.
Day 2: Cultural Delights and Gourmet Treats
Morning
Kickstart your day with a visit to the Art Institute of Chicago. Marvel at the world-class art collection, including works by Van Gogh, Monet and Grant Wood. Afterward, head to The Allis at Soho House for a stylish brunch.
Afternoon
Explore the trendy West Loop neighborhood. Visit Fulton Market Kitchen for a unique blend of art and culinary delights. Afterward, stop by Aba for an amazingly delicious Mediterranean lunch overlooking the city.
Evening
For a truly immersive dining experience, book a table at Oriole. This intimate restaurant offers a chef's tasting menu featuring exquisite dishes with a focus on seasonal ingredients. End the night with a stroll along the Chicago Riverwalk.
Day 3: Lakeside Luxury and Nightlife
Morning
Enjoy a leisurely morning at Lake Shore East Park, offering stunning views of Lake Michigan and the city skyline. Have breakfast Beatnik on the River, known for its exotic decor and upbeat atmosphere.
Afternoon
Take a boat tour on the Chicago River for a different perspective of the city. Afterwards, indulge in happy hour at Raised with some great cocktails and bites.
Evening
Cap off your luxurious Chicago experience with a visit to The Aviary. This avant-garde cocktail lounge, created by the team behind Alinea, offers inventive and visually stunning drinks. Afterward, head to a trendy rooftop bar like Chateau Carbide for panoramic views of the city lights.
Need to Know
For more travel tips, check out Fora Advisor Oluwaseyi Aladeselu's guide, How to Spend a Luxury Weekend in Chicago, Illinois.
Travel Advisor
Claudia Cox
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This guide is part of our ongoing series on travel to Chicago.