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4-Day Fun-Filled Guide to Chicago, USA

Explore the Windy City and discover its diverse culture, iconic architecture, and world-class cuisine.

03 May 2023

Chicago is a vibrant city full of diverse neighborhoods, impressive architecture, and a world-renowned food scene. Visitors can take in breathtaking views of the skyline from the Willis Tower Skydeck, stroll along the Lakefront Trail, and explore world-class museums and galleries. With something for everyone, a trip to Chicago is not to be missed.

Travel plan

• Check in to the swanky Warwick Allerton Hotel, located right on Chicago's famous Magnificent Mile.
• Satisfy your hunger pangs with deep-dish pizza at Giordano's, a Chicago institution since 1974.
• Walk off those calories by strolling along the lakefront at Navy Pier, where you can catch a ferris wheel or a fireworks show.
• Get your culture fix at the Art Institute of Chicago, home to some of the most iconic masterpieces in the world.
• Finish off the night with a drink at The Signature Room, a bar on the 95th floor of the John Hancock Center that offers panoramic views of the city.

• Start the day off with some coffee and breakfast at Intelligentsia, a hip coffee joint that helped kick off Chicago's third wave coffee scene.
• Head to Wicker Park and wander through its vintage shops, street murals, and food carts.
• Grab a sandwich from defunct deli-inspired sandwich joint, Lucky's during lunch.
• Hop on the CTA and head to Chinatown for a dumpling crawl and some unbeatable bubble tea.
• End the night at the Green Mill, a historic jazz venue that used to be a speakeasy during Prohibition.

• Kick off the day with brunch at Cindy's rooftop restaurant, where you'll have a stunning view of Lake Michigan and the city skyline.
• Take a boat tour down the Chicago River, where you'll learn about the city's history and see some impressive feats of architecture.
• Check out the shops along State Street, where you'll find everything from bargain stores to high-end retailers.
• Have a bite to eat at the Chicago French Market, where you can choose from a wide range of delicious food stalls.
• Take a trip up to the 103rd floor of the Willis Tower and step out onto The Ledge, a section of the skydeck that extends out from the building.

• Start the day with breakfast at Ann Sather, a Swedish restaurant known for their cinnamon rolls.
• Walk off your meal by checking out the street art in Pilsen, a neighborhood known for its Mexican culture.
• Grab a hot dog from The Weiner's Circle, a hotspot known for its rowdy late-night crowd.
• Get some popcorn from Garrett Popcorn Shops and hit the benches at Millennium Park.
• End the trip on a sweet note with a cupcake from Molly's Cupcakes. Don't miss the sprinkles bar!