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Day 1 MORNING Start the trip in Chicago’s downtown Loop with a local tradition: breakfast at the beloved Lou Mitchell’s, a city institution since 1923. It gets busy early, but those standing in line get a special treat: free doughnut holes while they wait, plus Milk Duds for the ladies. (1 hour) For sweeping views of the…

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Leading up to the Chicago Blues Festival, during May and June there will be several preview performances and film screenings held at the Chicago Cultural Center. The “official” Chicago Blues Festival preview on Daley Plaza will take place Monday, June 5, at noon. On opening night in Millennium Park on Friday, June 9, the festival…

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Opening night, August 31, will feature the music of Dizzy Gillespie, who appeared at the festival in 1980, 1984 and 1989. Gillespie’s tribute will feature his protégé Jon Faddis and the Chicago Jazz Festival Big Band featuring Chicago musicians and special guest artists Jimmy Heath, Ignacio Berrora, Antonio Hart and Todd Coolman. Thursday will also…

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The heart and soul of Chicago lives in our 77 vibrant neighborhoods and within the people who call them home. Start your exploration on the following pages and discover 51 communities, each with their own mix of historical sights and attractions, arts and culture, dining, nightlife, shopping, and most importantly, personality. Downtown Downtown is a…

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Heart-pumping thrills in the heart of the city? You bet — Chicago is the perfect place to tap into your inner adventurer. Here are three full day’s worth of sightseeing suggestions sure to raise your pulse. The 3-day Chicago itinerary packs in new sights like The 606 and the outdoor climbing wall at Maggie Daley…

Read More Urban Explorer Sightseeing Itinerary | Choose Chicago

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Heading to Chicago for a short trip but still want to see the sights? It can feel like you have to rush to do everything you want to do, but the truth is — Chicago is actually quite an easy place to get around and the major attractions are close to one another. We put…

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Looking for romantic things to do in Chicago? Here are three red-hot itineraries to keep you and your main squeeze toasty on even the coldest Chicago nights. Date night in Chicago — solved! DATE NIGHT OPTION 1: Bubbly Comedy Nuzzle up in the dazzling dining room or romantic patio at Old Town’s Perennial Virant, where the…

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