9. Chicago, ILGet More Info
Why go: There’s no better season than summer in Chicago, especially for music and baseball. Chicago is home to Pitchfork Festival (July 19-21), Lollapalooza (August 1-4), and the Chicago Jazz Festival (August 23-September 1); historic Wrigley Field is also open on non-game dates for behind-the-scenes tours.
Where to stay: Hotel Zachary is directly across the street from Wrigley Field and Gallagher Way. Their summer Architecture of Baseball Package includes accommodations in a room or suite with a view of the stadium, admission for two to the Wrigley Field Tour, and a one-of-a-kind reproduction of architect Zachary Taylor Davis’ original plan of Wrigley Field.
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