How to Have a Spectacular Day in Chicago

Galdones Photography

Start your day with the Blues Brunch at River Roast, an upscale pub on the Chicago River, to get a taste of great food and live music.

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Then head up to Wrigleyville, where we’ll rent you out a rooftop to watch the World Series–winning Cubs start their season. Make your way back south to the Art Institute, but not before a quick stop to the Gold Coast for luxury shopping on Oak Street.

Related: 8 Great Things to See and Do in Chicago

Kamil Galimski

Then have the Chicago Helicopter Experience pick you up for a tour of the city before letting chef Grant Achatz seduce your taste buds at Alinea.

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Finally, we’ll charter the Anita Dee ll yacht for a boat party with DJs William Galvan, Michael Serafini, and Bridget Marie. (Chicago is the birthplace of house, after all.) We’ll stock the yacht with Lou Malnati’s pizza for everyone.

A version of this article appears in the March 15, 2017 issue of Coins2Day as a sidebar in Black Book: Chicago, with the headline “The $10,000 Day.” We’ve included affiliate links into this article. Click here to learn what those are.