Worldwide icon-chevron-right North America icon-chevron-right United States icon-chevron-right Illinois icon-chevron-right Chicago icon-chevron-right Your 24-hour itinerary: The Baller

Your 24-hour itinerary: The Baller

You have money to burn (or you at least like to pretend that you do). These are the places where you can drop the most cash in 24 hours.

Terrace at Trump is one of the best rooftop bars in Chicago.
Photo: Jason Little Terrace at Trump is one of the best rooftop bars in Chicago.

Well, look who's fancy. You want to make it rain in Chicago? Easily done. Start with the most expensive brunch in Chicago, then get crazy-pricey spa treatments and eat at the most exquisite of Chicago restaurants. Sprinkle in some yacht-cruising, tiki drinks and stellar views of the city and you might as well be Kanye goddamn West.

Your 24-hour itinerary: The Baller

Restaurants, Coffee shops

9–10am: Hipster coffee and sweets at Caffé Streets

icon-location-pin Wicker Park

With its sleek Euro-sauna-in-space look and delicious, pricey coffee (brewed pour-over-style, of course), Caffe Streets in Wicker Park is the ideal place for ballers to start the morning. Nibble on a housemade croissant while you check your portfolio online.

Photograph: Dave Rentauskas
Restaurants, Soul and southern American

10am–noon: Brunch at Table Fifty-Two

icon-location-pin Rush & Division

Yes, you will pay $24 for chicken and waffles you can get elsewhere for less than $10. Why? Because they're beyond delicious here, and you leak money when turned on your side. Note: Brunch is only available on Sundays but if you go here on another day, pretend you're Oprah or something and just demand the brunch menu.

Shopping, Department stores

Noon–1pm: Buy a new wardrobe at Barneys New York

icon-location-pin Rush & Division

You've got time to kill before your spa appointment, so you might as well buy enough designer shoes and clothes to fill your closet(s) ten times over. Afterward, head to the top floor and have a glass of wine at ladies-who-lunch restaurant Fred's while you contemplate whether you should just go ahead and buy that Caribbean island you have your heart set on.

Jon Shaft
Health and beauty, Massage and body treatments

1–3pm: Get pampered at Elysian Spa

icon-location-pin Rush & Division

Housed within the Waldorf Astoria hotel in the Gold Coast, this spa and health club is among the poshest in town. Start with the Waldorf Signature Facial ($195 for 60 mins), then really let go with the ashiatsu massage ($210 for 60 mins), which has a therapist walking on your back while she holds onto bars above her. 


3–5:30pm: Rent a yacht and cruise around Lake Michigan

Smart ballers like you know that owning a boat is like throwing money into Lake Michigan. Much better to rent a yacht whenever you feel like taking to the high seas. Charter company Imagine Lifestyles offers a 34-foot yacht for $2,000 for four hours. A bargain!

Restaurants, Contemporary American

7–11pm: 12-plus courses at Alinea

icon-location-pin Lincoln Park

Get comfortable: Dinner at Alinea is indeed a four-hour affair, and the final bill will be at least $1,000 for two people. The menu changes contstantly, but you can rest assured your meal at the best restaurant in the country, maybe the world, is going to be flawless.

Bars, Cocktail bars

11pm–1am: Keep the party going at Three Dots and a Dash

icon-location-pin River North

Three Dots is not really known as a baller bar, but it can be if you are "invited" to sit at the private back bar away from the great unwashed, and if you order the Treasure Chest No. 3, a $385 cocktail served with a bottle of Dom. It's supposed to be shared with six to eight friends, but you and your date can take it down yourselves. Because that's what ballers do.

Photograph: Erica Gannett
Bars, Lounges

1–3am: Bottle service at Studio Paris

icon-location-pin River North

Yeah, bottle service is a bit of a douche move, but a baller night isn't really complete without it. You'll drop at least $500 here, but that retractable roof is pretty spectacular, right?