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Max Grinnell

As the days grow shorter and the air is inevitably cooler, it’s not too late to have that last summer fling with Chicago. Follow along as we offer up a rooftop bar or two to have an early evening drink, an afternoon with Chicago historical secrets, and live performances in a rather rarefied setting. No doubt you’ll find your own adventures, so let this be your place of departure—and the start of a great Chicago weekend.

Where to Stay

If you’re looking for a break from the usual Loop lodgings, the vintage, 1920s-era Hotel Lincoln is a stellar option (doubles from $200). You’ll be right across the street from the Green City Market, and mere floors from the hotel’s in-house cafe, Elaine’s Coffee Call. Up top, you’ll want to grab a drink at J. Parker, the hotel’s rooftop bar and restaurant, which offers up robust seasonal cocktail menu under the glass-paneled ceiling. The perfect end to your day will involve grabbing a libation here and watching the sunset over Chicago’s skyline.

With a design sentiment that might be described as “gritty chic,” the funky, boutique ACME Hotel has great perks that go along with that rock ‘n’ roll aesthetic (doubles from $200). There’s the “Bare Painted Ladies,” an installation created by local art students that guests can view when they look out their windows, a free thermos of coffee delivered to your room every day, and your own customizable Google Glass for exploring Chicago.

Related: The 12 Best Places to See the Sunset Around the World

What To See and Do

Head on over to the MCA on Fridays and Saturdays for one of their arresting weekend performances. You might find yourself listening to experimental jazz or find yourself watching a series of new one-act plays. On your way in, don’t miss the arresting work of Alexandre da Cunha in the plaza.

A heavy metal badge, a pair of eyeglasses, and a wooden cane are just a few of the items in Secret Lives of Objects, a remarkable exhibit at the Chicago History Museum—and they’re all connected to the “Crime of the Century,” Charlie Chaplin, and a corrupt alderman. It’s a fascinating way to get in touch with the Windy City’s past, and afterwards, you can wander over to the rest of the exhibits, like Vivian Maier’s Chicago and Chicago: Crossroads of America.

Jump on the train to Hyde Park, and celebrate seven female graffiti artists in Creatures from the Concrete, an expansive show at the Hyde Park Art Center that features work inspired by an intense concern with social justice issues. You’ll want to wander around the rest of the galleries, too, and check out one of their lectures or performances.

Who doesn’t love a distillery tour? The folks at Koval, the craft spirits producer in the Ravenswood neighborhood, offer an excellent tour through their whiskey, vodka, and gin selection every Wednesday, Saturday and Sunday. By the end of the tour, you’ll be able to tell the difference between white and aged whiskey, and the ins and outs of the distillation process.

Where to Eat and Drink

Drink on the outdoor patio at Fountainhead Chicago while watching the sunset from the rooftop. This low-key lounge has one of the deepest bourbon lists in the city, and hey, if you want rosé, that’s cool too—the wine list is also extensive.

Eat brunch outside at Barcocina on the weekend for some of the best people-watching in the city. Don’t miss the brioche French toast and their own iced coffee, which includes Herradura Silver Tequila and several other liquors.

Samples beers at the Half Acre Tap Room on Firkin Friday. Every Friday the crew at Half Acre in Lincoln Square taps a 10-gallon firkin (a small, 10-gallon cask) at noon. Its contents rotate, and may have hops insides, or something fruitier or more herbal, but whenever it’s done, it’s done. Bring some friends and stay awhile.

Before summer ends, make your way to Elle on the River, which is right outside the Langham Chicago. You can spend a late afternoon here that might become a long evening getting acquainted with their craft sodas (we’re partial to the pomegranate), house-made paletas, and a range of indulgent punches. Monday through Saturday they also have a happy hour that includes three tacos and a beer for $12.

Max Grinnell is a Chicago-based writer who covers several beats for Travel + Leisure. Follow him on Twitter at @theurbanologist.

Looking for more on things to do in Chicago? Read T+L’s Travel Guide: Chicago.

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