No one loves summer more than Chicagoans. Can you blame them? Just think back to winter in “Chiberia,” marred by foot-high snow, deep freezes and Lake Michigan’s blistering winds.
So once temps spike, locals open their patios, pools and beaches to bask in Chicago’s hottest season, nicknamed “Summertime Chi.”
And with upcoming musical events like Reggae Fest (Aug. 13) and North Coast (Sept. 4-6) and new venues popping up all over, now is prime time to bask in the Second City’s dog days of August and September — before it turns into an igloo.
Stay at The Peninsula Chicago
The hotel has sex appeal in spades.Courtesy of The Peninsula ChicagoThe Peninsula renovated its 331 guest rooms in April, and suites now sport orchids, sapphire curtains and art installations featuring hand-embroidered chrysanthemums, the city’s official flower (from $425/night). Each room also includes three tablet remotes that control just about everything. Despite the high-tech upgrades, the hotel retains its stellar hospitality. Doormen greet you and your guests by name, bartenders remember your favorite bottle of vino and maids tie your iPhone charger into a neat loop using silk ribbon emblazoned with the hotel’s name.
Eat at Parlor Pizza Bar
Grab a Sgt. Pepper slice at Parlor.Neil BurgerA decade ago, the city’s West Loop neighborhood was a ghost town of warehouses. But in the past four years, it has emerged as Chicago’s version of Manhattan’s Meatpacking District. Sleek new haunts set up shop, like this bougie pizza bar and beer garden. Opened last year, the industrial-chic restaurant includes a massive outdoor patio where yuppies bring their rescue dogs and sip French rosés in Champagne flutes and dine on perfectly crispy calamari ($16) served on metal skillets. Forget deep-dish pizza — try the eggs Benedict pizza ($14), which packs a savory, yolky bite.
People watch at Soho House Chicago
The rooftop’s pool scene heats up at Soho House.Soho House ChicagoLess stodgy and pretentious than New York’s outpost, Chicago’s iteration of the famed private members’ club for creative professionals opened in 2015. Members and hotel guests can bring up to three visitors. Though taking photos is technically prohibited, its rooftop pool is a prime Instagram spot, with its checkered floors, string lights and gorgeous panoramic view of downtown Chicago.
Shop at Azeeza US
Stop at local label Azeeza for classy clothes.Courtesy of AzeezaLast year, local womenswear designer Azeeza Khan debuted her first store right on Michigan Avenue’s Magnificent Mile, showcasing pieces that reflect her sleek, clean and minimalist aesthetic. Look for ultra-feminine frocks (from $995) and billowy off-the-shoulder tops ($795) throughout the irresistible boutique.
Drink at The Bassment




This massive basement speakeasy below a restaurant called the Hampton Social is decorated with electric guitars, Union Jack-patterned chaises and portraits of rock icons like Mick Jagger and Yoko Ono. Aimed at a sophisticated crowd, cocktails here are named after pop stars: The Aretha, for instance, is a punchy vodka-based drink with grapefruit, lime and cucumber, while the Million Dollar Negroni ($100) uses ultra-exclusive Nolet’s Reserve — touted as the world’s most expensive gin. Cheers!



