A St. Louisan’s guide to a summer weekend getaway in Chicago

Events & Exhibits

Georgia O’Keeffe: “My New Yorks” at the Art Institute Chicago | June 2–September 22

Georgia O’Keeffe might be best known for her flower paintings, but she also has an extensive collection of New York City scenes, the focus of Georgia O’Keeffe: “My New Yorks.” There will be a conversation between curator Annelise K. Madsen and scholar Wanda M. Corn on June 13 and garden party on June 14.

NASCAR Chicago Street Race | July 6 & 7

This July, the streets of Chicago will transform into a NASCAR racetrack, as NASCAR Chicago Street Race returns to the Windy City. This two-day event combines street racing with popular musical acts, including Keith Urban, The Black Keys, and The Chainsmokers. 

Millennium Park 20th Anniversary Celebration | July 18–21

To commemorate the 20th anniversary of Millennium Park, the Department of Cultural Affairs is hosting a four-day festival that will include new public art, dance performances, activities for families, workouts, and musical performances. The headliners include Fruko y Sus Tesos, Common, and The S&S Chicago Experience. 

Lollapalooza | August 1–4

This popular music festival has been a highlight of Chicago summers for over 30 years. The lakefront setting with views of the cityscape make this four-day musical event one not to miss. This year’s lineup of 170 musical acts includes SZA, Tyler, the Creator, The Killers, and Deftones. 


Outdoor Attractions

Kayaking on the Chicago River and Lake Michigan

Urban Kayaks offers a variety of paddling tours. Choose between the Riverwalk or Lakefront location; the company recommends starting on the river if you’re new to kayaking. Tours range from one to two hours and include happy hour, sunset, and historic tours. There’s also an introduction to paddling for newcomers, and if you’re starting from the Riverwalk Location, you can stay for lunch and a cocktail or head to nearby the River North neighborhood.

Rooftop Cinema Club

For a fun date or family night out, head to Rooftop Cinema Club, where you can enjoy a film and views of the city. The cinema shows an impressive lineup of classic films and new releases. This month’s offerings include Coming to America, Mean Girls, and Crazy Rich Asians. The doors open early, giving you time to enjoy the lounge area and play an assortment of lawn and table games. Given the cinema’s convenient location inside The Emily Hotel, don’t miss its rooftop cocktail bar, Selva, where you can order tacos and mezcal.

The Beach

Chicago’s lakefront stretches 26 miles and offers plenty of beaches, depending on your preferences. For a great view of the skyline, head to Oak Street Beach. This popular beach has volleyball tournaments, watersports rentals, and a lifeguard first aid station. Ohio Street Beach is conveniently located near Navy Pier. Because of the curved shoreline, its waters are calmer and great for families. Located alongside Lincoln Park, North Avenue Beach is the busiest of Chicago’s beaches, but it comes with all of the amenities: lockers, Wifi, water sports rentals, restrooms, and a lifeguard first aid station. You can even rent kayaks and jet skies at this location.

Wrigley Field 

One of baseball’s oldest stadiums, Wrigley Field is second in age only to Fenway Park in Boston. Visit the famous Chicago landmark to cheer on the St. Louis Cardinals when they face the rival Cubs on June 14–16 and August 1–4.


Hotels Bars & Restaurants

The Hoxton

The Hoxton is located in the popular Fulton Market neighborhood, the city’s former meatpacking district. Outside, the brick exterior echoes the warehouse aesthetic, but the interior includes a cozy living room space with a fireplace, plants, and plenty of seating. The two-story window behind the bar serves as a focal point, with views of the elevated “L” tracks that are perfect for trainspotting. The rooms have an industrial, mid-century feel with furniture and bedding designed by local artist Cody Hudson. Upstairs, you’ll find Cabra, a Peruvian-style restaurant serving up shareable plates by chef Stephanie Izard. 

The Gwen

The Gwen is a work of art, located in the landmark McGraw-Hill building, which dates to 1928. With Art Deco details, the hotel is named after Chicago-born female sculptor Gwen Lux, whose work can be seen inside. The hotel is part of Marriott’s Luxury Collection, which offers a unique connection to the locale. Upstairs at The Gwen offers rooftop dining in an Art Deco-inspired space. Grab a cocktail, share small bite plates, and enjoy the view.

theWit Chicago

Conveniently located near the Blue Line, Riverwalk, and many of Chicago’s main attractions, theWit offers a stylish yet affordable place to stay downtown. The rooms and suites are decorated in a modern monochrome with shades of white and cream, as well as bold pops of color. Travel + Leisure named Roof, located on the 27th floor, as one of the top three rooftop bars in the world. Go for the views, but stay for the music, synched with video screens and an impressive cocktail menu. 


Read More: 10 of the best rooftop bars in Chicago


Before You Go

To help prepare for your trip to Chicago, Choose Chicago has a new travel show that highlights the five different neighborhoods of the city. “The 77: A City of Neighborhoods,” which explores the history of these neighborhoods from the residents’ perspective. The series is available on YouTube.

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