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

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

Kayak the Chicago River, grab a drink at a rooftop bar, cheer on the Cardinals at Wrigley, and more.

Events & Exhibits

Events & Exhibits

“Willem de Kooning Drawing” at the Art Institute Chicago | Through September 20

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As one of the world’s most celebrated draftsmen, Willem de Kooning had an expansive drawing practice that is showcased in this exhibit. “Willem de Koonig Drawing” is the first solo exhibit at the Art Institute since 1969. With more than 200 artworks, the exhibit provides a glimpse at his famous works alongside lesser-known pieces.

Lollapalooza | July 30–August 2

This popular music festival has been a highlight of Chicago summers for more than 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 Lorde, Charli XCX, The Smashing Pumpkins, Olivia Dean, TheXX, among others.


Photography by Jen Roberts
Photography by Jen RobertsIMG_1551.jpg

Outdoor Attractions

Wrigley Field 

One of baseball’s oldest stadiums, Wrigley is second in age only to Fenway Park in Boston. You can tour the famous Chicago landmark, or if you want to cheer on the St. Louis Cardinals, they face the rival Cubs on July 3–5 and August 14–16.

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. 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.

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.


Courtesy of Chicago Athletic Association
Courtesy of Chicago Athletic Association

Hotels Bars & Restaurants

Chicago Athletic Association

Steeped in history that dates back to 1893 when this Venetian Gothic landmark was built as an exclusive athletic club, the Chicago Athletic Association blends old-world character with modern comforts. The 240 guest rooms and suites pay homage to its past with pommel horse benches, vintage-inspired furnishings, and stately gathering spaces. Cindy’s Rooftop, with its expansive outdoor terrace, offers sweeping views of Millennium Park and Lake Michigan. With a seasonal menu, creative craft cocktails, and unmatched views, it has rightfully become one of Chicago’s premier dining destinations.

LondonHouse Chicago

Located at the intersection of the Chicago River and Michigan Avenue, LondonHouse Chicago pairs timeless elegance with contemporary luxury in one of the most iconic locations. The hotel’s 452 rooms and suites offer views of the river, skyline, or Lake Michigan. LH Rooftop is one the city’s best vantage points. To ensure a table, reservations are strongly recommended.

Park Hyatt Chicago

Overlooking the Chicago Water Tower and Michigan Lake, Park Hyatt Chicago offers a luxury experience that feels like home. The 146 rooms and 36 suites feature large soaking tubs, custom artwork, and are pet-friendly. For more relaxation, book a massage in the spa and allow time to sit in the steam room or to soak in the hot tub. Perched over the Jane M. Byrne Plaza Park, NoMI Kitchen reimagines traditional midwestern dishes with a modern twist. The roasted pears accompanied with a whipped goat cheese and Rohan duck aren’t to be missed. 

Sheraton Grand Chicago Riverwalk

If you’re visiting Chicago over the Fourth of July weekend, this is where you want to stay. With views of the skyline, river, and lake, Sheraton Grand Chicago Riverwalk offers an easy way to see the fireworks–without the traffic. The indoor pool is a great additional feature, especially for families traveling with kids. 

Renaissance Chicago Downtown

Located in the Theatre District, directly across the river from the Marina Towers, Renaissance Chicago Downtown offers a luxury stay without the hefty price tag. The hotel’s prime location makes it an easy jumping off point for exploring the city, or if you prefer to stay in, take a dip in the heated indoor pool and enjoy a cocktail at Raised an Urban Rooftop Bar.


Read More: 10 of the best rooftop bars in Chicago