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

“My Frida Kahlo’s Month in Paris: A Friendship with Mary Reynolds” at the Art Institute Chicago | Through July 13

Find inspiration and tips for your next trip

Subscribe to the St. Louis Travel newsletter, covering big cities, small towns, and everywhere in between!

We will never send spam or annoying emails. Unsubscribe anytime.
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

In 1939, Frida Kahlo traveled to France, her first and only visit to Europe. She was invited by Surrealist André Breton, who was excited about her work and eager to showcase it in Paris. Although Kahlo found Paris to be uninspiring and longed to return home to Mexico, she forged a meaningful friendship with American bookbinder Mary Reynolds. This exhibit explores their friendship through paintings, photographs, and artifacts.

NASCAR Chicago Street Race | July 5 & 6

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 the Zac Brown Band.

Lollapalooza | July 31–August 3

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 Olivia Rodrigo, Tyler the Creator, Luke Combs, Sabrina Carpenter, and Cage the Elephant, 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 4–6 and September 26–28.

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, 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.


Photography by Jen Roberts
Photography by Jen RobertsIMG_2386.jpg

Hotels Bars & Restaurants

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 DowntownLocated 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