Chicago Skyline View

Our Favorite Things to do in Chicago

As you may know, the Candor Threads office is located in Chicago, IL. Even though we deal with cold winters and bad traffic, we love “The Windy City” and all it has to offer! Chicago is often called “The Second City” in comparison to New York City, but New York better watch out–the world has its eyes on Chicago.  Named 11th Best City in the World by TimeOut for 2025, and Best Big City in the U.S. by Conde Nast Traveler eight years in a row, Chicago is a force to be reckoned with!

 

 

Chicago became a city on May 4th, 1837 with the motto “Urbs in Horto“, Latin for “City in a Garden”. There wasn’t much green space at the beginning, but over time large parks and tree-lined residential streets became one of the city’s finest traits. Visitors are often surprised at how big Lake Michigan really is, giving an “oceanfront” feeling with many beaches and yet another nickname for the area, “The Third Coast”.

In Chicago, there is always something new to discover. The Candor Threads team has shared some of our top picks that you can note for your next trip to “The City of Big Shoulders”.

 

April’s Picks

April loves a museum day at the  Field Museum, which is one the largest natural history museums in the world. In addition to a rotation of special exhibits and Sue the T. Rex, the museum has vast collections that originate from the 1893 World’s Columbian Exposition. The museum is part of The Museum Campus, a 57 acre lakefront park that also includes the Shedd Aquarium, the Adler Planetarium, and Soldier Field. After a day viewing the wonders of the natural world, it’s great to take a refreshing stroll along the lakefront!

After spending time at the museum, you’re going to be hungry! April suggests Tweet in the Northside neighborhood of Uptown. Tweet serves comforting classic dishes made with fresh ingredients among the eclectic personal art collection of proprietor Michelle Fire. It’s the sister restaurant to Big Chicks, a cornerstone bar for Chicago’s LGBTQ+ community.

 

 

Becky’s Picks

Becky loves to get outside, and a great place to walk and get a great view is her first pick, the Chicago Riverwalk, where both locals and tourists alike take a stroll and enjoy the heart of downtown. The Riverwalk also has restaurants and public seating to take a rest and watch boats float down the river between the high rise architecture.

If you need another option for downtown dining, Becky suggests Aba in the West Loop. Their menu is full of Mediterranean- inspired delights with a California twist. As a bonus, the dining space includes a rooftop patio for city views while you dine.

For more rooftop views, head to the Wicker Park neighborhood to the Robey Hotel rooftop. Open to the general public, the hotel features two restaurants as well as the seasonal Cabana Club and UpRoom bars.

While you’re in Wicker Park, grab some caffeine at Wormhole Coffee. Their unique specialty beverages are a main attraction and the decor includes a real Delorean!

 

 

Jinna’s Picks

Jinna shares one of Chicago’s biggest secrets that many locals don’t even know about–the Chicago Pedway. Whether you visit during a winter freeze or a summer rainstorm, the Pedway has you covered (literally!). It’s an underground pedestrian walkway that connects more than 50 buildings, covering roughly 5 miles in the Loop. There are many guides to the Pedway’s secrets online, and it’s a great way to do some urban exploration downtown.
If you visit the city over Labor Day weekend, check out the Chicago Jazz Festival, four days of jazz performances that are open to the public at no cost! Performances take place at Millennium Park‘s Pritzker Pavilion and the Chicago Cultural Center. Many performers are local but big name performers are also brought in to play, and if you beat the crowds you can find a nice place to picnic under the park’s trees.

 

Kaitlin’s Picks

For a unique art viewing experience, Kaitlin recommends visiting the Art Institute of Chicago to see the Thorne Miniature Rooms. This is a wonderland of detailed miniature rooms that span centuries of interior decor and design. Created in the 1930s by artist Narcissa Niblack Thorne and a team of skilled artisans, the rooms are enchanting and beloved by young and old alike.

If you’re also a cinema buff, you can stay in the Loop and check out the Gene Siskel Film Center.  The center plays limited runs of classic and contemporary independent films. Or travel to Southport Corridor and visit the Music Box Theater, an historical movie theater built in August 1929. The interior is decorated like a Tuscan villa with a twinkling, star covered ceiling that will ignite the magic of any film viewing experience.

For coffee and curiosities, head to Logan Square to The Brewed, a horror-themed coffee shop that displays a rotating collection of horror memorabilia and handmade decorations. Next door is Bric-A-Brac Records, a record and collectibles store with wacky decor in an 80’s-90’s theme.

For a hearty meal befitting any Chicagoan, head to the Ukrainian Village to Tryzub. Their menu showcases the foods and culture of Ukraine in a modern (and tasty!) way. If you imbibe, Tryzub offers a wide array of infused spirits showcasing seasonal fruits and herbs.

 

 

 

Katie’s Picks

Katie loves outdoor events, including seeing the Cubs at Wrigley Field, summertime concerts, or walking the lakefront paths. For a unique way to see the city, set sail on one of the many architectural boat tours. It’s a delightful way to relax in the open air and learn about how the buildings shaped our downtown.
For exciting evening entertainment, check out a show at the Chicago Magic Lounge. Even the entryway is like magic–you enter through a secret laundromat into a retro-inspired speakeasy! Get up close and personal to performances of sleight-of-hand that will leave you mesmerized.
Beer and spirits connoisseurs should try Maplewood Brewery and Distillery, which is coincidentally not far from the Candor Threads office! Maplewood is Illinois’ first brewery and distillery under the same roof. Their lounge is a wonderful place to sample their beer, gin, whiskey, and cocktails.

We hope you find some hidden gems in our recommendations!  Let us know if you’ve traveled to any of these awesome places, or if you have other suggestions of your own – we’d love to add them to our list.  Happy travels, Windy City visitors.

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