Chicago, Illinois is a renowned tourist destination packed with famous attractions and landmarks. However, when you’ve had enough of Millennium Park and the Navy Pier, venture out to explore hidden gems situated close to most Chicago vacation rentals. Swing by lesser-known museums offering unique artifacts, or shop the day away at vinyl record shops and quaint bookstores. Find adventure and fun when exploring these secret spots on your next trip to the Windy City.

1. The Driehaus Museum

matilda and samuel nickerson's mansion
Source: driehausmuseum.org

It’s no secret that Chicago is home to many famous museums; however, one hidden gem is the Driehaus Museum. Just a few steps from the Magnificent Mile, this museum takes you back into the Gilded Age to admire the stained-glass dome in the gallery, the 17 different types of marble in the Main Hall, and the impressive architecture of the museum itself. Located at 40 East Erie Street, this hidden gem offers daytime hours Tuesday through Sunday for your family to explore Chicago’s history. While adults are charged an admission fee, children 12 and under are free.

2. The Hideout

hideout chicago
Source: hideoutchicago.com

After relaxing in your cozy Chicago vacation rental during the day, head out for some live entertainment at The Hideout, one of the city’s hidden gems for music lovers. Located between West Town and Noble Square, this dive bar has been rocking out since its opening in 1934. If you’re a fan of Indie, rock, punk, or country music, The Hideout is the perfect hangout when you want to cut loose and toss back a few brews with friends. Although this bar is easy to miss, since it looks like a house from the outside, once you’re inside, you can admire the memorabilia from well-known artists on the wall while tapping your toes to the live music.

3. Oz Park

dorothy at oz park
Source: Flickr/vikramjam

If you’re a fan of “The Wizard of Oz,” then this hidden gem in Lincoln Park is the obvious choice when you want to walk park trails and see bold statues of the Tin Man and Dorothy. Located at the intersection of W. Webster, N. Lincoln Avenue, and N. Larrabee Street, this neighborhood park brings the magic of the film to life. Stop in at the park’s administrative office during daytime hours to grab a map of the park that was revitalized in the 1970s to showcase the 1939 film. Take a stroll through the Emerald Gardens to see the blooming flowers, or let the kids jump around at Dorothy’s Playlot.

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4. Dusty Groove

dusty groove record store
Source: Flickr/Kyle Akerman

Head over to the south side and uncover some dusty gems when visiting the Dusty Groove, an internationally-known record store launched in the early 1990s by the radio station employees at the University of Chicago. Sort through the LPs and old 45 records that feature a mix of soul, jazz, world music, hip hop, and vintage blues. The store is a haven for vinyl junkies and sponsors special events with recording artists throughout the year. Open seven days a week, this hidden gem, located at 1120 N. Ashland Avenue, is a must-stop on your weekend getaway in Chicago.

5. The Wiener’s Circle

the wieners circle
Source: Facebook/The Wiener’s Circle

While The Wiener’s Circle may appear to be a family-friendly location, this Chicago hidden gem in the Lincoln Park neighborhood may not be appropriate for the kids in the wee hours of the evening. Known for its large dogs, this restaurant and hot dog stand is also famous for mistreating its customers with comical insults and profanity. Open until 5 a.m. on the weekends, The Wiener’s Circle, located at 2622 N Clark Street, serves up char-dogs and crispy French fries as well as a few snippy remarks to unsuspecting customers at all times of the day.

6. Chopin Theatre

chopin theatre
Source: Flickr/Connie

This hidden gem in Chicago has survived the test of time when many movie palaces have closed up for business. This attractive, ornate building features glossy white tile and a historic-looking interior to showcase architecture and design from its 1918 origins. Stop in at the Chopin Theatre, located at the triangle of Milwaukee Avenues, Ashland, and Division Street to see artifacts from the more than 100 productions that have been performed in this historic building that is now available for touring seven days a week.

7. Myopic Books

myopic book shop
Source: Flickr/Laurie Chipps

Own your book nerd characteristics by making a trip to Myopic Books, a long-standing used-book store and one of Chicago’s hidden gems. Attend one of the poetry reading events or the experimental music series hosted by the store’s original owner, or browse through the extensive holdings that include true crime, academic work, fiction, and books on politics and history. Open seven days a week for book enthusiasts, this novelty store is located at 1564 North Milwaukee Avenue.

8. The Secret Mermaid

the secret mermaid sculpture
Source: Facebook/Nok VL‎

Uncover one of Chicago’s secrets when traveling from your vacation rental to the bike path near the Oakwood-41st Street Beach to see the Secret Mermaid. This sculpture originated in 1986 when four sculptors secretly crafted the mermaid along the Chicago lakefront. The unauthorized piece was soon discovered by the U.S. Army Corps of Engineers and press coverage let the secret out. Now a permanent fixture in the city, this sculpture was once thought to be a leftover from a Gilded Age mansion until the sculptors came forward.

9. Wicker Park

wicker park
Source: Flickr/Adam Jones

Once known as the “Polish Gold Coast,” Wicker Park is a small park in the city that showcases the history of Chicago. Originating in the mid-1800s, this park, located at 1425 N. Damen Avenue, offers 4 acres to explore, as well as a field house, a children’s playground, a water spray feature, an ornamental fountain, and a community garden area. Let the kids slide and swing for a bit before heading over to the basketball courts for a family game. If you’re traveling with Fido, stop in at the dog-friendly area so he can roam freely.

 
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