
If you’re considering moving to Chicago, you’ve probably heard about a lot of the basics: the chilly winters, the green river in March, the renowned architecture, the summer days on Lake Michigan, the shows at Second City, and of course, the hot dogs and deep-dish pizza. But, there are a few things that you haven’t heard about before, though, and we’re here to make sure you don’t miss some of the best-kept secrets of the Windy City.
1. Chicago’s secret “Bat Cave“

With little information and only a few existing photos of this 2.5-mile street, this may be Chicago’s most well-kept secret. This exclusive express route is built alongside the Metra Electric/Illinois Central Railroad tracks and runs underneath Millennium Park and the Art Institute. Bypassing local traffic and Lake Shore Drive, this mini-highway, known as McCormick Place Busway, reduces travel time between downtown and the lakefront convention center to an average of just 8 minutes. Before you start jumping for joy, we should say that only a limited number of people have access to this unique road. It’s not open to the public, and the government officials and high-profile figures who do have access must have a pass to enter the secret route.
2. RM Champagne Salon

Yes, you read correctly, an entire salon dedicated to bubbly wine. If you’re a champagne enthusiast, head to the West Loop to enjoy this lavish 1,500-square-foot space tucked away in a secluded cobblestone alley. RM Champagne offers a huge selection of estate-grown wines, as well as a full dinner and cheese menu. But don’t start reaching for your shoes just yet – this salon has a long waitlist so making an advance RSVP is a must!
3. Historic Hotel Tour

Navy Pier and Willis Tower are a couple of Chicago’s most popular sights, but they’re also the most touristy. Skip them; you’re a local! Head to the Magnificent Mile for a tour of the Intercontinental Hotel, which was built in 1929 as the Medinah Athletic Club. This tour allows you to step back into the Roaring 20s with prohibition-era decor complete with crystal chandeliers, intricate wood carvings, and knights in shining armor. Not a guest of the hotel? No problem. Guests and non-guests can simply head to the concierge desk for a complimentary, self-guided audio tour.
4. Fairways Golf Bar

Okay, so this may not be a secret. But it’s definitely a gem. This reservations-only golf lounge offers an extensive food menu, a wide selection of craft beers and HD golf simulator flat screens. Now you can spend your Friday night with links & drinks at this laid-back environment.
*Update: Fairways has closed its Lincoln Park doors and is in the process of re-opening in a new (secret) location. We’re sure it’ll be just as good as the OG.
5. Hoosier Mama Pie Company


The Hoosier Mama Pie Company, located on Chicago Avenue, is an insanely-delicious bakery offering a plethora of baked goods made by hand. We can promise that these are some of the best pastries you’ve ever tasted!
6. Twin Anchors

Located in a historic Old Town building, Twin Anchors Restaurant & Tavern was founded in 1932, making it one of Chicago’s oldest restaurants. As one of Frank Sinatra’s favorite food stops, this restaurant has received a lot of publicity over the decades, even being featured in the motion picture, The Dark Knight. If you’ve yet to venture to this neighborhood tavern that serves some of the most tender, barbequed back-ribs you’ve ever tried, it’s a must-visit.
7. Millennium Park’s hidden garden

It’s no question that Millennium Park is a public attraction for many tourists, but it’s what lies beyond the park that makes it a hidden gem. Separated from the city bustle by a 15-foot-high hedge of conifers and trees, the Lurie Garden is an understated natural beauty that serves as the perfect environment for reading a book or enjoying a summertime picnic.
8. Andersonville’s Dinner Crawl

This Chicago-based event at the Swedish American Museum is a foodie’s dream come true! The Taste of Andersonville Dinner Crawl is an annual summertime event that allows you to enjoy your favorite neighborhood restaurants, find new spots to dine and meet lots of new people in the process. Are you a vegetarian? Don’t worry. The dinner crawl offers a variety of specialty plates to satisfy any dietary restriction or craving! The Dinner Crawl is just one of the reasons we think Andersonville is one of Chicago’s best neighborhoods.
9. Chicago’s Speakeasy Bar

If the Intercontinental Hotel tour doesn’t strike your fancy, check out the 1920’s themed speakeasy called Room 13. Located in a discreet alleyway entrance to the left of the Old Chicago Inn, you’ll find a red-lit gate with the “RM-13” logo. Knock on the door and you’ll be greeted by a doorman asking you for the password. Head inside and enjoy old slot machines and prohibition-era cocktails.
10. ROOFtop Bar on theWit


If you’re familiar with Chicago winters, you can probably agree that cold temperatures make you want to curl up and hibernate. That’s what makes Chicago the greatest city in the summer, and it has plenty of rooftop bars to go with the warm weather. Don’t wait until May to enjoy drinking with a view. Instead, curl up in front of the fireplace with a handcrafted cocktail at Chicago’s coziest rooftop bar. Offering both indoor and outdoor seating, the ROOF on theWit has striking views year-round, especially during St. Patrick’s Day.
11. The Chicago Pedway

Used by tens of thousands of pedestrians each day, the Pedway is a system of underground tunnels and overhead bridges that link more than 40 blocks in the Central Business District. This pedestrian way system connects to public and private buildings, CTA stations and commuter rail facilities. It might surprise a lot of Chicagoans that there’s a quicker and more convenient way to travel around the city – and it’s all underground.
Frequently asked questions about Chicago’s hidden gems
Some of the best free art exhibits in Chicago include the famous Bean located in Millennium Park, but that is a known tourist destination. For a hidden gem, check out the Wabash Arts Corridor, one of the best free art exhibits in Chicago.
Located in the Lincoln Park neighborhood, the Children’s Memorial Hospital parking garage offers incredible views of the Chicago skyline without the crowds.
The Chicago Magic Lounge is a 20th century-themed bar and performance venue that can be accessed through a laundromat facade. This speakeasy style venue is a can’t miss when visiting or living in Chicago.
Woolly Mammoth Antiques and Oddities and the Wicker Park Secret Agent Supply Company are two options for a unique shopping experience in Chicago.
Get to know the city of Chicago by exploring some of these letter known hidden gems. If considering a move to Chicago, you may also want to try a short-term rental before you commit. Short-term rentals can be a great way to experience the city, while getting a true taste of what life will be like as a new resident.
Looking for a rental in the Windy City? Zumper has thousands of homes and apartments for rent in Chicago.