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You probably know Chicago as the home of the Cubs baseball team and the delicious deep-dish pizza, or maybe you recognize it as the birthplace of skyscrapers and one of the biggest cities in the USA. What you might not know, though, is that the Windy City is also home to lush green spaces, long stretches of lakefront beaches, and countless speakeasies and dive bars.
If you’re planning a trip to the Midwest and want to get off the beaten track, you’re in luck! We’ve tracked down the 17 can’t miss hidden gems in Chicago.
1. Humboldt Park
There are many better-known neighborhoods to explore in Chicago which means that Humboldt Park often gets overlooked by tourists. Head here to experience vibrant Puerto Rican culture, eat delicious cuisine, sip cappuccinos at welcoming coffee shops, and admire colorful murals created by local artists.
2. Chicago Pedway
Navigating traffic as a pedestrian in huge cities is often a worry for tourists, but the Pedway ensures this isn’t an issue in Chicago. A series of underground tunnels and overhead bridges covers around five miles of the Central Business District, making it safe and easy to reach many parts of the Windy City without having to rely on taxis or public transport.
3. Graceland Cemetery
- Website: gracelandcemetery.org
- Address: 4001 N Clark St, Chicago, IL
- Opening hours: 8.00 am – 6.00 pm Monday to Friday / 9.00 am – 4.00 pm Saturday & Sunday
Graceland Cemetery is the final resting place of many of Chicago’s most famous architects, including Louis Sullivan, William Le Baron Jenney, and Fazlur Khan. The cemetery is enormous and makes a tranquil place for a quiet stroll when the hubbub of the city becomes too much.
4. Bucktown
For an alternative shopping destination to Michigan Avenue, head to the Chicago neighborhood of Bucktown. Here, you’ll find fashion-forward boutiques that’ll scratch your retail therapy itch without the crowds that the Magnificent Mile attracts.
Then once you’ve worked up an appetite, you can indulge in the global cuisine that’s also on offer here. You’ll find everything from Mexican and American to European and Asian restaurants in this neighborhood.
5. Chicago History Museum
- Website: chicagohistory.org
- Address: 1601 N Clark St, Chicago, IL
- Opening hours: 9.30 am – 4.30 pm Tuesday to Saturday / 12.00 pm – 5.00 pm Sunday
This fascinating museum is located in the Lincoln Park area and is where you can learn about how Chicago grew into the incredible city it is today. Exhibits of interest include the Great Chicago Fire, the Prohibition era, and the 1893 World’s Columbian Exposition.
6. Chicago Dive Bars
If you’ve had your fill of classy cocktail joints and craft beer bars, Chicago’s dive bar scene is ready to serve up a memorable night out. Here are two favorites:
Rossi’s
- Website: rossischicago.com/
- Address: 412 N State St, Chicago, IL
- Opening hours: 11.00 am – 2.00 am Sunday to Friday, 11.00 am – 3.00 am Saturday
This dive bar is located in River North, has been around for decades, and looks well past its best. Despite the wear and tear, this spot is beloved by the local post-work crowd and you’re unlikely to encounter another tourist here.
Hideout
- Website: hideoutchicago.com
- Address: 1354 W Wabansia Ave, Chicago, IL
- Opening hours: 5.00 pm – 12.00 am Tuesday to Thursday / 5.00 pm – 2.00 am Friday / 6.00 pm – 3.00 am, Saturday
This spot has been open since the 1930s and sits among several warehouses close to the Chicago River. It’s said to be a place for folks who don’t fit in elsewhere and you can expect quirky live music, comedy shows, and poetry readings here.
7. Chicago Botanic Garden
- Website: chicagobotanic.org
- Address: 1000 Lake Cook Rd, Glencoe, IL
- Opening hours: 8.00 am – 8.00 pm daily
Millennium Park and its famous “Bean” statue are at the top of most tourists’ must-visit list, but there are dozens of other green spaces to discover during your time in Chicago. The botanic garden has over 385 acres of diverse plants to explore, and the calm ambiance is a welcome change to the city’s busy urban areas.
8. Phyllis’ Musical Inn
- Website: facebook.com/phyllismusicalinn
- Address: 1800 W Division St, Chicago, IL
- Opening hours: 4.00 pm – 2.00 am Monday to Thursday / 3.00 pm – 2.00 am Friday / 2.00 pm – 3.00 am Saturday / 2.00 pm – 2.00 am Sunday
This was Wicker Park’s first live music venue and has been in operation since the 1950s. Much of the interior remains the same, taking patrons back in time as they step through the door. Live music offerings range from garage rock to jazz, and there’s also an open mic night if you want to show off your own musical talents.
9. International Museum of Surgical Science
- Website: imss.org
- Address: 1524 N Lake Shore Dr, Chicago, IL
- Opening hours: 9.30 am – 5.00 pm Monday to Friday, 10.00 am – 5.00 pm Saturday & Sunday
Once you’ve visited Chicago’s many world-class museums, head to this quirky spot. Here, you’ll find more than 600 historical paintings of surgeries as well as gory items such as heart valves preserved in jars.
10. Chicago Speakeasy
Alcohol flowed freely during America’s Prohibition era because gangsters like Al Capone were running the show. Chicagoans still enjoy drinking in speakeasies to this day, and you’ll find several dotted around the city. These two are particularly special:
The Milk Room
- Address: 12 S Michigan Ave, Chicago, IL
- Opening hours: 5.00 pm – 11.00 pm Wednesday to Saturday / 5.00 pm – 9.00 pm Sunday, Monday & Tuesday
This micro-bar seats just eight guests, making it the most exclusive speakeasy in the city. This bar’s claim to fame is its cocktail list made with rare vintage spirits and curated whiskies.
The Office
- Website: theaviary.com/the-office
- Address: 55 W Fulton Market, Chicago, IL
- Opening hours: 5.00 pm – 12.00 pm Sunday to Thursday / 5.00 pm – 1.00 am Friday & Saturday
This speakeasy is tucked away below the Aviary cocktail bar in the West Loop. For an unmatched experience, book a spot at the bar for Office Hour — a 60-minute experience featuring two cocktails with snack pairings.
11. Osaka Garden
- Website: www.chicagoparkdistrict.com/parks-facilities/japanese-garden
- Address: 6300 S Cornell Ave, Chicago, IL 60637
- Opening hours: 6.00 am – 11.00 pm daily
Osaka Garden is located in Jackson Park in the Hyde Park neighborhood. It was gifted to Chicago by Osaka, its sister city, and makes a peaceful place to take a stroll. Keen birders may also spot some of the 200+ species of birds that call this park home.
12. Artists of the Wall Painted Bench
- Address: 1096 W Pratt Blvd, Chicago, IL 60626
- Opening hours: 24 hours
Once you’ve visited the Chicago Art Institute, head to this unique al fresco art gallery. This concrete bench sits on Lake Michigan’s beachfront and features more than 150 murals that have been painted by local artists and residents.
13. Chicago Temple
- Website: chicagotemple.org
- Address: 77 W Washington St, Chicago, IL
- Opening hours: Sanctuary: 10.00 am – 2.00 pm Monday to Friday
Chicago Temple is the tallest church in the world and a fascinating sight to behold. Located in Downtown Chicago, this skyscraper features a gothic spire and has a central sanctuary that seats 1,000 people. Daily tours are available via the website.
14. Magnetic Attraction
- Website: navypier.org/location/magnetic-attraction
- Address: 600 E Grand Ave, Chicago, IL
- Opening hours: 10.00 pm – 8.00 pm Monday to Thursday / 10.00 pm – 10.00 pm Friday & Saturday / 10.00 pm – 7.00 pm Sunday
If you’re searching for souvenirs to commemorate your time in Chicago, swing by Magnetic Attraction on Navy Pier. This is home to the biggest selection of magnets in the Midwest so you’ll have no trouble finding unique trinkets here.
15. Ping Tom Park
- Website: chicagoparkdistrict.com/parks-facilities/tom-ping-memorial-park
- Address: 1700 S Wentworth Ave, Chicago, IL
- Opening hours: 6.00 am – 10.00 pm daily
This urban park is located in Chicago’s Chinatown on the South Side of the city. Head here to relax in the public green space and admire the pavilion, Chinese dragon poles, and red zigzag bridge. If you’re heading here during the summer, the water taxi is the quickest way to arrive.
16. Chicago Beaches
Chicago isn’t known as a beach destination but those in the know will tell you that it’s the perfect place to visit during the sunny summer months. Here are three of the best beaches on Lake Michigan:
Oakwood Beach
- Address: 4100 S. Lake Shore Drive, Chicago, IL
- Opening hours: 6.00 am – 11.00 pm daily / Swimming allowed 11.00 am – 7.00 pm
This is the newest beach on the South Side and it has great amenities. Lifeguards are on duty during permitted swimming times, and there is a beach house with restrooms. There’s also an on-site concession stand serving food and drinks for beachgoers who want to make a full day of it.
North Avenue Beach
- Address: 1601 N. Jean-Baptiste Pointe DuSable Lake Shore Drive, Chicago, IL 60611
- Opening hours: 24 hours / Swimming allowed 11.00 am – 7.00 pm daily
This is one of the most popular beaches among locals and it’s conveniently located near many of the city’s top tourist attractions. Head here for the spacious sandy area and the buzzy beachfront bars.
Loyola Beach
- Website: www.chicagoparkdistrict.com/parks-facilities/loyola-beach
- Address: 1230 W. Greenleaf Ave., Chicago, IL 60626
- Opening hours: 24 hours / Swimming allowed 11.00 am – 7.00 pm daily
Head further north, and you’ll find Loyola Beach. You should come here if you prefer a quiet, calm ambiance and space to spread out. There’s also a playground, a handy addition if you’re traveling with kids.
17. Green Mill Jazz Club
- Website: greenmilljazz.com
- Address: 4802 N Broadway, Chicago, IL
- Opening hours: 4.00 pm – 1.00 am Sunday to Friday, 2.00 pm – 1.00 am Saturday
This jazz hotspot was named as a nod to Moulin Rouge (Red Mill) in Paris and has hosted countless famous (and infamous) faces over its 100+ year history. Mobsters, including Al Capone have enjoyed the nightlife here, as well as stars like Frank Sinatra and Charlie Chaplin. You’ll find the Green Mill in the Uptown neighborhood.
Uncover the Many Chicago Hidden Gems
Chicago is an iconic city with some of the best-known tourist attractions right here within its city limits. But, if you’re an adventurous traveler, you’ll love discovering the Windy City’s hidden gems for yourself. Which will you unearth first?
