30 Top Downtown Chicago Hidden Gems | 2024 (with Photos)

Rosalia Ignatova

Rosalia Ignatova - Travel Writer

Published: June 30, 2023

Hey there! I'm Rose, and I'm thrilled to share my favorite hidden gems in downtown Chicago with you. From local hotspots to secret hideaways, get ready to uncover the best-kept secrets of the Windy City in this article.

Top Downtown Chicago Hidden Gems

Visiting Chicago offers a multitude of well-known attractions to explore.

The Loop, an area spanning more than 1.5 square miles between the picturesque shores of Lake Michigan and the winding Chicago River, is also bursting with iconic Chicago attractions.

From amazing exhibits at the Art Institute of Chicago to historic buildings and artworks in Millennium Park, here is a list of 30 hidden gems in Chicago that you won't want to miss on your next trip to the Windy City.

Most Recommended Thing to Do

Visit Navy Pier

Top Choice Hotel

The Ritz-Carlton, Chicago

Our Top Choice Restaurant


Our Top Choice Bar for Nightlife

Kingston Mines

Best Time to Visit

Summer months for vibrant festivals, mild weather explorations.

Average Temperature

Chicago's average temperature is often cold and fluctuating.

Transportation Options

Buses, trains, taxis, rideshares, bikes, scooters, walking, driving.

Average Cost ($, $$, $$$)


My Top Recommendation

For an extraordinary travel experience in Chicago, explore the iconic Magnificent Mile, where you can immerse yourself in a vibrant city atmosphere, surrounded by impressive skyscrapers and world-class shopping opportunities.

Dive into Chicago's rich cultural heritage by visiting the Art Institute of Chicago, home to a diverse collection of masterpieces from renowned artists such as Van Gogh and Monet, and take a leisurely stroll along the picturesque Millennium Park, where you can marvel at the stunning Cloud Gate sculpture and enjoy live performances at the Jay Pritzker Pavilion.

What You'll Need to Bring

  • Comfortable walking shoes
  • Weather-appropriate clothing
  • Valid identification and travel documents
  • Local currency and/or credit cards
  • Mobile phone and charger
  • Maps or navigation app
  • Umbrella or raincoat
  • Snacks and refillable water bottle
  • Camera or smartphone for capturing memories

What Not to Miss

  1. The Magnificent Mile
  2. Millennium Park and Cloud Gate
  3. Navy Pier
  4. The Art Institute of Chicago
  5. Willis Tower Skydeck
  6. Wrigley Field
  7. Grant Park and Buckingham Fountain
  8. Museum of Science and Industry
  9. Chicago Riverwalk
  10. The Field Museum

What to Avoid

  1. High crime areas
  2. Rush hour traffic
  3. Overpriced tourist traps
  4. Walking alone at night in certain neighborhoods
  5. Ignoring parking regulations
  6. Going without proper winter gear in cold months
  7. Trusting strangers with personal belongings
  8. Ignoring street signs and signals while driving
  9. Engaging in illegal activities
  10. Leaving valuables unattended in busy areas.

Hot Tip: Get the Chicago CityPASS

The Chicago CityPASS is a convenient and cost-effective way to explore the best attractions in Downtown Chicago.

It covers entry to the Shedd Aquarium, Skydeck Chicago, the Field Museum, and your choice of either the Art Institute of Chicago or the Museum of Science and Industry.

The Chicago CityPASS also includes a sightseeing cruise along the Chicago River, allowing you to marvel at the city's breathtaking skyline.

1. Walk Along the Chicago Lakefront Trail at Lake Michigan

Chicago Lakefront Trail at Lake Michigan

Stretching for 18 miles along the shores of Lake Michigan, the Chicago Lakefront Trail is a perfect blend of natural beauty, outdoor activities, and stunning views of the city skyline.

The Lakefront Trail provides a picturesque route for jogging and biking that takes you past beautiful beaches and lush green parks.

The trail offers a refreshing escape from the city, allowing you to immerse yourself in the natural beauty of Lake Michigan.

2. Hop on a Water Taxi at the Chicago River

Water Taxi at the Chicago River

A visit to Chicago wouldn't be complete without a ride on the water taxi, which navigates the Chicago River and Lake Michigan, providing stunning views of the city.

The water taxi offers a refreshing and leisurely mode of transportation, allowing you to sit back, relax, and take in the sights.

The water taxi stops at various locations along the river, including popular destinations in the city such as Navy Pier, Michigan Avenue, and the Museum Campus.

3. See the Views from the Centennial Ferris Wheel at Navy Pier

Views from the Centennial Ferris Wheel at Navy Pier

The Centennial Ferris Wheel at Navy Pier is a great attraction that offers breathtaking views of Chicago and Lake Michigan.

As you ascend over 60 meters into the air, this iconic Ferris wheel provides 360-degree panoramic views of Chicago's skyline and the shimmering lake.

Concerts are often held here, from Memorial Day to Labor Day, as well as New Year's Eve celebrations.

You can also find a drop tower and an old carousel, enjoy a show at the Chicago Shakespeare Theater, or unwind at the Navy Pier Beer Garden.

4. Stroll down the Chicago Riverwalk

Chicago Riverwalk

The Chicago Riverwalk, situated on the south bank of the Chicago River, is a pedestrian-friendly destination that extends 1.25 miles from Lake Michigan to Lake Street.

This scenic promenade allows visitors to immerse themselves in the urban atmosphere and appreciate the city's stunning architecture.

With its beautifully landscaped walkways and inviting riverfront cafes, The Chicago Riverwalk provides an ideal setting to relax and enjoy the captivating views.

Along the way, you'll encounter public art installations, boat tours of the Chicago River, and kayak rentals.

5. Attend the Food Festival in Grant Park

Food Festival in Grant Park

Grant Park is a sprawling oasis, spanning 319 acres along the shores of Lake Michigan. It begins at the eastern edge of the Loop and extends to the northern boundaries of the Near South Side.

This green space features iconic attractions, such as Buckingham Fountain, which delights visitors with its water displays.

The Petrillo Music Shell hosts a variety of events, including the renowned Grant Park Symphony, where free concerts can be enjoyed during the summer months.

Grant Park is also famous for hosting Chicago's annual food festival, the Taste of Chicago.

6. See The Cloud Gate in Millennium Park

Cloud Gate

Millennium Park, a vast green space located in the heart of downtown Chicago, captivates visitors with its iconic attractions.

One of the highlights at Millennium Park is "The Cloud Gate," a mesmerizing sculpture affectionately known as "The Bean."

During the winter months, visitors can lace up their skates and glide across the McCormick Tribune Ice Rink, located within Millennium Park.

Millennium Park also connects with the northwest corner of Grant Park.

7. Check out Frank Gehry's Jay Pritzker Pavilion

Frank Gehry's Jay Pritzker Pavilion

Designed by Canadian architect Frank Gehry, the Jay Pritzker Pavilion located within Millennium Park is another iconic landmark.

The venue hosts legendary music festivals like the Chicago Blues Festival, Chicago Jazz Festival, and the Millennium Park Summer Music Series.

With its distinctive stainless steel ribbons, the open-air amphitheater creates a visually stunning setting for outdoor performances.

8. Cool Off at The Crown Fountain in Millennium Park

Crown Fountain

Situated in the heart of Millennium Park, the Crown Fountain is an interactive sculpture that beckons visitors with its captivating design and engaging features.

The Crown Fountain features two towering 50-foot glass structures that showcase dynamic video images of Chicago residents.

You can see the faces of diverse individuals projected onto the towers, creating a mesmerizing visual display in Millennium Park that reflects the vibrant spirit of the city.

9. Walk along the Chicago Cultural Mile

Chicago Cultural Mile

South Michigan Avenue, also known as the Chicago Cultural Mile, is a stretch of Michigan Avenue that runs from the Art Institute of Chicago to the Museum Campus.

As you wander down South Michigan Avenue, you'll come across cultural institutions, such as the Chicago Cultural Center, the Symphony Center, and the Fine Arts Building.

Historic landmarks like the Auditorium Theatre and the historic Palmer House Hilton add a touch of grandeur to the surroundings.

10. Explore The Loop Retail Historic District

Chicago Board of Trade

The Loop Retail Historic District in Downtown Chicago is a captivating destination that blends history, culture, and retail experiences.

This district is home to iconic buildings such as the Chicago Board of Trade, the Chicago Cultural Center, and the Marshall Field and Company Building.

Art enthusiasts can explore numerous art galleries, while history buffs can delve into the past by visiting the Chicago History Museum.

The district is also a shopper's paradise, with an abundance of shops and boutiques.

11. Admire Impressionist Art at the Art Institute of Chicago

Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the country and offers an exceptional opportunity to admire a remarkable collection of Impressionist art.

The Art Institute houses an extensive selection of masterpieces by artists such as Monet, Renoir, Degas, and Cézanne.

If you are interested in learning more about the Impressionist movement, a visit to the Art Institute of Chicago allows for a profound and immersive experience with these iconic works.

Located at 111 S Michigan Ave, Chicago, the Art Institute is in a great spot for exploring Downtown Chicago.

12. Visit the Shedd Aquarium

Shedd Aquarium

The Shedd Aquarium, home to an impressive collection of over 30,000 animals, offers several distinct zones that showcase diverse aquatic environments.

Explore the Caribbean Reef, Polar Play Zone, and Waters of the World, where you can discover fascinating creatures from around the globe.

Delve into the local waters of Chicago and interact with rescued green sea turtles and anacondas, or even get the chance to touch giant rays.

For an immersive cinematic experience, visit the 4D theater at The Shedd Aquarium.

13. See Iconic Building on Michigan Avenue

Michigan Avenue

Michigan Avenue, also known as "The Magnificent Mile," is renowned for its luxurious shopping destinations, upscale boutiques, and high-end department stores. Michigan Avenue is also home to a wealth of cultural tourist attractions in Chicago.

You can visit the Art Institute of Chicago, the Tribune Tower, and the Chicago Water Tower, listed on the National Register of Historic Places and a symbol of resilience after the Great Chicago Fire.

You can also admire the skyscrapers that line the avenue, including the iconic Wrigley Building and the John Hancock Center.

14. Splurge on Designer Labels on The Magnificent Mile

Magnificent Mile

Stretching between Lake Shore Drive and the Chicago River, this iconic stretch of road offers an unparalleled shopping experience with over 450 retailers within walking distance.

Whether you're in search of high-end luxury brands or department stores within walking distance from each other, the Magnificent Mile has it all.

Beyond the incredible shopping opportunities, the Magnificent Mile is also home to exquisite dining establishments, world-class hotels, and renowned cultural attractions.

15. See Chicago from the Willis Tower Skydeck

View from the Top of the Willis Tower

The Willis Tower (formerly Sears Tower) once held the number one position as the tallest building in the world.

As the country's tallest Skydeck observatory, Willis Tower/ Sears Tower offers visitors unparalleled views of the city with floor-to-ceiling windows.

One of the main highlights of Willis Tower is "The Ledge,'' extending more than 1 meter out from the building, allowing visitors to enjoy panoramic views encompassing Lake Michigan and beyond.

16. Find the Historic Route 66 Sign

Historic Route 66 Sign

Located on East Adams Street in the Loop, this iconic sign marks the starting point of the legendary Route 66, the most iconic highway in the world.

Route 66 holds a special place in American culture, immortalized in films and songs as the epitome of the American spirit of adventure.

Originally spanning nearly four thousand miles from Chicago to Santa Monica in California, Route 66 was a symbol of opportunity, connecting landscapes across the United States.

17. Enjoy Live Music at Buddy Guy's Legends

Buddy Guy's Legends

Buddy Guy's Legends is a legendary blues club located in the heart of Chicago. As one of the city's premier live music venues, it offers a unique and authentic blues experience.

With a rich history and a reputation for showcasing both up-and-coming talent and world-renowned acts, Buddy Guy's Legends presents live performances seven nights a week.

The intimate setting creates an up-close and personal connection between the artists and the audience, allowing you to fully appreciate the raw talent at Buddy Guy's Legends.

18. Go Skating at Maggie Daley Park

Maggie Daley Park

Maggie Daley Park, spanning 20 acres near Lake Michigan, offers a wide array of activities for visitors to enjoy.

The highlight of the park is the half-kilometer-long ice skating ribbon, which provides an exhilarating skating experience. During the summer months, the green space is a roller skating area.

This Downtown Chicago park also boasts tennis courts and two rock-climbing structures that provide opportunities for both bouldering and lead-harnessed climbing.

19. Attend a Performance of the Chicago Symphony Orchestra

Chicago Symphony Orchestra

With a rich history dating back to 1891, the Chicago Symphony Orchestra has captivated audiences with its exceptional performances and remarkable talent ever since.

The Symphony Center itself is an architectural gem in Downtown Chicago, blending the charm of its original 1904 design with modern renovations.

The historical Orchestra Hall has served as the home of the Chicago Symphony Orchestra and the Chicago Symphony Chorus for many years.

20. See a Show at the Chicago Theatre

Chicago Theater

The Chicago Theatre is a historic landmark and an architectural gem located in the heart of Downtown Chicago.

Its grand marquee and iconic sign make it a recognizable symbol of the city's vibrant entertainment scene. The theater offers a wide range of shows, including Broadway productions, comedy acts, concerts, and more.

There is also the smaller Studio Theatre, which hosts intimate performances and events in Downtown Chicago.

21. Find Cool Hands-On Exhibits at the Chicago Children's Museum

Chicago Children's Museum

The Chicago Children's Museum is a top destination for families and children of all ages. Located on Navy Pier, this interactive museum offers a wealth of engaging experiences.

Children can explore the Dinosaur Expedition, where they can dig for fossils, and the Tinkering Lab, where they can engage in imaginative building and problem-solving.

The WaterWays exhibit allows kids to experiment with water, while the Treehouse Trails provides a multi-level play area for active exploration. If you are in Downtown Chicago with kids, this is the place to be.

22. Meet T Rex Sue at The Field Museum of Natural History

T Rex Sue at The Field Museum of Natural History

The Field Museum of Natural History at Grant Park's Museum Campus is a captivating destination that offers a journey through time and a deeper understanding of the natural world.

The museum is home to an amazing collection that spans millions of years of Earth's history, showcasing everything from dinosaur fossils and ancient Egypt to cultural artifacts from around the globe.

The museum's most famous resident, Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered, is a highlight not to be missed in Downtown Chicago.

23. Visit the Adler Planetarium

Adler Planetarium

The Adler Planetarium was established in the 1930s as the first planetarium in the United States and has a rich history of inspiring and educating visitors about space and astrophysics.

As you explore this Downtown Chicago museum, you'll encounter captivating hands-on exhibits that showcase celestial phenomena, space exploration, and the latest discoveries in the field.

One of the highlights of a visit to the Adler is the Doane Observatory, where visitors can peer through powerful telescopes and gaze at the stars on select Wednesday nights.

24. Spend Time at the Lincoln Park Zoo

Lincoln Park Zoo

Located just 2 miles north of the Loop in the vibrant North Side neighborhood of Lincoln Park, the Lincoln Park Zoo is a beloved attraction in the city.

As one of the oldest zoos in the United States, it holds a rich history and a commitment to wildlife conservation and education.

The zoo is home to nearly 200 species, including exotic animals from around the world, from majestic lions and playful penguins to graceful giraffes and colorful reptiles.

25. Try Chicago-style Popcorn

Chicago-style Popcorn

If you're looking for a unique and delicious snack in Downtown Chicago, be sure to visit the Garrett Popcorn Shop on East Madison Street.

This iconic shop is renowned for its mouthwatering Chicago-style popcorn, a delightful blend of two distinct flavors.

Combining cheesy kernels with caramel-coated ones, this popcorn creation offers a harmonious balance of savory and sweet that will tantalize your taste buds.

Garrett's flavor combination is both unexpected and utterly addictive and well worth the trip if you are in Downtown Chicago.

26. Have some Chicago Style Pizza

Chicago Deep Dish Pizza

With its deep-dish crust, generous amounts of cheese, chunky tomato sauce, and various toppings, Chicago-style pizza is a must-try for foodies visiting the city.

When it comes to finding the best Chicago-style pizza in Downtown Chicago, there are several renowned establishments worth visiting.

One iconic spot is Giordano's on Randolph Street, serving their famous stuffed deep-dish pizza since 1974. Another popular choice is Pizano's on Madison Street.

27. Shop in Macy's at State Street

Macy's at State Street

If you're in the mood for some retail therapy, visit Macy's in Downtown Chicago.

Located on State Street, within the Loop Retail Historic District, this iconic department store beckons shoppers with its vast selection and grandeur.

With a sprawling eight floors of retail space, Macy's in Downtown Chicago ranks as the second largest store in the world.

28. Visit the International Museum of Surgical Science

International Museum of Surgical Science

Housed in a historic mansion on Lake Shore Drive, the International Museum of Surgical Science explores the fascinating history of surgical science.

As you navigate through the museum's collections, you'll be transported through time, discovering the mysteries and pivotal moments that have shaped modern surgical practices.

This Downtown Chicago museum offers a thought-provoking interpretation of the ancient and contemporary healing practices of both Eastern and Western civilizations.

The museum is supported by Choose Chicago**,** the official destination marketing organization for Chicago, Illinois.

29. Dine in the Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

Located right on the Magnificent Mile, Millennium Knickerbocker Chicago is a premier 4-star hotel that offers an exceptional experience for visitors of the city.

The hotel features a stunning ballroom, adorned with a magnificent gold-gilded domed ceiling that exudes elegance and grandeur.

Guests can enjoy the spa and fitness center, indulge in delectable farm-to-table cuisine and immerse themselves in the ambiance of the Roaring Twenties in a 1920s-inspired cocktail bar.

30. Explore Printers Row in the South Loop

Printers Row in the South Loop

Located in the South Loop neighborhood of Chicago, Printers Row is a historic district that offers a unique and charming experience for visitors.

Printers Row is renowned for its beautiful architecture, with preserved buildings that exude a vintage charm that pose a contrast with much of Downtown Chicago.

Book lovers will enjoy the annual Printers Row Lit Fest, one of the largest book fairs in the country.

FAQs Relating to Downtown Chicago Attractions

Let's also explore some frequently asked questions relating to the top Downtown Chicago hidden gems.

What is Downtown Chicago known for?

Downtown Chicago is known for its world-class museums and theaters, and the Chicago Cubs team. Some notable Chicago landmarks include the Magnificent Mile, Millennium Park, Navy Pier, and Willis Tower.

The main neighborhoods in Downtown Chicago include the Gold Coast, The Chicago Loop, South Loop, Downtown Loop, West Loop, Magnificent Mile, Lakeshore East, Chicago River North, and Streeterville.

What is the most famous street in Downtown Chicago?

The famous street in Downtown Chicago is the Magnificent Mile. It is a section of Michigan Avenue that stretches from the Chicago River to Oak Street and is known for its high-end shops, restaurants, and cultural attractions.

What is the main part of Downtown Chicago?

The main part of Downtown Chicago is the Loop. It is the central business district of the city and is home to many iconic historic buildings, such as the Willis Tower, the Chicago Board of Trade Building, and the Chicago Cultural Center.

The Loop Retail Historic District within the Chicago Loop is particularly popular with visitors for shopping and sightseeing.

How do you explore Downtown Chicago?

To explore Downtown Chicago, one can take a stroll through the streets, take a Segway tour, hop on a sightseeing bus, or take a riverboat tour.

There are also various walking tours available in Downtown Chicago and many art galleries and museums to explore when visiting Chicago.

Summing Up: Downtown Chicago Hidden Gems

Exploring Downtown Chicago unveils a treasure trove of hidden gems. From the enchanting Chicago Riverwalk to the expansive Grant Park, there are endless opportunities for unforgettable experiences in the city.

See the mesmerizing Chicago skyline from the Willis Tower Skydeck, go shopping at State Street, and head to the art museums and theaters for a much-needed culture fix.

Plan your trip today and embark on a journey through the heart of the Windy City to uncover the magic that awaits.