Blake Walsh

40 Best Things to Do in Chicago, IL

  • Published 2023/02/13

See also: Where to Stay in Chicago

Architecture, sports, and live music are the three defining characteristics of Chicago, Illinois.

Visit the museums, parks, and grand avenues, where you can see a wide variety of stunning art, structures, and many more.

If you like sports, you may want to drop by the Wrigley Field and United Center to watch all sorts of ball games.

Interested to know more about this place?

Here are the 40 best things you can do in Chicago, Illinois:

See the Stunning Millennium Park

Millennium Park

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Capturing the modern-day spirit of Chicago is the shining Millennium Park, an award-winning park.

It is one of Chicago’s most popular tourist attractions

Discover the world’s largest green roof, Lurie Garden, binding perennials, bulbs, and grasses in a bold design.

View of Jay Pritzker Pavilion

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Or, catch a concert at the 11,000-capacity Jay Pritzker Pavilion, which the Chicago Symphony Orchestra and major music headliners frequent.

Millennium Park also offers bike rentals at McDonald’s Cycle Center, so you can explore the expansive Grant Park.

Visitors enjoying an event at Jay Pritzker Pavilion

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Feel the Nightlife at Puttery

Puttery is a venue for adults aged 21 and above that puts the game of putting in a fresh light and reshapes it with distinctive twists at each hole.

It’s an immersive adventure with friendly competition, networking, fine dining, specialty drinks, and excellent music.

Adults come here for an unforgettable night out, whether they play or not.

When you arrive at Puttery, check in with the concierge to schedule your tee time.

Afterward, unwind with a round of creative drinks and posh snacks in lounges, bar tops, communal tables, or terraces.

Its extensive bars provide a wide variety of drinks, including zero-proof beverages, glasses of champagne, course-specific specialty cocktails, and local brews.

Revisit Disnosaur’s History at the Field Museum of Natural History

Field Museum of Natural History

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Since 1893, the Field Museum of Natural History has collected over 24 million items.

This collection is a comprehensive look at the natural world, featuring excavated fossils, gemstones, and extinct specimens.

Exterior view of  Field Museum of Natural History

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Here, you’ll see themed halls like anthropological Ancient Americas and Ancient Egypt or art pieces related to the Tibetan and African cultures.

This museum is definitely a must-visit.

Exhibits at  Field Museum of Natural History /

Shop for Unique Items at Woolly Mammoth Antiques

Are you searching for one-of-a-kind gift items for loved ones or pieces to keep for yourself?

Browse a fascinating collection of unusual, humorous, and diverse things from the past at Woolly Mammoth Antiques & Oddities.

They are experts in vintage and antique taxidermy, anatomical supplies, medical equipment, books, toys, bones, skeletons, artwork, charts, maps, instruments, specimens, and more.

Woolly Mammoth is open Monday through Sunday from 12 p.m. to 5 p.m.

Visit the store to admire the innovative design elements included in the business’s retail space and the things for sale.

Visit Chicago Riverwalk


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Cutting through downtown along the Chicago River is the 1.25 miles long Chicago Riverwalk leading up to Wolf Point.

With a backdrop of stately buildings, terraces, dramatic bridges, and urban scenery, it is a must-visit for all photographers.

View of Chicago Riverwalk

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Keep an eye out for the Wrigley Building or Ellen Lanyon’s Gateway, where you’ll see plenty of architectural highlights and public art in the form of installations, graffiti, and tiled murals.

Chicago Riverwalk is incredibly evocative at night, with cafés and grill bars lighting up the walkway with date-night ambiance.

Visitors dining at a restaurant in the Chicago Riverwalk

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Admire the Breathtaking Views from 360 CHICAGO

View from 360 CHICAGO

Matt Kieffer from London, United Kingdom, CC BY-SA 2.0, via Wikimedia Commons

From the highest part of the former John Hancock Center, 360 CHICAGO offers the perfect perspectives of the Chicago skyline and Lake Michigan.

A thousand-foot vantage point above the renowned Magnificent Mile, the 360 CHICAGO Observation Deck provides phenomenal panoramic views of Chicago.

The tallest thrill coaster in Chicago, TILT, is on the observation deck.

View from the 360 CHICAGO

David Wilson from Oak Park, Illinois, USA, CC BY 2.0, via Wikimedia Commons

Being the only one of its type in the world, it provides guests with exceptional, downward-facing vistas from 1,030 feet.

The observation deck blends delicious drinks with stunning views.

Grab a drink, unwind, and take happy hour to a new level at 360 CHICAGO!

See Various Aquatic Animals at the Shedd Aquarium

Shedd Aquarium

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Sharing location with the Field Museum and Adler Planetarium, the Shedd Aquarium is an impressive collection of 30,000 aquatic creatures.

Visitors watching the fish at Shedd Aquarium

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Amazon Rising recreates the roots of rainforest trees to house anacondas, piranhas, and freshwater stingrays; the Wild Reef has four shark species.

You may also spend some time waving at the sea lions and sea otters at the Oceanarium.

A trainner interacting with a whale at Shedd Aquarium

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View the Collections at Driehaus Museum

Exterior view of Driehaus Museum

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Richard H. Driehaus Museum educates and inspires the worldwide community through discovery and active conversations in late-nineteenth- and early-twentieth-century art, architecture, and design.

The late Richard H. Driehaus, the Museum’s founder, had a passion for collecting, which is reflected in and inspired by the collection.

Stained glass at Driehaus Museum

victorgrigas, CC BY-SA 3.0, via Wikimedia Commons

The renovated Samuel Mayo Nickerson Mansion houses its permanent collection and occasional exhibitions, creating an immersive environment.

Tours cover the collections of the Museum, the special exhibition’s best bits, and the historical background and architecture of the building.

Private excursions led by guides are arranged upon request.

Watch a Performance at The Chicago Theatre

Chicago Theatre

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Bring home a snapshot of The Chicago Theatre’s iconic marquee and vertical sign, even if you’re passing by.

The red and yellow glowing boards have been featured in movies.

Much like its grand exterior, the performances held here are top-tier.

The grand interior of Chicago Theatre

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Pick from their extensive performing arts program, as varied as dance theatre and comedy acts.

Sometimes the venue also hosts talks by famous cultural figures.

Take an Interesting Tour with Nightly Spirits

Discover the most significant and genuine Chicago ghost tours, as there are many haunted spots in the city.

Nightly Spirits allows you to dig into the legendary city of Chicago’s mysterious past.

It is situated right in the center of Windy City.

The experienced storytellers serving as your guides will take you to several of the city’s most eerie locations along the route.

Are you prepared for the people or creatures you’ll run into on your adventurous journey?

On this one-of-a-kind journey, you will discover all of Chicago’s past, untold stories, and rich cultural legacy.

The most well-liked tour offered by Nightly Spirits merges a pub crawl with a ghost walk around the city’s famous center, allowing you to savor delectable beverages while learning about some of its most terrifying legends.

Have a Picnic at Grant Park

Grant Park

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Grant Park in autumn is beautiful, with broad litters of golden leaves sharp against the green shrubbery.

An open space home to some of Chicago’s top attractions, including Millennium Park, the Art Institute of Chicago, and Soldier Field, its cumulative 319 acres is coined “Chicago’s Front Yard.”

Rose garden at Grant Park

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There’s much to do within its boundaries, such as the annual Chicago Marathon and Taste of Chicago Festival.

Still, if you’re looking to unwind, there are plenty of quiet corners to hide in.

Aerial view of Grant Park

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Explore the Adler Planetarium

Adler Planetarium

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Within Adler Planetarium are displays of the Solar System and exhibits that detail the universe’s history.

The planetarium also hosts events when other planets come into view, presenting the mysterious at a closer distance.

Closer view of Adler Planetarium

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Climb to the Willis Tower Skydeck

Willis Tower Skydeck

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Willis Tower is considered the ‘world’s tallest building.’

Standing at 442 meters and a Skydeck at 412 meters, its view glances over four states of sectioned concrete.

Exterior view of Willis Tower Skydeck

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Watch the movie documenting how Willis Tower came to be and learn about other worthwhile Chicago architectures.

Your Willis Tower Skydeck experience doesn’t end with stunning views, as the four all-glass boxes of The Ledge will have you screaming.

A couple posing at Willis Tower Skydeck

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See a Wide Variety of Plants at the Garfield Park Conservatory

Garfield Park Conservatory

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Palms, ferns, succulents, and cacti can be found in this beautiful garden.

Eight indoor display groves make up the Garfield Park Conservatory.

Colorful sculpture at Garfield Park Conservatory

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Whether it is the softer lushness of the Fen Room or the dry brushes of the Desert House, the carefully sculpted spaces will melt your stress away.

Free up some time to participate in a free yoga session or watch gardening demonstrations.

View of Garfield Park Conservatory

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Have Fun at the Navy Pier

Navy Pier

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Jutting out where Chicago Portage meets Lake Michigan, the Navy Pier is a heavy-duty tourist attraction that offers multifaceted entertainment.

You’ll find splashes of green at the botanical garden Crystal Gardens, fairground amusements around the Centennial Wheel and Funhouse Maze, the Chicago Children’s Museum, and other sensory fun.

View of Navy Pier

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The Miller Lite Beer Garden will let you wash down craft beers with live music, and to satisfy your drama-seeking needs, visit the Chicago Shakespeare Theatre.

People strolling at Navy Pier

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Pay a Visit to Chicago Shakespeare Theatre

Chicago Shakespeare Theatre

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Fill up on drama at the non-profit Chicago Shakespeare Theatre down at Navy Pier.

Celebrating the works of Shakespeare with remarkable productions on-site and off-site, the company has earned three Laurence Olivier Awards over the years.

The theatre hosts two halls, the bigger one capable of seating 510 audiences.

Performance at Chicago Shakespeare Theatre

JenFulmer, CC BY-SA 4.0, via Wikimedia Commons

Catch classic productions like Macbeth and Hamlet, or go light with a fun Peter Pan musical.

It’s a relaxing activity to fill up your post-dinner schedule.

Exterior view of Chicago Shakespeare Theatre

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Take Pictures of the Japanese Macaques at Lincoln Park Zoo

Lincoln Park Zoo

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Visit Lincoln Park Zoo is one of the only free admissions parks in the United States.

Since 1868, this zoo has undergone constant revamps to provide the best habitats for its thousand-strong residents.

Ferocious tiger at Lincoln Park Zoo

Mobilus In Mobili, CC BY 2.0, via Wikimedia Commons

Gaze at lounging polar bears, grazing gazelles, ostriches, and hot-spring-loving Japanese macaques.

Signage at Lincoln Park Zoo

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Soak under the Sun at Oak Street Beach

Oak Street Beach

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You don’t have to go far for some waterside chilling as Oak Street Beach only stretches along the shore of Lake Michigan on North Lake Shore Drive.

There are lifeguards keeping things fun and safe.

Men playing volleyball at Oak Street Beach

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There are also bars and food joints nearby when you need fuel.

Spend a relaxing afternoon here.

Oak Street Beach on a busy summer day

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Visit the Chicago Cultural Center

Chicago Cultural Center


Chicago Cultural Center offers many reasons why people should visit it.

For one, it hosts thousands of exhibitions and programs annually, ranging from music, theatre, and film screenings to family-oriented events.

The building speaks heritage, the interior boasting marbled pillars, polished brass work, and hardwood.

Interior view of Chicago Cultural Center

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If the tiled archways aren’t enough to hold your attention, then it’s south and north domes surely will.

Look at the peerless stained glass Tiffany dome and the intricate Renaissance-style dome in appreciation of their fine artistry.

Beautiful architecture at Chicago Cultural Center

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Break boundaries at Maggie Daley Park

Maggie Daley Park

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Challenge yourself at Maggie Daley Park.

Named to the city’s former first lady, this relatively new recreational space sits on a corner of Grant Park.

Its unusual landscaping is attributed to architect Michael Van Valkenburgh, whose design stresses an unconventional play area for adults and children.

Rock climbing wall at Maggie Daley Park

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Among the ice skating ribbon, picnic nook, and mini-golf course, the Play Garden stands out.

Offering six fun zones, this park features a Watering Hole and an Enchanted Forest.

View of the Maggie Daley Park

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Watch a Basketball Game at United Center

United Center

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Professional hockey, basketball, and top-selling pop acts have blessed the halls of the United Center.

Serving as home turf for the Chicago Bulls and Blackhawks during on-seasons, this venue offers rock and pop concerts.

Front view of United Center

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While it may no longer be the headliner venue it once was, United Center is still significant.

Remember to grab a photo with Michael Jordan’s statue in the public atrium if you’re passing by.

Interior view of United Center

Gavindow, CC BY 3.0, via Wikimedia Commons

Visit the Historic Pullman Foundation

View of Pullman Center

Boven, CC0, via Wikimedia Commons

When we say visit the Historic Pullman Center, we mean start your South Side tour here.

Introducing George Pullman’s neighborhood (built to house his employees) through exhibits, the visitor center provides context on the area’s significance.

Once equipped with some knowledge of the neighborhood’s growth and preservation, set out on a self-guided tour to find film-featured historic buildings.

Wander around the Magnificent Mile

Magnificent Mile

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Magnificent Mile has an 8-block whirl of shopping, dining, and urban display.

Stroll down Michigan Avenue for your choice of cuisine and retail, which covers indie boutiques and high-end flagship stores.

While walking, see the Tribune Tower, Wrigley Building, and 875 N Michigan.

Shops at Magnificent Mile

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Tour The Art Institute of Chicago

The Art Institute of Chicago

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Art lovers will be familiar with the names of Nighthawks, American Gothic, and A Sunday Afternoon on the Island of La Grande Jatte – three celebrated works currently inhabiting the Art Institute of Chicago.

Outside of Paris, the most significant Impressionist and Post-Impressionist painting collection dwell, featuring Monet, Cezanne, Renoir, and van Gogh.

Interior view of Art Institute of Chicago

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Modernist contenders such as Pollock and Warhol and designs by Frank Lloyd Wright are also highlights of this institution.

You can expect more than just paintings; a wide range of Greek, Egyptian, and Etruscan artifacts run from mosaics to bronze items.

Exhibits at Art Institute of Chicago

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Watch Live Bands at Kingston Mines

Dip by Kingston Mines for some of the city’s best blues music.

This place is the oldest and largest operating blues club still thriving soulfully.

From night until dawn, energetic bands will have you swinging to their beats.

If Kingston Mines isn’t quite your venue, there are over 200 live music stages for you to browse through.

Include this place in your itinerary.

Take a River or Lake Cruise

Chicago River Cruise

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Lake Michigan and the Chicago River offer a unique way of seeing the city.

Embark on a tour through the city-crossing channel to spot some of Chicago’s architectural masterpieces.

River Cruise in Chicago

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Ranging from 45 minutes to a sedate 75-minute cruise, you have a selection of sightseeing trips.

Check out the Classic Lake Tour, Architecture Cruise, or Chicago River Architecture Cruise.

Cruise ship at Chicago

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Play Pokers at Logan Arcade

Logan Arcade has well-preserved collections of game machines.

It is housed inside a refurbished hardware store and old-time classics such as Pac-Man.

Mario Kart and Jurassic Park shooter games lure in younger crowds, whereas timeless pinball machines combine various period selections.

There’s even a bar to supplement with craft beers and cocktails for those who need an extra kick.

Cross The 606


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You might not consider this a conventional attraction, but The 606 is functional and visual.

An abandoned elevated railway track turned pedestrian and bicycle path, it is a 2.7-mile trek that links Logan Square, Humboldt Park, Bucktown, and Wicker Park.

View of the 606 trail

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Laugh Out Loud at Second City

chicago comedy

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Second City has birthed many comedians that have come to conquer this entertainment genre.

Alums include Tina Fey, Steve Carell, Stephen Colbert, and Amy Poehler; current members of this company are equally talented.

If you need some cheer-me-up, why not treat yourself to sketch comedy and improv acts?

Revisity the City’s History at Chicago History Museum

Chicago History Museum

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Chicago History Museum digs deep into Chicago’s history, delineating its origins, struggles, and transformation from outpost to metropolis.

Peruse the hall of Facing Freedom to grasp Chicago’s role in the fight for freedoms; it recounts the Civil War, the Women’s Suffrage movement, and labor unions’ rise from the mid-1800s to the 1970s.

Interior view of Chicago History Museum

Michael Barera, CC BY-SA 4.0, via Wikimedia Commons

But there’s more – experience an old-time jazz club firsthand and sit in Chicago’s first L train.

By merging historical displays with interactive cultural galleries, Chicago History Museum seeks to comprehensively understand the city’s rich heritage.

Lincoln's deathbed at Chicago History Museum

Adam Jones from Kelowna, BC, Canada, CC BY-SA 2.0, via Wikimedia Commons

Pay a Visit to Frederick C. Robie House

the Robie House

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Robie House represents early 20th-century Prairie-style residences.

Drawing inspiration from the spacious Midwest, this architecture uses open spaces, layered roofing, broad eaves, and balconies.

Entrance to Frederick C. Robie House

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In contrast, the use of art-glass and careful selection of furniture fittings and fireplaces evoke a cozy vibe in complement to its warm coloring.

Interior view of Frederick C. Robie House

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Catch a Game at Wrigley Field

Wrigley Field

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Built in 1914, Wrigley Field is recognizable by its unassuming exterior and ivy-clad outfield walls – although its manual scoreboard steals the limelight.

Outside view of Wrigley Field

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Its proximity to Lake Michigan makes the games doubly exciting, but the home team Chicago Cubs thrives on the thrill anyway.

Treat yourself to a game and round off the experience with a Chicago hot dog as you cheer the players on.

Statue of Erine Banes at Wrigley Field

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Go Bar Hopping in Boystown


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Chicago’s hottest LGBTQ neighborhood is calling the boys and girls to town.

If you’re searching for good grog and even better company, hustle your way through Boystown by thoroughly exploring the drinks menu of every watering hole.

Street view of Boystown

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From drag-show bars to fancy cocktail venues, you are guaranteed a night of laidback revelry.

Halloween decorations at Boystown

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Watch a Cinema at Music Box Theatre

Exterior view of Music Box Theatre

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Divorce mainstream Hollywood films and popcorn through Music Box Theatre’s art-house films and documentaries.

The natural buttered popcorn is yummy toppings on top of midnight screenings, cult classics, and director Q&As.

See the Lantern Slides at Stony Island Arts Bank

Exterior view of Stony Island Arts Bank

Altawati, CC BY-SA 4.0, via Wikimedia Commons

Did you know Stony Island Arts Bank was purchased for $1 and was transformed into an art and media archive?

It’s a miracle what one measly dollar could do; the bank is now home to 60,000 glass lantern slides and DJ Frankie Knuckles’ record collection.

The bizarre galleries also feature world-famous artists, and guests are carefully lectured before being allowed to wander around.

See a Submarine at the Museum of Science and Industry

Museum of Science and Industry

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The Museum of Science and Industry is nestled in the 1933 Old Palace of Fine Arts.

If you find its hulking structure inspiring, you’ll be blown away by the mind-boggling exhibits within the walls.

A distant view of the Museum of Science and Industry

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Some highlights include a World War II German U-505 submarine and the commercial aviation pioneer Boeing 727.

Complex scientific concepts are broken down for easy digestion in the Science Storms exhibit, whereas the coal mine replica takes you back to earlier industrial sets.

Submarine at Museum of Science and Industry

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Watch a Musical Concert at Chicago Symphony Orchestra

Facade of the Chicago Symphony Orchestra

ajay_suresh, CC BY 2.0, via Wikimedia Commons

Close your eyes and throw away all other distractions to appreciate a filling, resonant performance by one of the world’s most prestigious classical ensembles.

The shows are worth every dollar, featuring arrangements by the Chicago Symphony Orchestra and guest soloists.

Settle in the Grainger Ballroom, Buntrock Hall, or Orchestra Hall for an ear changing night at this historical landmark.

Final Thoughts

Beyond downtown, you’ll find a distinct environment with historic live music venues, cuisine, and attractions.

No matter your hobbies, Chicago has something to get you fired up.

Explore the city’s fascinating history, thriving commercial areas, and diverse nightlife.

Join the tours of the most well-known sights in the city!

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