Top 25 Things To Do in Chicago

From towering skyscrapers to deep-dish pizza, the Windy City serves up a feast of architecture, culture, and culinary delights.

West Parker
West Parker
July 18, 2024

Welcome to Chicago, where the city's innovative spirit reaches for the sky – quite literally. Picture yourself stepping onto a glass balcony 1,353 feet above the ground, the sprawling cityscape spread out beneath your feet. This heart-pounding experience at Willis Tower's Skydeck is just the beginning of what the Windy City has to offer.

As we descend from these dizzying heights, we'll explore how Chicago's rich history and forward-thinking attitude have shaped a metropolis that's as diverse as it is dynamic. From the birthplace of the skyscraper to the shores of Lake Michigan, from world-class museums to hidden neighborhood gems, Chicago invites you to write your own story in its ever-evolving narrative.

So grab a slice of deep-dish, lace up your walking shoes, and get ready to explore the very best of Chi-Town. Whether you're an architecture buff, a foodie, a culture vulture, or simply seeking the warmth of Midwestern hospitality, Chicago's got you covered. Let's dive in!

Step Out on The Ledge at Willis Tower Skydeck

Visitor on Willis Tower Skydeck glass balcony, looking down at Chicago cityscape from 1,353 feet high
Faced my fear of heights at Willis Tower Skydeck. The view was totally worth the wobbly knees!

Ready for a adrenaline rush? At Willis Tower's Skydeck, you'll find yourself standing on a glass balcony 1,353 feet in the air, with nothing but transparent flooring between you and the bustling streets below. As you step out onto The Ledge, feel your heart race as you take in panoramic views of four states. On a clear day, you can see up to 50 miles away! But it's not just about the views – interactive exhibits on the lower levels offer fascinating insights into Chicago's history and architecture. For an extra special experience, time your visit for sunset and watch the city transform as day turns to night.

  • Location: 233 S Wacker Dr, Chicago, IL 60606
  • Hours: 9 AM - 10 PM daily (March-September), 10 AM - 8 PM (October-February)
  • Admission: Adults $30-35, Children (3-11) $22-26

Why Visit: Experience Chicago from a breathtaking perspective that will leave you speechless.

Pro Tip: Book your tickets online in advance and opt for the early morning or late evening slots to avoid the longest lines.

Marvel at Masterpieces in the Art Institute of Chicago

Visitors observing Georges Seurat's "A Sunday on La Grande Jatte" at the Art Institute of Chicago
Spent hours at the Art Institute today. Can't believe I saw Seurat's masterpiece in person!

Step into a world where artistic genius comes alive at every turn. The Art Institute of Chicago houses an astounding collection that spans 5,000 years of human creativity. From the Impressionist masters to contemporary provocateurs, this museum is a feast for the eyes and the mind. Stand before Georges Seurat's pointillist masterpiece "A Sunday on La Grande Jatte" and try to count the tiny dots. Lose yourself in the swirling brushstrokes of Van Gogh's "The Bedroom." With over 300,000 works of art, you could spend days here and still discover new treasures. Don't miss the modern wing, where floor-to-ceiling windows offer a stunning juxtaposition of artwork and city views.

  • Location: 111 S Michigan Ave, Chicago, IL 60603
  • Hours: 11 AM - 5 PM daily (Thursday until 8 PM), closed Thanksgiving, Christmas, and New Year's Day
  • Admission: Adults $25, Teens (14-17) $19, Children under 14 free

Why Visit: Immerse yourself in one of the world's premier art collections, spanning centuries and continents.

Pro Tip: Download the museum's free app for self-guided tours and to create your own personalized art trail.

Snap a Selfie at Cloud Gate in Millennium Park

Visitors taking selfies at Cloud Gate (The Bean) sculpture in Millennium Park, Chicago
The Bean lives up to the hype! Pro tip: come early to beat the crowds and get the perfect shot.

Get ready to see yourself – and the city – in a whole new light at Cloud Gate, affectionately known as "The Bean." This massive, mirror-like sculpture by Anish Kapoor has become Chicago's most iconic photo op. As you approach, watch the skyline warp and bend across its gleaming surface. Duck underneath to find yourself in a hall of mirrors, where the boundaries between art, architecture, and viewer blur into a mesmerizing spectacle. But Cloud Gate is just the beginning of Millennium Park's wonders. Splash in the playful Crown Fountain, where digital faces spout water on hot summer days, or catch a free concert at the Frank Gehry-designed Jay Pritzker Pavilion. The park is Chicago's front yard, a place where art, nature, and urban life collide in spectacular fashion.

  • Location: 201 E Randolph St, Chicago, IL 60602
  • Hours: 6 AM - 11 PM daily
  • Admission: Free

Why Visit: Experience Chicago's most photogenic public art and enjoy the vibrant energy of the city's favorite gathering spot.

Pro Tip: Visit early in the morning to catch "The Bean" without crowds and see it reflect the sunrise.

Travel Through Time at The Field Museum

Visitors admiring SUE, the largest and most complete T. rex skeleton, at The Field Museum in Chicago
Met SUE at The Field Museum today. 67 million years old and still looking fierce!

Prepare for a journey spanning billions of years at The Field Museum, where natural history comes to life in spectacular fashion. Come face-to-face with SUE, the largest and most complete T. rex ever discovered. Marvel at her 40-foot-long skeleton and ponder what life was like 67 million years ago. But dinosaurs are just the beginning. Explore ancient Egyptian tombs, marvel at sparkling gemstones, and learn about cultures from around the globe. The museum's immersive exhibits transport you from the depths of the ocean to the far reaches of outer space. Don't miss the chance to shrink down to bug size in the Underground Adventure exhibit – it's a perspective-shifting experience that will change how you see the world beneath your feet.

  • Location: 1400 S Lake Shore Dr, Chicago, IL 60605
  • Hours: 9 AM - 5 PM daily, last admission at 4 PM
  • Admission: Basic Adult $40, Child (3-11) $29, Senior (65+) $35

Why Visit: Embark on an awe-inspiring journey through the history of our planet and its diverse inhabitants.

Pro Tip: Upgrade to the All-Access Pass to include special exhibits and a 3D movie – it's worth it for the full Field Museum experience.

Cruise the Chicago River on an Architecture Tour

Chicago's skyline viewed from architecture boat tour on Chicago River near Michigan Avenue Bridge
Best way to see Chicago? From the river! This architecture tour blew my mind.

Prepare to be blown away by Chicago's world-renowned skyline from a unique vantage point – right on the water. As you glide along the Chicago River, expert docents from the Chicago Architecture Center will reveal the stories behind the city's most impressive structures. From the world's first skyscraper to cutting-edge modern marvels, you'll gain a new appreciation for how architecture has shaped Chicago's identity. Learn how the river itself was engineered to flow backwards, and how this feat of human ingenuity transformed the city. As the sun sets, watch the skyline light up, turning the river into a canyon of twinkling lights. It's a perspective on Chicago you won't soon forget.

  • Location: Tours depart from Michigan Avenue and Wacker Drive
  • Hours: Multiple daily departures, seasonal schedule
  • Admission: Adults from $51, Children (5-12) from $30

Why Visit: Gain unparalleled insights into Chicago's architectural legacy while enjoying stunning views from the water.

Pro Tip: Opt for a twilight cruise to see the city transition from day to night – the skyline views are simply magical.

Ride the Centennial Wheel at Navy Pier

Navy Pier's illuminated Centennial Wheel at night, with Lake Michigan and Chicago skyline in background
Ended the day with a spin on Navy Pier's Centennial Wheel. The nighttime views are unreal!

Take a spin on Navy Pier's crown jewel, the 200-foot Centennial Wheel, for breathtaking views of the Chicago skyline and Lake Michigan. As you ascend in your climate-controlled gondola, the bustling pier and glittering lake unfold beneath you. But the Ferris wheel is just the beginning of Navy Pier's charms. Stroll along the South Dock, lined with restaurants and shops, or catch a show at the Chicago Shakespeare Theater. Kids will love the Chicago Children's Museum, while adults can sip craft beers at the Miller Lite Beer Garden. As night falls, the pier comes alive with twinkling lights and often, spectacular fireworks displays. It's a slice of pure Chicago magic, right on the lakefront.

  • Location: 600 E Grand Ave, Chicago, IL 60611
  • Hours: 10 AM - 8 PM Sunday-Thursday, 10 AM - 10 PM Friday-Saturday (hours may vary seasonally)
  • Admission: Free entry to pier, Centennial Wheel: Adults $18, Children (3-11) $15

Why Visit: Experience a perfect blend of family-friendly fun, stunning views, and lakefront ambiance at this iconic Chicago destination.

Pro Tip: Visit on a Wednesday or Saturday night in summer to catch the free fireworks show, best viewed from the Centennial Wheel.

Unleash Your Inner Scientist at the Museum of Science and Industry

Visitor exploring giant walk-through human heart exhibit at Chicago's Museum of Science and Industry
Felt like Ant-Man exploring this giant heart. Science is cool, folks!

Get ready to have your mind blown at the largest science museum in the Western Hemisphere. The Museum of Science and Industry is where curiosity runs wild and hands-on experiences reign supreme. Step inside a real German U-boat from World War II, feel the rush of a simulated tornado, or watch baby chicks hatch before your eyes. The mirror maze will challenge your perception, while the giant heart will make your own skip a beat. Don't miss the chance to descend into a coal mine or control a 40-foot tornado. With over 400,000 square feet of exhibits, there's enough here to keep both kids and adults entertained for hours. Who knew learning could be this much fun?

  • Location: 5700 S Lake Shore Dr, Chicago, IL 60637
  • Hours: 9:30 AM - 4 PM daily, extended hours seasonally
  • Admission: Adults $21.95, Children (3-11) $12.95

Why Visit: Ignite your curiosity with interactive exhibits that bring science and technology to life in spectacular fashion.

Pro Tip: Book tickets for the popular Coal Mine and U-505 Submarine tours in advance to avoid disappointment.

Meet the Animals at Lincoln Park Zoo

Visitors observing lions in their habitat at Lincoln Park Zoo, Chicago's free urban wildlife oasis
Can't believe this amazing zoo is free! Watched the lions for hours. A must-visit in Chicago.

Step into a 35-acre oasis in the heart of Chicago, where lions roar and monkeys swing from tree to tree. Lincoln Park Zoo, one of the oldest zoos in North America, offers a chance to connect with wildlife from around the globe – all without spending a dime. Watch polar bears dive and play in their state-of-the-art habitat, observe gorillas in their lush forest environment, or come face-to-face with a Komodo dragon. The zoo's commitment to conservation shines through in its naturalistic habitats and educational programs. As you wander the beautifully landscaped grounds, you'll forget you're in the middle of a bustling city. Don't miss the charming Kovler Lion House, a historic landmark that's home to big cats with even bigger personalities.

  • Location: 2001 N Clark St, Chicago, IL 60614
  • Hours: 10 AM - 5 PM daily (hours may vary seasonally)
  • Admission: Free

Why Visit: Experience the wonders of wildlife in a historic, beautifully maintained setting – all for free!

Pro Tip: Visit during feeding times for the best chance to see active animals and learn from keeper talks.

Bike or Stroll Along the Lakefront Trail

Cyclists on Chicago's Lakefront Trail near Belmont Harbor with Lake Michigan and city skyline in background
Cruised the Lakefront Trail on a rental bike. Best way to see the city and get some exercise!

Lace up your sneakers or hop on a bike for an invigorating journey along Chicago's stunning Lakefront Trail. This 18-mile paved path hugs the shores of Lake Michigan, offering breathtaking views of the skyline on one side and the vast expanse of the lake on the other. As you make your way from Hollywood Beach in the north to South Shore Beach in the south, you'll pass a string of attractions. Take a detour to explore the tranquil Montrose Bird Sanctuary, cool off at Oak Street Beach, or pause to admire the yachts at Belmont Harbor. The trail is a microcosm of Chicago life, where joggers, cyclists, and rollerbladers share the path with picnickers and sunbathers. It's the perfect way to experience the city's love affair with its lakefront.

  • Location: Runs along the Lake Michigan shoreline from Ardmore Street (5800 N) to 71st Street (7100 S)
  • Hours: Open 24/7

Why Visit: Experience Chicago's relationship with Lake Michigan while enjoying outdoor activities and stunning urban views.

Pro Tip: Rent a Divvy bike from one of the many stations along the trail for an easy and affordable way to explore.

Reach for the Stars at Adler Planetarium

Immersive star projection inside Adler Planetarium dome, showcasing wonders of the night sky
Mind = blown at Adler Planetarium. Felt like I was floating in space during the sky show!

Prepare for liftoff at America's first planetarium, where the wonders of the universe unfold before your eyes. The Adler Planetarium sits on the edge of Lake Michigan, offering stellar views of both the heavens and the Chicago skyline. Step into the domed theater and watch as billions of stars swirl overhead in mind-blowing detail. Ever wondered what it's like to be an astronaut? The Mission Moon exhibit lets you experience the thrills and challenges of space exploration firsthand. From ancient celestial navigation tools to cutting-edge space science, the Adler brings the cosmos down to Earth in captivating ways. Don't miss the opportunity to peer through the historic Doane Observatory telescope – on a clear night, you might glimpse the rings of Saturn or the moons of Jupiter.

  • Location: 1300 S Lake Shore Dr, Chicago, IL 60605
  • Hours: 9 AM - 4 PM daily (hours may vary seasonally)
  • Admission: Adults $19, Children (3-11) $8

Why Visit: Journey through space and time at America's first planetarium, with breathtaking shows and interactive exhibits.

Pro Tip: Plan your visit to coincide with one of the Adler After Dark events for an adults-only night of cocktails, entertainment, and unobstructed telescope viewing.

Climb the Historic Water Tower

Historic Chicago Water Tower among modern skyscrapers on Michigan Avenue, symbol of city's resilience
This beauty survived the Great Chicago Fire of 1871. Talk about standing strong!

Step back in time at one of the few buildings to survive the Great Chicago Fire of 1871. The Chicago Water Tower, a castle-like structure of yellowed limestone, stands as a proud symbol of the city's resilience. Climb the spiral staircase for a unique perspective on the Magnificent Mile below. Inside, the City Gallery showcases the work of local photographers and artists, adding a touch of modern creativity to this historic landmark. As you explore, imagine the tower as it once was – a crucial part of the city's early water system. Today, surrounded by sleek skyscrapers, it's a charming reminder of Chicago's past amid the bustle of the present.

  • Location: 806 N Michigan Ave, Chicago, IL 60611
  • Hours: 10 AM - 6:30 PM Monday-Saturday, 10 AM - 5 PM Sunday
  • Admission: Free

Why Visit: Experience a piece of Chicago's resilient history and enjoy local art in a unique, historic setting.

Pro Tip: Visit at night to see the tower beautifully illuminated, standing out against the modern cityscape.

Shop 'Til You Drop on the Magnificent Mile

Shoppers exploring the bustling Magnificent Mile outside Nordstrom on Michigan Avenue in Chicago
RIP my wallet. Couldn't resist the shops on the Magnificent Mile. At least window shopping is free!

Prepare your wallet and lace up your comfiest shoes for a shopping extravaganza on Chicago's most famous stretch of retail therapy. The Magnificent Mile, a 13-block section of Michigan Avenue, is a shopper's paradise where high-end boutiques rub shoulders with familiar brands. From the glittering wares of Tiffany & Co. to the latest tech gadgets at the Apple Store, there's something for every taste and budget. But shopping is just the beginning. Admire the neo-Gothic architecture of the Tribune Tower, or stop for a bite at one of the many world-class restaurants along the way. As you stroll, look up to appreciate the blend of historic and modern architecture that makes this thoroughfare truly magnificent.

  • Location: N Michigan Ave from the Chicago River to Oak Street
  • Hours: Most stores open 10 AM - 9 PM Monday-Saturday, 11 AM - 6 PM Sunday

Why Visit: Indulge in world-class shopping while soaking in the energy and architecture of Chicago's most famous street.

Pro Tip: For a unique perspective, take a break from shopping and enjoy afternoon tea at the historic Drake Hotel.

Catch a Cubs Game at Wrigley Field

Enthusiastic fans cheering in bleachers at Chicago Cubs game in iconic Wrigley Field baseball stadium
First time at Wrigley Field and I'm hooked! The energy here is electric. Go Cubs!

Step into a slice of baseball heaven at Wrigley Field, where the ivy-covered walls and hand-turned scoreboard transport you to a bygone era of America's favorite pastime. Built in 1914, this iconic ballpark is the second-oldest in the major leagues and oozes charm from every bleacher. Even if you're not a die-hard baseball fan, the energy of the crowd and the view of the Chicago skyline beyond the outfield create an unforgettable experience. Sink your teeth into a Chicago-style hot dog, join in the seventh-inning stretch, and cheer on the Cubs with the passionate locals. Win or lose, a day at Wrigley is a quintessential Chicago experience that captures the heart of the city.

  • Location: 1060 W Addison St, Chicago, IL 60613
  • Hours: Varies by game schedule, typically afternoon and evening games
  • Admission: Ticket prices vary, starting around $20 for bleacher seats

Why Visit: Experience the magic of baseball in one of America's most beloved and historic ballparks.

Pro Tip: If you can't score tickets to a game, take a behind-the-scenes tour of the ballpark to soak in its rich history.

Stroll and Dine Along the Chicago Riverwalk

Diners at City Winery on Chicago Riverwalk with skyscrapers in background
Found my new favorite spot in Chicago. Nothing beats dinner at City Winery on the Riverwalk!

Meander along the Chicago River on this picturesque pedestrian walkway, where the city's architectural marvels provide a stunning backdrop for a leisurely stroll or an al fresco meal. The Riverwalk stretches for 1.25 miles, offering a series of distinct "rooms" each with its own character and attractions. Rent a kayak for a unique perspective on the city, or simply watch the boats go by from one of the many waterfront cafes and bars. As day turns to night, the Riverwalk transforms into a twinkling wonderland, with the lights of the surrounding skyscrapers dancing on the water. It's the perfect spot to unwind after a day of sightseeing and soak in the city's vibrant energy.

  • Location: Along Wacker Drive from Lake Shore Drive to Lake Street
  • Hours: 6 AM - 11 PM daily

Why Visit: Experience Chicago from a unique riverside perspective, with plenty of options for dining, drinking, and recreation.

Pro Tip: Time your visit for the "Art on theMART," a nightly digital art projection on the massive facade of the Merchandise Mart.

Enjoy a Free Concert at Millennium Park

Large crowd enjoying free concert at Jay Pritzker Pavilion in Millennium Park, Chicago
Free concert at Millennium Park tonight. The music, the skyline, the crowd – pure magic!

Spread out a blanket on the Great Lawn of Millennium Park and let the sweet sounds of music wash over you. During the summer months, the Jay Pritzker Pavilion hosts a variety of free concerts, from classical symphonies to contemporary rock. The Frank Gehry-designed bandshell, with its billowing sheets of stainless steel, is a work of art in itself. As the music plays, watch the sky change colors over the Chicago skyline, creating a magical backdrop for the performance. It's a quintessential Chicago summer experience, where world-class culture meets laid-back Midwest charm. Bring a picnic, a bottle of wine, and good company for a perfect evening under the stars.

  • Location: 201 E Randolph St, Chicago, IL 60602
  • Hours: 6 AM - 11 PM daily, concert times vary
  • Admission: Free

Why Visit: Experience world-class music in a stunning outdoor setting, all for free.

Pro Tip: Arrive early to secure a good spot on the lawn, and don't forget to bring a low-back chair or blanket for seating.

Indulge in Deep-Dish Pizza at Lou Malnati's

Close-up of Lou Malnati's famous Chicago deep-dish pizza slice at their Gold Coast location
Finally tried real Chicago deep-dish at Lou Malnati's. It's like a pizza and a casserole had a baby!

Prepare your taste buds for a true Chicago culinary icon – the deep-dish pizza. At Lou Malnati's, a local institution since 1971, you'll discover why this hearty pie has captured the hearts (and stomachs) of locals and visitors alike. Sink your fork into layers of gooey cheese, tangy tomato sauce, and your choice of toppings, all nestled in a buttery, flaky crust. The pizza is so thick, it's more like a casserole than a traditional slice. As you savor each bite, you'll understand why Chicagoans defend their deep-dish with such passion. Be warned: one slice is often enough to satisfy even the heartiest appetite!

  • Location: Multiple locations throughout Chicago
  • Hours: Vary by location, typically 11 AM - 11 PM

Why Visit: Taste Chicago's most famous culinary creation at one of the city's most beloved pizzerias.

Pro Tip: Order your pizza when you arrive – the deep-dish takes about 45 minutes to prepare, but it's worth the wait!

Laugh Your Heart Out at The Second City

Engaged audience at comedy show on main stage at The Second City, Chicago's legendary comedy club
Laughed until it hurt at The Second City tonight. No wonder so many comedy legends started here!

Get ready for a night of side-splitting laughter at the legendary comedy club that launched the careers of countless stars, including Bill Murray, Tina Fey, and Stephen Colbert. The Second City has been the epicenter of improv and sketch comedy since 1959, and its stages continue to showcase the brightest up-and-coming talent. As you settle into your seat, you never know what to expect – each show is a unique blend of scripted sketches and off-the-cuff improv based on audience suggestions. The intimate theater ensures there's not a bad seat in the house, putting you right in the midst of the comedic action. Who knows? You might be watching the next big Hollywood star before they hit the big time.

  • Location: 1616 N Wells St, Chicago, IL 60614
  • Hours: Shows typically at 8 PM and 11 PM, schedules vary
  • Admission: Tickets start at around $30

Why Visit: Experience cutting-edge comedy at the birthplace of some of America's greatest comedic talents.

Pro Tip: For a more intimate experience, check out the shows in the smaller e.t.c. Theater upstairs.

Sample Local Flavors at Green City Market

Visitors exploring produce stands at Green City Market in Lincoln Park, Chicago's sustainable farmers market
Heaven for foodies! Green City Market has the freshest local produce and friendliest farmers.

Immerse yourself in Chicago's vibrant food scene at Green City Market, where local farmers and artisans showcase the best of the Midwest's bounty. Stroll through rows of colorful produce, fragrant flowers, and artisanal goods as the sweet aroma of fresh-baked bread and brewing coffee fills the air. Chat with passionate vendors about their wares, from heirloom tomatoes to small-batch cheeses. During the warmer months, the market sets up outdoors in Lincoln Park, creating a lively community gathering spot. In winter, it moves indoors but doesn't lose any of its charm. Keep an eye out for Chicago's top chefs, who often source their ingredients here and sometimes give cooking demonstrations.

  • Location: Lincoln Park (summer), 2613 W Lawrence Ave (winter)
  • Hours: 7 AM - 1 PM Wednesdays and Saturdays (May-October), 8 AM - 1 PM Saturdays (November-April)

Why Visit: Experience the flavors of the Midwest and connect with local food producers in a vibrant market atmosphere.

Pro Tip: Come hungry and make a meal of the various prepared food vendors, offering everything from organic crepes to farm-fresh smoothies.

Tour Frank Lloyd Wright's Home and Studio

Interior view of Frank Lloyd Wright's Studio in Oak Park, showcasing innovative Prairie style architecture
Toured Frank Lloyd Wright's home today. His attention to detail was next level. Architecture heaven!

Step into the mind of America's most famous architect at Frank Lloyd Wright's Home and Studio in Oak Park. This is where Wright developed his groundbreaking Prairie style, revolutionizing 20th-century architecture. As you wander through the rooms, you'll see how Wright's ideas about organic architecture took shape – from the open floor plans to the intricate art glass windows. The studio, where Wright and his apprentices worked, buzzes with creative energy. Outside, the neighborhood is a living museum of Wright's work, with the highest concentration of his buildings anywhere in the world. It's a pilgrimage site for architecture buffs and a fascinating glimpse into the life and work of a true American genius.

  • Location: 951 Chicago Ave, Oak Park, IL 60302
  • Hours: 10 AM - 4 PM Thursday-Monday (closed Tuesday-Wednesday)
  • Admission: Adults $20, Youth (3-17) $14

Why Visit: Explore the birthplace of Prairie School architecture and gain insights into the genius of Frank Lloyd Wright.

Pro Tip: Combine your visit with a self-guided walking tour of the Oak Park neighborhood to see other Wright-designed homes.

Groove to the Blues at Kingston Mines

Live blues performance on north stage at Kingston Mines, Chicago's oldest continuously operating blues club
Experiencing real Chicago blues at Kingston Mines. The music here gets into your soul!

Feel the rhythm of Chicago's soul at Kingston Mines, the city's oldest and largest continuously operating blues club. This no-frills venue has been serving up authentic Chicago blues seven nights a week since 1968. With two stages offering non-stop music, you're in for a night of foot-stomping, heart-thumping entertainment. The intimate setting puts you up close and personal with the performers, many of whom are local legends. As the wail of harmonicas and the twang of guitars fill the air, you'll understand why Chicago is known as the "Blues Capital of the World." Grab a plate of soul food, order a cold beer, and let the music transport you to the South Side of yesteryear.

  • Location: 2548 N Halsted St, Chicago, IL 60614
  • Hours: 7 PM - 4 AM daily
  • Admission: $15-$20, depending on the day

Why Visit: Experience authentic Chicago blues in a historic venue that's been keeping the tradition alive for over 50 years.

Pro Tip: If you're visiting in June, don't miss the Chicago Blues Festival in Millennium Park, the largest free blues festival in the world.

Explore Street Art in Pilsen

Visitor admiring street art mural on 16th Street in Chicago's Pilsen neighborhood, known for Mexican-American culture
Pilsen's street art is unreal. Every corner is an Instagram opportunity and history lesson in one!

Dive into Chicago's vibrant street art scene in Pilsen, a neighborhood where creativity spills onto every surface. This historically Mexican-American area has become an open-air gallery, with colorful murals adorning buildings, alleys, and underpasses. As you wander the streets, you'll encounter powerful pieces that speak to the community's heritage, social issues, and dreams for the future. The 16th Street railroad embankment is a must-see, featuring a mile-long stretch of murals by local and international artists. But the art is just part of Pilsen's charm – the neighborhood is also home to unique shops, authentic Mexican restaurants, and cutting-edge galleries. It's a feast for the eyes and the taste buds alike.

  • Location: Pilsen neighborhood, roughly bounded by 16th St, Cermak Rd, Halsted St, and Western Ave
  • Hours: Accessible 24/7

Why Visit: Immerse yourself in Chicago's vibrant street art scene and experience the cultural richness of one of the city's most dynamic neighborhoods.

Pro Tip: Join a guided mural walk to learn about the artists and the stories behind their creations.

Escape to the Tropics at Garfield Park Conservatory

Visitor exploring lush Fern Room inside Garfield Park Conservatory, Chicago's urban oasis
Escaped the city at Garfield Park Conservatory. It's like a prehistoric jungle in here!

Step into a lush oasis in the heart of the city at Garfield Park Conservatory, one of the largest and most stunning botanical conservatories in the nation. As you enter, you're transported from the urban jungle to a real one, complete with soaring palm trees, cascading waterfalls, and a riot of tropical flowers. Wander through the Fern Room, where prehistoric plants thrive in a misty landscape, or marvel at the vibrant blooms in the Show House. The Desert House offers a stark contrast with its collection of cacti and succulents. It's a year-round escape, especially welcome during Chicago's chilly winters. The conservatory's mission of urban agriculture is evident in its outdoor gardens and community programs, making it not just a beautiful space, but an educational one too.

  • Location: 300 N Central Park Ave, Chicago, IL 60624
  • Hours: 10 AM - 5 PM Wednesday-Sunday
  • Admission: Free (suggested donation $10)

Why Visit: Experience a tropical getaway without leaving the city in this stunning "landscape art under glass."

Pro Tip: Visit on a chilly or rainy day for a perfect indoor escape, or in winter to see the holiday flower show.

Marvel at The Rookery's Light Court

Stunning light court of The Rookery on LaSalle Street, showcasing intricate ironwork and Wright redesign
Stumbled upon this gem downtown. The Rookery's light court is a time machine to Chicago's golden age!

Step into a masterpiece of Chicago School architecture at The Rookery, where history and beauty intertwine in spectacular fashion. This 1888 building, designed by architectural legends Burnham and Root, features a stunning light court that will take your breath away. The soaring atrium, reimagined by Frank Lloyd Wright in 1905, bathes visitors in golden light filtered through intricate ironwork and marble. As you stand in the center, gazing up at the glass ceiling, you'll feel transported to the glamorous days of Chicago's architectural revolution. Don't miss the chance to ride in one of the building's lovingly maintained vintage elevators. The Rookery is a living testament to Chicago's architectural heritage and a must-see for anyone interested in design and history.

  • Location: 209 S LaSalle St, Chicago, IL 60604
  • Hours: 8 AM - 6 PM Monday-Friday
  • Admission: Free to enter lobby, guided tours available for a fee

Why Visit: Experience one of the most beautiful interior spaces in Chicago and a masterpiece of early skyscraper design.

Pro Tip: Time your visit for midday when the sun is highest to see the light court at its most dazzling.

Savor a Chicago-Style Hot Dog

Close-up of classic Chicago-style hot dog with traditional toppings at Portillo's on Ontario Street
First rule of Chicago hot dogs: NO KETCHUP! This "garden on a bun" from Portillo's is a flavor explosion.

Sink your teeth into a true taste of Chicago with the city's iconic hot dog. But be warned – asking for ketchup on this local delicacy is a serious faux pas! A proper Chicago-style hot dog starts with an all-beef frankfurter nestled in a steamed poppy seed bun. Then comes the "garden on a bun": yellow mustard, bright green relish, fresh chopped onions, juicy tomato wedges, a crisp pickle spear, spicy sport peppers, and a sprinkle of celery salt. The result is a flavor explosion that perfectly balances savory, spicy, and tangy notes. While you can find great dogs all over the city, locals swear by spots like Portillo's, Superdawg, and The Wieners Circle. It's more than just a quick bite – it's a cultural institution and a rite of passage for any Chicago visitor.

  • Location: Various hot dog stands throughout the city
  • Hours: Vary by location
  • Price: Typically $3-$5 per hot dog

Why Visit: Experience a true taste of Chicago with this perfectly balanced flavor bomb of a hot dog.

Pro Tip: For the full Chicago experience, pair your hot dog with a side of crispy, golden french fries and a cold local craft beer.

Gawk at the Corn Cob Towers of Marina City

Iconic "corn cob" towers of Marina City viewed from Chicago Riverwalk, showcasing unique mid-century architecture
Can't get over these "corn cob" towers. Marina City proves Chicago's architecture is anything but boring!

Crane your neck skyward to behold Marina City, a pair of cylindrical towers that have become icons of Chicago's skyline. Affectionately dubbed the "Corn Cob Towers" due to their unique shape, these 60-story buildings were revolutionary when completed in 1967. Designed by architect Bertrand Goldberg, they were the first urban high-rises to combine residential apartments with office space, a marina, and entertainment venues – a true "city within a city." The exposed parking levels at the base create a mesmerizing spiral effect that's irresistible to photographers. While you can't go inside unless you're a resident or hotel guest, the view from the Chicago Riverwalk or a river cruise is spectacular. At night, when the buildings are illuminated, they transform into glowing beacons of mid-century architectural ambition.

  • Location: 300 N State St, Chicago, IL 60654
  • Hours: Exterior visible 24/7
  • Admission: Free to view from outside

Why Visit: Marvel at one of Chicago's most distinctive architectural landmarks and a prime example of mid-century urban design.

Pro Tip: For a unique view of Marina City, enjoy a meal or drink at the House of Blues, located at the base of the western tower.

Structuring Your Chicago Adventure: A 7-Day Itinerary

Ready to tackle the Windy City but not sure where to start? We've got you covered with this week-long itinerary that'll help you make the most of your Chicago adventure. Remember, this is just a suggestion – feel free to mix and match based on your interests and energy levels!

Days 1-2: Downtown and the Loop

Kick off your Chicago experience in the heart of the city. Start at Millennium Park, where you can snap that obligatory selfie at Cloud Gate (aka "The Bean"). From there, it's a short walk to the Art Institute of Chicago for a culture fix. Spend your afternoon on an architecture river cruise for a unique perspective on the city's famous skyline. On day two, head to Willis Tower's Skydeck for breathtaking views, then explore the Chicago Riverwalk. Cap off your evening with a deep-dish pizza at Lou Malnati's – you've earned it!

Days 3-4: North Side

Time to venture north! Begin with a visit to Lincoln Park Zoo, one of the oldest zoos in North America. Afterwards, stroll through the charming Lincoln Park neighborhood. On day four, make your way to Wrigley Field for a Cubs game or a tour of this iconic ballpark. Spend your evening in Wicker Park or Logan Square, two of Chicago's trendiest neighborhoods, for dinner and drinks.

Days 5-6: South Side

The South Side deserves your attention too. Start with the Museum of Science and Industry, where you can easily spend a full day exploring. On day six, head to the historic Hyde Park neighborhood. Visit the DuSable Museum of African American History, then take a stroll around the beautiful University of Chicago campus. For dinner, try some authentic soul food at a local restaurant.

Day 7: Choose Your Own Adventure

For your final day, the choice is yours! You could:

  • Take a day trip to Frank Lloyd Wright's Home and Studio in Oak Park
  • Dive deeper into any neighborhoods you particularly enjoyed
  • Check out any attractions you missed, like the Adler Planetarium or the Field Museum
  • Simply relax on one of Chicago's beautiful beaches along Lake Michigan

End your trip on a high note with a comedy show at The Second City or some live blues at Kingston Mines.

Remember, Chicago is a city of neighborhoods, each with its own unique flavor. Don't be afraid to wander and discover your own favorite spots along the way. And don't worry if you can't fit everything in – it just means you'll have to come back!

From soaring skyscrapers to deep-dish delights, from laughs at The Second City to blues at Kingston Mines, Chicago offers a feast for all the senses. Whether you're an art lover, a foodie, a history buff, or simply in search of urban adventures, the Windy City will blow you away with its diverse attractions and welcoming spirit. So grab your walking shoes, bring your appetite, and get ready to fall in love with Chicago – a city that truly has it all. The question isn't whether you'll enjoy your visit, but how soon you can come back for more!

West Parker
West Parker
Article updated:
July 18, 2024 8:29 AM

West Parker, a Cornell University School of Hotel Administration graduate, has spent two decades as the secret weapon of the jet-set elite, crafting bespoke adventures that redefine luxury travel. Now a resident writer for Town & Tourist, this 45-year-old "Architect of Extraordinary Journeys" combines razor-sharp insights with unparalleled industry connections to deliver experiences that even the most discerning globetrotters can't help but rave about. West's expertise spans from exclusive real estate to fine dining, making him the go-to strategist for those who demand nothing but the extraordinary in their travels.

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