Chicago
"Explore Chicago’s iconic skyline, jazz-filled streets, and deep-dish delights, where the past and present collide."
🌆🌭🌊
US Dollar (USD) $
Apr – Oct
2.7 million
10.4°C
TWYS — The Best Travel Guides for Hidden Gems & Local Secrets
Chicago is a city of contrasts, where the old and new coexist. Its towering skyscrapers, like the Willis Tower, offer panoramic views of the city. In contrast, the rich blues and jazz culture continues to thrive, with legendary clubs that have hosted the likes of Muddy Waters and Buddy Guy. The city's food culture is just as diverse, from its signature deep-dish pizza to the internationally recognized Chicago-style hot dog. Whether you're visiting for its architectural wonders, live music, or culinary delights, Chicago promises an experience like no other.
1833 AD Modern city, developed during the 19th century.
8️⃣ Moderate to high cost of living, particularly in housing and food.
Illinois
O'Hare International Airport (ORD)
Minimal List TL;DR
TWYS curates the best places to SEE, EAT, DRINK, SHOP & MORE — uncover hidden gems, must-visit landmarks, top restaurants, unique bars, boutique shops, luxury stays, and networking spots.
The Art Institute of Chicago
4.9Field Museum
4.8Millennium Park & Cloud Gate (“The Bean”)
4.8Museum of Science and Industry
4.7Skydeck Chicago on Willis Tower
4.5Lincoln Park
4.5Girl & The Goat ($$$)
4.9Qing Xiang Yuan Dumplings ($$
4.8Lou Malnati’s Pizza ($$)
4.8Au Cheval ($$)
4.7Roister (brunch $$; dinner $$$$)
4.7Duck Duck Goat ($$-$$$)
4.6The Violet Hour
4.9
Places to See
Discover breathtaking landmarks, hidden gems, and offbeat sights that make every destination unforgettable.
Millennium Park, Art Institute of Chicago, Navy Pier, Chicago Theatre, and Field Museum. Chicago is famous for its architectural tours, jazz and blues music, and cultural diversity, offering a rich museum scene and vibrant public art.
Chicago’s skyline is home to over 1,100 high-rise buildings. The city is a pioneer in architecture, and visitors can experience its legacy in iconic structures like the Willis Tower. Chicago also holds an important place in music history, particularly for jazz and blues. The city’s contributions to these genres are monumental, with legends like Muddy Waters and Benny Goodman, making it a pilgrimage for music lovers worldwide.
Places to Eat
Savor the best local flavors, street food gems, and must-try dining spots curated for true food lovers.
🍕 Deep-Dish Pizza (Thick pizza with cheese and tomato sauce baked in a deep pan) 🌭 Italian Beef (Thinly sliced roast beef, often served in a sandwich with peppers) 🌭 Chicago-Style Hot Dogs (Hot dog topped with mustard, relish, and veggies) 🍿 Popcorn (Known for being caramel-coated or savory) 🌮 Tacos (Flour or corn tortillas filled with various meats and veggies)
Places to Drink
Unwind at vibrant bars, cozy cafés, and craft breweries, handpicked for the best drinks and atmosphere.
🎷 Jazz: The birthplace of modern jazz, with venues like The Green Mill. 🎸 Blues: Legendary clubs like Buddy Guy’s Legends. 🎶 House Music: Originated in the '80s, influential in global EDM culture. 🎤 Soul & Gospel: Soul Train vibes and churches with powerful gospel choirs.
Places to Network
Connect with like-minded travelers, digital nomads, and entrepreneurs at the best networking spots.
💰 Finance (home to Chicago Mercantile Exchange), 🏭 Manufacturing (a historic industrial center, with prominent manufacturing sectors in machinery and steel), 💻 Tech (growing tech hub with organizations like Groupon and Grubhub) - Chicago remains a powerhouse for finance and manufacturing but is rapidly embracing innovation, with tech startups flourishing. Networking in fintech and manufacturing sectors thrives here.
Chicago
Chicago’s skyline, a stunning silhouette against Lake Michigan, tells tales of architectural prowess and urban grit. From the jazz notes echoing in dimly lit bars to the aromatic delight of deep-dish pizza, the Windy City promises an adventure that transcends the ordinary. Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. With a wealth of iconic sights and neighborhoods to explore, there’s enough to fill a visit of days, weeks, or even months without ever seeing the end.
Places to Shop
Explore local markets, unique boutiques, and artisanal stores for one-of-a-kind finds.
Luxury
Indulge in high-end experiences, exclusive stays, and premium services tailored for refined travelers.
Local Chicago Treasures
Deep-dish pizza, jazz music, Millennium Park, architectural marvels, and a rich cultural scene.
Chicago is the birthplace of modern skyscraper architecture, with the Home Insurance Building, the world’s first skyscraper, completed in 1885. Known for its stunning skyline, the city boasts a rich architectural heritage, with landmarks like the Willis Tower (formerly Sears Tower) and the John Hancock Center. Chicago is also famous for its deep-dish pizza, jazz music, and Millennium Park. The city has a vibrant arts scene, numerous parks, and a deep cultural history that makes it one of America’s most influential cities.
Chicago, located on the shores of Lake Michigan, is an American metropolis known for its stunning skyline, rich history, and cultural vibrancy. As the birthplace of jazz and blues, Chicago’s music scene has been instrumental in shaping the sound of modern America. The city's architecture is equally iconic, with towering skyscrapers like the Willis Tower and the John Hancock Center defining its skyline. Chicago's diverse neighborhoods each offer a unique atmosphere, from the historic Gold Coast to the trendy neighborhoods of Wicker Park and Logan Square. Food lovers flock to the city to experience the world-famous deep-dish pizza, as well as a wide array of international cuisines. Chicago is also home to cultural institutions such as the Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry. Visitors can also enjoy its vibrant theater scene, with numerous plays, musicals, and comedy shows throughout the year. Whether you’re visiting for its history, culture, or food, Chicago is a city that offers something for everyone, with a unique blend of American spirit and global influence.
Watch Out
Skip
Avoid overrated tourist traps and discover alternative experiences worth your time.
Transportation
🚇 Efficient metro system (CTA), buses, and commuter trains. 🚲 Plenty of bike lanes along the lakefront and throughout downtown. 🚖 Taxis and ride-hailing services provide good connectivity. 🚶♂️ The city is walkable with vibrant pedestrian zones.
City Overview
Chicago is a city where rich history meets modern innovation, offering a captivating experience for every visitor. Known for its iconic skyline, Chicago is home to some of the most impressive architecture in the world, including the Willis Tower and the striking John Hancock Center. But beyond the skyscrapers, Chicago’s charm lies in its vibrant neighborhoods, dynamic food scene, and scenic location along the shores of Lake Michigan. A visit to Chicago wouldn’t be complete without experiencing its architectural brilliance. Take an architecture river cruise for a unique perspective on the city’s history and design, or stroll through Millennium Park, home to the famous Cloud Gate, also known as “The Bean.” For history buffs, The Art Institute of Chicago offers an extensive collection of works ranging from Impressionist masterpieces to contemporary installations. Food lovers will find Chicago to be a culinary haven. While the city is famous for its deep-dish pizza, its food scene extends far beyond, featuring innovative dishes at Michelin-starred restaurants and authentic global cuisines in neighborhoods like Pilsen and Greektown. Don’t miss the chance to try a Chicago-style hot dog or explore the lively atmosphere of Navy Pier, which also offers entertainment, shopping, and lakefront dining. Chicago’s neighborhoods are a testament to its diversity. From the vibrant murals in Pilsen to the historic charm of Old Town, each area has its own unique vibe. Wicker Park is a favorite for indie shops and cafes, while Lincoln Park offers a perfect blend of green spaces and urban attractions, including the Lincoln Park Zoo. Music enthusiasts can enjoy Chicago’s rich jazz and blues heritage at legendary clubs like Buddy Guy’s Legends. Whether you’re marveling at the city’s towering skyline, savoring its culinary delights, or enjoying a stroll along the Chicago Riverwalk, the city’s blend of history, culture, and innovation makes it an unforgettable destination.
Chicago
3 Day City Guide
🌆 Day 1: Chicago's Urban Exploration & Classic Eats 🕘 9:00 AM: Begin your day at Millennium Park 🌳, with the famous Cloud Gate (The Bean) 🪞 for some fun photo ops. 🕛 12:00 PM: Take the Chicago Architecture Boat Tour 🚤 to see the city’s impressive skyline and learn about its history. 🍴 2:00 PM: Stop for lunch at Lou Malnati’s 🍕 for Chicago’s iconic deep-dish pizza. 🕕 7:00 PM: Head to a South Loop jazz club 🎷 for an evening of live music and a laid-back vibe. 🌆 Day 2: Museums & Waterfront 🕘 9:00 AM: Visit the world-renowned Field Museum or Art Institute of Chicago 🖼️ for some cultural immersion. 🕛 12:00 PM: Afterward, head to Navy Pier 🎡, ride the Ferris wheel 🎡, and take in the lakefront views. 🕕 6:00 PM: In the evening, enjoy cocktails at a South Loop jazz club 🎶 for a taste of the city’s musical history. 🌆 Day 3: Local Vibes & Views 🕘 9:00 AM: Explore Wicker Park 🛍️ for unique boutiques, vibrant street art, and cool coffee spots. 🕛 12:00 PM: Head to the Lincoln Park Zoo 🦁, a lovely, free spot to relax and enjoy the animals. 🕕 6:00 PM: For a spectacular end to the day, enjoy sunset drinks at the Signature Room in the John Hancock Tower 🍸 with panoramic views of the city skyline.
Current Trends
🍴 West Loop restaurants: Known for its trendy food scene, home to celebrity chefs and Michelin-star restaurants like The Girl and The Goat. 🍻 Craft breweries: Chicago is a hub for craft beer lovers, with spots like Revolution Brewing and Half Acre leading the way. 🍸 Rooftop bars: Popular spots like Cindy’s Rooftop offer skyline views and craft cocktails. 🌱 Plant-based dining: Vegan restaurants like The Chicago Diner offer delicious, health-conscious food options. 🎤 Live music scene: Chicago’s jazz and blues clubs are thriving, especially along the South Loop’s iconic music row.
Local Events Guide
🎸 Chicago Blues Festival (June): The largest free blues festival in the world, celebrating the city's rich musical heritage. 🎤 Lollapalooza (August): A massive music festival attracting big-name artists and tens of thousands of fans. ✈️ Chicago Air and Water Show (August): A thrilling aerial display over Lake Michigan with breathtaking performances. 🏙️ Chicago Jazz Festival (September): A celebration of Chicago’s deep jazz history with performances from renowned artists. 🎨 Chicago Architecture Biennial (September): A global exhibition of cutting-edge architecture.
Local Insider Tips
🍺 Logan Square: Known for its cool breweries, this neighborhood is a haven for craft beer lovers. Check out quirky vintage shops and art galleries, then enjoy live music in intimate venues. 🌊 Riverwalk: Stroll along the Chicago River and enjoy scenic views, waterfront cafes, and public art installations. Don’t miss the chance to take a kayak tour for a unique perspective of the skyline. 🎨 Pilsen: This vibrant, artsy district is home to colorful murals, authentic Mexican food, and a rich cultural history. The National Museum of Mexican Art is a must-visit. 🍔 West Loop: Discover some of Chicago’s best restaurants in this trendy area, featuring world-renowned chefs and local favorites. 🏞️ Millennium Park: Beyond the famous Cloud Gate ("The Bean"), explore lesser-known sculptures and enjoy free concerts in the summer. The nearby Maggie Daley Park offers fun climbing walls and ice skating in winter.
Sustainable Travel
🚲 Divvy Bike Sharing: Eco-friendly bike rentals around the city. 🌳 Urban parks: Visit Lincoln Park or Garfield Park Conservatory. 🚇 Public transportation: The CTA (Chicago Transit Authority) operates electric buses and trains. 🍽️ Sustainable dining: Uncommon Ground restaurant is a leader in eco-friendly dining, with a rooftop farm. 🌱 Farmers markets: Support local vendors with fresh, sustainable products.
Chicago
TWYS: Your Ultimate Guide to Unique Travel Experiences & Insider Tips
Ready to see through a local’s eyes?
Our curated guide unveils top hidden gems, secret spots, and local favorites that you won’t find in typical travel guides.
Whether it’s a cozy café tucked away in a historic neighborhood, a scenic trail only known to insiders, or unique cultural sites, has so much more to offer beyond the tourist hotspots.
Dive into our off-the-beaten-path guide and discover the true heart —perfect for adventurous travelers, culture enthusiasts, and anyone looking for an authentic journey
Sign below for Fresh Updates
We will send you the latest curation of places and cities straight to your inbox along with access to the pop-up store & exclusive events.
Join us to stay connected. Read our updates
Each spot in our City guide is handpicked to help you experience the city like a local, avoiding the crowds and discovering the best-kept secrets.
From charming local eateries and breathtaking viewpoints to tucked-away art galleries and vibrant local markets, this guide lets you explore beyond the surface.
Follow our recommendations for an unforgettable adventure and see why these places stand out as favorites among locals.
For more unique experiences like these, explore our full collection of off-the-beaten-path city guides and make every trip a journey of discovery.
& More Cities to Explore:
