Chicago
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.
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US Dollar (USD) $
April to October
2.7 million
10.4
“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.”
Local Chicago
Deep-dish pizza, jazz music, and Millennium Park.
Chicago has the world’s first skyscraper, the Home Insurance Building, built in 1885, shaping modern architecture.
Chicago is a bustling metropolis on the shores of Lake Michigan, known for its skyline, history, and cultural richness. As the birthplace of jazz and blues, Chicago’s music scene is legendary, influencing global genres. The city’s architectural landscape is as iconic as its musical roots, with a blend of historic landmarks and modern skyscrapers. Chicago's diverse neighborhoods offer unique experiences, and its food scene is equally diverse, from deep-dish pizza to international cuisines.
Chicago’s skyline is home to 1,100 high-rises, and the city has played a pivotal role in the development of jazz and blues music, with artists like Muddy Waters and Benny Goodman.
Illinois
1833
O'Hare International Airport (ORD)
8
Places to See
Millennium Park, Art Institute of Chicago
Places to Eat
Deep-Dish Pizza, Italian Beef, Chicago-Style Hot Dogs, Popcorn, Tacos
Places to Drink
Jazz, Blues, House Music, Soul, Gospel
Places to Network
Finance, Manufacturing, Tech
Places to Shop
Luxury
Watch Out
Skip
Transportation
Efficient metro, buses
City Overview
Chicago blends a rich architectural heritage with vibrant neighborhoods, an innovative food scene, and Lake Michigan’s stunning backdrop. Known for its skyscrapers and deep-dish pizza, the city offers much more than meets the eye.
3 Day City Itinerary Guide
- Day 1: Morning: Millennium Park and Cloud Gate (The Bean). Afternoon: Chicago Architecture Boat Tour. Evening: Dinner at a deep-dish pizza spot like Lou Malnati’s. - Day 2: Morning: Field Museum or Art Institute of Chicago. Afternoon: Navy Pier and Ferris wheel. Evening: Jazz clubs in the South Loop. - Day 3: Morning: Explore Wicker Park. Afternoon: Lincoln Park Zoo. Evening: Sunset drinks at the Signature Room in the John Hancock Tower.
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.
Local Events Guide
- Chicago Blues Festival (June): The largest free blues festival in the world. - Lollapalooza (August): One of the largest music festivals in the US. - Chicago Air and Water Show (August): Stunning aerial displays over Lake Michigan.
Local Insider Tips
- Logan Square for local breweries and quirky vintage shops. - Riverwalk for waterside views and cafés. - Pilsen for colorful murals and authentic Mexican food.
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.
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 travellers, culture enthusiasts, and anyone looking for an authentic journey
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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.
