Currency
US Dollar (USD) $
Best Time
April to October
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.
Airport
O'Hare International Airport (ORD)
Minimal List TL;DR
🍕Dining/Pizza
Lou Malnati’s Pizza ($$)Chicago’s famous deep dish pizza can be found in this local favorite; be wary of long lines and expect at least a 40 minute wait
🍔Dining/Burger
Au Cheval ($$)the best burger in town” infamous for 2-5 hour waits; no reservations; Small Cheval ($) is a similar chain that offers the casual version of Au Cheval
🥟Dining/Asian Fusion
Duck Duck Goat ($$-$$$)Chinese fusion small plates; same chef as above; truly 10/10 creative and delicious.
🍷Cocktail Bar, American
The Violet HourCreative cocktails & small bites define this sophisticated, stylish bar.
🌆Casual Dining, American
Cindy’sHip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
Places to See
1600 N Lake Shore Dr, Chicago, IL 60613, United States
4.6
€-€€
Wednesday at 9:30pm | Saturday at 10:15pm.
Offers beautiful views of the city and the lake.
Vibe:
Beach volleyball, Scenic views
Tip:
Relaxed, Family-friendly
Get To:
Diverse public transport options
stunning skyline views in front of the beach; in the summertime, watch fireworks on Wednesday at 9:30pm and Saturday at 10:15pm.
111 E Wacker Dr, Chicago, IL 60601, United States
4.6
€-€€
10AM to 4PM
Learn about Chicago’s architectural history from experts.
Vibe:
Architectural insights, Scenic views
Tip:
Educational, Informative
Get To:
Various docks available
Awarded as one of the most popular tours in America, the tour is a must-do for those interested in the history of Chicago and how the city unfolded
2045 N Lincoln Park W, Chicago, IL 60614-4707
4.5
€-€€
6AM to 11PM
Home to the Lincoln Park Zoo and the Chicago History Museum
Vibe:
Outdoor activities, picnics, zoo visits
Tip:
Relaxed and Family-Friendly
Get To:
Accessible via Brown Line, Red Line
a residential neighborhood featuring a free Zoo, the famous Lincoln Park and Chicago’s “beach”
233 S Wacker Dr, Chicago, IL 60606, United States
4.5
€-€€
12 to 12:30AM
One of the tallest buildings in the Western Hemisphere.
Vibe:
Views of the skyline, Glass Ledge experience
Tip:
Thrilling, Awe-inspiring
Get To:
Adams/Wells station (0.6 miles)
photo opportunities of the skyline on a glass balcony extending four feet outside the 103rd floor
220 E Chicago Ave, Chicago, IL 60611, United States
4.5
€-€€
Temporarily closed
Engages visitors with contemporary art and culture.
Vibe:
Modern art exhibitions, Live performances
Tip:
Innovative, Thought-provoking
Get To:
Chicago Ave station (0.3 miles)
Downtown museum showcasing post-World War II paintings, sculptures, photos, videos & performances.
River North, Chicago, IL, USA
4.5
€-€€
6AM to 11PM
Home to the famous "Holy Name Cathedral" and many art installations
Vibe:
Fine dining, art galleries, river cruises
Get To:
Accessible via Brown Line, Red Line
great for fine dining, mainstream clubs, bars & lounges
1027 W Addison St, Chicago, IL 60613-4986
4.4
€-€€
6AM to 11PM
The famous Wrigley Field and the surrounding party atmosphere
Vibe:
Ballpark snacks, local brews
Get To:
Accessible via Red Line
a neighborhood built around its baseball stadium featuring many sports bars
Must Visit:
Millennium Park, Art Institute of Chicago
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.
Places to Eat
809 W Randolph St, Chicago, IL 60607, United States
4.9
€-€€
4:30 to 9:30PM
Known for its innovative approach to shared dining.
Vibe:
Goat empanadas, Seasonal dishes
Get To:
Damen station (0.3 miles)
small plates with adventurous ingredients, family style, 2-3 months prior reservations recommended.
http://www.girlandthegoat.com/439 N Wells St, Chicago, IL 60654, United States
4.8
€-€€
10:30AM to 10PM
Known for its iconic deep-dish pizza.
Vibe:
Deep-dish pizza, Malnati's salad
Get To:
Diverse public transport options
Tip:
Cozy, Family-friendly
Chicago’s famous deep dish pizza can be found in this local favorite; be wary of long lines and expect at least a 40 minute wait
https://www.loumalnatis.com/chicago-river-north2002 S Wentworth Ave #103, Chicago, IL 60616, United States
4.8
€-€€
11:30AM to 9PM
West Loop
Vibe:
Accessible via CTA bus 8, 65
Get To:
Specializes in hand-made dumplings and noodles
housemade dumplings with various choices for fillings.
http://qxydumplings.com/951 W Fulton Market, Chicago, IL 60607, United States
4.7
€-€€
10AM to 3PM | 4 to 9PM
Known for its innovative approach to wood-fired cooking.
Vibe:
Wood-fired meats, Seasonal dishes
Get To:
Damen station (0.5 miles)
amazing brunch alert; the BEST chicken and waffles I’ve ever had.
https://www.roisterrestaurant.com/800 W Randolph St, Chicago, IL 60607, United States
4.7
€-€€
12 to 9PM
Known for its elevated burger experience.
Vibe:
Cheeseburger, Duck fries
Get To:
Damen station (0.5 miles)
the best burger in town” infamous for 2-5 hour waits; no reservations; Small Cheval ($) is a similar chain that offers the casual version of Au Cheval
http://auchevalchicago.com/2540 W Armitage Ave, Chicago, IL 60647, United States
4.7
€-€€
10AM to 9PM
Wicker Park & Logan Square
Vibe:
Accessible via CTA bus 74, 49
Get To:
Offers authentic Cuban dishes and vibrant decor
Tip:
Cuban Sandwich, Empanadas
Great Cuban food with nice outdoor seatings.
http://www.90milescubancafe.com/857 W Fulton Market, Chicago, IL 60607, United States
4.6
€-€€
4:30 to 11PM
A unique take on Asian cuisine with a sharing concept.
Vibe:
Peking duck, Dumplings
Get To:
Damen station (0.5 miles)
Chinese fusion small plates; same chef as above; truly 10/10 creative and delicious.
https://duckduckgoatchicago.com/Must Try:
Deep-Dish Pizza, Italian Beef, Chicago-Style Hot Dogs, Popcorn, Tacos
Places to Drink
1520 N Damen Ave., Chicago, IL 60622, United States
4.9
€-€€
4 to 8PM
Wicker Park
Vibe:
Accessible via CTA bus 56, 70
Get To:
Speakeasy vibe with artisanal cocktails
Tip:
Cocktails, Small Plates
Creative cocktails & small bites define this sophisticated, stylish bar.
http://www.theviolethour.com/12 S Michigan Ave, Chicago, IL 60603, United States
4.5
€-€€
Temporarily closed
Loop
Vibe:
Accessible via CTA bus 3, 60
Get To:
Stunning rooftop views of Millennium Park
Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
http://www.cindysrooftop.com/
Music / Dance:
Jazz, Blues, House Music, Soul, Gospel
Places to Network
We'll be updating more places soon!
Key Industries:
Finance, Manufacturing, Tech
Chicago
“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
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Luxury
For More Tips Read Further
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.
Watch Out
Watch out for Crowded Areas
Skip
Skip Super Touristic Places
Off the beaten path places in
Chicago
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 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.
Explore the Best Off-the-Beaten-Path Experiences:
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
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Unlock the Hidden Side:
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 Visit:
27.2
5
Indian Rupee (INR) ₹
Local Mumbai
Vibe:
Mumbai is home to the world’s most expensive house, Antilia, which is owned by billionaire Mukesh Ambani.
Tip:
Mumbai is a city where the old and new coexist in perfect harmony, from its historic bazaars to its cutting-edge malls. The hustle and bustle are matched only by its vibrant nightlife, making it a global hub for both business and pleasure. The city’s street food is legendary, with dishes like Vada Pav and Pani Puri being some of the most iconic snacks. While Bollywood dominates the entertainment scene, the city is also home to rich cultural traditions, making it a true melting pot of art, food, and fashion. With iconic sites like Marine Drive and the Gateway of India, Mumbai offers a stunning view of the Arabian Sea. Mumbai is a city that never sleeps—its markets, restaurants, and nightlife hum with life at all hours of the day and night.
18.3
Jordanian Dinar (JOD) د.ا
Local Amman
Vibe:
Amman is home to the Roman Theatre, built in the 2nd century AD, which still hosts cultural events today.
Tip:
Amman is a city with a rich history that spans thousands of years. From the Roman Theatre to the Citadel, every street and building tells a story of the past. The city also blends modern amenities with traditional markets, making it an ideal place to experience both ancient and contemporary Jordanian life. Visitors can explore Amman’s many historic landmarks, enjoy delicious Arabic cuisine, or take a short trip to the nearby Dead Sea or Petra. Amman offers visitors a warm welcome and is a perfect base for exploring the wider country. The city's culture, food, and music make it an unforgettable destination.
Coastal Glamour
Vibe:
Built by the Romans, famous marina
Tip:
With its Mediterranean charm and luxurious appeal, Vilamoura offers the perfect combination of relaxation and adventure. Boasting one of Europe’s largest marinas, it is a prime location for yacht tours and upscale dining. The town’s rich history is evident in its Roman origins, which are complemented by modern amenities and stunning beaches. Whether you’re enjoying a round of golf, lounging by the sea, or dining at a Michelin-star restaurant, Vilamoura offers a high-end escape like no other.
Hidden Hamburg
Vibe:
Hamburg has more bridges than any other city in the world, even more than Amsterdam and Venice combined.
Tip:
Hamburg is a major port city with a fascinating blend of history and modernity. Visitors can explore the city's impressive harbor, famous Speicherstadt district, and rich maritime heritage. From the lively nightlife in the St. Pauli district to the world-class museums and art galleries, Hamburg offers a variety of experiences for visitors of all tastes. Whether you’re a history buff or a foodie, Hamburg has something to offer.
Tranquil
Vibe:
Nuragic civilization predates Roman Empire.
Tip:
Sardinia is a peaceful haven with breathtaking landscapes and a rich cultural history. Its ancient ruins and pristine beaches make it a unique destination for history buffs and nature lovers alike. Sardinia’s natural beauty and culture offer something for every traveler.
Hidden Rome
Vibe:
Rome has more fountains than any other city in the world, with over 1,500, including the iconic Trevi Fountain.
Tip:
Rome is a breathtaking city where history and culture come to life in every corner. The city boasts an unrivaled wealth of ancient monuments, world-class art, and iconic landmarks. From the mesmerizing Colosseum to the beautiful St. Peter’s Basilica, Rome's charm lies in its blend of past and present. Its streets are filled with lively cafes, beautiful boutiques, and open-air markets, making it an unforgettable destination that offers a perfect mix of ancient wonders and modern charm.
