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
📹Museum/Natural History
Field MuseumState-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
🏃Park/Trail
The 606A 2.7-mile elevated pedestrian path that connects Logan Square, Humboldt Park
🍴Food & Drink
West Loopknown for restaurants, brunch, bars, coffee shops, murals
🌳Neighborhood
Wicker ParkGreat for an evening stroll, jog or bike ride
🧆Arts & Culture
Wicker Park & Logan Squaredubbed for it’s artistic influences and experimental restaurants, independent boutiques, coffee shops & bars
🏙️Arts & Culture
Pilsena historically Mexican neighborhood with a variety of food options, murals, shops and museums
🌃Beach
North Avenue “Beach”stunning skyline views in front of the beach; in the summertime, watch fireworks on Wednesday at 9:30pm and Saturday at 10:15pm.
🏙️Tour/Experience
Chicago Architecture TouAwarded 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
🌳Nature & Recreation
Lincoln Parka residential neighborhood featuring a free Zoo, the famous Lincoln Park and Chicago’s “beach”
🍽️Art & Culture
River Northgreat for fine dining, mainstream clubs, bars & lounges
🏘️Sports & Entertainment
Wrigleyvillea neighborhood built around its baseball stadium featuring many sports bars
🛍️Shopping/Dining
Magnificent Milethe largest shopping district with various mid-range and high-end shops lined on Michigan Avenue.
🎡Entertainment
Navy PierFormer Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
🧆Dining/Fine Dining
Girl & The Goat ($$$)small plates with adventurous ingredients, family style, 2-3 months prior reservations recommended.
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
For More Places and regular updates, Subscribe today
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
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.
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:
9.6
6
Czech Koruna (CZK) Kč
Prague Unveiled
Vibe:
The Charles Bridge, a historic stone bridge, is adorned with 30 statues, many of which are replicas.
Tip:
Prague enchants visitors with its magical blend of old-world charm and modern-day vibrancy. Stroll through the historic Old Town, explore the winding streets, and discover the city’s rich cultural heritage. The music scene in Prague features a variety of genres, from classical to traditional folk. The city is also known for its stunning castles, including the Prague Castle, and its cozy beer halls, making it a must-visit destination for those who appreciate history, culture, and great food.
Paris Unseen
Vibe:
The Louvre is the world's largest art museum, housing over 35,000 works, including the Mona Lisa.
Tip:
Paris offers a rich blend of history, culture, and modernity, where visitors can wander through its cobbled streets, admire its grand architecture, and enjoy its delicious food and wines. The Seine River adds an enchanting charm to the city, especially at sunset when the city’s lights reflect on the water. Paris is not just the epitome of romance but also a city full of art, from the masterpieces at the Louvre to the avant-garde galleries scattered throughout the city. Paris' café culture invites visitors to relax and people-watch while sipping coffee or wine in the heart of the city. Whether it’s strolling through Montmartre or shopping along the Champs-Élysées, Paris offers something for everyone.
29
Medium
Indian Rupee (INR) ₹
Cultural & Coastal
Vibe:
Marina Beach is the longest natural urban beach in India.
Tip:
Chennai is a vibrant, multicultural city where tradition meets modernity. As the cultural capital of South India, the city is home to centuries-old temples, stunning colonial architecture, and the famous Marina Beach. The city’s music scene is dominated by Carnatic music, and the Chennai Music Season, held every December, celebrates the best of classical music and dance. Visitors can explore the city’s rich heritage through its temples, art galleries, and bustling local markets, or simply enjoy the beautiful coastal vistas. With its distinct blend of culture, cuisine, and history, Chennai offers a unique and immersive experience for every traveler.
Daring Frontier
Vibe:
Marseille is known for its stunning Mediterranean coastline and rich maritime heritage.
Tip:
Marseille is a crossroads of Mediterranean culture, known for its dynamic street life, maritime history, and stunning natural surroundings. With its blend of old and new, it’s a city that always feels alive and full of energy.
Amsterdam Views
Vibe:
Amsterdam has more than 1,500 bridges and is often referred to as the "Venice of the North."
Tip:
Amsterdam is a city that captivates with its artistic legacy and laid-back energy. The city’s free-spirited vibe is reflected in its iconic coffee shops, bike-friendly streets, and progressive culture. Whether you’re visiting the Anne Frank House, exploring the Van Gogh Museum, or enjoying a leisurely boat ride through its canals, Amsterdam offers a unique and unforgettable experience. Its multicultural influence can be seen in the diverse food offerings and music genres that permeate the city’s vibrant cultural scene.
Spiritual, Exotic
Vibe:
Famous for the Grand Palace
Tip:
The energy of Bangkok pulses through its busy streets, ancient temples, and vibrant food markets. The city's golden temples, bustling streets, and diverse cultural landscape make it a must-visit destination for travelers seeking history, food, and excitement.
