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
111 S Michigan Ave, Chicago, IL 60603, United States
4.9
€-€€
Temporarily closed
Home to the famous painting "A Sunday on La Grande Jatte" by Georges Seurat.
Vibe:
Impressionist paintings, Iconic sculptures
Get To:
Adams/Wells station (0.5 miles)
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
1400 S Lake Shore Dr, Chicago, IL 60605, United States
4.8
€-€€
Temporarily closed
Hosts the largest dinosaur fossil ever discovered.
Vibe:
Sue the T. rex, Ancient Egyptian artifacts
Tip:
Educational, Engaging
Get To:
Roosevelt station (0.6 miles)
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
1805 N Ridgeway Ave, Chicago, IL 60647, United States
4.7
€-€€
6AM to 7PM
A unique linear park that connects multiple neighborhoods.
Vibe:
Biking, Art installations
Get To:
Western Ave station (0.3 miles)
A 2.7-mile elevated pedestrian path that connects Logan Square, Humboldt Park
5700 S Lake Shore Dr, Chicago, IL 60637, United States
4.7
€-€€
Temporarily closed
Offers interactive experiences for all ages.
Vibe:
U-505 submarine, Science exhibits
Tip:
Interactive, Educational
Get To:
57th St. station (0.7 miles)
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
2363 N Milwaukee Ave, Chicago, IL 60647, United States
4.6
€-€€
6AM to 11PM
The "Wicker Park" itself features a picturesque park with a unique fountain
Vibe:
Indie boutiques, street art
Get To:
Accessible via Blue Line
dubbed for it’s artistic influences and experimental restaurants, independent boutiques, coffee shops & bars
1831 S Halsted St, Chicago, IL 60608-3455
4.6
€-€€
6AM to 11PM
Home to the "National Museum of Mexican Art" and vibrant street art
Vibe:
Tacos, art galleries
Tip:
Cultural and Colorful
Get To:
Accessible via Pink Line
a historically Mexican neighborhood with a variety of food options, murals, shops and museums
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:
Maritime
Vibe:
Member of the Hanseatic League.
Tip:
Bremen is a city of maritime history, where past and present merge. The town is filled with historic buildings and monuments that showcase its important role in trade and culture, from the Hanseatic League to its role in modern Germany.
Toledo Uncovered
Vibe:
Toledo was the capital of Spain until the 16th century and has a rich history of coexistence among religions.
Tip:
Toledo is a city of ancient history and religious harmony. With its winding streets, medieval churches, and fascinating blend of Christian, Jewish, and Muslim influences, Toledo offers a fascinating look into the past. Visitors can admire the famous Toledo sword-making tradition, visit historical landmarks such as the Alcázar and the Synagogue of El Transito, and experience the city’s vibrant cultural festivals.
10-35°C
High
US Dollar (USD) $
Cosmic
Vibe:
Home to NASA's Johnson Space Center
Tip:
Houston is a bustling metropolis where innovation meets diversity. Known for its rich history in space exploration, it also offers visitors a range of cultural experiences from art galleries and world-class museums to unique dining experiences. This city’s multicultural environment allows for a fusion of Southern comfort food, international cuisines, and diverse musical genres, including jazz and blues, making it a must-see for both foodies and music lovers.
Local Chicago
Vibe:
Chicago has the world’s first skyscraper, the Home Insurance Building, built in 1885, shaping modern architecture.
Tip:
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.
7°C – 16°C
Medium
Euro (EUR) €
Medieval Charm
Vibe:
Famous for its half-timbered houses and old town.
Tip:
Nuremberg's medieval charm, with its cobblestone streets and half-timbered houses, creates a unique atmosphere. The city’s rich history is reflected in its well-preserved monuments, museums, and the haunting memory of its role in World War II.
Chic
Vibe:
Home to Leonardo da Vinci’s "The Last Supper".
Tip:
Milan is a global hub for fashion, finance, and design. The city is filled with elegant architecture, high-end shops, and vibrant cultural landmarks. From art to fashion, Milan offers a wealth of experiences that cater to every interest.
