Chicago

"Explore Chicagoโ€™s iconic skyline, jazz-filled streets, and deep-dish delights, where the past and present collide."

๐ŸŒ†๐ŸŒญ๐ŸŒŠ

Currency

US Dollar (USD) $

Best Time

Apr โ€“ Oct

Population

2.7 million

Weather ยฐC

10.4ยฐC

TWYS โ€” 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.
State

Illinois

Year

1833 AD Modern city, developed during the 19th century.

Airport

O'Hare International Airport (ORD)

Cost of Living (10)

8๏ธโƒฃ Moderate to high cost of living, particularly in housing and food.

Minimal List TL;DR

TWYS curates the best places to SEE, EAT, DRINK, SHOP & MORE โ€” uncover hidden gems, must-visit landmarks, top restaurants, unique bars, boutique shops, luxury stays, and networking spots.
See
Museum/Art
๐ŸŽจ

The Art Institute of Chicago

4.9
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
See
Museum/Natural History
๐Ÿ“น

Field Museum

4.8
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
See
Park/Sculpture
๐ŸŒณ

Millennium Park & Cloud Gate (โ€œThe Beanโ€)

4.8
A public park located in the center of the city hosting outdoor moving screenings and festivals in the summer, and ice skating in the winter
See
Food & Drink
๐Ÿด

West Loop

4.7
known for restaurants, brunch, bars, coffee shops, murals
See
Museum/Science
๐Ÿ•น๏ธ

Museum of Science and Industry

4.7
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
See
Park/Trail
๐Ÿƒ

The 606

4.7
A 2.7-mile elevated pedestrian path that connects Logan Square, Humboldt Park
See
Waterfront
๐ŸŒ†

Chicago Riverwalk

4.7
A walk way through the city for skyline and waterfront view
See
Arts & Culture
๐Ÿ™๏ธ

Pilsen

4.6
a historically Mexican neighborhood with a variety of food options, murals, shops and museums
See
Neighborhood
๐ŸŒณ

Wicker Park

4.6
Great for an evening stroll, jog or bike ride
See
Art & Culture
๐Ÿฝ๏ธ

River North

4.5
great for fine dining, mainstream clubs, bars & lounges
See
Observation Deck
๐ŸŒ‡

Skydeck Chicago on Willis Tower

4.5
photo opportunities of the skyline on a glass balcony extending four feet outside the 103rd floor
See
Nature & Recreation
๐ŸŒณ

Lincoln Park

4.5
a residential neighborhood featuring a free Zoo, the famous Lincoln Park and Chicagoโ€™s โ€œbeachโ€
No FoMo
Entertainment
๐ŸŽก

Navy Pier

4.5
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
Eat
Dining/Fine Dining
๐Ÿง†

Girl & The Goat ($$$)

4.9
small plates with adventurous ingredients, family style, 2-3 months prior reservations recommended.
Eat
Casual Dining, Chinese
๐ŸฅŸ

Qing Xiang Yuan Dumplings ($$

4.8
housemade dumplings with various choices for fillings.
Eat
Dining/Pizza
๐Ÿ•

Lou Malnatiโ€™s Pizza ($$)

4.8
Chicagoโ€™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
Eat
Dining/Burger
๐Ÿ”

Au Cheval ($$)

4.7
the best burger in townโ€ infamous for 2-5 hour waits; no reservations; Small Cheval ($) is a similar chain that offers the casual version of Au Cheval
Eat
Casual Dining, Cuban
๐Ÿฅ™

90 Miles Cuban Cafe ($$

4.7
Great Cuban food with nice outdoor seatings.
Eat
Dining/Fine Dining
๐Ÿง‡

Roister (brunch $$; dinner $$$$)

4.7
amazing brunch alert; the BEST chicken and waffles Iโ€™ve ever had.
Eat
Dining/Asian Fusion
๐ŸฅŸ

Duck Duck Goat ($$-$$$)

4.6
Chinese fusion small plates; same chef as above; truly 10/10 creative and delicious.
Drink
Cocktail Bar, American
๐Ÿท

The Violet Hour

4.9
Creative cocktails & small bites define this sophisticated, stylish bar.
Drink
Fine Dining, American
๐ŸŽต

LondonHouse Chicago

4.6
Hip bar
Drink
Casual Dining, American
๐ŸŒ†

Cindyโ€™s

4.5
Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.

Places to See

Discover breathtaking landmarks, hidden gems, and offbeat sights that make every destination unforgettable.
๐ŸŽจ
The Art Institute of Chicago
Museum/Art
111 S Michigan Ave, Chicago, IL 60603, United States
4.9
โ‚ฌ-โ‚ฌโ‚ฌ
Temporarily closed
Home to the famous painting "A Sunday on La Grande Jatte" by Georges Seurat.
Vibe:
Impressionist paintings, Iconic sculptures
Tip:
Cultural, Inspiring
Get:
Adams/Wells station (0.5 miles)
Home to the famous painting "A Sunday on La Grande Jatte" by Georges Seurat.Home to the famous painting "A Sunday on La Grande Jatte" by Georges Seurat.The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
http://www.artic.edu/
๐Ÿ“น
Field Museum
Museum/Natural History
1400 S Lake Shore Dr, Chicago, IL 60605, United States
4.8
โ‚ฌ-โ‚ฌโ‚ฌ
Temporarily closed
Hosts the largest dinosaur fossil ever discovered.
Vibe:
Sue the T. rex, Ancient Egyptian artifacts
Tip:
Educational, Engaging
Get:
Roosevelt station (0.6 miles)
Hosts the largest dinosaur fossil ever discovered.Hosts the largest dinosaur fossil ever discovered.Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
https://www.fieldmuseum.org/
201 E Randolph St, Chicago, IL 60602, United States
4.8
โ‚ฌ-โ‚ฌโ‚ฌ
6AM to 11PM
Hosts various public art installations and concerts.
Vibe:
Cloud Gate photo opportunity, Jay Pritzker Pavilion concerts
Tip:
Lively, Artistic
Get:
Millennium Park station (0.2 miles)
Hosts various public art installations and concerts.Hosts various public art installations and concerts.Millennium Park & Cloud Gate (โ€œThe Beanโ€)
A public park located in the center of the city hosting outdoor moving screenings and festivals in the summer, and ice skating in the winter
https://www.cityofchicago.org/city/en/depts/dca/supp_info/chicago_s_publicartcloudgateinmillenniumpark.html
๐Ÿด
West Loop
Food & Drink
West Loop, Chicago, IL, USA
4.7
โ‚ฌ-โ‚ฌโ‚ฌ
6AM to 11PM
Hosts the famous "Chicago Food Truck Festival" and has a lively arts scene
Vibe:
Gourmet food, craft cocktails
Tip:
Hip and Energetic
Get:
Accessible via Pink Line, Green Line
Hosts the famous "Chicago Food Truck Festival" and has a lively arts sceneHosts the famous "Chicago Food Truck Festival" and has a lively arts sceneWest Loop
known for restaurants, brunch, bars, coffee shops, murals
https://www.hotspotrentals.com/the-ultimate-guide-to-chicagos-west-loop-neighborhood/
๐Ÿ•น๏ธ
Museum of Science and Industry
Museum/Science
5700 S Lake Shore Dr, Chicago, IL 60637, United States
4.7
โ‚ฌ-โ‚ฌโ‚ฌ
Temporarily closed
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
http://www.msichicago.org/
๐Ÿƒ
The 606
Park/Trail
1805 N Ridgeway Ave, Chicago, IL 60647, United States
4.7
โ‚ฌ-โ‚ฌโ‚ฌ
6AM to 7PM
A 2.7-mile elevated pedestrian path that connects Logan Square, Humboldt Park
http://the606.org/
๐Ÿ™๏ธ
Pilsen
Arts & Culture
1831 S Halsted St, Chicago, IL 60608-3455
4.6
โ‚ฌ-โ‚ฌโ‚ฌ
6AM to 11PM
Home to the "National Museum of Mexican Art" and vibrant street art
Vibe:
Tacos, art galleries
Tip:
Cultural and Colorful
Get:
Accessible via Pink Line
Home to the "National Museum of Mexican Art" and vibrant street artHome to the "National Museum of Mexican Art" and vibrant street artPilsen
a historically Mexican neighborhood with a variety of food options, murals, shops and museums
https://ru.hotels.com/go/usa/pilsen-chicago
๐Ÿฝ๏ธ
River North
Art & Culture
River North, Chicago, IL, USA
4.5
โ‚ฌ-โ‚ฌโ‚ฌ
6AM to 11PM
Home to the famous "Holy Name Cathedral" and many art installations
Vibe:
Fine dining, art galleries, river cruises
Tip:
Trendy and Lively
Get:
Accessible via Brown Line, Red Line
Home to the famous "Holy Name Cathedral" and many art installationsHome to the famous "Holy Name Cathedral" and many art installationsRiver North
great for fine dining, mainstream clubs, bars & lounges
https://www.choosechicago.com/neighborhoods/river-north/
Must Visit:

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.

Chicagoโ€™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 cityโ€™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.
๐Ÿง†
Girl & The Goat ($$$)
Dining/Fine Dining
809 W Randolph St, Chicago, IL 60607, United States
4.9
โ‚ฌ-โ‚ฌโ‚ฌ
4:30 to 9:30PM
Known for its innovative approach to shared dining.
Vibe:
Goat empanadas, Seasonal dishes
Get:
Damen station (0.3 miles)
Tip:
Energetic, Chic
Known for its innovative approach to shared dining.Known for its innovative approach to shared dining.Girl & The Goat ($$$)
small plates with adventurous ingredients, family style, 2-3 months prior reservations recommended.
http://www.girlandthegoat.com/
๐Ÿ•
Lou Malnatiโ€™s Pizza ($$)
Dining/Pizza
439 N Wells St, Chicago, IL 60654, United States
4.8
โ‚ฌ-โ‚ฌโ‚ฌ
10:30AM to 10PM
Known for its iconic deep-dish pizza.
Vibe:
Deep-dish pizza, Malnati's salad
Get:
Diverse public transport options
Tip:
Cozy, Family-friendly
Known for its iconic deep-dish pizza.Known for its iconic deep-dish pizza.Lou Malnatiโ€™s Pizza ($$)
Chicagoโ€™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-north
๐ŸฅŸ
Qing Xiang Yuan Dumplings ($$
Casual Dining, Chinese
2002 S Wentworth Ave #103, Chicago, IL 60616, United States
4.8
โ‚ฌ-โ‚ฌโ‚ฌ
11:30AM to 9PM
Fresh homemade dumplings with authetic flavour
Vibe:
Accessible via CTA bus 8, 65
Get:
Specializes in hand-made dumplings and noodles
Tip:
Dumplings, Noodles
Fresh homemade dumplings with authetic flavourFresh homemade dumplings with authetic flavourQing Xiang Yuan Dumplings ($$
housemade dumplings with various choices for fillings.
http://qxydumplings.com/
๐Ÿง‡
Roister (brunch $$; dinner $$$$)
Dining/Fine Dining
951 W Fulton Market, Chicago, IL 60607, United States
4.7
โ‚ฌ-โ‚ฌโ‚ฌ
10AM to 3PM | 4 to 9PM
Known for its innovative approach to wood-fired cooking.
Vibe:
Wood-fired meats, Seasonal dishes
Get:
Damen station (0.5 miles)
Tip:
Lively, Rustic
Known for its innovative approach to wood-fired cooking.Known for its innovative approach to wood-fired cooking.Roister (brunch $$; dinner $$$$)
amazing brunch alert; the BEST chicken and waffles Iโ€™ve ever had.
https://www.roisterrestaurant.com/
๐Ÿ”
Au Cheval ($$)
Dining/Burger
800 W Randolph St, Chicago, IL 60607, United States
4.7
โ‚ฌ-โ‚ฌโ‚ฌ
12 to 9PM
the best burger in townโ€ 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/
๐Ÿฅ™
90 Miles Cuban Cafe ($$
Casual Dining, Cuban
2540 W Armitage Ave, Chicago, IL 60647, United States
4.7
โ‚ฌ-โ‚ฌโ‚ฌ
10AM to 9PM
Wicker Park & Logan Square
Vibe:
Accessible via CTA bus 74, 49
Get:
Offers authentic Cuban dishes and vibrant decor
Tip:
Cuban Sandwich, Empanadas
Wicker Park & Logan SquareWicker Park & Logan Square90 Miles Cuban Cafe ($$
Great Cuban food with nice outdoor seatings.
http://www.90milescubancafe.com/
๐ŸฅŸ
Duck Duck Goat ($$-$$$)
Dining/Asian Fusion
857 W Fulton Market, Chicago, IL 60607, United States
4.6
โ‚ฌ-โ‚ฌโ‚ฌ
4:30 to 11PM
A unique take on Asian cuisine with a sharing concept.
Vibe:
Peking duck, Dumplings
Get:
Damen station (0.5 miles)
Tip:
Lively, Colorful
A unique take on Asian cuisine with a sharing concept.A unique take on Asian cuisine with a sharing concept.Duck Duck Goat ($$-$$$)
Chinese fusion small plates; same chef as above; truly 10/10 creative and delicious.
https://duckduckgoatchicago.com/
Must Try:

๐Ÿ• Deep-Dish Pizza (Thick pizza with cheese and tomato sauce baked in a deep pan) ๐ŸŒญ Italian Beef (Thinly sliced roast beef, often served in a sandwich with peppers) ๐ŸŒญ Chicago-Style Hot Dogs (Hot dog topped with mustard, relish, and veggies) ๐Ÿฟ Popcorn (Known for being caramel-coated or savory) ๐ŸŒฎ Tacos (Flour or corn tortillas filled with various meats and veggies)

Places to Drink

Unwind at vibrant bars, cozy cafรฉs, and craft breweries, handpicked for the best drinks and atmosphere.
๐Ÿท
The Violet Hour
Cocktail Bar, American
1520 N Damen Ave., Chicago, IL 60622, United States
4.9
โ‚ฌ-โ‚ฌโ‚ฌ
4 to 8PM
Creative bar with cocktails and small bites
Vibe:
Accessible via CTA bus 56, 70
Get:
Speakeasy vibe with artisanal cocktails
Tip:
Cocktails, Small Plates
Creative bar with cocktails and small bitesCreative bar with cocktails and small bitesThe Violet Hour
Creative cocktails & small bites define this sophisticated, stylish bar.
http://www.theviolethour.com/
๐ŸŽต
LondonHouse Chicago
Fine Dining, American
85 E Wacker Dr, Chicago, IL 60601, United States
4.6
โ‚ฌ-โ‚ฌโ‚ฌ
12 to 9PM
Hip bar for seafood and steak
Vibe:
Accessible via CTA bus 1, 121
Get:
Rooftop bar with stunning views of the river
Tip:
Steak, Seafood
Hip bar for seafood and steakHip bar for seafood and steakLondonHouse Chicago
Hip bar
https://www.hilton.com/en/hotels/chilhqq-londonhouse-chicago/?SEO_id=GMB-QQ-CHILHQQ&y_source=1_MzI2NDc5Ni03MTUtbG9jYXRpb24uZ29vZ2xlX3dlYnNpdGVfb3ZlcnJpZGU%3D
๐ŸŒ†
Cindyโ€™s
Casual Dining, American
12 S Michigan Ave, Chicago, IL 60603, United States
4.5
โ‚ฌ-โ‚ฌโ‚ฌ
Temporarily closed
Stylish bar for cocktails and brunch
Vibe:
Accessible via CTA bus 3, 60
Get:
Stunning rooftop views of Millennium Park
Tip:
Brunch, Cocktails
Stylish bar for cocktails and brunchStylish bar for cocktails and brunchCindyโ€™s
Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
http://www.cindysrooftop.com/
Music & Dance:

๐ŸŽท Jazz: The birthplace of modern jazz, with venues like The Green Mill. ๐ŸŽธ Blues: Legendary clubs like Buddy Guyโ€™s Legends. ๐ŸŽถ House Music: Originated in the '80s, influential in global EDM culture. ๐ŸŽค 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.
We'll be updating more places soon!
Key Industries:

๐Ÿ’ฐ Finance (home to Chicago Mercantile Exchange), ๐Ÿญ Manufacturing (a historic industrial center, with prominent manufacturing sectors in machinery and steel), ๐Ÿ’ป 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

Chicagoโ€™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, thereโ€™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.
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Luxury

Indulge in high-end experiences, exclusive stays, and premium services tailored for refined travelers.
For More Tips Read Further

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 worldโ€™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 Americaโ€™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, Chicagoโ€™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 youโ€™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

Watchย out for Crowded Areas
Avoid overrated tourist traps and discover alternative experiences worth your time.
Skip Super Touristic Places

Off the beaten path places in

Chicago

Transportation

๐Ÿš‡ Efficient metro system (CTA), buses, and commuter trains. ๐Ÿšฒ Plenty of bike lanes along the lakefront and throughout downtown. ๐Ÿš– Taxis and ride-hailing services provide good connectivity. ๐Ÿšถโ€โ™‚๏ธ 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, Chicagoโ€™s charm lies in its vibrant neighborhoods, dynamic food scene, and scenic location along the shores of Lake Michigan. A visit to Chicago wouldnโ€™t be complete without experiencing its architectural brilliance. Take an architecture river cruise for a unique perspective on the cityโ€™s history and design, or stroll through Millennium Park, home to the famous Cloud Gate, also known as โ€œThe Bean.โ€ 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. Donโ€™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. Chicagoโ€™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 Chicagoโ€™s rich jazz and blues heritage at legendary clubs like Buddy Guyโ€™s Legends. Whether youโ€™re marveling at the cityโ€™s towering skyline, savoring its culinary delights, or enjoying a stroll along the Chicago Riverwalk, the cityโ€™s blend of history, culture, and innovation makes it an unforgettable destination.

Chicago

3 Day City Guide

๐ŸŒ† Day 1: Chicago's Urban Exploration & Classic Eats ๐Ÿ•˜ 9:00 AM: Begin your day at Millennium Park ๐ŸŒณ, with the famous Cloud Gate (The Bean) ๐Ÿชž for some fun photo ops. ๐Ÿ•› 12:00 PM: Take the Chicago Architecture Boat Tour ๐Ÿšค to see the cityโ€™s impressive skyline and learn about its history. ๐Ÿด 2:00 PM: Stop for lunch at Lou Malnatiโ€™s ๐Ÿ• for Chicagoโ€™s iconic deep-dish pizza. ๐Ÿ•• 7:00 PM: Head to a South Loop jazz club ๐ŸŽท for an evening of live music and a laid-back vibe. ๐ŸŒ† Day 2: Museums & Waterfront ๐Ÿ•˜ 9:00 AM: Visit the world-renowned Field Museum or Art Institute of Chicago ๐Ÿ–ผ๏ธ for some cultural immersion. ๐Ÿ•› 12:00 PM: Afterward, head to Navy Pier ๐ŸŽก, ride the Ferris wheel ๐ŸŽก, and take in the lakefront views. ๐Ÿ•• 6:00 PM: In the evening, enjoy cocktails at a South Loop jazz club ๐ŸŽถ for a taste of the cityโ€™s musical history. ๐ŸŒ† Day 3: Local Vibes & Views ๐Ÿ•˜ 9:00 AM: Explore Wicker Park ๐Ÿ›๏ธ for unique boutiques, vibrant street art, and cool coffee spots. ๐Ÿ•› 12:00 PM: Head to the Lincoln Park Zoo ๐Ÿฆ, a lovely, free spot to relax and enjoy the animals. ๐Ÿ•• 6:00 PM: For a spectacular end to the day, enjoy sunset drinks at the Signature Room in the John Hancock Tower ๐Ÿธ with panoramic views of the city skyline.

Current Trends

๐Ÿด West Loop restaurants: Known for its trendy food scene, home to celebrity chefs and Michelin-star restaurants like The Girl and The Goat. ๐Ÿป Craft breweries: Chicago is a hub for craft beer lovers, with spots like Revolution Brewing and Half Acre leading the way. ๐Ÿธ Rooftop bars: Popular spots like Cindyโ€™s Rooftop offer skyline views and craft cocktails. ๐ŸŒฑ Plant-based dining: Vegan restaurants like The Chicago Diner offer delicious, health-conscious food options. ๐ŸŽค Live music scene: Chicagoโ€™s jazz and blues clubs are thriving, especially along the South Loopโ€™s iconic music row.

Local Events Guide

๐ŸŽธ Chicago Blues Festival (June): The largest free blues festival in the world, celebrating the city's rich musical heritage. ๐ŸŽค Lollapalooza (August): A massive music festival attracting big-name artists and tens of thousands of fans. โœˆ๏ธ Chicago Air and Water Show (August): A thrilling aerial display over Lake Michigan with breathtaking performances. ๐Ÿ™๏ธ Chicago Jazz Festival (September): A celebration of Chicagoโ€™s deep jazz history with performances from renowned artists. ๐ŸŽจ Chicago Architecture Biennial (September): A global exhibition of cutting-edge architecture.

Local Insider Tips

๐Ÿบ 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. ๐ŸŒŠ Riverwalk: Stroll along the Chicago River and enjoy scenic views, waterfront cafes, and public art installations. Donโ€™t miss the chance to take a kayak tour for a unique perspective of the skyline. ๐ŸŽจ 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. ๐Ÿ” West Loop: Discover some of Chicagoโ€™s best restaurants in this trendy area, featuring world-renowned chefs and local favorites. ๐Ÿž๏ธ 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

๐Ÿšฒ Divvy Bike Sharing: Eco-friendly bike rentals around the city. ๐ŸŒณ Urban parks: Visit Lincoln Park or Garfield Park Conservatory. ๐Ÿš‡ Public transportation: The CTA (Chicago Transit Authority) operates electric buses and trains. ๐Ÿฝ๏ธ Sustainable dining: Uncommon Ground restaurant is a leader in eco-friendly dining, with a rooftop farm. ๐ŸŒฑ Farmers markets: Support local vendors with fresh, sustainable products.

Chicago

TWYS: Your Ultimate Guide to Unique Travel Experiences & Insider Tips

Explore the Best Off-the-Beaten-Path Experiences:
โ€
Ready to see through a localโ€™s eyes?
Our curated guide unveils top hidden gems, secret spots, and local favorites that you wonโ€™t find in typical travel guides.
Whether itโ€™s a cozy cafรฉ 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 โ€”perfect for adventurous travelers, culture enthusiasts, and anyone looking for an authentic journey

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Unlock the Hidden Side:
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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.

More Cities to Visit:

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Dubai
Dubai Hidden Gems
United Arab Emirates
28.5ยฐC
UAE Dirham (AED) ุฏ.ุฅโ€Ž
Dubai is a modern metropolis that offers the worldโ€™s largest shopping mall, the Dubai Mall, complete with an indoor ice rink and aquarium. Known for its luxurious lifestyle, Dubai features towering skyscrapers like the Burj Khalifa, the tallest building in the world. The city is also famous for its opulent hotels, desert safaris, and vibrant nightlife. Dubai blends modern architecture with rich cultural traditions, offering a unique experience to visitors. Its innovative approach to architecture, retail, and tourism continues to set global trends.
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Nuremburg
Medieval Charm Nuremburg
Germany
7ยฐC โ€“ 16ยฐC
Euro (EUR) โ‚ฌ
Nuremberg, one of the most historically significant cities in Germany, played a pivotal role in medieval European politics. The city is home to the Nuremberg Castle, a major landmark, and the Nuremberg Trials, which were held after World War II to prosecute war criminals. The Old Town (Altstadt) is full of medieval charm, with cobbled streets, half-timbered houses, and the beautiful St. Lorenz Church. Known for its famous Christmas market, Nuremberg is also renowned for its bratwurst, gingerbread cookies, and its role in the production of high-quality toys
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Napoli
Naples Unveiled Treasures
Spain
16.6ยฐC
Euro (EUR) โ‚ฌ
Naples is home to an ancient underground city, with Roman ruins, catacombs, and tunnels that are open to the public. The cityโ€™s rich history can be seen in its historic buildings, including the Royal Palace and the Naples National Archaeological Museum. Naples is the birthplace of pizza and offers some of the best pizza in the world. The city is also a gateway to Pompeii, the Amalfi Coast, and Mount Vesuvius. Naples is a vibrant city with a unique mix of ancient history, delicious cuisine, and Mediterranean charm.
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Berlin
Berlin Hidden Gems
Germany
9.9ยฐC
Euro (EUR) โ‚ฌ
Berlin is a city that seamlessly blends history with modernity, featuring over 1,700 parks, including the famous Tiergarten. Known for its diverse culture, rich history, and vibrant arts scene, Berlin is also home to iconic landmarks like the Berlin Wall Memorial and Brandenburg Gate. With a unique mix of historical sites and cutting-edge architecture, the city is an international hub for innovation, technology, and culture, offering visitors a fascinating glimpse into Germanyโ€™s past and present.
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Madrid
Artistic Madrid Culture
Spain
15.1ยฐC
Euro (EUR) โ‚ฌ
Madrid, Spainโ€™s capital, is known for its grand historic buildings, including the Royal Palace and Prado Museum. As the worldโ€™s oldest restaurant, Sobrino de Botรญn, established in 1725, serves traditional Spanish cuisine in a historic setting. The city is home to lush green parks, including Retiro Park, and boasts a vibrant nightlife scene. Madridโ€™s food culture is world-renowned, with tapas bars, markets, and elegant dining options. The city is a blend of old-world charm and modern vibrancy, offering a rich cultural experience.
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San Francisco
SF Hidden Spots Discovery
United States of America
15.1ยฐC
US Dollar (USD) $
San Francisco is famous for its picturesque Golden Gate Bridge, diverse neighborhoods, and vibrant arts scene. The city has more than 200 parks, including Golden Gate Park, which is larger than New York's Central Park. Known for its cable cars and tech startups, San Francisco is a global leader in innovation and technology. Its rich history is intertwined with the California Gold Rush and the LGBT rights movement, while its stunning bay views, iconic architecture, and thriving cultural scene continue to draw visitors from around the world.
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Leipzig
Cultural Hub Leipzig
Germany
8ยฐC โ€“ 18ยฐC
Euro (EUR) โ‚ฌ
Famous for its annual Leipzig Book Fair, Leipzig has long been a center of culture and learning in Germany. The city is home to a thriving arts scene, with numerous galleries, theaters, and music venues. Leipzigโ€™s rich history is reflected in its stunning architecture, including the Monument to the Battle of the Nations. Itโ€™s also known for its contributions to music, being the home of composer Johann Sebastian Bach and the site of his famous St. Thomas Church performances.
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Shanghai
Urban Shanghai Wonders
China
17.1ยฐC
Chinese Yuan (CNY) ยฅ
Shanghai is home to the iconic Shanghai Tower, the tallest building in China and the second tallest in the world at 632 meters. The city blends futuristic architecture with traditional Chinese culture, offering a dynamic mix of the old and new. Visitors can explore the historic Bund, walk along the Huangpu River, and shop in luxury malls. Shanghai is a hub for finance, innovation, and culture, boasting a vibrant arts scene and world-class museums. With its bustling streets, stunning skyline, and rich history, Shanghai is one of the worldโ€™s most exciting cities.
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Rugen
Island Haven Rugen
Germany
10ยฐC โ€“ 18ยฐC
Euro (EUR) โ‚ฌ
Rรผgen Island is home to Jasmund National Park, known for its unique chalk formations and stunning coastal views. The park, a UNESCO World Heritage Site, is famous for its ancient beech forests and dramatic cliffs, such as the famous Kรถnigsstuhl. Rรผgen also boasts beautiful beaches, charming villages, and historic lighthouses, making it a popular destination for nature lovers and hikers. The islandโ€™s rich biodiversity and striking landscapes make it one of Germanyโ€™s most scenic regions.
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Jaipur
Regal & Royal Jaipur
India
25ยฐC
Indian Rupee (INR) โ‚น
Jaipur, often called the โ€œPink City,โ€ is renowned for its beautiful pink-hued buildings, opulent palaces, and rich royal heritage. This historic city in Rajasthan is home to iconic landmarks such as the Amber Fort, City Palace, and Hawa Mahal. Jaipurโ€™s bustling markets offer vibrant textiles, jewelry, and handicrafts, and the cityโ€™s cultural traditions, including folk music and dance, provide visitors with a glimpse into Rajasthanโ€™s regal past. Jaipur's blend of history, architecture, and culture makes it a must-visit destination in India.