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If you’re in Chicago and looking for little gems mixed with must-see spots and well-known addresses, follow our lead.

FOR THE DRINKS & ATMOSPHERE

The Aviary is a must-visit for cocktail lovers — creative, innovative, and often ranked among the best on the mixology scene. For a more intimate atmosphere, head downstairs to the speakeasy, The Office.

To take in views of the lake and Chicago’s iconic skyline while sipping a cocktail at sunset, make your way to Cindy’s Rooftop, perched on the 13th floor of the Chicago Athletic Hotel.

If you prefer to enjoy your drink with live music, Kingston Mines is a true Chicago classic. This world-renowned nightclub in Lincoln Park is famous for its outstanding blues performances — an absolute must.

Gus Sip & Dip is the perfect place to experience the authentic tavern vibe, with just the right touch of elegance. Located in the heart of River North, this beloved local spot operates on a first-come, first-served basis.

Step into the retro-chic atmosphere of Gilt Bar, a Chicago institution since 1910, where the food is just as impressive (don’t miss the carrot cake). For a more intimate, dimly lit experience, slip through a hidden door to the basement and discover The Library, the establishment’s cozy speakeasy.

FOR A DELICIOUS MEAL

It’s impossible to visit Chicago without trying one of its culinary icons: deep-dish pizza — that thick, buttery-crusted indulgence that’s finger-licking good. We recommend grabbing a slice at Lou Malnati’s or Giordano’s.

Treat yourself to the ultimate fine-dining experience at Oriole, helmed by chef-owner Noah Sandoval. With two Michelin stars and a uniquely intimate dining room, this restaurant offers minimalist dishes that highlight the pure flavors of top-quality ingredients.

Under the direction of chef Sarah Grueneberg, Monteverde boldly reimagines Italian classics, earning it a spot among the city’s 50 best restaurants.

At Schwa, in the Wicker Park neighborhood, expect a truly avant-garde, and proudly eccentric, gastronomic experience. Chef Michael Carlson and his team have earned a Michelin star for their creative, boundary-pushing cuisine.

Elske, a Michelin-starred gem in the West Loop run by chefs David and Anna Posey, serves a Scandinavian-inspired menu that celebrates seasonal ingredients with a perfectly balanced mix of classic and modern flavors.

A hidden treasure in Bridgeport, The Duck Inn is a beloved modern brasserie offering inventive dishes in a cozy, off-the-beaten-path setting.

And finally, let serendipity guide you through the neighboring districts of Logan Square and Avondale, where you’ll find a wealth of authentic and accessible culinary gems waiting to be discovered.

FOR A COFFEE BREAK

Stroll through Andersonville, along Clark Street, where the charm of
small-town shopping comes to life with cozy cafés and independent boutiques.

Specialty coffee, fine teas, pastries — you’ll find it all at Soloway Coffee. Even better, this neighborhood café in Lincoln Park has that extra touch of soul that makes it truly special.

Recently opened in Avondale, Milli by Metric is a delightful community hub created by the team behind Metric Coffee. Set in a beautiful stone building, it’s a place where people share more than just great flavors — a must-visit.

Stop at the Altar Café, located inside the Altar Home concept store, centered around decor and interior design. It's so pretty and peaceful you'll never want to leave.

THE TYPICAL MUST-DO

Take a stroll along the Chicago River to admire the city’s remarkable architectural diversity — a blend of Art Deco, modernism, and other eclectic styles.

Head to the downtown business district to see The Bean (officially known as Cloud Gate), an unmissable sculpture located in Millennium Park.

For breathtaking views of the city, visit the Skydeck at the Willis Tower or 360 Chicago, the observatory perched on the 93rd floor of a skyscraper.

Depending on the season, unwind at Montrose Beach, a beautiful urban escape right by the water.

Walk south along the lakefront to explore the historic and elegant Gold Coast, known for its signature brownstone buildings lining Astor Street.

And don’t miss Prairie Avenue, another heritage-rich street, home to elegant 19th-century mansions that tell the story of Chicago’s storied past.

FOR A LIVELY STROLL

Explore the neighborhoods of Lincoln Park, especially Clark Street, lined with shops and charming independent bookstores. Wander through Hyde Park, Bronzeville, and South Loop to soak in the city’s local flavor.

Recently named one of the coolest neighborhoods in the world by Time Out magazine, Avondale is not to be missed. For an artsy adventure, head to Pilsen, a culturally rich district filled with galleries, colorful murals, and lively outdoor markets.


FOR SHOPPING

If you’re after luxury, designer brands, and elegant window displays, Oak Street (in the Gold Coast) is Chicago’s premier shopping destination.

For something more local and independent, wander through Wicker Park, stop by Cotélac, in Lincoln Park, or browse Una Mae in Bucktown. These neighborhoods are full of unique boutiques and creative finds.

In West Loop – Fulton Market, you’ll discover contemporary art galleries, cutting-edge fashion boutiques, and concept stores like Morlen Sinoway Atelier, Patagonia x Worn Wear, and SVRN, among others.

FOR A PERFECT NIGHT’S SLEEP

Set in the former IBM Tower designed by Mies van der Rohe, The Langham Chicago is a refined, design-forward hotel offering spectacular views of the river and downtown skyline. Ranked among Forbes’ most luxurious hotels, it was also named the Best Hotel Bar in the United States by USA Today.

With its stylish vibe and blend of vintage and contemporary design accents, the ACE Hotel remains a top choice for those who love to stay at the heart of the action. Located in the lively Fulton Market district, it’s the perfect base for exploring the city on foot, surrounded by art exhibits, live music, and vibrant cafés.

For a more local and artistic atmosphere, spend a night at The Robey in the charming Wicker Park neighborhood. This boutique hotel, housed in an Art Deco building full of character, offers stunning city views, best enjoyed from its rooftop pool and bar.