Why You’ll Love It

You'll need to wait in line for this one because Au Cheval and their "Best Cheeseburger in the U.S." award from Bon Appetit have put this old-school-style eatery on the map. The burger in question starts with beef patties perfectly grilled to medium

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Dripping in decadence and old-world style, this undeniably sophisticated cocktail lounge brings the elegance of London's cocktail scene to the Windy City in breathtaking detail. The interior is draped in blue velvet from the curtains to the furniture

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As the only Filipino restaurant in America with a Michelin Star, Kasama is all about community and togetherness, with its husband-and-wife chef team offering dishes that are so authentic and nostalgic to the Filipino community that diners have shed a

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This boisterous dining room that's practically buzzing with conversational energy was developed by brothers Oliver and Nicolas Poilevey of French bistro Le Bouchon, who have married traditional French fare with a few tasty twists of modernity. Conver

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Southern comfort food has never been more sophisticated than the dishes served at Virtue in Hyde Park. Led by Chef Erick Williams, Virtue is his first solo project where he combines his love for Southern cooking with the history and art that surround

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Lazy Bird may sound like a laid-back dive bar, but this basement space in The Hoxton Hotel is anything but. Moody lamp light blended with deep brown accents and bright pops of royal blue give this intimate, 65-seat cocktail lounge an air of sophistic

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As a master of Italian cooking, Chef Evan Funke and his dedication to old-world culinary techniques have made Tre Dita one of the most decadent dining destinations in Chicago. The restaurant interior features massive 40-foot windows with panoramic vi

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Uncover this dark, ornate, windowless speakeasy that drops the cheesy tourist vibes and embraces French flair without the formality, blending sultry jazz with Chesterfield-styled sofas. The elaborate, dimly lit wood and exposed brick walls are illumi

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Stashed away in a former speakeasy sits Milk Room, an award-winning, eight-seat micro bar that utilizes vintage spirits and rare ingredients to create the perfect historical drinking experience. Full rare bottles decades in the making are also availa

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Intimate and steeped in history, The Sparrow breathes new life into a nearly 100-year-old Art Deco apartment building by bringing the original lobby bar back to life. The exotic touches, dimly lit chandeliers, and vintage hotel accents give this cock

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Maxwell's Trading is one of the most unique eateries in Chicago, with a dedication to sustainability so deep that they even have a vegetable garden and bee hive on the roof as a part of the Roof Crop organization. The main dining space is airy and br

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As the only restaurant in Chicago to make the 2024 New York Times list of the best restaurants in America, Asador Bastian is a must-visit. Putting a Spanish twist on the classic steakhouse experience, Asador Bastian embraces every aspect of Basque co

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Uniquely located in what looks to be an aged warehouse down a brick-paved alley, Green Street Smoked Meats is known for bringing Texas spices and style all the way to Chicago. Immediately, you are welcomed into a rustic, old western-inspired interior

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Two-time Top Chef contestant, Chef CJ Jacobson is bringing a light California style of cooking to Chicago’s dinner plates. His style consists of hyper-seasonal and localized ingredients to create Mediterranean-style meals, developing flavor profiles

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Lula Cafe has been a leader in the farm-to-table restaurant community since it opened its doors in 1999. Now, over 20 years later and with two extra storefronts worth of space, Lula is a staple of the Logan Square culinary community. Their seasonal,

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As one of the only four Ralph Lauren restaurants in existence, the Chicago location has become a local staple in a usually tourist-focused neighborhood. The classy, sophisticated interior is filled with the same luxury the clothing line provides: lea

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Created by Stephanie Izard, (James Beard Award Winner, Iron Chef Title Winner, and Top Chef’s first fan favorite), Little Goat Diner is an adorable new vintage-styled restaurant that is serving up a wide range of creative, gourmet comfort food classi

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A honky-tonk hangout mixed with great bourbon and authentic Mexican street food? Count us in. Created by Executive Chef-Partner Paul Kahan and Culinary Director Chris Miller, Big Star is all about open air, lively crowds, and good food & drinks.

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Led by James Beard Award-winning chef and pasta expert Sarah Grueneberg, Monteverde is dedicated to the craft of cooking authentic Italian fare using traditional techniques and the best ingredients possible. The entire operation centers around the cu

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Experience Greek food at its finest with Andros Taverna, a contemporary, sophisticated-yet-approachable spot where seafood reigns supreme, and the spreads with wood-fired pita should never be skipped. Their commitment to authenticity means that they

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The Magnificent Mile in Chicago, nestled along North Michigan Avenue, is where the city’s energy and elegance come together. This mile-long stretch is not just a shopping district; it’s an experience. From high-end boutiques to flagship stores, it’s

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As the Official River Cruise of the Chicago Architecture Foundation, Chicago's First Lady is one of the best ways to tour the Windy City. Their entire vessel is designed after early 20th-century luxury yachts with a full bar, plenty of snacks availab

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For 65 years, Second City has been responsible for launching the careers of countless actors and comedians who have become household names. This makes it the oldest improvisational theater troupe continuously based in Chicago– providing training, edu

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For a rejuvenating spa experience unlike anything you've ever experienced, AIRE Ancient Baths is where you can surround yourself with Chicago's distinct, historic style while renewing your body and soul. The spa is located in a meticulously restored

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Hidden within Chicago’s Garfield Park, the Garfield Park Conservatory feels like you’ve stumbled right into Jumanji. This glass-encased wonderland is a tropical oasis with a touch of Windy City grit, featuring lush fern rooms, exotic cacti, and a pal

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The Green Mill is a genuine glimpse into Chicago’s Prohibition past, where jazz legends played, and Al Capone had his own booth. With its velvet-curtained stage, vintage posters, and a bar that's been around for over a century, it feels like stepping

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Situated in the historic Washington Park neighborhood, the DuSable Black History Museum, aptly named after the city's Haitian-born founder, is a pivotal institution dedicated to celebrating and preserving African American history and culture.As a tra

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The Field Museum, which first opened its doors in 1894, has since grown into a true treasure trove of natural history, with a collection that now boasts nearly 40 million artifacts and specimens. As you wander through its massive stone halls, you'll

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Chicago's Riverwalk is where nature, art, and architecture combine to create one of the city's most beloved landmarks. Since the 1970s, this fantastic pedestrian destination has won multiple awards for its urban design, architecture, and lighting whi

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The Lincoln Park Zoo has been an iconic part of Chicago since it opened in 1868. Its dedication to connecting guests with nature continues to this day by offering free, yes, free admission to all visitors. The zoo houses over 200 animals, including a

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Chicago's popular North Avenue Beach boasts a distinctive beach house with 22,000 square feet of space. The sleek, ocean liner-inspired building offers stunning views of the city, featuring upper decks and portholes. Dedicated in May 2000 by Mayor Ri

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Summer fun in Chicago takes to the waters of Lake Michigan with The Playpen, a hotspot for boating enthusiasts, where calm waters, skyline views, and party vibes reign supreme. The Playpen offers a range of boats to rent, from sailboat charters to lu

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Take in the breathtaking views and soaring heights from the 103rd floor of the Willis Tower. Formerly known as the Sears Tower, this landmark is the tallest building in Chicago and is the third tallest in the Western Hemisphere. The Skydeck offers st

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Windy offers a unique sailing experience aboard an authentic tall ship on a secure waterway, presenting guests with thrilling skyline sails featuring diverse experiences. From captivating architecture tours revealing the hidden history of the Windy C

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The Starbucks Reserve is anything but your typical coffee shop. This Chicago Roastery is a true haven for coffee aficionados seeking an immersive deep dive into the world of coffee. From the moment one steps inside, the sensory delight of freshly gro

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Established in 1968, the club first opened its doors as a modest coffee house, evolving through several phases before becoming the first to bring blues music to the north side of Chicago. By 1980, it had found its current home, where live music has b

Why You’ll Love It

What started as a discovery during a family vacation turned into one of the largest museums focused on science and science education in the world. Since opening in 1933, the Griffin Museum of Science and Industry, (or Griffin MSI for short), has offe

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After successfully convincing the railroad to donate the land rights, Mayor Richard M. Daley unveiled plans for what would become Millennium Park in 1998. Since its grand opening in 2004, the park has transformed into a beloved urban oasis, offering

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The Shedd Aquarium is more than just a prominent indoor aquarium, it’s a deep dive into the wonders of the aquatic world without ever leaving town. Since opening its doors on May 30, 1930, the Shedd has been home to around 32,000 fascinating creature

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The WNDR Museum offers an immersive, multi-sensory blend of art and technology, inviting everyone to embrace the idea that we're all artists in our own right. At WNDR, you’re not just a spectator—every step you take and interaction you have becomes p

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The only word to truly describe the St. Regis Hotel in Chicago is decadent. This luxury, 5-star stay is an exclusive retreat filled with lavish amenities that will delight even the most affluent of tastes. At the heart of every St. Regis hotel is the

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The Peninsula Chicago, a renowned five-star hotel celebrated for its traditional Asian service, has become a cornerstone of Chicago’s hospitality scene, excelling in everything from accommodations to corporate events and celebrations.With its deep lo

Why You’ll Love It

The newly revamped Four Seasons Chicago is more than just a place to rest your head—it’s a vibrant hub of culture, fashion, and energy where iconic luxury meets the bold spirit of the city. Think of it as a living, breathing tribute to everything tha

Why You’ll Love It

Created for the discerning traveler, the Park Hyatt Chicago offers a luxurious stay filled with elevated experiences, premium residential-style suites complete with unobstructed views of Lake Michigan, and a plethora of bespoke amenities. Each room a

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This hotel is as historic to Downtown Chicago as it is iconic, and as a Hilton property, guests can expect all of the fantastic amenities and modern touches that the brand is known for providing. Here's a bit of a history lesson about the Palmer Hous

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Chicago's iconic Fulton Market district is home to Nobu Hotel Chicago, where the city's artistic pulse meets the world-renowned Nobu spirit. Opened in June 2020, this hotel perfectly blends luxury with a sleek, minimalist design. With 115 rooms and s

Why You’ll Love It

The Ritz-Carlton, Chicago, presents an iconic location that harmoniously blends the city, the lake, and the sky within a vibrant and opulent environment. Nestled in the heart of Chicago's Gold Coast, this hotel carries a legacy that has been treasure

Why You’ll Love It

Situated in the historic 1929 Art Deco Carbide & Carbon Building, Pendry Chicago seamlessly blends the charm of the past with modern sophistication in the heart of the vibrant Loop neighborhood. With sleek contemporary interiors, distinctive culi

Why You’ll Love It

The Emily Hotel in the Fulton Market of Chicago offers guests a boutique hotel experience that is as trendy as it is comfortable. Their modern, minimalist rooms offer a cozy escape from the bustling city streets with amenities like Malin + Goetz prod

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The Hoxton, Chicago, is the kind of place that makes you feel right at home—if your home has chic vibes, art-covered walls, and a rooftop perfect for soaking up the sunshine. Tucked away in the Fulton Market District, this cozy retreat blends comfort

Why You’ll Love It

The Langham, Chicago, is a distinguished hotel in downtown's River North neighborhood, housed in the iconic IBM Building. Since its opening in 2013, it has become known for its elegant accommodations, thoughtful dining experiences, and exceptional am

Why You’ll Love It

Opened in 2009 in Chicago’s prestigious Gold Coast neighborhood, this hotel combines charming chateau-style architecture with an unbeatable location, just steps from vibrant Rush Street and a block from the world-famous Magnificent Mile. Choose from

Why You’ll Love It

Arlo Chicago, which opened in 2023, is the newest kid on the block, but with some serious history under its belt. Once known as Hotel Julian, this fresh take on a Chicago stay is set in the beautifully reimagined 1916 Atlantic Bank building, blending