Architecture, Steakhouses, and Cocktail
Curated Lists Editorial Overview
Chicago's world-famous skyline by foot, its legendary steakhouses, and a cocktail bar scene that invented the mixology renaissance
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16 pinned placesFeatured Places
Discover the best spots in this carefully curated guide. Each location has been personally visited and vetted to ensure an authentic and memorable experience.
Chicago Athletic Association - The Unbound Collection by Hyatt
Housed in a stunning Venetian Gothic skyscraper, the Chicago Athletic Association Hotel is a captivating blend of history and modern luxury. Its grand ballrooms and iconic rooftop bar offer breathtaking views of Millennium Park, making it a perfect spot for a cocktail after a day of architectural exploration.
Smith & Wollensky - Chicago
This classic steakhouse nestled along the Chicago River boasts a sleek, polished interior and a welcoming, clubby ambiance. Known for its dry-aged steaks and extensive wine list, it's a quintessential destination for steak lovers looking to indulge in a slice of Chicago's culinary history.
The Art Institute of Chicago
Not only is this museum home to an impressive collection of architectural drawings and designs, but its stunning Beaux-Arts structure is a masterpiece in itself. After wandering through its vast galleries, visitors can enjoy a cocktail at the museum's café, where art and mixology meet.
The Signature Room at the 95th®
Perched high above the city in the John Hancock Center, The Signature Room offers diners an unparalleled view of Chicago's skyline while enjoying an exquisite meal. The atmosphere is upscale and refined, making it an ideal spot to sip on a cocktail while marveling at the architectural wonder below.
Gene & Georgetti
As one of Chicago's oldest steakhouses, Gene & Georgetti embodies the spirit of the city's culinary heritage. With its vintage decor and a menu that highlights perfectly cooked steaks, this establishment has been a favorite of locals and celebrities alike since 1941, offering a nostalgic journey through the city's dining history.
The Green Mill
A historic jazz club that dates back to the Prohibition era, The Green Mill retains its original charm with plush seating and a timeless bar. Known for its expertly crafted cocktails and live music, it's a place where the spirit of Chicago's past mingles with its vibrant nightlife.
Cindy's Rooftop
Located atop the Chicago Athletic Association Hotel, Cindy's Rooftop is a stylish sanctuary that offers sweeping views of Lake Michigan and Millennium Park. With a focus on seasonal ingredients, cocktails here are as refreshing as the view, making it a perfect spot for a sunset drink amidst the city's architectural splendor.
Ruth's Chris Steak House
Situated in a sleek, modern building, Ruth's Chris combines a contemporary vibe with classic steakhouse flair. Known for its signature sizzling steaks served on 500-degree plates, it offers an upscale dining experience complemented by an impressive selection of wines and cocktails.
The Whale
A lively cocktail bar with an emphasis on craft drinks, The Whale Chicago is set in a beautifully restored building that features exposed brick and industrial design. Its inventive cocktails and warm atmosphere create a perfect retreat after exploring the architectural gems nearby.
Chicago Union Station
An architectural marvel, Chicago Union Station is a grand transportation hub that showcases stunning Beaux-Arts design. Visitors can admire its iconic Great Hall, a perfect backdrop to enjoy a quick cocktail at one of the nearby bars before embarking on their architectural walking tour.
Tavern On Rush
This upscale steakhouse located in the Gold Coast is known for its lively atmosphere and classic American fare. With its inviting patio and expansive bar, it’s a great spot to enjoy a well-crafted cocktail while soaking in the vibrant energy of the surrounding architecture.
Chicago History Museum
This museum provides a window into the architectural evolution of Chicago, featuring exhibits that highlight the city’s rich history. After exploring its captivating displays, visitors can enjoy cocktails at its café, where the past meets the present in a stylish setting.
The Aviary
A culinary cocktail experience, The Aviary offers an innovative approach to mixology in a stunning setting. With high ceilings and modern decor, guests are treated to theatrical presentations of drinks that are as much art as they are refreshment, making it a must-visit for cocktail enthusiasts.
Chicago Riverwalk
The Chicago Riverwalk is a vibrant promenade that showcases the city’s architectural beauty from a unique perspective. Lined with restaurants and bars, it’s an ideal place to stroll and enjoy a cocktail while soaking in views of the stunning high-rises that define Chicago's skyline.
Benny's Chop House
An upscale steakhouse that exudes elegance, Benny's Chop House is known for its impeccable service and perfectly cooked steaks. The sophisticated atmosphere is complemented by a well-curated cocktail menu, making it a favorite among those seeking a refined dining experience in the heart of Chicago.
Field Museum
Beyond its impressive exhibits, The Field Museum is an architectural masterpiece featuring a grand hall that captivates visitors. After exploring the wonders of natural history, guests can unwind at the museum’s café, where cocktails are served with a side of inspiration drawn from the building's grandeur.
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How often is this guide updated? ▾
This guide was last updated on April 11, 2026. We regularly review and refresh our guides to ensure all places are still open and worth visiting.
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