It’s no secret Chicago’s a palate-pleasing destination for food, balancing the old cuisine with the new, and bridging fine dining with casual eats.
The city’s many vibrant, ethnic neighborhoods host everything from schnitzel at The Berghoff’s longtime downtown location to dim sum in Chinatown. There’s tacos in Pilsen, deep-dish pizza in River North, and Chicago-style hot dogs at North Side and South Side institutions alike. The hit Hulu show “The Bear” also catapulted what Chicagoans have known for years, and the city’s Italian beef sandwiches, thin, slow-cooked beef with gravy on top of French bread, are legendary.
Another layer to Chicago is its rich architectural history. This includes skyscrapers and Art Deco marvels in the Loop dating back to the late 1800s, and the world’s tallest structure designed by a female architect, unveiled in 2023. Many of Chicago’s best restaurants are tucked into these amazing structures. That means in one swoop visitors can enjoy an artfully plated meal and an immersive peek into world-class architecture.
For a deep dive into Chicago’s culinary scene and its architectural marvels, here’s where to book a table. Not only for a unique look at famous spots, but an equally famous eatery too.
Travelle in Ludwig Mies van der Rohe’s Building at 330 N. Wabash
The Building
Perched above the Chicago River in River North, the 52-story skyscraper at 330 N. Wabash Ave. remains the late German-American architect Ludwig Mies van der Rohe’s final design, though it wasn’t completed until three years after his death in 1972. With a black exterior, the edifice may seem familiar due to cameos in Ozark’s first episode and in the 2008 Batman film The Dark Night. Because of the iconic facade, the building is easy to find.
Inside the lobby a miniature bust of van der Rohe’s likeness resides, designed by Italian sculptor Marino Marini. It’s a pleasing nod to this godfather of Modern architecture, who also once held the title of head of Illinois Institute of Technology’s architecture department, where many of his designed buildings remain.
The Restaurant
The Langham, Chicago, from the Hong Kong-based luxury hotel company, fills the 2nd through 13th floors. It’s here you’ll find Travelle, the hotel’s fine-dining restaurant. The dimly lit, elegant lounge is a popular spot for after-work social events and date nights, as well as for hotel guests to unwind. Relaxation aside, with the high price points it’s far from a rowdy happy-hour venue.
The same goes for the dining room, marked by a stand-alone, glass-walled wine cellar. Order everything from Korean-style 24-hour beef to herb-crusted Colorado lamb to tuna poke lettuce cups. Most diners, however, come here for the view, and an eclectic cocktail served in the adjacent Travelle Lounge. Short on time? Enjoy the new Luxury Line Cocktails, an experiential pairing of inventive cocktails with food such as oysters or wagyu beef tartare.
Cindy’s Rooftop in Chicago Athletic Association
The Building
The architect Henry Ives Cobb was a founding member of Chicago Athletic Association, which started out as a men’s club in 1890, and later included a football team of the same name in 1892. Cobb himself, through his architecture firm Cobb and Frost, left an imprint on Chicago not only with this beautiful Victorian Gothic building, but through his other projects as well.
In 2015 the building welcomed a 240-room hotel that’s part of Hyatt’s Unbound Collection, located at 12 S. Michigan Ave. Today it not only showcases the history of the fantastic edifice, but is home to a trendy glass-enclosed eatery as well.
The Restaurant
Make a trip to the buzzy Cindy’s Rooftop, which resides on the 13th floor and overlooks Millennium Park and Lake Michigan. The terrace remains open year-round, with crackling fire pits during the winter months.
The menu leans toward new American, with fried chicken sliders playing truffled deviled eggs and seasonal homemade ice cream. Lunch and dinner are served daily, along with weekend brunch, late-night snacks, and a mid-day menu, ensuring there’s never a break in service.
From oysters on the half-shell to a half-roasted chicken to a whole fried branzino, many dishes are designed for sharing. Cocktails bear sassy names and demonstrate the bar staff’s creativity, such as Helicopter Parenting and No Soup For You. Also check out the wide variety of zero-proof mocktails.
Skydeck Chicago in Willis Tower
The Building
The former Sears Tower, which debuted in 1973 as the catalogue retailer’s headquarters, is now known as the Willis Tower. Located in Chicago’s Loop at 233 S. Wacker Dr., the 110-story building was designed by architect Bruce Graham and engineer Fazlur Rahman Khan and at the time held the title of the world’s tallest building.
That honor held for over two decades, and though it’s now marked at the 23 tallest, the edifice remains just as impressive. However, the building also includes Skydeck, the highest observation deck in the United States. It provides sweeping views of the city, and on clear days 50 miles of land is visible. Step out on The Ledge, one of the five glass floor balconies on floor 103, which extend 4.3 feet from Willis Tower. Each comprises three layers of half-inch thick glass laminated into one seamless unit.
The Restaurant
Celebrate Chicago’s rich culinary history with an iconic deep-dish pie from Giordano’s Pizza. Chicago-style pizza showcases a thick, buttery crust and rich layers of cheese, and this may be the highest location visitors can enjoy it. The pizza is part of Skydeck Chicago’s three-course dinner service, which also includes a salad, soft drink, and dessert.
Book a spot on Thursday or Friday at 9:30 p.m. and enjoy the meal on the 103rd floor. It’s served after hours so guests get to experience the space and view without a crowd. Don’t worry if that’s too late, there’s also a 6 p.m. seating on the 99th floor. Just make sure to reserve in advance, space is limited and a hot ticket item.
Marshall’s Landing in The Merchandise Mart
The Building
During the Art Deco era Chicago experienced a major growth spurt, especially in the architecture world. In 1930, The Merchandise Mart (222 W. Merchandise Mart Plaza) debuted in the Loop, based on a design by Alfred P. Shaw while he was an employee of the architecture firm Graham, Anderson, Probst & White. At the time it was clocked as the world’s largest building, boasting 4.2 million square feet. Inside contained a wholesale space for the department store, Marshall Field’s.
Shaw employed limestone, terra cotta, and bronze, each folded in rows of decorative zig-zags as well as octagonal towers for glam effects. While many of the showrooms are only available to wholesale trade, two floors are open to the public, including a weekday restaurant.
The Restaurant
The 12,000-square-foot Marshall’s Landing embodies the power-lunch concept with velvet booths and greenery suspended from high ceilings surrounded in natural light. Weekdays, between 8 a.m. and 7 p.m., the menu spans lattes and pastries to kick start the day, and winds down with cocktails and shareable plates at night. In between you’ll find a hearty lunch menu featuring comfort foods such as a turkey club sandwich, poke bowl, market omelet, and chicken fries, which are just chicken strips tossed in sriracha aioli and ranch.
Miru and Tre Dita in The St. Regis Chicago
The Building
Jeanne Gang, of Studio Gang Architects, made history with The St. Regis Chicago (401 E. Wacker Dr.), the world’s tallest structure designed by a female architect. Located in Chicago’s Lake Shore East area near downtown, the hotel towers 101 stories up, making it the third-tallest in Chicago.
Gang completed the building in 2020, giving the edifice a teal-ish color thanks to gorgeous glass panels in different hues. It also features three interconnected towers of varied heights that blend seamlessly to one another.
The Restaurant
Within the 191-room hotel, which first welcomed guests in 2023 and occupies the first 10 floors (with residences above), are two fine-dining restaurants. First we tap into the Japanese spot Miru, an all-day concept with some of the best sushi around. Look for dishes including A5 wagyu tartare on milk bread toast, smoked pork belly skewers, duck yakisoba, breakfast bao, and Hokkaido sea urchin.
On the Italian side, Tre Dita opens for dinner only, and is run by executive chef Evan Funke, a two-times James Beard nominated chef. Funke previously worked at Mother Wolf in Hollywood, Calif., cooks for Vanity Fair’s annual Oscar Party, and also has a documentary about him titled, Funke.
Here diners can enjoy house-baked focaccia and seasonal, handmade Tuscan-style pastas. For a more casual meal, next door you’ll find the intimate Bar Tre Dita. Dip in here for drinks and small plates, either a precursor to your evening or a delicious after thought.
FireLake Chicago in Aqua Tower
The Building
Located in Lake Shore East, the 82-story Aqua Tower (225 N. Columbus Dr,) features an open-air, green-roof terrace with a fire pit and gardens. Created by Studio Gang Architects, irregularly shaped concrete pieces on the building’s exterior emulate a work of sculpture, and the limestone outcroppings mirror Lake Michigan’s shoreline nearby. Another unique design feature are the asymmetrical balconies decorating the facade. When unveiled in 2009, the Aqua Tower nabbed a lot of attention for its edgy design.
The Restaurant
Since 2020 FireLake Chicago has been the restaurant inside Aqua Tower, and serves wood-fired Midwestern fare for breakfast, lunch, and dinner. The eatery also does weekend brunch and offers an express lunch menu. Make sure to get the two-pound pretzel, an Instagram-worthy dish to say the least. Other hot menu items include the smoked pork ribs, cheese curds with spicy ranch, branzino, and rotisserie chicken flat bread. The restaurant also serves afternoon tea, a rarity in Chicago, and the tiny sandwiches and cakes on tiered platters are as design-centric as the building.
