Featured image: Samantha Labrecque Semle
Chicago is Midwestern-charm-meets-big-city, and is located on the shores of Lake Michigan. Well-known and loved for its vibrant culture, deep-dish pizza, and bold architecture, we’re sharing the best places to eat, where to stay, and things to do while in the Windy City.
Where to Stay
Chicago Athletic Association
If you want to be in the heart of the city—also known as The Loop—but still enjoy a relaxing and welcoming stay, Chicago Athletic Association is a sure bet. Located directly across from Millennium Park and The Bean, Chicago Athletic Association is a historic landmark turned luxury hotel. Originally established in 1893 as an exclusive men’s sports club, the building features dark wooden elements in a Venetian Gothic style.
The guest rooms and suites are moody, yet cozy, complemented with more dark wood molding, vintage-inspired furnishings, leather chairs, and Carrara marble in the bathroom. As a nod to the men’s sports club, boxing-style robes are available to guests for lounging. The hotel’s on-site dining options are plenty, with Cindy’s rooftop restaurant, the Game Room bar, and Shake Shack on the ground level, too.
Where to Eat
Ciccio Mio
Ciccio Mio is a cozy and intimate Italian-American restaurant in Chicago’s River North neighborhood. This Hogsalt restaurant group spot is known for its cozy, supper club-style ambiance and hearty dishes like the lasagna and spicy vodka rigatoni, plus their fior di latte gelato for dessert. The restaurant is on the smaller size and has been recognized with a Michelin Bib Gourmand, so reservations are the way to go and can be made twenty-one days in advance.
Coda di Volpe
Coda di Volpe, meaning “tail of the fox,” is a Southern Italian restaurant located in the Lakeview neighborhood. The restaurant’s name is inspired by a white grape variety native to Italy’s Campania region. A familiar corner spot, Coda di Volpe serves a menu of delicious Neapolitan-style pizzas, handmade pastas, and house-cured meats. The restaurant also features an extensive wine list and cocktails, which can be perfectly paired with a pie or some pasta.
Armitage Alehouse
Far and away our favorite restaurant in Chicago, is Armitage Alehouse. Outside, it’s Lincoln Park, but inside the doors of the restaurant, it’s London circa 1926. Another Hogsalt-owned restaurant, the interior is dark and moody, with a large fireplace, dim lighting, and cozy seating. The menu features a unique fusion of British and Indian cuisines, with menu standouts including a variety of pot pies with a bone marrow center, tikki masala, and a double cut pork chop. There’s wine, some British-style draughts, and cocktails, but whatever you do, don’t skip the sticky date cake for dessert. Reservations are highly recommended and the restaurant is often fully booked.
Kasama
Kasama is a Michelin-starred Filipino restaurant known for its thirteen-course tasting menu. By day, however, it operates as a bakery and café offering Filipino pastries. Our menu favorites include the longanisa, egg, and cheese breakfast sandwich, apple hand pie, ham and cheese Danish, and really, any pastry you can get your hands on. (They are also known for their black truffle croissant!). The restaurant opens at 9 a.m. for counter service, but we recommend arriving around 7:45 a.m. if you’re visiting on a week day, because the line to enter gets long… and for good reason!
The Purple Pig
This centrally-located, Mediterranean-inspired restaurant is a great place to stop in for some shareable plates and a glass of vino. Think: cheese, swine, and wine. Order a cured meats and cheese board for the table, then choose-your-own adventure with a meat-focused main dish. If you only order one thing on the menu, let it be the ravioli. It’s a pillowy pasta pocket stuffed with beef short rib, bone marrow, brown butter, and red wine jus.
Bavette’s Bar & Boeuf
Bavette’s Bar & Boeuf is widely considered one of Chicago’s best restaurants and is a sought-after Windy City steakhouse. While the restaurant is larger than it’s other Hogsalt-owned counterparts, Bavette’s is a dimly lit space featuring dark woods and leather seating. The perfect place for a celebration or just a dinner on the town, you can’t go wrong with any of their cuts. The double wagyu cheeseburger is a must-order (a farm fresh egg and thick cut bacon accompaniments, too!), which is said to be very similar to their famous sister restaurant’s, 4 Charles Prime Rib, in New York City.
Meadowlark
Meadowlark is a dimly-lit cocktail haven exuding vintage charm. An intimate cocktail bar located in the Logan Square neighborhood, Meadowlark is nestled behind an unmarked door with speakeasy vibes. The cocktail menu is as unique as it is creative. Think: the pizza party, a savory yet funky and bubbly concoction.
Bar Tre Dita
Luxe and sophisticated, this stylish and upscale bar located in The St. Regis Chicago is adjacent to its’ primary Tuscan restaurant, Tre Dita. The cocktail bar offers Italian-inspired drinks, an expansive whiskey list, and modern elegance for a night out on the town. The seating is plush and the drinks are delightful, but the traditional Tuscan handmade pasta is the star of the show.
Small Cheval
A spinoff to Au Cheval, Small Cheval is the acclaimed restaurant’s younger sibling. The fast-casual burger joint has multiple locations, but you can find the same thing at each one: juicy burgers, crispy fries, and casual vibes.
Cindy’s Rooftop
Cindy’s Rooftop is located atop the Chicago Athletic Association Hotel, offering panoramic views of Millennium Park and The Bean. The chic rooftop restaurant and bar has a glass atrium and large terrace, making it the perfect place to kickback with a pre-dinner drink or trendy date night spot.
Pequod’s Pizza
Chicago is known for deep dish pizza and that’s a fact. Pequod’s Pizza has a slice in that! Their pan-style, deep-dish pizza comes in several sizes (to share or not, we aren’t judging!), each with a caramelized cheesey crust. Toppings can be added and the pizzas can be ordered for dine-in or carry-out. Founded in 1970 in Morton Grove, the Chicago location opened in 1992 and has become a local favorite ever since.
Bar Mar
Part of chef José Andrés’ culinary empire, Bar Mar is a sleek seafood-focused restaurant and bar. The nautical-inspired décor and octopus sculpture hanging above the bar lend to a contemporary yet stylish theme, while the menu features seafood fare with Spanish and Latin American influence. Try some selections from the raw bar or opt for elevated versions of the classics like a lobster roll or sea scallops.
DeNucci’s
This neighborhood restaurant is approachable and warm, which is everything an Italian-American restaurant should be. A classic vibe with old-school flair, DeNucci’s serves up hearty dishes like lasagna bolognese, cacio e pepe, New York-style and Sicilian pizzas, and more. If the weather is nice, request a table on their outdoor patio for some great people watching and limoncello spritz sipping.
Aleez Café
Allez Café is a cozy coffee shop known for its standout breakfast sandwich, which is made with a soft potato roll filled with a silky egg patty, thick cut bacon, melted gouda cheese, a house-made hash brown, and onion aioli with a jalapeño jam. There’s plenty of caffeinated beverages, but if you’re looking for a bite on the lighter side, try one of their pastries.
Tzuco
Upscale meets approachable at this Mexican restaurant. Led by chef Carlos Gaytán—the first Mexican chef to earn a Michelin star—Tzuco’s menu showcases dishes of Gaytán’s heritage from Huitzuco, Guerrero. If you’re going for brunch, we suggest ordering the avocado flatbread, the chilaquiles, and the duck waffle to start your day off strong.
Trivoli Tavern
Tucked in a back courtyard in the popular West Loop neighborhood, Trivoli Tavern is a cozy Hogsalt-owned restaurant with a timeless atmosphere. It’s moody with dark wood, a candlelit ambiance, and plush seating, creating an intimate setting reminiscent of classic supper clubs. The menu follows suit, with dishes like prime rib, steaks and chops, sushi, and more. In the front of the restaurant, there’s a casual lobster bar slinging out shellfish and seafood forward snacks, too.
Three Dots and a Dash
This hidden tiki bar is a popular spot known for its rum-forward cocktails and tropical vibes. Drinks are garnished in fun vessels and mugs, with large format options available for groups. The bar’s name is a nod to Morse code for the letter “V” for victory.
Things to Do
Architectural Boat Tour
A must-do while in Chicago, an architectural boat tour is the best way explore the city’s skyline via the Chicago River. Hop aboard one of Wendella’s ships and learn about the city’s architectural heritage, iconic landmarks, and more from a knowledgable guide. Founded in 1935, Wendella is one of the city’s oldest family-owned tour boat operators.
Lincoln Park Zoo
Not just for littles, Lincoln Park Zoo is a wildlife escape in an urban setting for both the kiddos and kids at heart. Nestled in Lincoln Park, the zoo is free to enter and is home to hundreds of species, including lions, gorillas, polar bears, giraffes, and more. The family-friendly spot also features immersive habitats, a nature boardwalk, café, and more.
The Art Institute of Chicago
Prepare to spend all day in the Art Institute, because this museum houses a large and diverse collection. If you’re short on time, however, it’s still worth the visit: here you will find masterpieces by Monet, Picasso, and Van Gogh, plus the iconic American Gothic by Grant Wood and A Sunday on La Grande Jatte by Georges Seurat.There’s also the Arts of Ancient Egypt, Arts of the Americas, and more collections to explore, plus a modern wing. The museum offers a great one-hour guide to maximize your time.
A Game at Wrigley Field
Take us out to the ball game! One of the most iconic and historic ballparks in Major League Baseball, Wrigley Field is home to the Chicago Cubs. A perfect way to spend an afternoon, take in the sights and sounds of America’s favorite past time with a Chicago-style hot dog and Cracker Jacks while watching nine innings of ball. Known for its ivy-covered outfield walls, manually operated scoreboard, and seventh-inning stretch rendition of “Take Me Out to the Ball Game,” (often led by a special guest or the team’s organist), watching a game at Wrigley evokes the nostalgia of summer’s past.
Stroll the Riverwalk
Running along the Chicago River through the heart of the city, the Riverwalk is a 1.25-mile pedestrian promenade that spans from Lake Street to Lake Michigan. The bustling and vibrant walking path provides stunning views of the city’s skyline, and is dotted with restaurants and bars like Tiny Tapp, Pizzeria Portofino, City Winery, and more.
Explore the City
The best way to navigate a new place is to get lost exploring! Chicago has plenty of neighborhoods, restaurants, and activities to discover, so stroll around the city to find your favorite spots. Check out The Magnificent Mile, a busy and premier stretch of Michigan Avenue known for its luxury shops. Or, opt for the more quiet and scenic neighborhood of Lincoln Park. There’s also the Lakefront Trail which is a popular walking/biking/running path along Lake Michigan and of course, Millennium Park, an urban green space housing the famous Cloud Gate sculpture, aka The Bean!
