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Chicago has always been considered one of America’s greatest food cities—one where fully loaded hot dogs, deep-dish pizza, and ultra-luxe 18-course tasting menus are revered in the same dining scene. You could practically fill a travel itinerary with places to get Italian beef sandwiches (à la The Bear) alone. The city's restaurants, cafés, and bars reflect the diversity of Chicago's neighborhoods, and knowing where to stay is the key to having convenient access to the best spots.
Here we break down some of the most commonly trafficked neighborhoods in the Windy City and highlight where to stay so you can hit the must-visit eateries on your list.
The West Loop up through West Town
The West Loop was once an industrial zone and meatpacking district but has transformed into a lively dining and nightlife hub. Restaurant Row on the main stretch of Randolph Street is filled with restaurants and bars that have taken over old warehouse spaces. The neighborhood's also conveniently located near Chicago’s west side via the CTA Blue Line (or a quick car ride), which is home to many of the neighborhoods like Logan Square and Wicker Park with the city’s greatest places to eat.
Selecting the West Loop as your home base means you can grab chai and chili cheese toasties at Swadesi for brunch, indulge in chili-crisp-laden claypot rice with pork belly at Maxwells Trading for dinner, and end the night with a whiskey highball at Japanese bar Kumiko. If you venture northwards, there’s the cult-followed Kasama for Filipino pastries and longanisa sausage breakfast sandwiches, Lula Café for James Beard Award-winning brunch with impeccable hospitality, Akahoshi Ramen (a Best New Restaurant of 2024) for transcendent ramen, and Feld for the freshest seasonal tasting menu in town.
The first thing you’ll notice upon entering the Chicago Hoxton, which is just a stone's throw away from restaurants on Randolph Street and the Fulton Market District, is its stylish clientele. The hotel's vibrant energy draws a mix of locals and travelers, who meet up with friends or work remotely at the artfully-designed lobby's communal tables or coffee bar.
The socializing flows into the dining spaces scattered throughout the building: Cabra, chef Stephanie Izard’s Peruvian rooftop spot, has bright ceviches and savory goat empanadas; Cira is a Mediterranean crowd-pleaser in the lobby; and Lazy Bird's basement lounge offers live music and cocktails. Plus, there’s a rooftop pool, a rarity in the neighborhood.
The Hoxton has four options for rooms (Snug, Cosy, Cosy Up, and Roomy). None are palatial in size (the largest rooms are 300 square feet), but all are modern and stylish, with leather headboards, brass lighting, and retro-styled speakers.
Visited by Joseph Hernandez
This 11-room, three-story property located in the former Historic Free Methodist Publishing House is private and low-key while still being in the center of it all in the West Loop. While the space is now a bed and breakfast, it has lived many lives—as the Walter Rudolph Casket Factory in the 1930s through 1950s and the Museum of Holography from 1976 to 2009. You can feel that historic charm in its current iteration, even after the hotel’s renovation in 2016. There’s original wood paneling and maple flooring, but the property now feels updated to suit a modern day traveler.
Design varies with each room, which are named after Chicago literary figures, and the communal third-floor living room, meant for lingering, has a grand piano and double-sided fireplace. There’s also a wine bar, the Press Room, in the basement. Because of the property’s intimate size, it’s a great option for a buyout so a big group or wedding party can all stay together.
Visited by Joseph Hernandez
Down by the River
The Loop and River North are bustling business and tourist areas. You can access most CTA rail lines (including the Blue Line, which runs to the airport) and walk to iconic landmarks like Millennium Park and the “Bean,” the Art Institute of Chicago, and the Riverwalk. Of course, you'll need to eat when you’re checking landmarks off your to-see list.
Walk in at Gus’ Sip & Dip (a BA Best New Bar of 2025) for no-fuss classic cocktails and a Wagyu beef dip in a tavern setting, or delight in Indian fine dining at Indienne (a Best New Restaurant of 2023). You can’t miss a daytime stop at Doma, a Croatian café with a dynamite breakfast sandwich and destination-worthy hashbrowns. Plus, River North is home to many Chicago classics like Rick Bayless’s Topolobampo and Shaw’s Crab House. We recommend a quick trip south to Chinatown for an MSG martini and neon-drenched vibes at Nine Bar.
The Chicago Athletic Association offers an elevated members club experience without the steely pretension. It’s also one of the most gorgeous properties in town. The common spaces in this Venetian Gothic building include a game room and a historic basketball court (a holdover from the property’s previous life as an actual athletic club). As for dining, Cindy’s Rooftop offers cocktails with unbeatable views of Millennium Park on a year-round terrace that's enclosed by a photo-worthy glass atrium, and the cozy Drawing Room in the 19th-century-inspired lobby has all-day fare in a space you wish were your living room. The hotel also just debuted Midosuji, an eight-seat omakase counter with two seatings a night.
The nods to history continue in the guestrooms, where vintage leather pommel horses serve as benches and wrought iron and rich wood accents evoke a fin-de-siècle opulence. The larger Holy Cow Suites, including a bi-level option complete with two bedrooms and a separate living area, are great for families, while solo travelers or couples can opt for single or double bed quarters. If there weren’t already enough reasons to stay here, the hotel couldn’t sit in a better location with access to the Art Institute, Lake Michigan, and a multitude of museums. It’s undoubtedly the city's best place for design and history lovers to stay.
Visited by Joseph Hernandez
The Pendry Chicago sits in the Loop’s Art Deco Carbide & Carbon building, a 1929 architectural icon with a dark stone façade and gold trim. The hotel got a luxe upgrade in 2021 and its service is inviting from the moment you step onto the curb, where your bags will be whisked away to your room and a welcome drink placed in your hand before you even reach the check-in desk. Plus, there’s a concierge text service for recommendations from the hotel even while you're exploring. The sizable rooms offer a restrained elegance, with white marble bathrooms, mid-century modern furniture, and black-and-white photos of striking architecture on the walls.
The property also offers three dining experiences (a bistro with a mean steak frites, a rooftop bar with expansive views, and a cozy living room-like lobby bar), and you shouldn't skip a stop at Château Carbide for a cocktail with live music.
Visited by Kate Kassin
Gold Coast and Upward
Lake Michigan's shoreline offers some of Chicago's best scenic strolling and people watching. The stretch between Lakeview and Lincoln Park to the north and Gold Coast in the south in particular is abundant with exquisite food and top-notch hotels. Start at the top in Lakeview with esquite biscuits and smoked vanilla bean lattes at Loba Pastry or shakshuka buns at Cafe Yaya, a new spot from the team behind Middle Eastern hit Galit. Lincoln Park is also home to many of the bucket-list tasting menu spots like Alinea. Most of the hotels that provide easy access these gems are located in Gold Coast and they’re some of the best in the city.
Even with new hotels cropping up in Chicago (seemingly by the day), the elegant Peninsula remains a fixture in the upper echelon of must-stay properties. The Peninsula sits right off the Magnificent Mile, the one-mile stretch with top shopping, dining, and accommodations on Michigan Avenue that's on every visitor's itinerary. The stately, residential-style rooms, with a couch and dining table even in the smallest, are at least double the size of others you'll find on this list, and many feature views of the Hancock building or Water Tower Place.
While there’s no shortage of dining options, our favorite is Z Bar for cocktails (like the gin-based signature drink the Z) in a picturesque setting perched right above the Magnificent Mile. And while the property's eateries, decor, and amenities are impeccable, it's the service that truly sets it apart and makes it worth the splurge. We're talking friendly and engaged staff, on-demand concierge recommendations through the hotel's text service, and flexible check-in and check-out times (as early as 6:00 a.m. and as late as 10:00 p.m.—unheard of these days!).
Visited by Joseph Hernandez
If you’re hoping to explore Chicago by foot, the Thompson makes an excellent home base. Situated on a side street off the busy Magnificent Mile, the hotel feels protected from frenetic shoppers and commuters but is still just one block from Oak Street shopping.
The vibe here is sleek and contemporary with no frills, making it a perfect option for both business and leisure travelers. There are plenty of accommodation options, from multiroom suites to generously sized one-king or two-double-bed rooms. All are spacious and sophisticated, with velvet seating and leather headboards and bathrooms stocked with D.S. & Durga products and plush robes. If you’re in a room on a higher floor, you might just luck out with a view of Lake Michigan.
Visited by Kate Kassin
Additional reporting from Joseph Hernandez