The Windy City is a magnet for culture seekers, home to some of the country’s most captivating museums, parks, and art galleries. It’s also full of top hotels, many set near the Magnificent Mile in soaring skyscrapers or historic buildings that date back to the 1920s. Here are the best places to stay in Chicago, bookable with Culture Trip.
This hipster hotel lies in the trendy Wicker Park neighborhood, in a former 1900s warehouse and tower. Choose from annex lofts or tower rooms, with various mid-century furniture, vintage phones, art-deco bronze lifts, and lofty ceilings. Highlights include the rooftop bar and pool with views of the Chicago skyline, free guest bikes, and a fashionable lobby with huge windows. Don’t miss the ground-floor Cafe Robey, which serves American hot dogs.
Set in the heart of the lively Fulton Market district, The Hoxton has 182 mid-century-style rooms with floor-to-ceiling windows that showcase skyline views. Expect a warehouse feel, with concrete ceilings and paneled leather headboards, as well as bedding from Chicago local Cody Hudson. “The Working From” co-working space buzzes with activity, as does the Peruvian rooftop restaurant Cabra Cevicheria and Lazy Bird Cocktail Bar, which has live music on the weekends.
Come to Conrad Chicago for a glamorous stay on a peaceful street just off Michigan Avenue. Previously an office, the 20-story building retains its glassy exterior but has been redesigned by French firm Pierre-Yves Rochon with a statement staircase, lobby with bone China sculpture, and elegant furnishings. Rooms and suites come in earthy tones with awe-inspiring city views and black granite bathrooms. Head to Baptiste & Bottle for a bourbon tasting session.
The four-star Eaglewood Resort and Spa lies in Itasca, just north of Chicago’s central hub. Golf fans come to try out the 18-hole championship, par 72 course, set among lakes and trees. Treat yourself to a pamper session at the spa with a sauna and outdoor pool deck. There’s also a bowling alley and restaurant. Rooms and suites are decked out in cherry and mahogany wood with balconies and patios to show off golf course views.
Calling all fitness fanatics: the Hotel at Midtown is a world-leading health resort with facilities spread over three levels. Check out the multiple pools, boxing ring, fitness studios, and gyms, as well as 16 tennis courts. Originally built as the world’s largest tennis club, there’s even a suite created by Venus Williams’ design firm. Rooms have a clean, minimalist design with graffiti art and skyscraper views. Guests can dine at the healthy Chromium farm-to-table restaurant.
Hotel Zachary is the place to stay if you’ve come to watch the Chicago Cubs play baseball. The boutique hotel is just steps from Wrigley Field and its premium rooms even offer tantalizing glimpses of the action. On game days, the hotel’s bars and restaurants are filled with excitable fans. Hotel Zachary is named for the Chicago architect who designed Wrigley Field, Zachary Taylor Davis and is filled with baseball memorabilia, exposed pipes, and brick walls.
Just north of Chicago’s center, the Lincolnshire is a fancy golf and spa resort brought to you by the Marriott. Following a $28m renovation, the 175-acre (70ha) resort is modern and sleek, with a spa, five restaurants, and three outdoor pavilions. The main draw is the 18-hole PGA Championship golf course but there’s also a pool, tennis courts, and award-winning live musical theatre at the in-house Marriott Theatre.
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It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.
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Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.
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Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.
Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.