Make the most of life in the Loop and soak up some of Chicago’s finest attractions with our guide to the best hotels for sightseeing, business and everything in between.
The bustling chunk of downtown Chicago – just east of the city’s wonderfully grand Union Station – is known as the Loop. It operates as the city’s central business district but is also packed with heavyweight Chicago sights, such as the Adler Planetarium, Art Institute of Chicago and Chicago Cultural Center. Hotels in the Loop reflect these two sides and are built to help guests get things done – whether that’s work, play or a bit of both – all bookable on Culture Trip.
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Looking for an expert's perspective?Uncover my top 3 recommended places from each continent on the map.
1. GuatemalaAn express adventure for those with limited time off. Prepare yourself incredible experiences. You will hike a volcano, visit mayan temples and witness a ceremony and take in beautiful colonial Antigua.
2. BelizeA quick trip not too far away for those seeking a relaxing mini break. You will have plenty of free time to relax but also some awesome activities to experience the rainforest and the caribbean sea.
3. MexicoAn exciting mini trip exploring the lesser known colonial towns of central Mexico. This is hte perfect trip for someone with limited time off and still wants to turn on explorer mode and do something different.
1. EcuadorA remarkable 8 days adventure through the Andes and the Amazon rainforest. The best choice for adventure seekers wishing to visit the 2 most iconic areas of South America, in only 1 week and no flights.
2. PeruAn alternative itinerary to classic Peru, from Cusco to Arequipa. This itinerary is great combination of highlights Cusco and Machu Picchu with the lesser known Arequipa and Colca Canyon.
1. ItalyThe ultimate Italian experience from the vibrant streets of Naples to the breathtaking sceneries of the Amalfi Coast followed by Matera and down to Puglia with its golden beaches, intense flavours and fascinating destinations.
2. ScotlandEmbark on this great adventure starting from London all the way to Scotland with a true Scottish experience made of breathtaking sceneries, whisky tasting and ..lots of fun! Ideal for train lovers and explorers.
3. PortugalA wonderful train journey around Portugal, from the romantic city of Porto to the Douro Valley, to the beautiful Aveiro all the way to Lisbon and Sintra. The perfect trip to train, culinary and culture lovers.
1. South KoreaDiscover incredible temples, mountains and modern cities on this 10 day adventure. This trip is perfect for those seeking immersion in the cuisine, culture and natural wonders of South Korea.
2. ThailandFrom Bankgok to Angkor Wat to Ho Chi Minh City and everything in between - adventure through the heart of South-East Asia. Taste the delights, see history brought to life and unwind on a Mekong River cruise.
3. Sri LankaA fantastic adventure that showcases Sri Lanka's fantastic landscapes, wildlife and flavours. With 3 epic rail journeys, 3 UNESCO heritage sites and time to relax, this trip has loads to offer at a great price
1. MoroccoAn epic journey across Morocco: from Casablanca to Marrakech, through the blue city of Chefchaouen to the wonders of the desert and deep to the High Atlas Mountains - this trip has it all! Ideal for true explorers!
2. EgyptFrom Cairo to Aswan, this trip brings the land of the pharaohs to life. You'll visit the Pyramids, Valley of the Kings and Luxor Temple and cruise down the Nile in style. This is the perfect way to explore Egypt.
This business-focused hotel is in the very heart of the Loop and the city’s business district. But it’s not just the location that makes it a no-brainer for business travelers, as the hotel goes the extra mile with its many work-focused amenities.
The highlight is the Club Living Room – a private lounge with collaborative workspaces, super-fast free wi-fi, individual workstations and free coffee and tea. Dog-owners can bring two canine buddies at no extra charge and when business hours are over, you’re minutes away from the Art Institute of Chicago and the Chicago Symphony Orchestra’s HQ.
It’s all about the location at this quietly cool venue, which is ideal for exploring downtown Chicago at its most lively. Headline attractions like Willis Tower and Cadillac Palace Theatre are a few minutes away on foot – and Grant Park and the Museum of Contemporary Art Chicago are also within easy reach.
Stay hydrated on your excursions with free purified water on every floor of the hotel – just one of the many inviting features to make your life easier. Other great extras include gym and yoga equipment delivered to your room along with an eye mask, earplugs and an in-room ambient sound system to help you drift off after a busy day.
There’s definitely a touch of the Mad Men aesthetic to this elegant number, whose stylish retro glamour and art deco features pay homage to the hotel’s historic roots, dating back to 1894. Rooms are more modern, with subtle nods to vintage style.
When you manage to tear yourself away, take advantage of the free bike hire to explore the bustling downtown surroundings. Refuel at one of the many eateries on the heralded Restaurant Row – which is literally on your doorstep thanks to the Allegro’s location on Randolph Street.
Being listed on the National Historic Register is a boon for any hotel, but the 19th-century Hotel Blake doesn’t play on its historic status too much, instead opting for a classic feel in its neat and comfy rooms. The location on Printer’s Row is another big selling point, as you’ll be minutes – sometimes moments – away from some of Chicago’s best bits.
The Auditorium and Grant Park’s mighty Buckingham Fountain are nearby, surrounded by bus stops and stations on the city’s comprehensive L Train network – meaning that everything else is within easy reach.
All rooms are crisp, clean and stylish, offering welcome features like robes and ergonomic chairs, while higher-grade options boast whirlpool bathtubs and wine stations – a perfect combination if ever we heard of one.
Named after the distinctive grey Georgia Marble that helps give the hotel its class, the Kimpton Gray is a sleek operation in every sense. As well as looking the part with its opulent decor, the hotel has seriously on-point amenities: custom-designed bikes for adults and micro-scooters for kids, seasonal book recommendations delivered to your room, a fitness center with a Peloton and pop-up art installations – the list really is endless.
Don’t miss the gorgeous cocktail bar, Vol. 39, which nails mid-20th century grandeur and has become a destination spot in its own right. Try an old-fashioned or a negroni and you’ll understand why.
A bright, warming lobby makes Fairfield Inn an inviting place to step into and that atmosphere continues throughout the rest of the building. Rooms are cozy and modern and if you want extra space, a studio suite offers a separate living area to stretch out in.
A big bonus here is the daily free breakfast, meaning you can start the day hassle-free and save a few bucks in the process. For other meals, in-house restaurant Ēma serves up colorful Mediterranean mezze platters and Fairfield is surrounded by restaurants and bars offering a great range of global cuisines.
Aesthetically styled on Italian Renaissance architecture, this four-star boutique venue boasts an unashamedly grand and glorious air that also tips its top hat to the roaring 1920s – the decade in which the hotel was built.
Set directly on Chicago’s lively Magnificent Mile, crammed with upmarket stores and restaurants, gives the hotel a further buzz. But you’ll be forgiven for staying in and visiting the M Avenue Lounge – an update of the hotel’s nightclub that once hosted the likes of Frank Sinatra, Bing Crosby and Lucille Ball.
Enjoy riverside life at this smart hotel, which is a great bet for business travelers and anyone looking to max out their Chicago sightseeing time. You’ll be steps away from the southern end of the Magnificent Mile if you want hustle, bustle and retail therapy and a few minutes in the other direction takes you to Grant Park and then Millennium Park, where you’ll find Anish Kapoor’s Cloud Gate sculpture.
Rooms are comfy and all feature smart TVs and unlimited free bottled water. Business travelers can power through the day in comfort at the Club Living Room, a private lounge built for efficient working – and efficient snacking thanks to fruit, granola bars and wasabi peas – before unwinding with Wine @ 5: a happy hour showcasing tipples from local wineries.
For more stays in Chicago, check out accommodation for the savvy traveler or indulge in one of the many great spa retreats – bookable on Culture Trip. Fill your day with the best outdoor activities in Chicago or head to the beach if the weather is on your side, before getting the best out of the local American restaurants.
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I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!
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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.