Summer spots with views of Lake Michigan and sky-high places for late-night libations line up in this Illinois city.
Chicago has always marched to its own beat and the Second City is second to none when it comes to rooftop revelry. Although the summers are short, the nights are long as many of the hotels, restaurants and hotspots turn their open-air rooftops into cozy centers for cocktails, cuisine and conversation, whatever the season. So, head up to see this architecturally arresting city from above and get a soaring snapshot from these rooftop haunts.
Destinations Unlocked:Let our travel expert Stefano help you find your perfect Culture trip
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.
Modern luxury and an address amid the vibrant restaurants, shops and theaters around the Loop allows the Pendry to capture Chicago’s spirit. With sweeping city views and a distinguished bar with digestifs for the discerning drinker, Pendry delivers an experience that showcases Chicago in a new light. For the best views in the warmer months, head up to Cote D’Azur-like rooftop restaurant Château Carbide, where the light, airy feel is as intoxicating as the champagne selection.
A true taste of Chicago involves deep-dish pizza and Italian beef, but those with a refined palate know all too well that an opportunity to dine at Nobu should never be missed. Head up to the rooftop of Nobu Hotel for an elevated dining experience found nowhere else in the Midwest. Whitefish tiradito, based on the Peruvian ceviche-like dish, mini wagyu tacos and lamb anticucho (street-food-style Andean skewers) are just a few of the delicious plates you’ll plow through en route to a chocolate sobacha cake. The extensive wine selection lets you refill a whim while drinking in the rooftop atmosphere.
Nobu rarely leaves room in your stomach but if you’re game for a nightcap, ARIE has a shaker at the ready. A chic, playful vibe blows through the rooftop of Hyatt Centric, allowing you to appreciate the amazing city views without taking this breathtaking backdrop too seriously. The chill and chatty crowd will convince you to stay until last call and one too many of their Second City cocktails may sway you to follow your new friends to other rooftop haunts around the Loop.
It’s a refreshingly odd feeling sitting on the rooftop of the Hoxton: you’re planted deep within the heart of the city in the Fulton Market district and yet feel a million miles away from the rush of the streets below. Maybe it’s the floor-to-ceiling windows in your room that set a slow pace or the chill vibes on the sundeck that keep you cool at the pool. Whichever it is, as you munch on crab causa, goat empanadas and other Peruvian-inspired bites at the Cabra Cevicheria, you’ll feel delightfully content at this rooftop roost.
Heads up, sports fans: the best way to see the Cubbies in action is from the Wrigley View Rooftop. This game-changing experience hits a home run, whether you’re catching nine innings or a late-night concert, you’ll have a full view of the field and a full buffet to keep you going. You’ll need a group to rent out this space, but trust us: it’s the ultimate outing for those who love the Windy City, America’s favorite pastime and an all-round unforgettable experience.
You’ll feel in your element the moment you check into the Godfrey. Chic guest rooms have both wet bars and workstations, allowing you to work and play during your stay. Its prime location is ideal for knocking off the tourist trail: the Gold Coast, Navy Pier and Riverwalk are all within a few Subway stops. Head up to the I|O Rooftop Lounge to scan the skyline and snack on a dangerously decadent s’mores martini made with rum, cold-brew coffee and the signature sweets.
You’ll have to head almost down to Chinatown to reach Reggie’s, but the extra Subway stops are worth it. This no-frills bar has live local music, tons of pub grub and a beer list that pleases its mixed crowd. It’s way too easy to spend hours on the rooftop here, knocking back a few pints. If you happen to be in town for a concert or a sporting event, let the free shuttle bus be your designated driver so you can indulge safely.
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meet our Local Insider
HOW LONG HAVE YOU BEEN A GUIDE?
WHAT DO YOU LOVE ABOUT YOUR JOB?
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.
WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?
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!
Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.
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Connect with like-minded people on our premium trips curated by local insiders and with care for the world
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.