From the Chicago skyscrapers on the shores of Lake Michigan to quaint villas along the Illinois River, visitors to the Prairie State have a great choice of vacation venues, with townhouses that place you next to the action, riverside villas with the marina lifestyle and contemporary homes for group trips. Whether you’re looking for a base in the city or a waterside haven, here’s our pick of vacation rentals in Illinois – bookable on Culture Trip.
The large double bedrooms in this house in this stylish Bucktown home are spread over two floors with varnished wooden floors and stylish touches, roll-top baths and exposed brickwork. Downstairs, watch dinner come together while perched at the kitchen island – or on warmer days, the garden with outdoor kitchen and seating area is the perfect place to gather. Guests in search of a Chicago deep dish will love the proximity to the much-loved family-owned restaurant My Pi Pizza.
As the name suggests, this fun, nautical-inspired home on the banks of the Illinois River in Heritage Harbor is perfect for dipping your toes in the water. Bunk beds in the second bedroom make this vacation rental ideal for small families, and with on-site amenities including an outdoor pool, there is plenty to do other than watch the boats go by from the deck. You’ll find everything you need to cook family dinners here – or try the Red Dog Grill on the marina for a night out.
Escape to the waterfront for a couples getaway in Heritage Harbor. Accommodating four guests, this vacation rental in Illinois with two double bedrooms and two bathrooms has chunky rustic furniture and a quaint kitchen with a dining table under a hand-blown pendant light. Lounge the day away on a pontoon boat or sit around the firepit, before coming back for a drink on the deck.
This two-bedroom apartment is conveniently located if you’re looking for a vacation rental close to DePaul University. Memory foam beds, exposed brickwork and a compact kitchen dining area make it a cozy place to stay with a lot to explore nearby. Sports fans can catch a game of baseball at Wrigley Field – or explorers can head to Lincoln Park Zoo or the Chicago History Museum.
Sleeping up to six guests in two double bedrooms and an extra sofa bed, this comfortable home in Heritage Harbor is ideally placed for all the activities on offer. For the adventurous, there’s kayaking, kite flying, hiking and even skydiving. Or take a more sedated approach and spend the afternoon craft beer or wine tasting. And when you just want some me time, chill at home and watch the world go by from your sunny porch – it’s your vacation, after all.
The teal wooden fronting on this vacation rental perfectly reflects the river, and the interior has been given just as much thought. A light and airy spot, Casa Margarita is a two-bedroom, two-bathroom vacation rental on the water’s edge. Open-plan living, neutral earthy tones and elegant design touches such as wooden floors, paneled doors and linen headboards make this a stylish home from home.
Watch the comings and goings in the marina from this one-bedroom villa, wandering straight out onto your private deck from bed. Downstairs, a kitchen with breakfast nook and cozy sitting room makes this vacation rental the perfect spot for two – but with the option of inviting a friend to stay on the sofa bed and enjoy the views with you.
Spacious and contemporary, this townhouse on the Illinois River close to Ottawa sleeps up to eight people and delivers everything you want from a vacation. All bedrooms have a view of the water and there’s even a bar for fixing sundowners to enjoy on the large deck. This vacation rental comes with parking and enough attractions and activities nearby to keep everyone entertained – including kayaking, fishing and boat trips.
This pet-friendly riverfront home offers plenty of living space for larger groups. A double-height kitchen and living area complete with a chandelier and open fireplace seem like the center of the action – until you discover the games room upstairs with its own bar, plump sofas and card table. For quieter moments, bask in the sunny reading nook overlooking the water, or on the rear deck that backs onto it.
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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.
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