Chicago Morning
8 guests
4 bedrooms
Printer's Row, Chicago
Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.
Chicago Vista
6 guests
2 bedrooms
Rush & Division, Chicago
Step inside The Leto, where classic charm mingles with vibrant culture in the bustling Streeterville neighborhood of Chicago. This locale promises an immersive experience into not only traditional Chicago history but also the nuances of Italian villa architecture and other globally inspired design details.
The Heart of the Loop
16 guests
8 bedrooms
Chicago Loop, Chicago
Welcome to a holiday getaway nestled right in the heart of Chicago’s vibrant Financial District. Just steps from iconic attractions, revel in the rich history of the city through its grand architecture and marvel at the stunning skyline from this retreat.
The Skyline's Vision
14 guests
6 bedrooms
Fulton River District, Chicago
When you bring everyone to Chicago, you want a space that matches the occasion, and these skyline retreats near Fulton Market do exactly that. By day, the city is yours to explore: coffee and street art in the West Loop, vintage hunting at Randolph Street Market, picnics in Union Park, or a culinary crawl through some of the best restaurants in the Midwest.
Explore the 100 most perfect homes in our collection
Airbnb is a shot in the dark. We meticulously vet all our homes in Illinois to ensure you won’t waste your precious holiday. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Illinois Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.
