Culture Haven
12 guests
4 bedrooms
Rush & Division, Chicago
Welcome to The Hermes! Nestled in the vibrant Streeterville neighborhood, classic charm meets culture and bustling downtown lifestyle in the heart of The Windy City.
Luxury Long Stay Rentals in Chicago
We selected the 36 homes worth renting in this location
Home spotlights in Chicago
Chicagoan Idyll
6 guests
3 bedrooms
River West, Chicago
This modern penthouse is stylish, well-located, and boasts sensational skyline views – how can you go wrong? You'll find it near the West Loop, known for its top-notch restaurants and vibrant nightlife.
Westside Retreat
7 guests
3 bedrooms
River West, Chicago
Welcome to our charming haven, nestled in the vibrant neighborhood of River West, Chicago. This urban oasis offers a serene escape from the bustling city, allowing you to experience the best of both worlds.
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.
We selected the top 3% holiday homes in Chicago Long Stay Rentals
Explore the 36 most perfect homes in our collection
View on map
Check upcoming rates & availability for Chicago Long Stay Rentals
Frequently asked questions
Explore our collection of luxury Extended Stay Rentals available for you to rent in Chicago, Cook County, Illinois, United States. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Chicago, Cook County, Illinois, United States collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.
Search our collection