Compare Cottages, Resorts, & Rentals in Chicago, Illinois, USA
About Chicago Vacation Rentals
There are over 11678 amazing vacation rentals available in Chicago. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Chicago.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Chicago, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Chicago. The average size of places to stay near Chicago is approximately 736.78 ft², with prices averaging US $345 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Chicago. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods Chicago, IL
Frequently Asked Questions About Chicago?
What are the top cottages, summer homes, and lake houses in Chicago?
- The Sono Chicago
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 55th Floor Penthouse with Award-Winning Views
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- 51st Floor MagMile Penthouse Views Balcony Pool
- 2-Story Penthouse Views, Fireplace, Pool, Gym
- NEW LUXURY PENTHOUSE CONDO
How many rentals, hotels, or resorts are available in Chicago?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 11678 properties listed by Vacation Cottage in the Chicago area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Rental Cottages and Private Getaways in Chicago, Illinois | 1548 |
| The Loop Rental Cottages and Private Getaways in Chicago, Illinois | 717 |
| Near North Side Rental Cottages and Private Getaways in Chicago, Illinois | 617 |
| South Loop Rental Cottages and Private Getaways in Chicago, Illinois | 366 |
| Near South Side Rental Cottages and Private Getaways in Chicago, Illinois | 351 |
| River North Rental Cottages and Private Getaways in Chicago, Illinois | 332 |
| Lakeview Rental Cottages and Private Getaways in Chicago, Illinois | 266 |
| West Loop Rental Cottages and Private Getaways in Chicago, Illinois | 214 |
| Lincoln Park Rental Cottages and Private Getaways in Chicago, Illinois | 154 |
| Hyde Park Rental Cottages and Private Getaways in Chicago, Illinois | 103 |
| Logan Square Rental Cottages and Private Getaways in Chicago, Illinois | 87 |
| Edgewater Rental Cottages and Private Getaways in Chicago, Illinois | 78 |
| Rogers Park Rental Cottages and Private Getaways in Chicago, Illinois | 74 |
| O'Hare Rental Cottages and Private Getaways in Chicago, Illinois | 50 |
| Wrigleyville Rental Cottages and Private Getaways in Chicago, Illinois | 49 |
| Wicker Park Rental Cottages and Private Getaways in Chicago, Illinois | 46 |
