Compare Cottages, Resorts, & Rentals in Downtown Chicago, Chicago, Illinois, USA
About Downtown Chicago Vacation Rentals
There are over 2548 amazing vacation rentals available in Downtown 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 Downtown 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 Downtown 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 Downtown Chicago. The average size of places to stay near Downtown Chicago is approximately 688.07 ft², with prices averaging US $385 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Downtown 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 Downtown Chicago, IL
Frequently Asked Questions About Downtown Chicago?
What are the top cottages, summer homes, and lake houses in Downtown Chicago?
- 52nd Floor MagMile Penthouse VIEWS Fireplace Pool
- 55-56 Mag Mile Penthouse
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- 51st Floor MagMile Penthouse Views Balcony Pool
- 53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
- Magic Factory Loft 2West
- Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
- Million Dollar Views! Luxury Downtown Skyhouse!
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- Magic Factory Loft 3East 4 Bd/4 Ba Families Groups
How many rentals, hotels, or resorts are available in Downtown Chicago?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 2548 properties listed by Vacation Cottage in the Downtown Chicago area for the year 2025, 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 Downtown Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| The Loop Rental Cottages and Private Getaways in Chicago, Illinois | 1338 |
| Near North Side Rental Cottages and Private Getaways in Chicago, Illinois | 751 |
| Near West Side Rental Cottages and Private Getaways in Chicago, Illinois | 398 |
| South Loop Rental Cottages and Private Getaways in Chicago, Illinois | 390 |
| River North Rental Cottages and Private Getaways in Chicago, Illinois | 386 |
| Near South Side Rental Cottages and Private Getaways in Chicago, Illinois | 377 |
| West Town Rental Cottages and Private Getaways in Chicago, Illinois | 339 |
| West Loop Rental Cottages and Private Getaways in Chicago, Illinois | 239 |
| Streeterville Rental Cottages and Private Getaways in Chicago, Illinois | 212 |
| Lincoln Park Rental Cottages and Private Getaways in Chicago, Illinois | 175 |
| University Village / Little Italy Rental Cottages and Private Getaways in Chicago, Illinois | 109 |
| Old Town Rental Cottages and Private Getaways in Chicago, Illinois | 64 |
| River West Rental Cottages and Private Getaways in Chicago, Illinois | 54 |
| Gold Coast Rental Cottages and Private Getaways in Chicago, Illinois | 45 |
| Lakeshore East Rental Cottages and Private Getaways in Chicago, Illinois | 735 |
| Near East Side Rental Cottages and Private Getaways in Chicago, Illinois | 735 |
