Top Rated Activities & Tours in Chicago
Chicago Vacation Rentals, Hotels, & Places to Stay
About Chicago Vacation Rentals
There are more than 12084 places to stay that are available in Chicago. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Chicago.
Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Varoom's places in Chicago, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Chicago. Places to stay near Chicago are 744.71 ft² on average, with prices averaging US $376 a night.
Varoom helps you discover places to stay and suggests things to do to create great travel memories in Chicago. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Top Rental Accommodation Types in Chicago
| Type | Count |
|---|---|
| Holiday Apartments | 5972 |
| Vacation Homes | 3300 |
| Cottages | 50 |
| Villas | 25 |
Use these Quick Filters to Find a Vacation Rental in Chicago
★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Chicago today.
Weather in Chicago, IL
View the weather forecast for Chicago before booking your Chicago Vacation Rentals to confirm your best time to go.
Top Attractions Around Chicago, IL
Varoom offers a large selection of top attractions around Chicago . Research things to do on your vacation before you visit Chicago.
Other Places to Stay in Chicago, IL
Complexes around Chicago, IL
Frequently Asked Questions About Chicago?
What are the top vacation rentals in Chicago?
We have scoured the web to find you options in Chicago. If you plan on staying near or in the Chicago area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the Top Places to Stay 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 vacation rentals have private pools in Chicago?
We have found 334 places to stay that feature a private swimming pool in or near Chicago. Some of the best places to stay that feature or have access to a swimming pool are:
- You Favorite Vacation Spot in New Lenox
- Lux Apts with Lake Views and Top Amenities
- Stay One Chicago
- Grand 1800s Victorian Gem: Updated/by Downtown
Which vacation homes in Chicago are best for families?
If you are looking for a place to stay that is family-friendly in Chicago, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Chicago:
How many Varoom vacation rentals are available in Chicago?
Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2026 is over 12084 in the Chicago area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1486 |
| The Loop Vacation Rentals in Chicago, Illinois | 660 |
| Near North Side Vacation Rentals in Chicago, Illinois | 640 |
| South Loop Vacation Rentals in Chicago, Illinois | 384 |
| Near South Side Vacation Rentals in Chicago, Illinois | 369 |
| River North Vacation Rentals in Chicago, Illinois | 358 |
| Lakeview Vacation Rentals in Chicago, Illinois | 274 |
| West Loop Vacation Rentals in Chicago, Illinois | 186 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 167 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 101 |
| Logan Square Vacation Rentals in Chicago, Illinois | 80 |
| Edgewater Vacation Rentals in Chicago, Illinois | 75 |
| Rogers Park Vacation Rentals in Chicago, Illinois | 70 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 55 |
| O'Hare Vacation Rentals in Chicago, Illinois | 54 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 50 |
