Chicago Accommodations - Hotels & Rentals
About Chicago Vacation Rentals
Discover More than 11830 Incredible Getaway Rentals Available in Chicago. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Chicago.
Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Chicago, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Chicago. The Average Size of Places to Stay Near Chicago is 737.47 ft², with Prices Averaging US $355 per Night.
Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Chicago. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.
Top Hotels & Vacation Rentals in Chicago
| Type | Count |
|---|---|
| Holiday Apartments | 5807 |
| Vacation Homes | 3244 |
| Cottages | 49 |
| Villas | 24 |
Use these Quick Filters to Find a Vacation Rental in Chicago
★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Chicago with Online Reservations.
Weather in Chicago, IL
View the weather forecast for Chicago before booking your Chicago Vacation Rentals to confirm your best time to go.
Activities ChicagoGuest Reviews Local Attractions
A Large Selection of Hotels and Vacation Rentals from Around the World ChicagoGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey
Find Hotels & Vacation Rentals in these Cities and Neighborhoods
Frequently Asked Questions About Chicago?
What are the top hotels, lake houses & vacation rentals in Chicago?
We provide an array of great vacation destinations in Chicago. If you are looking to stay in or around the Chicago area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals 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 Hotels & Vacation Rentals have private pools in Chicago?
We have 327 Hotels & Vacation Rentals featuring a private pool in and near Chicago. Some of the best destinations to stay that feature or have access to a swimming pool are:
- ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
- Stay One Chicago
- ENVITAE 3BR Downtown Luxurious Suite Views & Pool
- Premier Penthouses and Apartment with Captivating Views of Millennium Park
Which hotel, lake house, or vacation rental in Chicago is best for families?
Searching for a family-friendly getaway in Chicago? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Chicago?
Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 11830 in the Chicago area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1548 |
| The Loop Vacation Rentals in Chicago, Illinois | 717 |
| Near North Side Vacation Rentals in Chicago, Illinois | 617 |
| South Loop Vacation Rentals in Chicago, Illinois | 366 |
| Near South Side Vacation Rentals in Chicago, Illinois | 351 |
| River North Vacation Rentals in Chicago, Illinois | 332 |
| Lakeview Vacation Rentals in Chicago, Illinois | 266 |
| West Loop Vacation Rentals in Chicago, Illinois | 214 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 154 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 103 |
| Logan Square Vacation Rentals in Chicago, Illinois | 87 |
| Edgewater Vacation Rentals in Chicago, Illinois | 78 |
| Rogers Park Vacation Rentals in Chicago, Illinois | 74 |
| O'Hare Vacation Rentals in Chicago, Illinois | 50 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 49 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 46 |
