Stay If You Dare - Vacation Rentals in Chicago
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Luxury Places to Stay in Chicago
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Top-Rated Vacation Rentals with a Pool in Chicago
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Pet-Friendly Vacation Rentals in Chicago
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Large Vacation Homes & Villas in Chicago
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Wheelchair Accessible Vacation Homes in Chicago
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Chicago Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Chicago
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About Chicago Vacation Rentals
With more than 7855 Chicago vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Stayifyoudare and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chicago.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Stayifyoudare Chicago, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chicago. Places to stay near Chicago are 749.07 ft² on average, with prices averaging US $427 a night.
Stayifyoudare makes it easy and safe to find and compare vacation rentals in Chicago with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Chicago
| Type | Count |
|---|---|
| Holiday Apartments | 5131 |
| Vacation Homes | 1172 |
| Hotels | 898 |
| B&B | 53 |
| Hostels | 13 |
| Resorts | 10 |
| Villas | 8 |
| Cottages | 5 |
| Others | 3 |
| Cabin Rentals | 2 |
Use these Quick Filters to Find a Vacation Rental in Chicago
★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chicago.
Weather in Chicago
View the weather forecast for Chicago before booking your Chicago Vacation Rentals to confirm your best time to go.
Top Attractions Around Chicago, IL
Stayifyoudare offers a large selection of top attractions around Chicago. Research things to do on your vacation before you visit Chicago.
Other Places to Stay Near Chicago, IL
Complexes around Chicago, IL
Chicago Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chicago?
There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chicago:
- The Sono Chicago
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- NEW LUXURY PENTHOUSE CONDO
- Great Location-Beautiful Friendly Andersonville Neighborhood
- Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- Magic Factory Loft 2West
- NEW LUXURY CONDO WITH PATIO DECK
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- 4BR Old Town Chicago Loft | Walk to Wells St
How many vacation rentals have private pools in Chicago?
There are 101 vacation rentals with private pools near Chicago. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Chicago are best for families?
If you are looking for a family-friendly vacation home in Chicago, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chicago:
How many vacation rentals are available in Chicago?
Currently, the total number of properties listed in 2026 is over 7855 in the Chicago area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chicago.
