Stay If You Dare - Vacation Rentals in Downtown Chicago
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- TV
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
Luxury Places to Stay in Downtown Chicago
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
Top-Rated Vacation Rentals with a Pool in Downtown Chicago
- Air Conditioner
- Pool
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pet Friendly
- Pool
Pet-Friendly Vacation Rentals in Downtown Chicago
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Pet Friendly
- TV
- Security/Safety
Large Vacation Homes & Villas in Downtown Chicago
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- Parking
- Pet Friendly
Wheelchair Accessible Vacation Homes in Downtown Chicago
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- TV
- Wheelchair Accessible
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
Downtown Chicago Vacation Rentals and Airbnb Places to Stay Under $200
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Security/Safety
- Wellness Facilities
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pool
- TV
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Pet Friendly
- Pool
Instantly Bookable Vacation Homes in Downtown Chicago
- Air Conditioner
- TV
- Security/Safety
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Parking
- TV
- Pet Friendly
- TV
- Balcony/Terrace
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
About Downtown Chicago Vacation Rentals
With more than 2821 Downtown 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 Downtown Chicago.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Stayifyoudare Downtown 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 Downtown Chicago. Places to stay near Downtown Chicago are 736.14 ft² on average, with prices averaging US $471 a night.
Stayifyoudare makes it easy and safe to find and compare vacation rentals in Downtown 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 Downtown Chicago
| Type | Count |
|---|---|
| Holiday Apartments | 1747 |
| Hotels | 630 |
| Vacation Homes | 326 |
| Resorts | 9 |
| Hostels | 5 |
| B&B | 3 |
| Cabin Rentals | 2 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Downtown 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 Downtown Chicago.
Weather in Downtown Chicago
View the weather forecast for Downtown Chicago before booking your Downtown Chicago Vacation Rentals to confirm your best time to go.
Other Places to Stay Near Downtown Chicago, IL
Complexes around Downtown Chicago, IL
Downtown Chicago Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Downtown Chicago?
There are a lot of options in Downtown Chicago. If you plan on staying in the Downtown 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 Downtown Chicago:
- Magic Factory Loft 2West
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- 4BR Old Town Chicago Loft | Walk to Wells St
- Gorgeous 3BR River North Condo - Free Parking
- Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
- City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
- Smart Home in Logan Square by the 606 Trail
- Modern West Loop Gem-City Views & Prime Location 6
- Spacious 4BR Central Apartment w/Skyline Views
- Bee's Knees - Ritzy, 1924 Chicago Bungalow
How many vacation rentals have private pools in Downtown Chicago?
There are 71 vacation rentals with private pools near Downtown Chicago. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Downtown Chicago are best for families?
If you are looking for a family-friendly vacation home in Downtown 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 Downtown Chicago:
How many vacation rentals are available in Downtown Chicago?
Currently, the total number of properties listed in 2026 is over 2821 in the Downtown Chicago area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Downtown Chicago.
