Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Self-catering
Fabulous
3 reviews
AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Heater, Hot Tub, Internet, Laundry
Wellness Facilities, Tv, Business Services, Barbecue/Outdoor Cooking, Security/Safety, Entertainment, Guest Services
AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
Apartments, Luxury, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Self-catering
Very Good
30 reviews
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
Guest Services, Air Conditioner, Security/Safety, Entertainment, Internet, Tv, Pet Friendly
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
Apartments, Luxury, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family
Superb
17 reviews
Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals
Fabulous
42 reviews
Apartments, Luxury, Accommodations, Pools, Parking, Serviced apartments, 4-star, Lodgings, Vacation rentals
Superb
100 reviews
![Luxurious Haven in the Heart of Chicago! [32 Day+]](https://q-xx.bstatic.com/xdata/images/hotel/max500/465724021.jpg?k=2d4dd6cfe76384ba1411faf05d253a59e491e7aa89b037982f9caea1ddb3a812&o=)
Balcony/Terrace, Parking, Wheelchair Accessible, Pool, Kitchen, Internet, Air Conditioner
AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry
AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry
Exceptional
1 reviews
AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry
AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry
AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry
AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
AC, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Laundry
AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Downtown Chicago.
VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
Some of the best vacation rentals with pool in Downtown Chicago are:
You can explore 165 verified vacation rentals with a pool in Downtown Chicago. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.
Prices for vacation rentals with a pool in Downtown Chicago vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $87 per night, with private pool homes and peak travel periods often costing more.
Many rentals in Downtown Chicago offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.
Yes, some vacation rentals with pools in Downtown Chicago welcome pets. Currently, 68 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.
Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.
Vacation rentals with pools in Downtown Chicago often include additional outdoor features such as Pool, Wellness Facilities, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.
Some vacation rentals in Downtown Chicago offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.