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
Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Arcade, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
Barbecue/Outdoor Cooking, Accessibility, Guest Services, Sports/Activities, Internet, Tv, Air Conditioner
AC, Arcade, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay
Wellness Facilities, Tv, Business Services, Barbecue/Outdoor Cooking, Security/Safety, Entertainment, Guest Services
AC, Arcade, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
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, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
Superb
6 reviews
Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Crib, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
Exceptional
10 reviews
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking
Guest Services, Air Conditioner, Security/Safety, Entertainment, Internet, Tv, Pet Friendly
AC, Arcade, Barbecue, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen
Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Dryer, Elevator, Fitness Equipment, Heater, Internet, Kitchen, Living Area, Microwave
AC, Elevator, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, TV
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 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 in Downtown Chicago are:
You can explore 2163 verified vacation rentals in Downtown Chicago. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.
Vacation rental prices in Downtown Chicago vary depending on the season, property size, and location. Rates typically start from around $87 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.
Most vacation rentals in Downtown Chicago include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.
Yes, many vacation rentals in Downtown Chicago welcome pets. Currently, 57 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.
For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.
Vacation rentals in Downtown Chicago often include amenities such as Wellness Facilities, Accessibility, and Fireplace/Heating. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.
You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.