Need a flexible short-term rental in Chicago? Browse fully furnished stays tailored for extended holidays, digital nomad bases, or business travel. Compare verified options to secure a convenient setup for your visit.
Apartments, Accommodations, Serviced apartments, Lodgings, Vacation rentals, Places to stay, Self-catering
Good
461 reviews
AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking
Exceptional
4 reviews
Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals
Fabulous
42 reviews
AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking
Exceptional
2 reviews
Apartments, Accommodations, Lodgings, Vacation rentals, Places to stay
AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking
Exceptional
4 reviews
Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Self-catering
Fabulous
3 reviews
AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking
Exceptional
3 reviews
Apartments, Accommodations, Serviced apartments, 3-star, Lodgings, Vacation rentals, Places to stay, Self-catering
Good
365 reviews
AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking
Exceptional
3 reviews
Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Crib, Dryer, Elevator, Heater, Internet, Kitchen, Microwave, No Smoking
Exceptional
1 reviews
Barbecue/Outdoor Cooking, Accessibility, Guest Services, Sports/Activities, Internet, Tv, Air Conditioner
AC, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet
Superb
5 reviews
Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater
Exceptional
2 reviews
Apartments, Luxury, Accommodations, Pools, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family
Superb
17 reviews
AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater
AC, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet
Exceptional
4 reviews
AC, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet
Exceptional
8 reviews
AC, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet
Exceptional
5 reviews
Pro Tip:
OwnerDirectVacationRental 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 Short Term Rentals in Chicago.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our short term rentals stand out?
Every short term rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best short term rentals in Chicago are:
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 Short-term Rentals in Chicago
You can explore 2204 verified short-term rentals in Chicago, including apartments, houses, and furnished stays suitable for both travel and temporary living.
Short-term rental prices in Chicago vary depending on location, property size, and travel dates. Rates typically start from around $115 per night, with higher prices for premium properties or peak seasons.
Many short-term rentals in Chicago include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.
Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Chicago, booking earlier can help secure better options.
In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.
Short-term rentals in Chicago often include amenities such as Accessibility, Wellness Facilities, and Fireplace/Heating, providing a comfortable and convenient stay.
Short-term rentals in Chicago are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.