the Americas · Whole-home rentals on VRBO
Vacation rentals in Chicago
Skip the hotel corridor. Whole-home whole-home rentals in Chicago give you a private front door, a full kitchen, and space for everyone travelling with you. Browse VRBO's whole-home inventory for Chicago, or compare hotels on Expedia if you'd rather have daily service.
Affiliate links · prices may change · the price you pay is the same.
Staying in a Chicago neighbourhood rather than a hotel district puts cafés, bakeries and everyday life on your doorstep — the version of United States that locals actually live in.
Browse by home type in Chicago
Villas in Chicago
Private pool. Full staff optional. Just you.
Cabins in Chicago
Wood-stove nights, star-filled skies, no signal.
Cottages in Chicago
Small, cozy, thatched-roof or lake-facing.
Luxury villas in Chicago
Full staff, infinity pool, zero compromises.
Private pool villas in Chicago
Your own pool. No loungers to fight for.
Mansions in Chicago
Room for the whole crew, and then some.
Glamping in Chicago
Nature without the sleeping bag.
Farmhouses in Chicago
Slow mornings, long tables, open country.
Penthouses in Chicago
Top floor, skyline views, private terrace.
Pet-friendly villas in Chicago
Bring the dog. Everyone's invited.
Family villas in Chicago
Fenced pool, bunk room, space for everyone.
Condos in Chicago
Resort amenities, apartment prices, beach out front.
Common questions
When is the best time to rent a vacation rental in Chicago?
Demand and prices peak in late spring through early autumn (May–September), so book a few months ahead for those dates. Shoulder-season weeks either side are the sweet spot for availability and value on VRBO.
Is a vacation rental in Chicago better value than a hotel?
For two people on a short trip, a central hotel can be cheaper. For families, groups, or stays of several nights, a whole-home vacation rental in Chicago usually wins on price per person once you factor in the kitchen and shared living space — compare both before you book.