Discover a selection of 1,500 holiday rentals in Downtown Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 199 per night, and flats & apartments and houses are popular options for a stay in Downtown Chicago. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — Downtown Chicago
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

Can I find a vacation rental around Downtown Chicago?

Yes, our 2021 property listings offer a large selection of 1,337 vacation rentals near Downtown Chicago. From 1,135 flats & apartments to 180 houses, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best places to stay near Downtown Chicago are on Vrbo.