Holiday Rentals in Chicago, IL

$310 per night is how much a holiday rental in Chicago costs, on average. $85 per night was the cheapest price recently found by our users, though anything for $308 per night or less is a good deal. Keep in mind that Chicago holiday rental prices fluctuate throughout the year: the most expensive month to book is July, and the cheapest time to book is December.

The best holiday rental in Chicago is The Chicago Hotel Collection - Millennium Park, according to our user data. 6 users from HotelsCombined gave the The Chicago Hotel Collection - Millennium Park a 4.3/10 rating.

If you’re looking to stay close to Chicago O'Hare Intl Airport for your trip to Chicago, then consider booking a Distinct Lincoln Park Suites by Sonder holiday rental. This holiday apartment is just 20.4 km away from the Chicago airport.

Downtown is the best part of the city to stay in if you’re looking for a holiday rental in Chicago. The 4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena is our most popular holiday rental in this neighbourhood. While there are other neighbourhoods throughout Chicago, 6% of HotelsCombined users searched for rentals in Downtown in the past 12 months, making it a popular choice.

The Chicago Hotel Collection - Millennium Park is the most popular Chicago holiday rental near Navy Pier (the city’s most popular landmark). It’s a 2.0 km trip from The Chicago Hotel Collection - Millennium Park to Navy Pier. While there may be other holiday rentals near Navy Pier, The Chicago Hotel Collection - Millennium Park received high marks (4.3/10) from 6 users.

Yes, there is 1 holiday rental in Chicago with “Pool” listed as an amenity, the most popular being the The Penthouse at Grand Plaza rental based on user data.

If you’re looking to book a Guest house holiday rental in Chicago, then you have 16 to choose from. We recommend looking at Hollywood Rentals Llc as it’s currently the most popular Guest house rental among our users.