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Holiday rentals in Chicago, IL

Find deals on 2,639 holiday rentals in Chicago, IL

Chicago, IL, United States
4 Jun — 5 Jun2
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Top rentals in Chicago

Find the perfect holiday rental for your stay in Chicago
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Vacation rentals in popular neighbourhoods in Chicago

Below are the most popular neighbourhoods in Chicago to stay in, as well as some of the best vacation rentals in each area

Hostels and cheap hotels in Chicago

These hotels and hostels usually make for a cheap way to stay in Chicago

Get the best value holiday rental in Chicago

These Chicago holiday rentals have the best prices for their ratings

momondo's favourite holiday rentals in Chicago

Learn more about these user-preferred holiday rentals in Chicago

Useful insights on Chicago holiday rentals

Get a quick overview on price and accommodation trends for your visit in Chicago

Lowest Holiday Rental Price

The cheapest price for a room in Chicago found in the last 7 days is €52/night. This rate is available with 5430 Happy Home.

When to book a holiday rental in Chicago

Check out the information below to find the best deal on a holiday rental in Chicago
Low seasonOctobercheapest month to stay
High seasonJulymost expensive time to stay
76%expected price decrease
56%expected price increase


€82 - €752

Cheapest day of weekTuesdayis the cheapest day of the week to book
Highest day of weekThursdayis the most expensive day of the week to book

Best neighbourhoods to book a holiday rental in Chicago

Below are the average prices for holiday rentals in the most popular neighbourhoods in Chicago


€191 - €206

CHEAPEST NEIGHBOURHOOD IN CHICAGONear North Side4% cheaperHoliday rentals in Near North Side are the cheapest in Chicago at just €191 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGONear West Side3% more expensiveNear West Side has the highest priced holiday rentals in Chicago with properties averaging €206 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGONear North Side34% more users visitedMore momondo users search for holiday rentals in Near North Side than any other neighbourhood in Chicago

Information about staying in Chicago

Read these important travel tips before booking a vacation rental in Chicago

How long do people typically book holiday apartments for in Chicago?

Those choosing holiday rental apartments in Chicago typically book for at least 4 nights.

When is the best time to book a holiday rental in Chicago?

October is typically when Chicago holiday apartment and rental property prices are at their lowest, with prices around 76% lower than the Chicago peak season.

What’s the best area of Chicago to book a holiday rental in?

The most popular areas to book Chicago holiday rentals in are Edgewater, Lincoln Park, and West Town.

How many operators does momondo search for hotels in Chicago?

When did momondo last update prices for hotels in Chicago?

Prices for hotels in Chicago were last updated today.

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