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Holiday rentals in Chicago, IL

Find deals on 2,645 holiday rentals in Chicago, IL

Chicago, IL, United States
26 Jun — 27 Jun2
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Top rentals in Chicago

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

Below are the most popular neighbourhoods in Chicago to stay in, as well as some of the best holiday 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


Average Length of Stay

3 days
The cheapest price for a room in Chicago found in the last 7 days is £42/night. This rate is available with 5430 Happy Home.
On average, people stay for 3 days when lodging at holiday rentals in Chicago. The average accommodation price for 3 days in Chicago in the past week is £68.

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 seasonFebruarycheapest month to stay
High seasonDecembermost expensive time to stay
72%expected price decrease
64%expected price increase


£51 - £495

Cheapest day of weekThursdayis the cheapest day of the week to book
Highest day of weekSaturdayis 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


£164 - £176

CHEAPEST NEIGHBOURHOOD IN CHICAGONear North Side4% cheaperHoliday rentals in Near North Side are the cheapest in Chicago at just £164 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 £176 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGONear North Side32% 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 holiday rental in Chicago

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

On average, people book holiday rentals in Chicago for stays of around 3 nights.

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

Holiday apartments in Chicago are often cheapest in February - rental prices can be around 72% lower than the average during this period.

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

Near South Side, Lake View, and Lincoln Park are typically the most popular places to rent holiday apartments in Chicago.

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 are updated daily.

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