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Vacation rentals in Chicago, IL

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

Chicago, IL, United States
28 Jun — 29 Jun2
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Top rentals in Chicago

Find the perfect vacation 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 vacation rental in Chicago

These Chicago vacation rentals have the best prices for their ratings

momondo's favourite vacation rentals in Chicago

Learn more about these user-preferred vacation rentals in Chicago

Useful insights on Chicago vacation rentals

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

Lowest Vacation Rental Price

C$ 72
The cheapest price for a room in Chicago found in the last 7 days is C$ 72/night. This rate is available with 5430 Happy Home.

When to book a vacation rental in Chicago

Check out the information below to find the best deal on a vacation rental in Chicago
Low seasonMaycheapest month to stay
High seasonJulymost expensive time to stay
74%expected price decrease
82%expected price increase


C$ 117 - C$ 2,519

Cheapest day of weekTuesdayis the cheapest day of the week to book
Highest day of weekSundayis the most expensive day of the week to book
C$ 108
C$ 356

Best neighbourhoods to book a vacation rental in Chicago

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


C$ 285 - C$ 307

CHEAPEST NEIGHBOURHOOD IN CHICAGONear North Side4% cheaperVacation rentals in Near North Side are the cheapest in Chicago at just C$ 285 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGONear West Side3% more expensiveNear West Side has the highest priced vacation rentals in Chicago with properties averaging C$ 307 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGONear North Side32% more users visitedMore momondo users search for vacation 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 vacation apartments for in Chicago?

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

How much does a vacation rental apartment in Chicago cost?

The price of a vacation apartment in Chicago depends on the number of guests, locations and required amenities - for a standard apartment in Chicago you can expect to pay around C$ 970 per night.

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

Vacation apartments in Chicago are often cheapest in May - rental prices can be around 74% lower than the average during this period.

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

Near West Side is the most popular area of Chicago to book a rental apartment in. Lincoln Park and Logan Square are also sought-after places to stay.

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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