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Holiday rentals in Chicago, IL

Find deals on 2,584 holiday rentals in Chicago, IL

Chicago, IL, United States
24 Jul — 25 Jul2
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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

₹ 4,065

Average Length of Stay

4 days
The cheapest price for a room in Chicago found in the last 7 days is ₹ 4,065/night. This rate is available with 5430 Happy Home.
On average, people stay for 4 days when lodging at holiday rentals in Chicago. The average accommodation price for 4 days in Chicago in the past week is ₹ 29,061.

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 seasonJanuarycheapest month to stay
High seasonJunemost expensive time to stay
58%expected price decrease
54%expected price increase


₹ 4,609 - ₹ 23,728

Best neighbourhoods to book a holiday rental in Chicago

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


₹ 17,312 - ₹ 19,319

CHEAPEST NEIGHBOURHOOD IN CHICAGONear North Side6% cheaperHoliday rentals in Near North Side are the cheapest in Chicago at just ₹ 17,312 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGONear West Side4% more expensiveNear West Side has the highest priced holiday rentals in Chicago with properties averaging ₹ 19,319 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 vacation rental in Chicago

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

4 nights is the typical length of a Chicago holiday rental booking.

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

The cheapest month to rent a holiday apartment in Chicago is usually January. The cost of your apartment or rental property can be around 59% cheaper in January vs. the high 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 Near North Side, Grand Boulevard, and Edgewater.

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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