Hotels in Chicago

Holiday rentals in Chicago, IL

Find deals on 2,524 holiday rentals in Chicago, IL

Chicago, IL, United States
28 Feb — 29 Feb2
Fri 23/2
Tue 27/2

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Top rentals in Chicago

Find the perfect holiday rental for your stay in Chicago
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Best neighbourhoods to book a holiday rental in Chicago

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


₹ 16,560 - ₹ 19,043

CHEAPEST NEIGHBOURHOOD IN CHICAGOLake View7% cheaperHoliday rentals in Lake View are the cheapest in Chicago at just ₹ 16,560 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGONear West Side7% more expensiveNear West Side has the highest priced holiday rentals in Chicago with properties averaging ₹ 19,043 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGONear North Side30% more users visitedMore momondo users search for holiday rentals in Near North Side than any other neighbourhood in Chicago

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

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 seasonJulycheapest month to stay
High seasonJunemost expensive time to stay
64%expected price decrease
50%expected price increase


₹ 3,243 - ₹ 17,859

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

Useful insights on Chicago holiday rentals

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

Lowest Holiday Rental Price

₹ 4,479
The cheapest price for a room in Chicago found in the last 7 days is ₹ 4,479/night. This rate is available with 5430 Happy Home.

Information about staying in Chicago

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

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

The cheapest month to rent a holiday apartment in Chicago is usually July. The cost of your apartment or rental property can be around 64% cheaper in July 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 Lincoln Park, Lake View, and Near North Side.

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.

momondo's favourite holiday rentals in Chicago

Learn more about these user-preferred holiday rentals in Chicago

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