Vacation rentals in Chicago, IL

Find deals on 2,452 vacation rentals in Chicago, IL

Chicago, IL
Sep 26 — Sep 272
Wed 9/27
Sun 10/1

Compare 3M+ hotel and accommodation options.

Top rentals in Chicago

Find the perfect vacation rental for your stay in Chicago
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Best neighborhoods to book a vacation rental in Chicago

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


$165 - $248

CHEAPEST NEIGHBORHOOD IN CHICAGOHyde Park24% cheaperVacation rentals in Hyde Park are the cheapest in Chicago at just $165 per night on average
MOST EXPENSIVE NEIGHBORHOOD IN CHICAGOLincoln Park12% more expensiveLincoln Park has the highest priced vacation rentals in Chicago with properties averaging $248 per night
MOST POPULAR NEIGHBORHOOD IN CHICAGONear North Side77% more users visitedMore momondo users search for vacation rentals in Near North Side than any other neighborhood in Chicago

Vacation rentals in popular neighborhoods in Chicago

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

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 SeasonAprilcheapest month to stay
High SeasonJulymost expensive time to stay
61%expected price decrease
53%expected price increase


$107 - $590

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

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

Useful insights on Chicago vacation rentals

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

Lowest Vacation Rental Price

The cheapest price for a room in Chicago found in the last 7 days is $31/night. This rate is available with Homestay - Eva's International Home.

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?

The average length of a vacation rental booking in Chicago is 7 nights.

How much does a vacation rental apartment in Chicago cost?

A vacation rental in Chicago will generally cost around $136 per night. This figure is taken from average apartment rental searches in Chicago and prices will vary according to the required size, facilities, and location of the rental.

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

The cheapest month to rent a vacation apartment in Chicago is usually April. The cost of your apartment or rental property can be around 62% cheaper in April vs. the high season.

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

Lincoln Park is the most popular area of Chicago to book a rental apartment in. Logan Square and Hyde Park 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 refresh daily.

momondo's favorite vacation rentals in Chicago

Learn more about these user-preferred vacation rentals in Chicago

Vacation rentals in other cities in Illinois

Check out vacation rental prices for these other cities that are also in Illinois

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.