Top Hotels
Neighborhoods
FAQs
Hotels in Chicago

Holiday rentals in Chicago, IL

Find deals on 2,633 holiday rentals in Chicago, IL

Chicago, IL, United States
27 Apr — 28 Apr2
Mon 22/4
Fri 26/4

Compare 3M+ hotel and accommodation options.


Top rentals in Chicago

Find the perfect holiday rental for your stay in Chicago
Price
$81
$640
Review Score
0+
6+
7+
8+
9+

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

$81
The cheapest price for a room in Chicago found in the last 7 days is $81/night. This rate is available with 5430 Happy Home.

Best neighbourhoods to book a holiday rental in Chicago

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

Price

$332 - $347

CHEAPEST NEIGHBOURHOOD IN CHICAGONear North Side2% cheaperHoliday rentals in Near North Side are the cheapest in Chicago at just $332 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 $347 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGONear North Side31% 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?

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

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

December is often the cheapest month to rent a holiday apartment in Chicago. Prices per night can be around 73% below average at this time.

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

Near North Side and Logan Square are classic choices for holiday rentals in Chicago. Recently, many users have found good rental properties in Lake View too.

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.


Save money when you book holiday rentals with momondo
Best deals on hotels
Best deals on hotels
See deals from 3M+ hotels and accommodations in one place.
Free cancellation
Free cancellation
Use our filter to find stays with free cancellation.
Millions of reviews
Millions of reviews
Check ratings based on millions of real guest reviews.
Price Alerts
Price Alerts
Not ready to book? Create a price alert to track prices.

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
Mon 22/4
Fri 26/4
Email me momondo's favourite deals