Vacation rentals in Chicago, IL
Find deals on 3,108 vacation rentals in Chicago, IL
momondo compares 3M+ hotel and accommodation options.
Top rentals in Chicago
Find the perfect vacation rental for your stay 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
Downtown
Search rentals in Downtown23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Chicago, IL, United States
4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena
Chicago, IL, United States
O'Hare
Search rentals in O'HareLuxurious New Remodeled
Chicago, IL, United States
Personal Gym Luxury Balcony Condo
Chicago, IL, United States
Rogers Park
Search rentals in Rogers ParkChicago Getaway
Chicago, IL, United States
Urban Chicago Vacation Rental Condo Near Beach!
Chicago, IL, United States
Urban Chicago Escape about 1 Mi to Local Beaches!
Chicago, IL, United States
Lincoln Park
Search rentals in Lincoln ParkHistoric Old Town One Bedroom Suite
Chicago, IL, United States
Suite 1 on Southport 4 Queen Beds
Chicago, IL, United States
Chicago Condo Near Lincoln Park and DePaul!
Chicago, IL, United States
Near North Side
Search rentals in Near North SideAurelien Spacious Apartments in the Heart of Gold Coast
Chicago, IL, United States
Sonder by Marriott Bonvoy The Opal Apartments River North
Chicago, IL, United States
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
The Avondale Attic
Chicago, IL, United States
MTM Fully Furnished Rental in Old Town - 2 beds
Chicago, IL, United States
Personal Gym Luxury Balcony Condo
Chicago, IL, United States
Logan Square: Chic, Comfy 1st Floor 2 Bdrm Apt! Parking Incld!
Chicago, IL, United States
Mccormick Place Modern Loft With An Amaz
2036 South Michigan Avenue 712, Chicago, IL, United States
momondo's favorite 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 | $31 |
|---|---|
Average Length of Stay | 4 days |
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 Season | February | cheapest month to stay |
| High Season | November | most expensive time to stay |
| 65% | expected price decrease | |
| 76% | expected price increase |
Price | $154 - $1,864 |
|---|
| Cheapest day of week | Monday | is the cheapest day of the week to book |
| Highest day of week | Friday | is the most expensive day of the week to book |
| $245 | ||
| $339 |
Best neighborhoods to book a vacation rental in Chicago
Below are the average prices for vacation rentals in the most popular neighborhoods in Chicago
Price | $389 - $481 |
|---|
| CHEAPEST NEIGHBORHOOD IN CHICAGO | Loop | 7% cheaper | Vacation rentals in Loop are the cheapest in Chicago at just $389 per night on average |
| MOST EXPENSIVE NEIGHBORHOOD IN CHICAGO | Near North Side | 13% more expensive | Near North Side has the highest priced vacation rentals in Chicago with properties averaging $481 per night |
| MOST POPULAR NEIGHBORHOOD IN CHICAGO | Near North Side | 35% more users visited | More momondo users search for vacation rentals in Near North Side than any other neighborhood 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?
The average length of a vacation rental booking in Chicago is 4 nights.
How much does a vacation rental apartment in Chicago cost?
A vacation rental in Chicago will generally cost around $127 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 February. The cost of your apartment or rental property can be around 66% cheaper in February vs. the high season.
What’s the best area of Chicago to book a vacation rental in?
Downtown is the most popular area of Chicago to book a rental apartment in. O'Hare and Rogers Park are also sought-after places to stay.
How many operators does momondo search for hotels in Chicago?
The number of operators available for hotels in Chicago is 3,551 as of July 2025.
When did momondo last update prices for hotels in Chicago?
Prices for hotels in Chicago refresh daily.