Holiday rentals in Chicago, IL
Find deals on 3,108 holiday rentals in Chicago, IL
momondo compares 3M+ hotel and accommodation options.
Top rentals in Chicago
Find the perfect holiday rental for your stay 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
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 Escape about 1 Mi to Local Beaches!
Chicago, IL, United States
Apartment by the lake
Chicago, IL, United States
Lincoln Park
Search rentals in Lincoln ParkHistoric Old Town One Bedroom Suite
Chicago, IL, United States
Chicago Condo Near Lincoln Park and DePaul!
Chicago, IL, United States
Entire Building-Walk To Lincoln Park Or The Beach
Chicago, IL, United States
Lincoln Park Living - Suite 2
Chicago, IL, United States
Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover
Chicago, IL, United States
Near North Side
Search rentals in Near North SideSonder by Marriott Bonvoy The Opal Apartments River North
Chicago, IL, United States
Chic River North Retreat
Chicago, IL, United States
Aurelien Spacious Apartments in the Heart of Gold Coast
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 holiday rental in Chicago
These Chicago holiday rentals have the best prices for their ratings
The Avondale Attic
Chicago, IL, United States
Peaceful Beachfront Loft Rooftop Gym
Chicago, IL, United States
Fully furnished bedroom near medical district and UIC
Chicago, IL, United States
Mccormick Place Modern Loft With An Amaz
2036 South Michigan Avenue 712, Chicago, IL, United States
Luxurious New Remodeled
Chicago, IL, United States
Pulaski Point Properties
Chicago, IL, United States
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 | $47 |
|---|
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 season | February | cheapest month to stay |
| High season | November | most expensive time to stay |
| 65% | expected price decrease | |
| 77% | expected price increase |
Price | $225 - $2,836 |
|---|
| Cheapest day of week | Thursday | is the cheapest day of the week to book |
| Highest day of week | Sunday | is the most expensive day of the week to book |
| $318 | ||
| $926 |
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 | $591 - $732 |
|---|
| CHEAPEST NEIGHBOURHOOD IN CHICAGO | Loop | 7% cheaper | Holiday rentals in Loop are the cheapest in Chicago at just $591 per night on average |
| MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGO | Near North Side | 13% more expensive | Near North Side has the highest priced holiday rentals in Chicago with properties averaging $732 per night |
| MOST POPULAR NEIGHBOURHOOD IN CHICAGO | Near North Side | 35% more users visited | More 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?
5 nights is the typical length of a Chicago holiday rental booking.
When is the best time to book a holiday rental in Chicago?
February is often the cheapest month to rent a holiday apartment in Chicago. Prices per night can be around 65% below average at this time.
What’s the best area of Chicago to book a holiday rental in?
Near North Side and West Town are classic choices for holiday rentals in Chicago. Recently, many users have found good rental properties in Edgewater too.
How many operators does momondo search for hotels in Chicago?
As of July 2025, there are 3,551 operators available to choose from for hotels in Chicago.
When did momondo last update prices for hotels in Chicago?
Prices for hotels in Chicago are updated daily.