Top rentals in Chicago
Find the perfect holiday rental for your stay in Chicago
Holiday rentals in popular neighbourhoods in Chicago
Below are the most popular neighbourhoods in Chicago to stay in, as well as some of the best holiday 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
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
Near North Side
Search rentals in Near North SideChic River North Retreat
Chicago, IL, United States
Brownstone in Gold Coast - Downtown
Chicago, IL, United States
Aurelien Spacious Apartments in the Heart of Gold Coast
Chicago, IL, United States
Lincoln Park
Search rentals in Lincoln ParkHistoric Old Town One Bedroom Suite
Chicago, IL, United States
Entire Building-Walk To Lincoln Park Or The Beach
Chicago, IL, United States
Chicago Condo Near Lincoln Park and DePaul!
Chicago, IL, United States
Lincoln Park Living - Suite 2
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
Fully furnished bedroom near medical district and UIC
Chicago, IL, United States
Pulaski Point Properties
Chicago, IL, United States
Econo Lodge
Rockford, IL, United States
Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking
Chicago, IL, United States
Cabin 101 by 747 Lofts
Chicago, IL, United States
Mccormick Place Modern Loft With An Amaz
2036 South Michigan Avenue 712, 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 | £34 |
|---|
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 | September | most expensive time to stay |
| 58% | expected price decrease | |
| 69% | expected price increase |
Price | £111 - £851 |
|---|
| Cheapest day of week | Monday | is the cheapest day of the week to book |
| Highest day of week | Thursday | is the most expensive day of the week to book |
| £144 | ||
| £255 |
Information about staying in Chicago
Read these important travel tips before booking a holiday rental in Chicago
How long do people typically book holiday apartments for in Chicago?
On average, people book holiday rentals in Chicago for stays of around 5 nights.
When is the best time to book a holiday rental in Chicago?
Holiday apartments in Chicago are often cheapest in February - rental prices can be around 58% lower than the average during this period.
What’s the best area of Chicago to book a holiday rental in?
Near West Side, Downtown, and Near North Side are typically the most popular places to rent holiday apartments in Chicago.
How many operators does momondo search for hotels in Chicago?
The number of operators available for hotels in Chicago is 3,551 as of May 2025.
When did momondo last update prices for hotels in Chicago?
Prices for hotels in Chicago are updated daily.