Vacation rentals in Chicago, IL
Find deals on 3,110 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 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
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 vacation rental in Chicago
These Chicago vacation 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 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 | C$ 64 |
|---|
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 | September | most expensive time to stay |
| 58% | expected price decrease | |
| 69% | expected price increase |
Price | C$ 204 - C$ 1,572 |
|---|
| 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 |
| C$ 266 | ||
| C$ 472 |
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?
On average, people book vacation rentals in Chicago for stays of around 3 nights.
When is the best time to book a vacation rental in Chicago?
Vacation 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 vacation rental in?
Near West Side is the most popular area of Chicago to book a rental apartment in. Downtown and Near North Side are also sought-after places to stay.
How many operators does momondo search for hotels in Chicago?
There are 3,551 operators available for hotels in Chicago as of April 2025.
When did momondo last update prices for hotels in Chicago?
Prices for hotels in Chicago were last updated today.