Vacation rentals in Chicago, IL
Find deals on 2,623 vacation rentals in Chicago, IL
Compare 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
Lincoln Park
Search rentals in Lincoln ParkThe Neighborhood Hotel - Lincoln Park
2616 North Clark Street, Chicago, IL, United States
Hyde Park
Search rentals in Hyde ParkLogan Square
Search rentals in Logan SquareNear North Side
Search rentals in Near North SideApartment in River North Downtown Chicago
Chicago, IL, United States
Lake View
Search rentals in Lake ViewChicago Guest House on Henderson Street
1330 West Henderson Street, Chicago, IL, United States
Hostels and cheap hotels in Chicago
These hotels and hostels usually make for a cheap way to stay in Chicago
The Pinnacle - Peace, Perfection, Practicality
2441 North Avers Avenue, Chicago, IL, United States
Chicago Guest House on Henderson Street
1330 West Henderson Street, Chicago, IL, United States
Get the best value vacation rental in Chicago
These Chicago vacation rentals have the best prices for their ratings
Cabin 101 by 747 Lofts
Chicago, IL, United States
The Neighborhood Hotel - Lincoln Park
2616 North Clark Street, Chicago, IL, United States
The Avondale Guesthouse
Chicago, IL, United States
Logan Square: Chic, Comfy 1st Floor 2 Bdrm Apt! Parking Incld!
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 | $29 |
|---|
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 | June | cheapest month to stay |
| High Season | December | most expensive time to stay |
| 72% | expected price decrease | |
| 55% | expected price increase |
Price | $106 - $833 |
|---|
| Cheapest day of week | Tuesday | is the cheapest day of the week to book |
| Highest day of week | Thursday | is the most expensive day of the week to book |
| $103 | ||
| $905 |
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 | $215 - $233 |
|---|
| CHEAPEST NEIGHBORHOOD IN CHICAGO | Near North Side | 5% cheaper | Vacation rentals in Near North Side are the cheapest in Chicago at just $215 per night on average |
| MOST EXPENSIVE NEIGHBORHOOD IN CHICAGO | Lake View | 3% more expensive | Lake View has the highest priced vacation rentals in Chicago with properties averaging $233 per night |
| MOST POPULAR NEIGHBORHOOD IN CHICAGO | Near North Side | 38% 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 $271 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 June. The cost of your apartment or rental property can be around 72% cheaper in June vs. the high season.
What’s the best area of Chicago to book a vacation rental in?
Lincoln Park is the most popular area of Chicago to book a rental apartment in. Hyde Park and Logan Square 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 3,047 as of August 2024.
When did momondo last update prices for hotels in Chicago?
Prices for hotels in Chicago refresh daily.