Vacation rentals in Chicago, IL
Find deals on vacation rentals in Chicago, IL
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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 ParkLincoln Park Living - 3 Queen Beds - Sleeps 6
1147 West Diversey Parkway, Chicago, IL, United States
2 New Construction Suites Same Place
Chicago, IL, United States
Suite 2 on Southport 4 Queen Beds
Chicago, IL, United States
Hyde Park
Search rentals in Hyde ParkCozy Studio in Hyde Park-Walk to Lake & University
Chicago, IL, United States
Enchanting 4-bedroom apartment with AC in vibrant Chicago Hyde Park
Chicago, IL, United States
Near South Side
Search rentals in Near South SideLuxury Studio Apartment with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field
Chicago, IL, United States
South Loop 3 Bedroom Apt
Chicago, IL, United States
South Loop 2 Bedroom Apt
Chicago, IL, United States
North Center
Search rentals in North CenterRelaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover
Chicago, IL, United States
The Lyons' Lair
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
Sonder The Burnham
555 West Jackson Boulevard, Chicago, IL, United States
Private Basement Suite-Completely separate from the rest of the house
Chicago, IL, United States
Kasa Lake Shore Chicago
446 East Ontario Street, 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
Average Length of Stay | 3 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 | March | cheapest month to stay |
| High Season | April | most expensive time to stay |
| 80% | expected price decrease | |
| 52% | expected price increase |
Price | $70 - $726 |
|---|
| Cheapest day of week | Thursday | is the cheapest day of the week to book |
| Highest day of week | Saturday | is the most expensive day of the week to book |
| $264 | is the average per night cost for a vacation rental on this day | |
| $394 | is the average per night cost for a vacation rental on this day |
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 | $257 - $311 |
|---|
| CHEAPEST NEIGHBORHOOD IN CHICAGO | Near North Side | 12% cheaper | Vacation rentals in Near North Side are the cheapest in Chicago at just $257 per night on average |
| MOST EXPENSIVE NEIGHBORHOOD IN CHICAGO | Loop | 6% more expensive | Loop has the highest priced vacation rentals in Chicago with properties averaging $311 per night |
| MOST POPULAR NEIGHBORHOOD IN CHICAGO | Loop | 30% more users visited | More momondo users search for vacation rentals in Loop 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 3 nights.
How much does a vacation rental apartment in Chicago cost?
A vacation rental in Chicago will generally cost around $323 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 January. The cost of your apartment or rental property can be around 46% cheaper in January 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. Lincoln Park and Hyde 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 2,630 as of October 2026.
When did momondo last update prices for hotels in Chicago?
Prices for hotels in Chicago refresh daily.