Chicago Vacation Rentals

Find the best deals on 2,613 vacation rentals in Chicago

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Top rentals in Chicago

Find the perfect Chicago vacation rental for your needs
Beautiful, Large single family home just 4 miles from downtown
Beautiful, Large single family home just 4 miles from downtown
C$ 463
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Premier Luxury at The Coast
Premier Luxury at The Coast
C$ 127
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Aqua Chicago
Aqua Chicago
C$ 122
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Staycation Wright in our Oak Park Beauty
Staycation Wright in our Oak Park Beauty
C$ 249
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New! Upscale 2br In Gold Coast By Domio
New! Upscale 2br In Gold Coast By Domio
C$ 254
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Opulent 3bdr2bth Old Town Luxury + Parking prmts
Opulent 3bdr2bth Old Town Luxury + Parking prmts
9.6
C$ 785
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Beautiful Room in Chicago
Beautiful Room in Chicago
7.1
C$ 113
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Royal Studio w/ Pool Close to 360 Chicago
Royal Studio w/ Pool Close to 360 Chicago
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When to book a vacation apartment in Chicago

Check out the tips below to find the best deal on a Chicago vacation rental property
Low Season
April
High Season
July

cheapest month to stay

36%

expected price decrease

most expensive time to stay

50%

expected price increase

Price
C$ 226 - C$ 690
Highest day of week
Friday
Cheapest day of week
Tuesday

avg. price over the last two weeks

Average price (weeknight)

C$ 294

avg. price over the last two weeks

avg. price over the last two weeks

Average price (weekend night)

C$ 325

avg. price over the last two weeks


Cheapest vacation rentals in Chicago

Our lowest-priced vacation apartments and property rentals for a cheaper way to stay in Chicago
New! Upscale 2br In Gold Coast By Domio
New! Upscale 2br In Gold Coast By Domio
C$ 254

Chicago vacation apartments & rental properties FAQ

How long do people typically book vacation apartments for in Chicago?

On average, people book vacation rentals in Chicago for stays of around 2 nights.

How much does a vacation rental apartment in Chicago cost?

Around C$ 250 per night is the typical cost of a vacation apartment in Chicago - note that if you are booking an apartment for a larger group or require more rooms and facilities in your rental, the price will likely be higher.

When is the best time to book a vacation rental in Chicago?

If you can be flexible on booking dates, vacation apartments and rental properties in Chicago can be as much as 36% cheaper in April.

What’s the best area of Chicago to book a vacation rental in?

The most popular areas to book Chicago vacation rentals in are Logan Square, Near North Side, and Grand Boulevard.