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Chicago Monthly Rentals

Find the perfect home in Chicago
Chicago
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Best Vacation Home Deals in Chicago

Apartment University Village / Little Italy
Dec 1 - Dec 8
-55%
$2,259
$1,008 for 7 nights
Apartment ∙ 8 guests ∙ 3 bedrooms
Wonderful Rental Apartment in University Village / Little Italy with Yard
5.0
"Excellent" (307 ratings)
University Village / Little Italy, Chicago, Illinois, United States
Details
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House Sheffield Neighbors
Sep 9 - Sep 16
-28%
$5,228
$3,764 for 7 nights
House ∙ 8 guests ∙ 3 bedrooms
House in Sheffield Neighbors
5.0
"Excellent" (19 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
Details
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Aparthotel Near North
Apr 21 - Apr 28
-32%
$7,470
$5,105 for 7 nights
Aparthotel ∙ 8 guests ∙ 3 bedrooms
Aparthotel in Near North with Grill, Pool & Sauna, Near John Hancock Center
4.9
"Excellent" (144 ratings)
Near North, Chicago, Illinois, United States
Details
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House Lake View East
Feb 17 - Feb 24
-36%
$4,141
$2,667 for 7 nights
House ∙ 20 guests ∙ 6 bedrooms
House in Lake View East with Grill & Yard
5.0
"Excellent" (13 ratings)
Lake View East, Chicago, Illinois, United States
Details
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Apartment University Village / Little Italy
Oct 27 - Nov 3
-53%
$3,602
$1,680 for 7 nights
Apartment ∙ 8 guests ∙ 4 bedrooms
Apartment in University Village / Little Italy
5.0
"Excellent" (227 ratings)
University Village / Little Italy, Chicago, Illinois, United States
Details
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House Jefferson Park
Jan 19 - Jan 26
-55%
$2,451
$1,095 for 7 nights
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Jefferson Park with Yard
5.0
"Excellent" (36 ratings)
Jefferson Park, Chicago, Illinois, United States
Details
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Aparthotel Near North
Jan 13 - Jan 20
-35%
$2,997
$1,953 for 7 nights
Aparthotel ∙ 4 guests ∙ 1 bedroom
Aparthotel in Near North with Grill & Pool, Close to John Hancock Center
5.0
"Excellent" (184 ratings)
Near North, Chicago, Illinois, United States
Details
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Apartment Lake View East
Apr 8 - Apr 15
-73%
$2,481
$661 for 7 nights
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Lake View East
4.4
"Very good" (12 ratings)
Lake View East, Chicago, Illinois, United States
Details
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Apartment Near North
Jan 6 - Jan 13
-65%
$4,065
$1,438 for 7 nights
Apartment ∙ 5 guests ∙ 2 bedrooms
Apartment in Near North with On-Site Parking, Near John Hancock Center
4.9
"Excellent" (23 ratings)
Near North, Chicago, Illinois, United States
Details
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Monthly Rentals in Chicago: Top Accommodations

Apartment Roscoe Village
Aug 26 - Sep 2
$1,280 for 7 nights
Apartment ∙ 4 guests ∙ 2 bedrooms
Family Friendly Rental Apartment in Roscoe Village with Grill & Yard
5.0
"Excellent" (153 ratings)
Roscoe Village, Chicago, Illinois, United States
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Apartment Logan Square
Jul 7 - Jul 14
$778 for 7 nights
Apartment ∙ 4 guests ∙ 3 bedrooms
Sunny Rental Apartment in Logan Square with Grill
4.6
"Outstanding" (41 ratings)
Logan Square, Chicago, Illinois, United States
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House Hollywood Park
Sep 23 - Sep 30
$1,839 for 7 nights
House ∙ 5 guests ∙ 2 bedrooms
Entire House in Hollywood Park with Free Parking
5.0
"Excellent" (10 ratings)
Hollywood Park, Chicago, Illinois, United States
Details
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The Weather in Chicago

max.
Min.
31°
17°
8 days 8
max.
Min.
35°
20°
7 days 7
max.
Min.
45°
29°
9 days 9
max.
Min.
59°
40°
9 days 9
max.
Min.
70°
50°
8 days 8
max.
Min.
81°
60°
9 days 9
max.
Min.
84°
65°
8 days 8
max.
Min.
83°
64°
8 days 8
max.
Min.
76°
56°
8 days 8
max.
Min.
65°
46°
7 days 7
max.
Min.
48°
33°
8 days 8
max.
Min.
35°
22°
9 days 9
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Frequently Asked Questions

Chicago Monthly Rentals: How much does it cost to rent a vacation home in Chicago?

You can get an incredible rental from $207 and get discounts up to 53%!

Can I find a vacation home for a group for Chicago Monthly Rentals?

in Chicago, medium-sized groups and families should look for Apartment rental since they fit 4 guests.

How many home rentals in Chicago are available to book for a month or longer?

There are more than 9,081 accommodations for rent in Chicago. The best time to find availability for longer stays is in August when home rentals have high availability.

Can you book seasonal vacation rentals in Chicago have a pool?

Absolutely, more than 28% of accommodations in Chicago come with a pool.

How much does a monthly vacation rental in Chicago cost?

Rates for vacation rentals in Chicago over a longer period can range from $78 per night, but many hosts offer discounts for stays of 14 days or longer.

What types of vacation homes are available for Chicago Monthly Rentals?

We would advice browsing our selection of House rental and Apartment rental for Chicago Monthly Rentals.

Average Nightly Rental Prices in Chicago

Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental Availability Information in Chicago

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