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Chicago Monthly Rentals

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Monthly Rentals with pools

Monthly Rentals with pools

Monthly Rentals with parking

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Pet-Friendly Monthly Rentals

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Top-rated monthly rentals in Chicago

Browse our top rated monthly rentals offers

House Uptown
$30,590 for 28 nights
House ∙ 21 guests ∙ 6 bedrooms

Vacation Home in Uptown with Yard, Patio & Grill

5.0
Outstanding (146 ratings)
Uptown, Chicago, Illinois, United States
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Condo West Town
$9,880 for 28 nights
Condo ∙ 9 guests ∙ 2 bedrooms

Condo in West Town with Private Terrace + Skyline View

5.0
Outstanding (208 ratings)
West Town, Chicago, Illinois, United States
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Apartment Portage Park
$2,661 for 28 nights
Apartment ∙ 10 guests ∙ 3 bedrooms

Family Friendly Private Apartment in Portage Park with Yard, Grill & Patio

5.0
Outstanding (102 ratings)
Portage Park, Chicago, Illinois, United States
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Best Deals and Discounts on Monthly Rentals

Save up to 38%

House North Austin
Mar 20 - Apr 17
-35%
$11,549
$7,465 for 28 nights
House ∙ 12 guests ∙ 4 bedrooms

Nice House in North Austin with Yard, Grill & Patio

North Austin, Chicago, Illinois, United States
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Apartment Heart of Chicago
Mar 20 - Apr 17
-38%
$6,444
$4,016 for 28 nights
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Heart Of Chicago with Free Parking

4.5
Excellent (19 ratings)
Heart of Chicago, Chicago, Illinois, United States
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Apartment Ukrainian Village
May 4 - Jun 1
-17%
$7,980
$6,584 for 28 nights
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Ukrainian Village with Yard & Patio

5.0
Outstanding (1 rating)
Ukrainian Village, Chicago, Illinois, United States
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Monthly Rentals in Chicago: Top Accommodations

House West Town
$7,434 for 28 nights
House ∙ 10 guests ∙ 3 bedrooms

House in West Town with Grill & Patio, Queen Sofabed

4.9
Outstanding (50 ratings)
West Town, Chicago, Illinois, United States
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Apartment Heart of Chicago
$12,809 for 28 nights
Apartment ∙ 8 guests ∙ 3 bedrooms

Lovely Apartment in Heart Of Chicago

5.0
Outstanding (2 ratings)
Heart of Chicago, Chicago, Illinois, United States
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House Pullman
$4,480 for 28 nights
House ∙ 7 guests ∙ 4 bedrooms

Pleasant House in Pullman with Yard, Patio & Grill

4.7
Excellent (28 ratings)
Pullman, Chicago, Illinois, United States
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House Near North Side
$15,364 for 28 nights
House ∙ 11 guests ∙ 3 bedrooms

House in Near North Side with Free Garage + City View

5.0
Outstanding (2 ratings)
Near North Side, Chicago, Illinois, United States
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Condo Lake View
$14,071 for 28 nights
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Lake View with Patio & Grill

Lake View, Chicago, Illinois, United States
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Condo South Shore
$5,873 for 28 nights
Condo ∙ 8 guests ∙ 4 bedrooms

Beautiful Condo in South Shore with Grill

South Shore, Chicago, Illinois, United States
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House Goose Island
$7,434 for 28 nights
House ∙ 14 guests ∙ 3 bedrooms

Charming Vacation Home in Goose Island with Sauna, Grill & Patio

4.9
Outstanding (47 ratings)
Goose Island, Chicago, Illinois, United States
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Apartment Grand Boulevard
$2,882 for 28 nights
Apartment ∙ 8 guests ∙ 2 bedrooms

Charming Rental Apartment in Grand Boulevard

4.9
Outstanding (93 ratings)
Grand Boulevard, Chicago, Illinois, United States
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Apartment Uptown
$4,900 for 28 nights
Apartment ∙ 4 guests ∙ 1 bedroom

Rental Apartment in Uptown with Grill & Pool + Incredible Views

5.0
Outstanding (25 ratings)
Uptown, Chicago, Illinois, United States
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Budget-friendly monthly rentals in Chicago

Our top value vacation rentals for monthly rentals

Condo East Village
$6,225 for 28 nights
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in East Village

4.8
Outstanding (35 ratings)
East Village, Chicago, Illinois, United States
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House Near North Side
$15,364 for 28 nights
House ∙ 11 guests ∙ 3 bedrooms

House in Near North Side

4.0
Very good (1 rating)
Near North Side, Chicago, Illinois, United States
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House Lincoln Park
$15,225 for 28 nights
House ∙ 24 guests ∙ 4 bedrooms

Vacation Home in Lincoln Park with Grill, Patio & Yard

5.0
Outstanding (171 ratings)
Lincoln Park, Chicago, Illinois, United States
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Stay Cool: Monthly Rentals with Air Conditioning

House  Pulaski Park
$7,194 for 28 nights
House ∙ 9 guests ∙ 2 bedrooms

Charming House in Pulaski Park

4.4
Very good (3 ratings)
Pulaski Park, West Town, Chicago
Air conditioning
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House  Pulaski Park
$22,774 for 28 nights
House ∙ 16 guests ∙ 7 bedrooms

Wonderful House in Pulaski Park with Private Parking

4.8
Outstanding (10 ratings)
Pulaski Park, West Town, Chicago
Air conditioning
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Condo  Lake View
$7,120 for 28 nights
Condo ∙ 6 guests ∙ 3 bedrooms

Condo in Lake View with Grill, Yard & Patio

5.0
Outstanding (99 ratings)
Lake View, Chicago, Illinois, United States
Air conditioning
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Stay connected: Monthly Rentals with internet

Condo  East Village
$11,238 for 28 nights
Condo ∙ 6 guests ∙ 3 bedrooms

Nice Condo in East Village

East Village, Chicago, Illinois, United States
Internet
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House  Gold Coast
$7,272 for 28 nights
House ∙ 9 guests ∙ 2 bedrooms

House in Gold Coast, Close to John Hancock Center

5.0
Outstanding (1 rating)
Gold Coast, Chicago, Illinois, United States
Internet
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House  Wrightwood Neighbors
$3,356 for 28 nights
House ∙ 6 guests ∙ 1 bedroom

Vacation Home in Wrightwood Neighbors

Wrightwood Neighbors, Chicago, Illinois, United States
Internet
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Monthly Rentals with kitchens

House  East Garfield Park
$15,248 for 28 nights
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in East Garfield Park

4.8
Outstanding (10 ratings)
East Garfield Park, Chicago, Illinois, United States
Kitchen
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Apartment  Grand Boulevard
$5,040 for 28 nights
Apartment ∙ 6 guests ∙ 3 bedrooms

Beautiful Apartment in Grand Boulevard with Yard

4.2
Very good (11 ratings)
Grand Boulevard, Chicago, Illinois, United States
Kitchen
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House  South Shore
$6,085 for 28 nights
House ∙ 16 guests ∙ 3 bedrooms

Lovely House in South Shore with Private Terrace

5.0
Outstanding (12 ratings)
South Shore, Chicago, Illinois, United States
Kitchen
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Monthly Rentals with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Bed and breakfast Sheffield Neighbors
$6,409 for 28 nights
Bed and breakfast ∙ 8 guests ∙ 1 bedroom

Bed & Breakfast in Sheffield Neighbors with Yard, Jacuzzi & Grill

4.7
Excellent (95 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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House Lake View
$4,227 for 28 nights
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Lake View with Grill, Patio & Yard

4.7
Excellent (53 ratings)
Lake View, Chicago, Illinois, United States
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House University Village / Little Italy
$14,000 for 28 nights
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home in University Village / Little Italy with Jacuzzi

5.0
Outstanding (96 ratings)
University Village / Little Italy, Chicago, Illinois, United States
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Monthly Rentals in Chicago for Any Type of Traveler

Looking to accommodate a group of eight or more people in Chicago?

Start browsing our available Monthly Rentals for large groups and plan the perfect vacation! April is the most affortable time to stay in Chicago with a big group, when nightly prices for Monthly Rentals will range from $197 to $542 per night. Find luxurious Monthly Rentals for big groups in Chicago, complete with private pool, large kitchen, and plenty of space to enjoy. HomeToGo offers numerous Monthly Rentals in Chicago with seven or more bedrooms and seven or more bathrooms.

Trying to plan a big family vacation in Chicago?

Many Monthly Rentals in Chicago will cost around $669 per day for a family of 8 people but you can find lots of affordable options in Chicago to choose from. Many Monthly Rentals in Chicago come with family-friendly amenities, including game rooms, private pools, jacuzzi, and many others. Chicago has lots of fun family-friendly activities to do, including hiking, swimming, biking, and many other activities. Browse HomeToGo's selection of roomy Monthly Rentals in Chicago, able to house a big family with 7+ beds and many restrooms. Start your search for family-friendly Monthly Rentals today!

Planning a remote vacation in Chicago with your partner?

Browse HomeToGo's best Monthly Rentals for romantic getaways in Chicago now! The cheapest time to book is April with prices starting at $67 per day. You can find lots of fun things to try with your partner during your private trip, including swimming, hiking, biking, and many other outdoor activities. Book luxurious Monthly Rentals in Chicago for a private retreat, equipped with hot tub, sauna, and a amazing view of Chicago's stunning scenery.
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Information about Chicago Monthly Rentals

📏 Average home size 86 m²
🥳 Busiest month April
🛏️ Popular home types Apartment rental and House rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months January and February
🌧️ Rainiest months March and April

Frequently Asked Questions

Chicago Monthly Rentals: What is the cost per night of stay?

The average cost for a vacation home in Chicago is usually around $197 and $542 per night.

Chicago Monthly Rentals: can I find a vacation home suitable for a group?

Usually the size of a Apartment rental is 86 m² and can fit 4 guests on average which is great for medium-sized groups and families.

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

There are more than 9,663 homes to rent in Chicago. The best time to find availability for longer stays is in September when home rentals have high availability.

Chicago Monthly Rentals: what kinds of vacation rentals can I book?

There are 2,013 Apartment rentals and 575 House rentals available in Chicago.

How much does a mid-term vacation rental in Chicago cost?

Prices for vacation rentals in Chicago over a longer period start from $67 per night, but many hosts can offer discounts for stays of 14 days or longer.

Can you book seasonal vacation rentals in Chicago come with a pool?

Of course, more than 24% of accommodations in Chicago come with a pool.

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