Chicago Monthly Rentals

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• Chicago Monthly Rentals

Choose from a fantastic selection of monthly rentals

Price per night

Up to $100

$100 - $199

From $200

Distance to center

1 km

2 km

5 km

Rating

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4+

Bedrooms

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1 bedroom

2+ bedrooms

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Popular amenities for Chicago Monthly Rentals

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Monthly Rentals with internet

Monthly Rentals with pools

Monthly Rentals with parking

Pet-Friendly Monthly Rentals

Top-rated monthly rentals in Chicago

Browse our top rated monthly rentals offers

Jan 6 - Jan 13

$658 for 7 nights

Condo ∙ 5 guests ∙ 2 bedrooms

Condo in The Gap

4.8

Outstanding (29 ratings)

The Gap, Chicago, Illinois, United States

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Jan 20 - Jan 27

-16%

$2,905

$2,450 for 7 nights

House ∙ 10 guests ∙ 5 bedrooms

Wonderful House in Palmer Square with Grill

4.9

Outstanding (6 ratings)

Palmer Square, Chicago, Illinois, United States

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Jan 27 - Feb 3

-42%

$7,752

$4,482 for 7 nights

House ∙ 17 guests ∙ 6 bedrooms

Family Friendly Vacation Home in Bridgeport with Delightful Barbecue

4.7

Excellent (3 ratings)

Bridgeport, Chicago, Illinois, United States

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Best Deals and Discounts on Monthly Rentals

Save up to 63%

Dec 10 - Dec 17

-63%

$3,583

$1,339 for 7 nights

House ∙ 12 guests ∙ 4 bedrooms

Nice House in North Austin with Yard & Grill

North Austin, Chicago, Illinois, United States

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May 8 - May 15

-55%

$2,458

$1,108 for 7 nights

House ∙ 10 guests ∙ 3 bedrooms

House in Humboldt Park with Pool, Grill & Sauna + Degree Views

Humboldt Park, Chicago, Illinois, United States

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Jan 6 - Jan 13

-20%

$1,794

$1,435 for 7 nights

House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Beverly with Grill

4.2

Very good (14 ratings)

Beverly, Chicago, Illinois, United States

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Monthly Rentals in Chicago: Top Accommodations

Dec 16 - Dec 23

$693 for 7 nights

Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment in Washington Park

Washington Park, Chicago, Illinois, United States

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Feb 24 - Mar 2

$350 for 7 nights

Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in West Ridge

West Ridge, Chicago, Illinois, United States

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Mar 1 - Mar 8

$643 for 7 nights

Apartment ∙ 5 guests ∙ 2 bedrooms

Entire Rental Apartment in Palmer Square with Free Parking

Palmer Square, Chicago, Illinois, United States

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Jan 6 - Jan 13

-59%

$1,913

$787 for 7 nights

House ∙ 8 guests ∙ 3 bedrooms

Wonderful Vacation Home in The Island with Yard

The Island, Chicago, Illinois, United States

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Dec 16 - Dec 23

-73%

$2,849

$761 for 7 nights

Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Tri-Taylor

Tri-Taylor, Chicago, Illinois, United States

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Jan 13 - Jan 20

-66%

$6,725

$2,319 for 7 nights

House ∙ 8 guests ∙ 3 bedrooms

House in Washington Park with Yard

Washington Park, Chicago, Illinois, United States

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Dec 15 - Dec 22

-78%

$2,747

$604 for 7 nights

House ∙ 9 guests ∙ 4 bedrooms

House in Douglas

Douglas, Chicago, Illinois, United States

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Dec 16 - Dec 23

-61%

$1,980

$774 for 7 nights

Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Heart Of Chicago with Free Parking

Heart of Chicago, Chicago, Illinois, United States

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Dec 23 - Dec 30

-57%

$3,542

$1,530 for 7 nights

House ∙ 8 guests ∙ 2 bedrooms

House in River North with Private Parking, Next to Magnificent Mile + Panoramic Views

3.0

(4 ratings)

River North, Chicago, Illinois, United States

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Budget-friendly monthly rentals in Chicago

Our top value vacation rentals for monthly rentals

Nov 2 - Nov 9

$1,961 for 7 nights

House ∙ 10 guests ∙ 3 bedrooms

House in West Town with Grill, Queen Sofabed

West Town, Chicago, Illinois, United States

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Dec 15 - Dec 22

-41%

$2,160

$1,269 for 7 nights

Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Near North, Next to John Hancock Center

Near North, Chicago, Illinois, United States

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Mar 16 - Mar 23

$840 for 7 nights

Apartment ∙ 8 guests ∙ 3 bedrooms

Rental Apartment in Washington Park

Washington Park, Chicago, Illinois, United States

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Monthly Rentals with Kitchens

Jan 6 - Jan 13

-56%

$6,994

$3,073 for 7 nights

Condo ∙ 14 guests ∙ 7 bedrooms

Condo in Wicker Park

Wicker Park, Chicago, Illinois, United States

Kitchen

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Jan 6 - Jan 13

-71%

$5,974

$1,756 for 7 nights

Apartment ∙ 12 guests ∙ 4 bedrooms

Apartment in Heart Of Chicago

Heart of Chicago, Chicago, Illinois, United States

Kitchen

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Jan 20 - Jan 27

-62%

$6,482

$2,450 for 7 nights

House ∙ 16 guests ∙ 7 bedrooms

Wonderful Vacation Home in Cragin with Yard

Cragin, Chicago, Illinois, United States

Kitchen

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Stay Connected: Monthly Rentals with Internet

Mar 2 - Mar 9

-39%

$1,087

$665 for 7 nights

Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Greater Grand Crossing

Greater Grand Crossing, Chicago, Illinois, United States

Internet

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Jan 13 - Jan 20

-75%

$3,218

$789 for 7 nights

Apartment ∙ 6 guests ∙ 2 bedrooms

Stylish Rental Apartment in Wrigleyville + Lake View

Wrigleyville, Chicago, Illinois, United States

Internet

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Jan 20 - Jan 27

$852 for 7 nights

Condo ∙ 9 guests ∙ 3 bedrooms

Condo in West Lakeview

West Lakeview, Chicago, Illinois, United States

Internet

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Stay Cool: Monthly Rentals with Air Conditioning

Dec 15 - Dec 22

-39%

$1,962

$1,201 for 7 nights

House ∙ 14 guests ∙ 3 bedrooms

Charming Vacation Home in Goose Island with Sauna & Grill

Goose Island, Chicago, Illinois, United States

Air conditioning

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Oct 19 - Oct 26

$2,655 for 7 nights

Apartment ∙ 7 guests ∙ 3 bedrooms

Apartment in West Loop with Grill

5.0

Outstanding (1 rating)

West Loop, Chicago, Illinois, United States

Air conditioning

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Jan 5 - Jan 12

-78%

$6,302

$1,385 for 7 nights

House ∙ 12 guests ∙ 5 bedrooms

House in West Town

West Town, Chicago, Illinois, United States

Air conditioning

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Monthly Rentals with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Nov 23 - Nov 30

-40%

$1,317

$795 for 7 nights

Condo ∙ 6 guests ∙ 2 bedrooms

Spacious Condo in Rogers Park with Private Garden

Rogers Park, Chicago, Illinois, United States

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Mar 2 - Mar 9

-24%

$2,475

$1,890 for 7 nights

House ∙ 4 guests ∙ 2 bedrooms

House in Andersonville with Yard, Grill, Hot Tub

Andersonville, Chicago, Illinois, United States

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Dec 16 - Dec 23

$341 for 7 nights

Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed & Breakfast in Englewood with Jacuzzi & Grill

Englewood, Chicago, Illinois, United States

Free cancellation

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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! January is the most affortable time to stay in Chicago with a big group, when nightly prices for Monthly Rentals will range from $205 to $604 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 $604 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 January with prices starting at $45 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.

Information about Chicago Monthly Rentals

💳 Highest rates	in October
🥳 Busiest month	November
🛏️ Popular home types	House rental and Apartment rental
🌡️ Hottest months	84 °F in July and August
❄️ Coldest months	January and February
🌧️ Rainiest months	March and April

Frequently Asked Questions

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

You can find more than 9,366 accommodations for rent in Chicago. The best time to find availability for longer stays is in December when home rentals have high availability.

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

We would advice checking out our incredible selection of House rental and Apartment rental for Chicago Monthly Rentals.

Chicago Monthly Rentals: What is the nightly cost of a stay?

On average, you can get a great vacation home for somewhere between $205 and $604 and find discounts up to 67%!

Can I find a vacation rental for a large group for Chicago Monthly Rentals?

Usually the size of a Apartment rental is 83 m² and may fit 4 people on average which is great for medium-sized groups and families.

How much does a monthly vacation home rental in Chicago cost?

Cost of a longer stay in vacation rental in Chicago range from $45 per night, but many hosts offer discounts for stays of 14 days or longer.

Do many mid-term rentals in Chicago include a pool?

Definitely, more than 25% of accommodations in Chicago offer a pool.

Searching for something else?

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