Chicago Monthly Rentals - HomeToGo base64Hash Chicago Monthly Rentals - HomeToGo

Chicago Monthly Rentals

Find the perfect home in Chicago
Anytime
1 guest
Anytime
1 guest

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • Cabin
    • House

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Bedrooms

    • Any
    • 1 bedroom
    • 2+ bedrooms

  • Booking Options

    • Instant Booking

  • Services

    • WiFi
    • Pool
    • Parking
    • Kitchen
    • TV
    • Air conditioning
    • Balcony/patio
    • Washing machine
    • Microwave
    • Hot tub
    • Fireplace
    • Dishwasher
    • Yard
    • Sauna
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Chicago Monthly Rentals: Recommended rentals

Chicago Monthly Rentals: find your perfect rental from just $80 per night!

House Goose Island
Jun 14 - Jul 12
House ∙ 14 guests ∙ 3 bedrooms

Children-friendly charming vacation home with sauna, patio & BBQ | City view | Perfect for remote work

Goose Island, Chicago, Illinois, United States
$340
per night
Outstanding(52 ratings)
$340
per night
View deal
Condo Lincoln Park
Sep 6 - Oct 4
Condo ∙ 8 guests ∙ 5 bedrooms

Family-friendly condo with garden & patio

Lincoln Park, Chicago, Illinois, United States
$506
per night
Outstanding(37 ratings)
$506
per night
View deal
Apartment Rush & Division
Sep 6 - Oct 4
Apartment ∙ 7 guests ∙ 3 bedrooms

Family-friendly rental apartment with terrace | Close to John Hancock Center | City view

Rush & Division, Chicago, Illinois, United States
$467
per night
Outstanding(7 ratings)
$467
per night
View deal
Apartment Wicker Park
Jul 31 - Aug 28
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment | Good for workation

Wicker Park, Chicago, Illinois, United States
$420
per night
Excellent(4 ratings)
$420
per night
View deal
Apartment Near North
Sep 6 - Oct 4
Apartment ∙ 7 guests ∙ 2 bedrooms

Holiday apartment with terrace | Near John Hancock Center | City view

Near North, Chicago, Illinois, United States
$142
per night
Good(22 ratings)
$142
per night
View deal
Apartment Heart of Chicago
Sep 6 - Oct 4
Apartment ∙ 8 guests ∙ 2 bedrooms

Holiday apartment with patio, grill & hot tub

Heart of Chicago, Chicago, Illinois, United States
$182
per night
Outstanding(5 ratings)
$182
per night
View deal
Condo Rogers Park
Sep 6 - Oct 4
Condo ∙ 8 guests ∙ 4 bedrooms

Fully equipped condo with garden, barbeque & jacuzzi | Nature view | Pets are welcome

Rogers Park, Chicago, Illinois, United States
$297
per night
Outstanding(246 ratings)
$297
per night
View deal
House Avalon Park
Jul 3 - Jul 31
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly vacation home | Suitable for remote work

Avalon Park, Chicago, Illinois, United States
$469
per night
Outstanding(1 rating)
$469
per night
View deal
Apartment Streeterville
Sep 6 - Oct 4
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with terrace | Near John Hancock Center | City view | Good for workation

Streeterville, Chicago, Illinois, United States
$309
per night
Excellent(38 ratings)
$309
per night
View deal
House Bronzeville
Jul 31 - Aug 28
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with patio | Suitable for remote work

Bronzeville, Chicago, Illinois, United States
$583
per night
Outstanding(30 ratings)
$583
per night
View deal
Apartment River West
Sep 6 - Oct 4
Apartment ∙ 7 guests ∙ 4 bedrooms

Apartment with barbeque | City view

River West, Chicago, Illinois, United States
$835
per night
$835
per night
View deal
Apartment West Loop
Sep 6 - Oct 4
Apartment ∙ 8 guests ∙ 4 bedrooms

Rental apartment with terrace & BBQ

West Loop, Chicago, Illinois, United States
$1,056
per night
$1,056
per night
View deal
Aparthotel Near North
-15%
Sep 6 - Oct 4
Aparthotel ∙ 6 guests ∙ 3 bedrooms

Fully equipped beautiful aparthotel with terrace, barbeque & sauna | Next to John Hancock Center | City view

Near North, Chicago, Illinois, United States
$1,009$674
per night
Outstanding(250 ratings)
$1,009$674
per night
View deal
House South Chicago
Mar 2 - Mar 30
House ∙ 5 guests ∙ 4 bedrooms

Charming house with 4 rooms for 5 persons

South Chicago, Chicago, Illinois, United States
$280
per night
$280
per night
View deal
Condo Roscoe Village
Sep 6 - Oct 4
Condo ∙ 10 guests ∙ 5 bedrooms

Fully equipped condo

Roscoe Village, Chicago, Illinois, United States
$415
per night
Good(50 ratings)
$415
per night
View deal
Show all 11,235 properties

Popular amenities for Chicago Monthly Rentals

Find the perfect home for your stay

Monthly Rentals with internet

Monthly Rentals with internet

Monthly Rentals with pools

Monthly Rentals with pools

Monthly Rentals with parking

Monthly Rentals with parking

Pet-Friendly Monthly Rentals

Pet-Friendly Monthly Rentals

Top-rated monthly rentals in Chicago

Browse our top rated monthly rentals offers

Condo Grand Boulevard
Jul 3 - Jul 31
$210
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo | City View | Perfect for Remote Work

5.0
Outstanding(28 ratings)
Grand Boulevard, Chicago, Illinois, United States
View deal
Apartment Streeterville
Jul 3 - Jul 31
$440
per night
Apartment ∙ 6 guests ∙ 4 bedrooms

Rental Apartment with Terrace | Close to John Hancock Center | City View

4.7
Excellent(27 ratings)
Streeterville, Chicago, Illinois, United States
View deal
Apartment Near West Side
Jan 2 - Jan 30
-30%
$524
$312
per night
Apartment ∙ 10 guests ∙ 3 bedrooms

Family-Oriented Apartment with Grill

5.0
Outstanding(4 ratings)
Near West Side, Chicago, Illinois, United States
Free cancellation
View deal

Best Deals and Discounts on Monthly Rentals

Save up to 54%

House Fifth City
Feb 26 - Mar 26
-54%
$279
$173
per night
House ∙ 5 guests ∙ 3 bedrooms

Children-Friendly Beautiful Vacation Home with Garden, Barbeque & Patio | Perfect for Remote Work

4.9
Outstanding(18 ratings)
Fifth City, Chicago, Illinois, United States
View deal
Apartment Fulton Market
Jan 23 - Feb 20
-34%
$740
$280
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Wonderful Holiday Apartment with Patio

5.0
Outstanding(2 ratings)
Fulton Market, Chicago, Illinois, United States
View deal
Apartment South Austin
Apr 1 - Apr 29
-26%
$397
$273
per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Holiday Apartment with Yard

5.0
Outstanding(1 rating)
South Austin, Chicago, Illinois, United States
Free cancellation
View deal

Budget-friendly monthly rentals in Chicago

Our top value vacation rentals for monthly rentals

Condo Pulaski Park
Jul 3 - Jul 31
$304
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with 3 Rooms for 8 Persons

4.4
Very good(10 ratings)
Pulaski Park, West Town, Chicago
View deal
Condo River North
Mar 31 - Apr 28
-34%
$1,233
$458
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo | Near John Hancock Center

5.0
Outstanding(68 ratings)
River North, Chicago, Illinois, United States
View deal
Apartment Washington Park
Jun 22 - Jul 20
$103
per night
Apartment ∙ 3 guests ∙ 3 bedrooms

Holiday Apartment with Barbeque & Patio | Good for Workation

Washington Park, Chicago, Illinois, United States
View deal

Monthly Rentals with Yards

House Lake View
Feb 15 - Mar 15
$875
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with patio, barbecue & garden | Suitable for remote work

5.0
Outstanding(11 ratings)
Lake View, Chicago, Illinois, United States
Yard
View deal
House Oakland
Jun 22 - Jul 20
$505
per night
House ∙ 10 guests ∙ 7 bedrooms

Vacation Home with Terrace, Barbeque & Yard | Lake View

4.9
Outstanding(12 ratings)
Oakland, Chicago, Illinois, United States
Yard
View deal
House Grand Boulevard
Mar 1 - Mar 29
$535
per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly pleasant house with yard & barbecue | Perfect for remote work | Pet-friendly

5.0
Outstanding(7 ratings)
Grand Boulevard, Chicago, Illinois, United States
Yard
View deal
See all offers

Monthly Rentals with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Aparthotel Near North
May 1 - May 29
$1,043
per night
Aparthotel ∙ 7 guests ∙ 4 bedrooms

Aparthotel with jacuzzi, barbecue & patio | Near John Hancock Center | City view

5.0
Outstanding(213 ratings)
Near North, Chicago, Illinois, United States
View deal
House West Town
Apr 1 - Apr 29
$335
per night
House ∙ 10 guests ∙ 5 bedrooms

Fully equipped house with BBQ, hot tub & terrace | City view

4.9
Outstanding(58 ratings)
West Town, Chicago, Illinois, United States
View deal
Condo Rogers Park
Jul 3 - Jul 31
$265
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, yard & hot tub | Lake view

4.8
Outstanding(214 ratings)
Rogers Park, Chicago, Illinois, United States
View deal

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 $133 to $719 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 $583 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 $80 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

📏 Average home size 92 m²
😎 Least busy month March
🛏️ Popular home types Apartment rental and House rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months January and February
🌧️ Rainiest months 9 rainy days in March and April

Chicago Monthly Rentals: frequently asked questions

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

HomeToGo offers incredible vacation rentals, with prices as low as $80 per night.

Chicago Monthly Rentals: are there many vacation rentals available for large groups?

Usually the average Apartment rental size is 92 m² and may fit 5 people on average which is ideal for medium-sized groups and families.

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

You can find more than 11,235 homes to rent in Chicago. The best time to find availability for longer stays is in March when home rentals have high availability.

Chicago Monthly Rentals: what kinds of vacation rentals are available?

You can choose from 2,399 Apartment rentals and 653 House rentals in Chicago on HomeToGo.

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

Cost of a longer stay in vacation rental in Chicago start from $80 per night, but many hosts can offer discounts for stays of 14 days or longer.

Can you book monthly vacation home rentals in Chicago include a pool?

Absolutely, over 23% of accommodations in Chicago offer a pool.

Check out more vacation options

Discover other popular accommodation types

Check out other vacation accommodation options in Chicago

Vacation rentals near Chicago with popular amenities

Check out vacation rentals with popular amenities in Chicago

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