Choose from a fantastic selection of monthly rentals
Popular amenities for Chicago Monthly Rentals
Find the perfect home for your stay
Top-rated monthly rentals in Chicago
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Best Deals and Discounts on Monthly Rentals
Save up to 63%
Monthly Rentals in Chicago: Top Accommodations
Budget-friendly monthly rentals in Chicago
Our top value vacation rentals for monthly rentals
Monthly Rentals with Kitchens
Stay Connected: Monthly Rentals with Internet
Stay Cool: Monthly Rentals with Air Conditioning
Monthly Rentals with Hot Tubs
Rentals Featuring Jacuzzis and Whirlpools
Monthly Rentals in Chicago for Any Type of Traveler
Looking to accommodate a group of eight or more people in Chicago?
Trying to plan a big family vacation in Chicago?
Planning a remote vacation in Chicago with your partner?
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.