Monthly Rentals in South Loop, Chicago

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Guest favourite
Flat in Near South Side
4.84 out of 5 average rating, 61 reviews

Modern 2BR Chicago Stay near McCormick & Willis

KaeRating, 5 stars2 weeks ago
We initially were staying with another host, but they canceled last minute. Milan was kind enough to help us out with the cleaning fee so we could afford the difference in price, and was an absolute gem after that as well! The apartment was clean, cozy, and in walking distance to everything we needed (including a ton of food and the convention center for C2E2) and had a lovely patio we spent some evenings on. The host checked up on us frequently and was understanding with a minor hiccup we had with a remote. Will look to them if we come back to Chicago again!
Guest favourite
Flat in Little Italy
4.95 out of 5 average rating, 41 reviews

Spacious Studio in Little Italy, Near West Loop

MaríaRating, 5 stars2 weeks ago
best hospeje option in Chicago .. host the best care I've had for a lot in America
Superhost
Flat in The Loop
5 out of 5 average rating, 3 reviews

*BRAND NEW* Luxury Apt in Downtown Chicago

DaneRating, 5 stars9 months ago
The place was wonderful. Quiet, beautiful views, clean, nice river walk, close to good restaurants, great amenities and people at the front desk. It was definitely worth the price, I paid more for a previous Airbnb that wasn't half as good. When I move back to Chicago this space is definitely at the top of my list. Victor was also fantastic to deal with. He was extremely accommodating, always prompt to respond (even late at night), very friendly, low maintenance, and generous. He's everything you want in a host, I cannot recommend him enough!
Private room in Little Italy
4.81 out of 5 average rating, 69 reviews

Sunny Place with Restaurants Around the Corner

bassamRating, 5 stars12 months ago
roseanna is a great host we had a wonderful stay

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.

Stay near South Loop, Chicago's top sights

Millennium Park1,243 locals recommend
Shedd Aquarium673 locals recommend
The Field Museum657 locals recommend
Willis Tower Skydeck348 locals recommend
Au Cheval620 locals recommend
Girl & The Goat496 locals recommend
*Some exclusions may apply in certain geographies and for some properties.
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