Condo vacation rentals in Cook County

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Popular amenities for Cook County condo rentals

Weekly condo rentals

Top guest favorite
A detailed map displays central Skokie, highlighting various locations such as restaurants and shops along major streets. Key landmarks are marked, including public transport routes and parks, indicating convenient access to amenities and attractions in the area.
Condo in Skokie
4.98 out of 5 average rating, 40 reviews

Free Parking Balcony, Weekly 5% & Monthly 20% Off

InesRating, 5 stars2 weeks ago
We enjoyed our stayed. The place was very clean and comfortable. Mark was great at communicating and accommodating. We would stay there again.
Superhost
A coffee station features a Keurig coffee maker next to a cup decorated with Chicago-themed designs. A carousel of coffee pods is displayed nearby, and a sign above reads "coffee bar." The countertop is styled with a small potted plant.
Condo in Stickney
4.9 out of 5 average rating, 20 reviews

2BR Chicago Escape | 20 min DT, Parking, Laundry

DerekRating, 5 stars5 months ago
We enjoyed our stay! The location was perfect for going into the city and being able to escape the hustle and bustle. The hosts were friendly and easy to work with. We appreciated the cleanliness and furnishings of the condo.
Guest favorite
The exterior of a modern three-story condo is depicted, showcasing a facade of light-colored brick and large windows. Lush green leaves partially frame the top of the image, while a bright sky with scattered clouds forms the backdrop.
Condo in Chicago
4.93 out of 5 average rating, 61 reviews

Amazing Fun Condo, City view next to 606 Trail!

StephRating, 5 stars3 days ago
Ken’s place was a great stay! Such a unique home with so much to see inside—decor, art, photos, and trinkets. We enjoyed relaxing in the space between exploring the city. Would recommend to anyone who is considering staying in Chicago!
Top guest favorite
Condo in Chicago
4.97 out of 5 average rating, 59 reviews

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit

TammyRating, 5 stars2 weeks ago
Chip and Lito's place is a dream! Spacious, clean, quiet, and convenient to restaurants, the "L", and the beach. Apartment is very well appointed, yet not cluttered. The shower is awesome! It was very nice to have a full kitchen, with coffee makers and dishwasher. I definitely plan to stay here the next time I visit Chicago!
Superhost
Condo in Chicago
4.76 out of 5 average rating, 21 reviews

2 BR GetAway, 15mins to Loop + private parking

KrystynRating, 5 stars3 weeks ago
Absolutely loved our stay! The place was cozy, clean, and exactly as described. Michael was super welcoming and made us feel right at home.
Guest favorite
A kitchen drawer is shown with a smooth wooden base, containing several black utensils, including a slotted spoon and a spatula. A green oven mitt with a broccoli pattern rests on a cutting board, which is positioned in the corner of the drawer.
Condo in Westmont
4.9 out of 5 average rating, 30 reviews

Hidden Gem

AzadehRating, 5 stars2 days ago
Easy and clear instructions upon check in, space was clean and comfortable. The kitchen had a brand new fridge, a toaster, coffee maker, dishwasher and microwave that really came in handy, they also had new utensils/plates/cups that we were able to use. Our host was very responsive and kind throughout our stay, and was available to answer our questions/requests. Very happy we found this place, I slept in the room facing the back (parking lot) so my only recommendation is if you’re a light sleeper, to bring earbuds, but that had nothing to do with the rental itself and more of a personal preference. Also they had brand new towels for us!!
Guest favorite
The exterior of a three-story condominium building is displayed, featuring a mix of stone and glass elements. A prominent entrance is framed by tall windows on each floor. The surrounding area is landscaped with trees, providing a natural contrast to the architectural design.
Condo in Chicago
4.78 out of 5 average rating, 37 reviews

Entire Cozy Home in the Heart of Bronzeville

NgocRating, 5 stars1 month ago
This is a beautiful Airbnb, everything was absolutely clean and spotless. Plentiful amenities. We loved our stay, thank you for having us!!
Guest favorite
A private outdoor balcony features a wooden deck with a table and two wire chairs. A decorative pendant light hangs above. Lush greenery creates a natural backdrop, softly framing the space with a view of the surrounding neighborhood.
Condo in Chicago
4.95 out of 5 average rating, 44 reviews

Grand Avenue Apt 2/west Loop & Newly Renovated!

GenevieveRating, 5 stars2 weeks ago
This is a comfortable apartment, with good-sized rooms, comfortable beds, and good blinds and curtains. The bathroom is well-maintained and clean. The kitchen knives are sharp, and the stove, microwave, and dishwasher all work well. The outdoor patio is a nice plus. Although grocery stores are not exactly at your doorstep, it is a few blocks' walk to a couple of strips of nice restaurants. For light sleepers, it's advisable to sleep in the main bedroom, rather than the smaller second bedroom, as this room is on the street side and thus close to urban levels of traffic / traffic noise.

Pet-friendly condo rentals

Superhost
A spacious living area is highlighted by large windows offering expansive views of the city skyline. A comfortable sofa and two accent chairs are positioned around a coffee table. A dining table with several chairs is visible beside a colorful wall art piece that adds a touch of personality.
Condo in Chicago
4.82 out of 5 average rating, 129 reviews

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

NareshRating, 5 stars2 weeks ago
Great location right next to the train station and walking distance to lakeside. Well stocked apartment, king beds were very comfortable. Host was quick in addressing an issue with AC unit. Very nice stay in a good location in downtown Chicago, we thoroughly enjoyed the convenience and comfort of the place!
Top guest favorite
The entryway features a wooden door with a glass panel, leading to a cozy living space. Gray walls complement modern kitchen cabinetry and stainless steel appliances. A comfortable sofa, adorned with white pillows and a soft throw blanket, sits invitingly in the foreground. Decorative elements add character.
Condo in Chicago
4.99 out of 5 average rating, 175 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

RebecaRating, 5 stars2 days ago
I can't recommend this Airbnb enough! From the moment I walked in, I felt right at home. The place was not only extremely clean, but also beautifully decorated with a very welcoming atmosphere. The space is also very spacious, which was a huge plus. The host was incredible, super kind and helpful. There’s so many restaurant and fun bars in the area so there was always something to do on our down time. Thanks again Will for sharing your amazing space!
Guest favorite
An open patio space features a light blue sofa adorned with decorative pillows in vibrant colors. A round wooden table sits nearby, complemented by a stylish green side table. Soft lighting from large windows enhances the cozy atmosphere of the room.
Condo in Chicago
4.94 out of 5 average rating, 124 reviews

Urban Oasis | Great for Families w/ Kids

RichardRating, 5 stars2 weeks ago
Place was great. Clean and well laid out with plenty of room. Enjoyed our stay. Location was further than we thought from our places we planned to visit. They were cutting down and grinding a tree first thing Saturday morning. Convenient cafe right around corner had good breakfast food and coffee. Ubers were fast getting us and to where we needed to go. Parked car and left all weekend. Neighborhood was a little rough with homeless and panhandlers but they left us alone. Great walks to Soldier field and Northern Island. Alex provided all the amenities you need plus some Heinkens to cool us down. We had no issues so we did not need to contact Alex at all but yoyu got to remember the location is on 17 Place not Street so we almost walked into the wrong house and when the dog started barking at us we knew something was up. LOL!!!
Top guest favorite
A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.
Condo in Chicago
4.98 out of 5 average rating, 118 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

RebeccaRating, 5 stars1 week ago
One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!
Superhost
The exterior of a two-story condominium is shown, featuring light grey siding and white trim. The entrance is framed by a pathway bordered by manicured greenery and flower pots. Large windows provide natural light, and a well-maintained lawn enhances the welcoming appearance.
Condo in Portage
4.81 out of 5 average rating, 168 reviews

Marina Condo near Lake Michigan

AnnaRating, 5 stars6 months ago
Met our needs very well. There was a little restaurant on the premesis.
Top guest favorite
Condo in Chicago
4.92 out of 5 average rating, 346 reviews

Susie's Space. 2BR easy parking & pet friendly

MatthewRating, 5 stars3 weeks ago
Really liked it, nice location, plenty of room, comfortable, good kitchen. Getting around using buses and the subway was also very easy.
Top guest favorite
A vibrant seating area is showcased with a blue couch adorned with colorful throw pillows and a brown leather sofa. A small black coffee table rests on a patterned area rug, which features geometric designs. Large windows allow natural light to fill the space.
Condo in Chicago
4.97 out of 5 average rating, 117 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

CherannRating, 5 stars2 weeks ago
Very close to public transit, grocery stores, and restaurants. Quiet neighborhood and comfortable sleeping.
Superhost
A spacious living area is highlighted by a large sectional sofa positioned around a light area rug. Natural light filters through the floor-to-ceiling windows, while a sleek TV is mounted on the wall. Decorative plants and modern furnishings add to the inviting atmosphere.
Condo in Chicago
4.81 out of 5 average rating, 140 reviews

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

BilalRating, 5 stars5 days ago
Great place to live..!! Thanks kyriako.

Condo rentals with a pool

Guest favorite
An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

AaronRating, 5 stars4 weeks ago
I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.
Guest favorite
Condo in Evanston
4.95 out of 5 average rating, 106 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

JasonRating, 5 stars1 month ago
Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!
A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.
Condo in Chicago
4.4 out of 5 average rating, 10 reviews

voco: Balcony & City View

BrookeRating, 5 stars3 weeks ago
Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.
A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.
Condo in Lombard
4.84 out of 5 average rating, 56 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

LelandRating, 5 stars5 months ago
Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.
An outdoor pool area features a clear, blue body of water surrounded by lounge chairs. Lush greenery is placed in large planters along the perimeter, with a backdrop of modern high-rise buildings and a cloudy sky.
Condo in Chicago
4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars25 months ago
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.
Guest favorite
The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars2 months ago
I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favorite
An outdoor swimming pool is surrounded by lounge chairs, offering a relaxing space. Trees are strategically placed around the area, and large glass walls provide views to the inside. Sunlight reflects off the water, enhancing the serene setting.
Condo in Evanston
4.91 out of 5 average rating, 125 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

NinaRating, 5 stars2 months ago
We had a great stay at Michelle’s “Heart of Evanston.” I loved the indoor garage parking option with easy in and out. If you have a large vehicle /SUV, maneuvering in and out of the spot may be challenging depending if the spot over is occupied. We have a mid-size SUV and had no issues. The room was easily accessed from the garage and we had no issues getting in. The place was clean and well organized. I loved that it smelled clean and also had a faint hint of bleach in the bathroom. It was a little warm in the bedrooms at night but we used the air conditioning to bring the temperature down. Town is very walkable and we enjoyed the local restaurants (Taco Diablo, Bat 17, Bennison’s bakery). We found the town to be very quiet - almost too quiet for what we expected but after our visit to Northwestern found out it was spring break for the students. Michelle was available for any questions and always replied promptly. We had a great stay and would stay again!
A cozy living area features a sectional sofa adorned with pillows and a throw pillow inscribed with 'Enjoy.' A round coffee table holds decorative items, while framed art showcases serene designs on the wall. A small dining area is visible in the background.
Condo in Lombard
4.91 out of 5 average rating, 46 reviews

Pond View, Washer Dryer, Non Smoking Community

AsgharRating, 5 stars6 months ago
Place was neat and very clean, enjoyed our stay, location was great as it was near all the malls and restaurants in Lombard and Oakbrook.

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