
Condo vacation rentals in Cook County
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Top-rated condo rentals in Cook County
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Popular amenities for Cook County condo rentals
Weekly condo rentals

Free Parking Balcony, Weekly 5% & Monthly 20% Off
We enjoyed our stayed. The place was very clean and comfortable. Mark was great at communicating and accommodating. We would stay there again.

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

Amazing Fun Condo, City view next to 606 Trail!
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!

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

2 BR GetAway, 15mins to Loop + private parking
Absolutely loved our stay! The place was cozy, clean, and exactly as described. Michael was super welcoming and made us feel right at home.

Hidden Gem
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!!

Entire Cozy Home in the Heart of Bronzeville
This is a beautiful Airbnb, everything was absolutely clean and spotless. Plentiful amenities. We loved our stay, thank you for having us!!

Grand Avenue Apt 2/west Loop & Newly Renovated!
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

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

RockStar Pad W3A BoysTown/Wrigley Field/Parking
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!

Urban Oasis | Great for Families w/ Kids
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!!!

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

Marina Condo near Lake Michigan
Met our needs very well. There was a little restaurant on the premesis.

Susie's Space. 2BR easy parking & pet friendly
Really liked it, nice location, plenty of room, comfortable, good kitchen. Getting around using buses and the subway was also very easy.

Steps from the Lake, Lovely 3-Bedroom Condo
Very close to public transit, grocery stores, and restaurants. Quiet neighborhood and comfortable sleeping.

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach
Great place to live..!! Thanks kyriako.
Condo rentals with a pool

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

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

voco: Balcony & City View
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.

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony
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.

30 E. Huron #2603 Private Residence
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.

Just remodeled apartment close to airport and mall
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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

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

Pond View, Washer Dryer, Non Smoking Community
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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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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