
Condo vacation rentals in Illinois
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Top-rated condo rentals in Illinois
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Chic and Charming Vintage Condominium in Lincoln Park
The apartment was perfect for what we needed and super walkable to all transit options we utilized. Also a cozy and roomy enough place for 5 people to unwind together at the end of the night. Great food options surround you too! Wake up and go downstairs to Corner Kitchen, or order late night pizza at Pequods next door. Love the balcony the apartment has! Perfect city stay. Colin was a communicative and thorough host. We will be back!

A Stones Throw from U Chicago South Campus!
Great location within walking distance of University of Chicago and in a safe neighbourhood. Basement apartment with 2 bedrooms. Bed was comfortable & extra pillows & blankets were provided. Toilet & kitchen facilities were slightly dated but functional. Appreciated the use of washer/dryer & complimentary coffee/tea. Very hospitable host!

NEW! Spacious Modern 5 BD Condo
Great place for our Chicago spring break trip. House photos were current, it had listed amenities, and was 2 blocks walk to the Blue line and plenty of shops/restaurants were walking distance. Nice neighborhood close to the action. I would note a few things for people considering this house : 1) Parking was readily available near the unit during daytime hours, but was trickier in the evenings/weekends. We did (eventually) always find a spot somewhere nearby when we drove places. 2) Layout of bedrooms is: main floor king bedroom with private shower bathroom; main floor queen, main floor full bath. Basement has other king, two queen rooms, and other full bathroom. 3) The quiet hours in the rules make even more sense when you realize this unit is 1st/basement and someone else (with little kid(s) lives on 2/3. It worked well for us since we had kids with us too so our noisy times were mostly in sync. 4) Ally was super responsive when we had questions or issues. A+ for that!

Dream Condo steps from Wrigley Field!
I would definitely stay here again! Walking distance from Wrigleyville bars, restaurants and stadium. Comfortable, clean and quiet.

Logan Square Beauty with 2 Bedrooms W/parking
We really enjoyed our three nights in Matt's roomy upstairs apartment. Great to have a space in his garage; the car stayed parked there while we took the blue line downtown each day. It was an easy 10 minute walk to the Logan Square station. If you're flying into or out of O'Hare, it would be convenient, since the airport is the last stop on the blue line.

Ultra clean/cozy condo, 10 mins south of Downtown!
Eugene is an amazing host that is very communicative and flexible. This property looked just like the pictures, clean, safe and bigger than expected. The property is in walking distance of two amazing restaurants Taqueria Varitas and a breakfast place called peaches. 10/10 highly recommend!

The Broadway Special - 2 Bd/1 Bath Smart-Condo!
I had a great stay at Newell’s place! The home was clean, cozy, and just as described in the listing. Check-in was smooth, and communication with Newell was quick and helpful the whole time. The neighborhood felt safe and peaceful, and I appreciated the extra touches like fresh towels, local recommendations, and a fully stocked kitchen. Whether you’re passing through or staying for a bit longer, this is definitely a spot I’d book again. Thanks for the hospitality, Newell!
Pet-friendly condo rentals

816 PLZN Luxury Apt | Rooftop | Garage Parking
such a great lovely place to stay thank you for the great hospitality!

Studio Apartment
It was a great stay 10/10! Barb sent very thorough and easy instructions on how to get to the house! When I arrived she showed me around and was very friendly and welcoming! The house was very clean and neat and my favorite thing about the stay was all of the lovely flowers and decor! I will be staying here again!

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT
Wonderful, everything was clean and lots of fun stuff nearby I recommend anyone book here it’s a great stay

Urban Oasis | Great for Families w/ Kids
We had a very good stay for a friends wedding a few blocks away in Chicago. As it is very modern, cozy, and clean. Alex's response time is very quick to whatever may arise. We would highly recommend staying there. Thanks for the stay!

Downtown Mich Ave #7| Park View Penthouse +gym
Beautiful spot, cannot be be beat, was a block away from our favorite pizza spot and a few blocks from our dumpling place. The rooftop view is stunning, panoramic view of the city. As for the apt — it was very well laid out, maximizing all of the space and the softest couch we’ve had in any Airbnb to date. Hosts were in constant communication and we were only there for a long weekend university visit. Very happy with the place, would use again this summer or for any future visits to the city.

Cozy 1bdr Rogers Park, Loyola, Northwestern.
Love this place! It’s peaceful, walkable, plenty of things to do in the area and close to the Lake. Will definitely be back to stay here and visit family. Thanks Kaye, for always being responsive and helpful.

Susie's Space. 2BR easy parking & pet friendly
We loved our stay here. The place was very comfortable and spacious. The area was close to restaurants either walking distance or a short drive. Parking was super easy and Susan was very accommodating with us having 2 cars. Would highly recommend this place!

Pets OK | Walk Score 95 | Desk | 1,750ft² |W/D
Great stay!! Perfect location and it suited our family and dogs wonderfully while we weee in Chicago for 4 nights. I passed this listing along to a friend who is looking to stay in the same area. Overall great experience and we loved our time there!
Condo rentals with a pool

Beautiful Lake Galena Views - Walk to Stonedrift S
We just returned from a 3-night stay at this incredible Airbnb, and I can't recommend it enough! Our group of four had an absolute blast – it truly exceeded all our expectations. First and foremost, the cleanliness was top-notch. You could tell the hosts take pride in maintaining a space that makes guests feel welcome and comfortable from the moment they step inside. The amenities were thoughtfully curated – we didn't want for a single thing during our stay. From the kitchen to the bedrooms to the living areas, every detail was considered to create a home-away-from-home atmosphere. But what really made our stay special was the peaceful surroundings. The quiet, relaxing environment was the perfect antidote to our busy lives. We left feeling refreshed and rejuvenated. If you're looking for a stress-free, comfortable getaway... look no further. We can't wait to come back and create more amazing memories.

Modern Feel Condo 2 bd /2 bath 1 car garage
Damon's place was perfect for us! Really nice and cozy and had all we needed. Damon was super nice and helpful. Highly recommend

Lake Links Loft in Galena, Illinois
Our family had a fantastic job at Dan's place. The location is great - close enough to the Eagle Ridge Inn and Owners Club, but very private location with a beautiful view of the lake. The unit had everything we need and was much larger than the pictures made it seem. Galena had great shopping and restaurants. Galena Territory Owners Club indoor pool was perfect for the kids. I'd recommend staying here anytime we make it back to Galena Territory!

Long Bay Point Unit C5
My husband and I stayed here for 4 nights. It's a 10 min drive from downtown Galena in a quiet wooded area with paved trails that you can take to the nearby amenities. The place was clean, quiet, and the bathtub was amazing! The gym and indoor/outdoor pool are very nice but about 1.5 miles from the condo which wasn't stated anywhere (or at least not anywhere we saw) and was a little disappointing but overall wasn't a huge deal. The restaurant is a short walk through the trails or you can drive to it. It's right next door. Also, the initial message you get after booking with the rules and asking to email them out of the app was a little daunting and not normal for Airbnb bookings. It just had a less "homey" experience that you expect from Airbnb. It made me slightly nervous but after everything I would certainly stay here again.

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! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

Harbor Inn- The Oriole Suite
The place was clean and just as it was described.

The Getaway - Chic 2bd Condo, Golf, Pool & More
It was a very nice place. Peaceful and beautiful inside and out. Lots of things to do. Had a great overall experience.
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