Condo vacation rentals in West Side

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Popular amenities for West Side condo rentals

Weekly condo rentals

Guest favorite
Condo in Chicago
4.93 out of 5 average rating, 68 reviews

Urban Oasis Getaway. 6 stops to downtown!

LydiaRating, 5 stars1 week ago
The hosts are great—very responsive and accommodating. It’s a lovely space, with a fully functioning kitchen and very walkable to a close cta stop that’s a quick 30 minutes downtown. Area around the place is lower income, so if you’re not used to being in a city, you maybe feel less comfortable. Would recommend if you’re comfortable with urban environments though!
Top guest favorite
Condo in Chicago
5 out of 5 average rating, 30 reviews

Private rooftop | Breathtaking skyline view

BrianRating, 5 stars1 week ago
The space was exactly as advertised, roof top patio was awesome. Location was great and Anna was easy to work with. Definitely recommend, we would stay here again.
Superhost
Condo in Chicago
4.69 out of 5 average rating, 230 reviews

Studio flat in the heart of Chicago's Gold Coast

CoreyRating, 5 stars2 weeks ago
everything was extremely nice, unfortunately the knob to change from shower to faucet was detached so we could not utilize the very large beautiful bathtub. The front porch light also needs to be replaced, we opted to leave the front door open to be able to see outside after dark. Other than that everything was extremely nice. Still worthy of a five-star review.
Guest favorite
Condo in Chicago
4.9 out of 5 average rating, 86 reviews

Welcome to the Chi! Close to Downtown

MartelRating, 5 stars3 weeks ago
Enjoyed my stay at Jasna's. Great unit in a great location
Guest favorite
Condo in Chicago
4.93 out of 5 average rating, 61 reviews

Amazing Fun Condo, City view next to 606 Trail!

StephRating, 5 stars1 day 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!
Superhost
Condo in Chicago
4.89 out of 5 average rating, 37 reviews

Rustic Cozy Haven in West Town

KatieRating, 5 stars6 days ago
Yara was a great host! Very responsive, clear instructions to get into the Airbnb. The place was spacious and very clean, looked exactly like the photos. Would definitely stay there again!
Top guest favorite
Condo in Chicago
5 out of 5 average rating, 27 reviews

Quick Drive to Downtown Chicago & Early Check-In

RupalRating, 5 stars1 week ago
Thomas was a wonderful host who truly went above and beyond. He gave us excellent recommendations for vegetarian restaurants, which we really appreciated. It was our first time visiting Chicago, and Thomas’s support throughout our trip made a big difference. The Airbnb was thoughtfully stocked with everything a guest might need—even umbrellas! Highly recommended.
Superhost
Condo in Chicago
4.8 out of 5 average rating, 20 reviews

Modern Design 2bd Garden Condo Near United Center

EmilyRating, 5 stars5 days ago
This was a nice quiet place to stay that is near the city. It was about a $30 Uber to get downtown, so much cheaper than parking a car. Would stay again!

Pet-friendly condo rentals

Superhost
Condo in Chicago
4.82 out of 5 average rating, 128 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!
Guest favorite
Condo in Chicago
4.92 out of 5 average rating, 120 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

RachaelRating, 5 stars4 days ago
Our stay was fantastic. We have three children and everyone was comfortable. The location was perfect, the hosts were clear communicators and quick to respond. We would stay here again in a heartbeat.
Guest favorite
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!!!
Guest favorite
Condo in Chicago
4.91 out of 5 average rating, 163 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

AngeliqueRating, 5 stars1 week ago
Great host and great stay! Beautiful home. Thank you so much!
Top guest favorite
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!
Guest favorite
Condo in Chicago
4.92 out of 5 average rating, 238 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

EllenRating, 5 stars2 weeks ago
What a great find! I'm talking about the room AND the host! The beds were very comfortable and the amenities were all we needed. The artwork was wonderful and the design of the rooms (lamps, table, chairs etc) were great. I especially loved the small room heater, it looked like a mini fireplace, I want one for my room at home! Kaye has thought out what a guest needs with all kinds of extras (covers for the chairs for pets), extra blankets, packet full of local information, and clear instructions. She was responsive when I had questions or needs. I was glad to meet her as well, easy to talk with and a very interesting person who knows Chicago extremely well. If I make it back this way, I would definitely stay here again.
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 stars2 weeks ago
Really liked it, nice location, plenty of room, comfortable, good kitchen. Getting around using buses and the subway was also very easy.
Superhost
Condo in Chicago
4.79 out of 5 average rating, 224 reviews

Modern Luxury In Old Town - Sleeps 4

AlexanderRating, 5 stars3 weeks ago
I had a great stay! The Airbnb was easy to get to and in a fantastic location within walking distance to restaurants, bars, gyms, and public transportation. The space was very clean and well-maintained. Would definitely recommend and stay here again!

Condo rentals with a pool

Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

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

AaronRating, 5 stars3 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!
Condo in Chicago
4.33 out of 5 average rating, 9 reviews

voco: Balcony & City View

BrookeRating, 5 stars2 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.
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.
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
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
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!
Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 99 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

AileenRating, 5 starstoday
Space was clean and in a charming, walkable city. The view in the living room was beautiful. The neighbors were quiet. The coffee in the condo and in the lounge was surprisingly delightful. Our group of friends had a great time, and this would be a perfect place for a family.

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