
Condo vacation rentals in Northwest Side
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Top-rated condo rentals in Northwest Side
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Popular amenities for Northwest Side condo rentals
Weekly condo rentals

Urban Oasis Getaway. 6 stops to downtown!
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!

Apartment in Chicago
Me and my friends had a great time during our stay! The place was clean, well-kept, and in a great location—close to everything we needed. The host was very responsive and helpful throughout. Would definitely recommend!

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.

Lincoln Square Condo
Allen's place is great, I stayed for five days and loved it! My highest compliment is that it's super well-equipped, to the point it feels lived-in (in a good way). For example, the kitchen is stocked better than mine, you'll find it easy to make a meal here. The rest of the unit is well thought out, too. My one piece of advice is to pay reallyyy close attention to the check-in instructions. There are multiple entrances to the complex, and they look similar. You might end up trying the wrong lockbox 10 times if you're not careful :) Overall, I highly recommend this place! Friendly neighbors as well!

Spacious 3BR • Great for Groups • Fast WiFi • Pets
Sofia and Brendan were great hosts; very accommodating and on time with their communication. The kitchen was fully stocked with dishes, pots, pans and silverware. They even had a water pitcher to filter water which we greatly appreciated. Also some tea, coffee, creamer and snacks were available. The hosts added an additional bed to the extra sleeping area which was a really nice surprise as this was not visible on the pictures. Plenty of blankets and towels were provided. Aside from some pet hair getting stuck to our clothes from the furniture, the place was very clean and smelled great. Pets are noted on the website so that was not a too much of a surprise. Nothing that would prevent us from returning. But if you have pet allergies or this would bother you, something to note. The condo was about 20 minute walk to the metro. Overall, we were very happy with our stay and would absolutely return. Thank you Sofia and Brendan for a great stay!

Modern 2 Bedroom Walk Up Condo in Irving Park
I stayed here for 3 nights and was in town for the Chicago Marathon. Tons of restaurants within walking distance and the bus stop is a short walk, which will drop you at the Red Line train to get you downtown. Place was clean and very cute. Laundry room is a bonus!

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!

Quick Drive to Downtown Chicago & Early Check-In
Thomas is an amazing host! He was very proactive in communicating right from the start of the trip ,was very welcoming and warm. This Airbnb house is spic and span. It is very clean , beautifully decorated and has everything you need to be comfortable in a home. The Kitchen is stocked with all vessels , has basic pantry supplies and has a gas for cooking warm meals. Thomas and his wife were also very thoughtful and considerate and left us a basket full of snacks and coffee pods - that was a really sweet gesture from their end.The coat closet has umbrellas , incase you need one , which I thought was very considerate as well. Thomas also regularly checked in on us to ensure we had a smooth stay - his check in and checkout instructions were uber clear and made it possible to check in and check out without any hassles. There is a starbucks and a bunch of small restaurants on a 10 - 13 min walk from the house.Overall , I would highly recommend his house to other guests.
Pet-friendly condo rentals

Chic and Charming Vintage Condominium in Lincoln Park
We had a terrific stay and would definitely recommend it to others. Great location, especially if you are doing anything around Lincoln Park, DePaul, etc. The dedicated parking space was really helpful (there are 2 of them, but we only had one car). We had six people and were very comfortable. Colin is very responsive as well.

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
We were staying in Chicago for a concert at Soldier Field. It was extremely walkable and easy to navigate. The condo is just right with the 2 bedrooms and king sized beds. The provided keurig coffee machine and coffee was nice. Easy walk to Roosevelt station for local transportation.

RockStar Pad W3A BoysTown/Wrigley Field/Parking
My dad and I were on a baseball road trip and this was a perfect place for a cubs game! About a 15 minute walk. Will was responsive and friendly, and the place might have been one of the coolest bnbs. Such a fun and relaxing spot. Would easily stay again!

Urban Oasis | Great for Families w/ Kids
Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT
Everything went well. Place was very nice and the host was very responsive when I needed help and accommodative as well. Highly recommend if needed a place near downtown.

City Hideaway
A really cute, cozy apartment in a great location. Brock was wonderful and very responsive. There was always parking, and it was close to everything. Children upstairs were a bit noisy during the day but overall, my stay was enjoyable and I would definitely recommend the place.

Ultra clean/cozy condo, 10 mins south of Downtown!
Great host and great stay! Beautiful home. Thank you so much!

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

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.

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.

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
You can walk to Northwestern University, and the surrounding environment is clean and comfortable.The house is fully furnished, I love cooking in the kitchen.Our whole family had a great week here.Would stay again.

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
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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- 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
- Wicker Park
- Willis Tower
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center