
Vacation rentals with a patio in North Side
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Top-rated patio rentals in North Side
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Apartment rentals with a patio

Midcentury, comfy 2bed/2bath
Diana was great. She was immediately responsive to any question or if I needed anything. She was also very friendly and just made staying at her place very comfortable. The place has a lot of space, which is really nice. The 608 walkway is 2 blocks away and is a great walk, and allows you to exit at various points and visit the Logan Park area, and get food, etc... Getting to Wrigley or thr Frank Lloyd Wright house is a quick drive (arnd 5/6 miles). I didnt want to leave and really enjoyed my stay at Diana's place.

Lovely 2bedroom 1bath Apt and outdoor seating.
One of the nicest, cleanest apartments we have ever rented. Very spacious and modern. We loved the back patio and the decor throughout. Close to pretty much everything! Would definitely rent this one again!

Andersonville's Secret Garden: 2 beds, 1 bath
Great stay in Chicago, Andersonville is a really fun and charming area with lots of cool shops and restaurants. Easy walk to the L. The apartment is beautiful, love the rooftop deck, especially!

Chic Penthouse In Perfect Wrigleyville Location
Super cute place in a safe neighborhood. The owner's were super nice and communicated with us quickly. We had everything we needed!

Logan Square 2BR Garden Unit
Kimberly house was beyond clean and spotless. Exactly what I love when booking a Airbnb. She was very responsive and instructions were very clear. The neighborhood was quiet and peaceful. The crib look exactly like her pictures and super clean! I def would stay here again.

Modern Lakefront Retreat with Breathtaking Views!
Great 1st floor town home on the boarder between Rogers Park and Evanston, right on the waters of Lake Michigan. Lots of sunlight (and able to watch the sunrise over Lake Michigan in the morning) and a couple of parks next door. The bathrooms (especially the showers) were great--full size, nice water pressure. I was able to work remotely while I was there without any issues. As others have noted, parking is on the street; but if you're proactive or book with Spot Hero or similar, it's very manageable. I really enjoyed my stay!

Logan Square Oasis
Really liked the neighborhood. Was a short walk to the blue line. The place was perfect and will come back again.

Private City Hideaway
great stay! loved the place, would definitely recommend
House rentals with a patio

Division St Designer Home In Heart of Wicker Park
I traveled to Chicago for work and had a nice three-day stay here. The Airbnb is in a great location, clean, and well-equipped with thoughtful amenities. I particularly enjoyed the small library!

Alluring Avondale Abode
Beth was an amazing host! Super easy to work with! The place was beautiful, immaculate and comfortable. Would definitely stay there again!

Garden/unit/1+1/cosy
First time staying at an Air Bnb and it was amazing. Instructions were very clear and the place had everything we needed!

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
We were 4 adult and 1 dog and we stayed at Matthew's place, everything went smooth and easy to feel at home, parking spot and great location of the house make us everything easier, it was so fast to get to the downtonw in lees than 20 minutes. Matthew was always responsive to all our questions, I definitely will search for this place to sray on my next trip to chicago.

LAVISH LINCOLN PARK Home w/ Patio +attached garage
Nicole and Matt’s place is a well-located, spacious apartment perfect for a family of four adults. Situated near Lincoln Park, it’s within walking distance to the park and a fantastic selection of restaurants. Nicole and Matt were also kind enough to provide recommendations and we did enjoy a couple of them. The apartment is clean, well-maintained, and fully equipped for a comfortable 4-day stay. The hosts were very responsive and provided clear check-in instructions. One consideration: the unit is spread over three levels, with the master bedroom on the top floor—potentially challenging for those with mobility issues. The second bedroom, located on the ground floor, lacks natural light and feels a bit confined. Overall, we had a pleasant and convenient stay.

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath
We had a truly wonderful stay at Casa22. The home is beautiful, luxurious, and impeccably maintained — everything was clean, spotless and thoughtfully arranged. It had all the essentials we needed for a comfortable extended stay with our family, including a well-equipped kitchen, and spacious layout. The hosts, Narcis and Gabriel, were fantastic — extremely responsive, clear in their communication. They provided detailed instructions that made check-in, check-out, and everything in between seamless. The neighborhood is quiet, safe, and very family-friendly, with easy access to main roads — a great location if you're planning to explore Chicago without the stress of city parking. Having a car made it easy to get around, and the area itself felt peaceful and well-kept. If you're visiting the Chicago area and looking for a clean, elegant, and well-managed place to stay, I highly recommend Casa22. We would absolutely love to return!

Unique porcelain-enamel paneled "Lustron" home
We enjoyed our 2nd visit as much as the 1st. Great location! Wonderful hosts! Cool house! Comfortable beds! Beautiful serene backyard. (=

BoHo House - A Chic, 1903 Chicago Workers Cottage
My family and I had a fantastic stay! The space was exactly as described; clean, stylish, and thoughtfully designed. Check-in was smooth, and Adam was super helpful throughout our visit. We especially appreciated the backyard for our dogs . The location was perfect. It was close to everything we needed but still quiet and peaceful. Would absolutely stay here again and highly recommend to anyone visiting the area!
Condo rentals with a patio

Interior Designer’s 2bd 2bath w Private Backyard
A Designer’s Dream – Absolute Perfection! This home is truly exceptional—every detail reflects thoughtful design and top-tier quality. It’s a designer’s dream, with stunning décor, a comfortable and beautifully clean space, and every amenity you could possibly need. The furnishings and finishes are stylish and well appointed, making the entire experience feel luxurious and relaxing. But the real showstopper? The backyard! It’s like a second living room—lush, tranquil, and designed for ultimate comfort and enjoyment. We loved spending time out there and honestly didn’t want to leave. It's so much better than anything a hotel could even begin to provide! We will absolutely be back!

The Ramblers Inn, Northside NEW Reno w/parking!
Easy check in and close to LUC which is what we needed. Clean and comfortable. Bonus that it included parking.

Logan Square Beauty with 2 Bedrooms W/parking
Very nice place. Looked professionally cleaned. Matt was prompt with his replies and managed to accomodate a late check out, which was helpful. 10 mins walk to Logan Square station where you can catch blue line to downtown.

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
I was coming to Chicago to just have a quiet weekend away from work and the stresses of home. I wanted a few days to enjoy urban life peacefully doing a few things I enjoy. This spot checked off all the boxes for peaceful and private but also re adorably we'll located to hit all of the spots around Chicago. The place was exactly as pictured and clean. couldn't have been easier and I would stay here again. hosts were responsive. it was a great few days.

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
This was a fabulous place to stay! My brother and I could easily walk to the "L" and head downtown. The pizza place right downstairs was delicious - we ate there twice in three days! The beds were comfortable, the couch and living room set up was cozy. I would absolutely stay there again!

💥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!

Modern Chicago Movie Themed Apt
We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

Chic Home! Walk to Nightlife-Comedy-Restaurants!
Jackie's place was great, right next to Lincoln park and lots to do nearby. Would definitely recommend staying here!
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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
- Garfield Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
- Things to do North Side
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