
Vacation rentals with outdoor seating in West Side
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Top-rated outdoor seating rentals in West Side
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House rentals with outdoor seating

Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
the house looked better than the pictures and the house was bigger than expected the heated floors were a great luxury I'd recommend to stay here but also recommend the owners 1 thing 1 the toilets need to be changed u have to wait like 5 mins in-between flushes they were very low pressured got irritating also the basement had a flood under the carpets near the pool table which made me not play pool bc I was standing in a soaked carpet which is an easy fix for future guest I'd recommend staying here if u want to be close to the city but not be in the heart of it and want to have easy parking n access to ur car

Chicago River House -BBQ Oasis now open!
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!

Floresitas Oasis, your home in Chicago
Lizbeth was an amazing host. She’s responsive and attentive. The place was exceptional clean and had an amazing smell. I was there to celebrate my birthday and was pleasantly surprised upon entry when I was greeted with a personalized birthday message, fresh flowers and a bottle of wine. Anytime I reached out to Lizbeth, she responded expeditiously. Again, very attentive. My husband and I will definitely stay at her beautiful Oasis again. We felt comfortable and completely safe. Everything we wanted to do was a quick drive from the location. If you’re considering staying at her home, you will not regret it. If I could give more than 5 stars, I would. Thanks Lizbeth for being an incredible host Until the next time…

Sunny Historic Cottage on the Park
We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.

Private Logan Square Garden Apt
Was a very nice and relaxing place to stay after spending time in the city! Really close to multiple bus stops which made the public transport really easy to access. The inside was very clean and nice, the bed is extremely comfortable! Would stay again!

Boho Chic Coach House 30Min to downtown W/ Parking
I enjoyed my stay. It was clean and pleasant. Marilyn was very friendly and quick to respond to any questions I had. I would recommend staying at this Airbnb! Great time!

Clean, Cozy 1st Floor Flat, Kitchen, Parking
Great get away especially anyone in the architectural field. Great location in the suburbs of Chicago and has a great connecting train station near by that takes you into the heart of Chicago. Overall great stay!

Beautiful Chicago Greystone
Great place to accommodate a big group. Close enough to the city if you don’t want to be in the heart of the city. Responsive host
Apartment rentals with outdoor seating

Logan Square 2nd Floor Chicago Victorian
We had an amazing stay at Kitty’s place! From the moment we arrived, she made us feel so welcome. She even decorated the house for my fiancée’s birthday and left us treats, which was such a sweet touch. Her recommendations were super helpful and made our trip even better. The house was full of books and art that made it feel really special, and the beds were super comfy. The separate entrance was great for privacy, and street parking was easy to find, which was a big plus. Thank you so much for all the little things that made our stay unforgettable. We would love to stay here again very soon!

Cozy Luxurious Beauty - 10 Min to Downtown Chicago
Freddie was a great host. He responded right away when I had a little confusion & smoothed everything. The inside was beautiful & created a comfortable space to return after being out and about.

Great Location & Bright 2BR+2BA | Mapletree Suites
Loved the area! Super close to restaurants and where our daughter lives do it was a great location

Breathtaking & Chic Oasis Loc in Desirable Old Twn
I loved everything about my stay ! Very nice and clean and the host were amazing

Sun filled tranquil 2 br great part of Logan Sq.
This was a very nice stay. It was super clean and in a great neighborhood. Thank you for hosting!

Charming retreat w/ fireplace
This place was amazing!! Felt right at home as soon as we got there. The neighborhood is very quiet and chill, there’s a ton of great mexican food/stores, and just a couple blocks from the pink line and bus stop. Great home base just outside of the chaos of downtown but easy to get anywhere you wanna go! The place itself was comfortable and felt very roomy. Only thing is there are some upstairs neighbors who you WILL hear walk, talk, breathe… but we didn’t have trouble dealing with it and still slept well. Plus they had two cute little doggies who came to say hi, which is a huge plus! Overall 10/10 would stay again and would always recommend to anyone visiting Chicago.

Belmont Pleasures - hot tub / arcade gaming room
Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.

Ukrainian Village Garden Retreat
Marc’s place was exactly as listed. The cleanliness was amazing. Not one speck of dust in sight. We thought the place was really cute. Was walkable to a few restaurants and cafe’s in the area. Street parking was available but we opted to use the garage since we didn’t drive our vehicle much. The garage was clean and secure and is a shared space with 2 other vehicles (I’m guessing the owner uses the other spots). This is a downstairs unit so you may hear people upstairs but nothing that was bothersome whatsoever. This place was perfect for what we needed during our 4 day stay. Would definitely come back again.
Condo rentals with outdoor seating

Luxe 2BR Cozy Suite | Skyline Views near McCormick
Milan runs a professional Airbnb service and promptly responded to all our queries. We stayed at Apartment No. 605 which, was clean and had all the required amenities for a comfortable stay.

3 BR Summer GetAway, 15mins to Loop+Gated Parking
Close to the green line for easy transportation.

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
Great place! Everything was clean, in a good location and they communicated well.

Logan Square Beauty with 2 Bedrooms W/parking
Matt is a great host. Open, responsive and informative…everything you want really when on vacation

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
John's place is great, just as described. Very clean and location is perfect (across the street from Pequod's). Check in/out was easy and communication was good.

Susie's Space. 2BR easy parking & pet friendly
Susan’s home was comfortable, clean, well-equipped, and aesthetically pleasing. The bed I slept in was one of the most comfortable of my entire life—I prefer a soft mattress. As far as location goes, the street was quiet, good for walking our dog, and close enough to public transport. Plenty of buses were available. We used street parking for our car and never had problems with finding a close spot to the house whenever we did take the car out. We enjoyed the stay greatly and will stay again. Thank you, Susan!

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!

Spacious 4 Bedroom Condo
We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.
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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
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
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