Holiday rentals with a patio in Downtown Chicago

Find and book unique Holiday Accommodation with Outdoor Verandahs on Airbnb

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Popular amenities for Downtown Chicago Holiday Houses with Outdoor Verandahs

Apartment rentals with a patio

Superhost
Apartment in Chicago
4.87 out of 5 average rating, 106 reviews

Lovely 2-bedroom apartment in Pilsen

HameedahRating, 5 stars2 days ago
Conveniently located, ease of access to public transport, clean and comfortable.
Guest favourite
Apartment in Chicago
4.94 out of 5 average rating, 69 reviews

Spacious! 3 bedroom apartment in Edgewater!

PatrickRating, 5 stars1 month ago
Awesome apartment in the Loyola Chicago neighborhood. Easy access to the loop with the red line. Host is super responsive. The place was spotless and well stocked when we arrived.
Guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 103 reviews

Spacious 1BR Garden Apt & Parking

TomásRating, 5 stars2 weeks ago
Mikael's place was amazing. Unlike most places listed around Hydde Park in Chicago, Mikael's place had from great reviews and they were totally right. The place is very well kept, spacious, practical, with very calm surroundings. I had great sleep and having breakfast while looking at the garden was a big plus for me too. I had no issues regarding privacy or noise which is something commonly brought up in listings in this sector, especially in old buildings. Mikael was also very responsive and kind. If I ever go back to Chicago I would definitely consider staying here again.
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 107 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

DarenRating, 5 stars1 week ago
A very nice and welcoming place to stay!
Guest favourite
Apartment in Chicago
4.89 out of 5 average rating, 38 reviews

River North | Rooftop With In & Out Parking | 3

ErinRating, 5 stars1 week ago
Awesome place to stay. It was very clean and in a perfect place to explore the city. Great restaurants right nearby but also close to train stops for easy access to other areas. TAIMS was always super responsive.
Top Guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 40 reviews

2 Room Apartment in Vintage Bldg

AudréanneRating, 5 stars2 weeks ago
We loved the apartment. It is ideally situated and was perfect for our little dog. The area is really nice an peaceful. It was also easy to get downtown via the red line. Karen was a fantastic host. We appreciated all the little gestures and the fact that she had saved a parking spot for us upon our arrival. We would come back anytime.
Superhost
Apartment in Glenview
4.86 out of 5 average rating, 28 reviews

1 Bedroom Apartment/free parking

DarrenRating, 5 stars2 months ago
We stayed at Karolinas apartment for 7 months and she was a wonderful host. She quickly addressed any problems. For example, we locked our keys in the apartment. I texted her and a new set of keys were promptly delivered. The apartment itself is super comfortable. Great furniture and appliances and we enjoyed the outdoor balcony. I would highly recommend renting from Karolina and this apartment specifically. We have no complaints and our stay was wonderful. Thank you Karolina!
Guest favourite
Apartment in Chicago
4.95 out of 5 average rating, 21 reviews

Tree-Lined Street Near the Lake!

KarenRating, 5 stars1 month ago
This place has the best location. It was easy for me to take the Brown line and get around town. Cute coffee shop bakery on the corner. Mark and Carmen where friendly when we meet in the garden. Nice stay!

Holiday House Rentals with a Verandah

Superhost
Home in Chicago
4.93 out of 5 average rating, 40 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JoannaRating, 5 stars3 weeks ago
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗
Guest favourite
Home in Hazel Crest
4.87 out of 5 average rating, 23 reviews

Your Peaceful,Joyful,Cozy, Relaxing, Experience

AdenikeRating, 5 stars2 days ago
i enjoyed my stay at Erica’s home. house was clean convenient location, nearby stores, movies etc. Erica also is very proactive when i had any questions with anything. I look forward to staying again in the future.
Superhost
Home in Chicago
4.86 out of 5 average rating, 102 reviews

Casa PLZN Location | Entire Home | Garage Parking

AuraRating, 5 stars2 weeks ago
Happy that this place was available! It was comfortable, clean, and roomy, right in Pilsen. Excellent communication and overall great spot.
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

PaulRating, 5 stars5 days ago
rob and sue were great hosts. easy, timely communication. the house has everything you’ll need and is spacious and quiet, despite being close to some busy streets. walkable to diners, restaurants, and some shopping. . will definitely book again.
Guest favourite
Home in Chicago Ridge
4.92 out of 5 average rating, 128 reviews

Quiet cul-de-sac with huge fenced in backyard

JoeRating, 5 starstoday
Tom provides an excellent place to stay when coming to the Chicago Ridge – Oak Lawn – Evergreen Park area. On a quiet cul-de-sac in a residential neighborhood. Easy access and everything works great.
Top Guest favourite
Home in Chicago
4.9 out of 5 average rating, 39 reviews

Suburban Feel with a City Vibe

IngessonRating, 5 stars1 week ago
I am very happy to have rented for the holidays it is really beautiful Very clean quiet area
Guest favourite
Home in Downers Grove
4.89 out of 5 average rating, 44 reviews

Spanish décor w/ modern twist & fenced yard

RichardRating, 5 stars6 months ago
This rental perfectly served our needs for a one month stay visiting family in Downers Grove. Everything was as described. Here are a few things future renters will appreciate knowing: • This location will work best if you have a car. • To be able to watch TV, we needed to use an on-line service for which we have our own paid subscription. If there was a way to access local Chicago stations without a paid service, we could not figure it out. • You will likely need to read the directions in the owner’s guide to figure out how to set the thermostat to your preferred temperature. • The unit would work best for four or fewer people, as the dining table is in the kitchen and only has room to easily seat four people. However, the living room is large and could potentially be used as an overflow seating area if there were more diners. • If you plan to spend time in downtown Chicago, it is probably best to take the train from the Belmont Metra station. Day parking is $3.
Superhost
Home in Lake Zurich
4.78 out of 5 average rating, 23 reviews

*3BRHouse*Kids Game Room*Patio

PriscillaRating, 5 stars1 month ago
Very comfortable stay she responded very quickly to my message I would recommend and would be back to visit real soon thanks for everything

Holiday condos with a patio

Superhost
Condo in Chicago
4.84 out of 5 average rating, 184 reviews

Loft-Like Wicker Park Condo Steps from the Cta!

KathyRating, 5 stars1 month ago
Great place! Very well kept and clean. Tom is very responsive from the time you book. Just be mindful that as stated there is NO where to park if you drive. All in all such a great neighborhood.
Guest favourite
Condo in Chicago
4.89 out of 5 average rating, 112 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars3 weeks ago
Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend
Guest favourite
Condo in Chicago
4.92 out of 5 average rating, 114 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

KristinaRating, 5 stars1 week ago
This was a great place to stay while in town with friends for a weekend! Walkable to great restaurants and shops, and the place was extremely clean and filled with natural light. Comfy beds and good shower pressure. Would stay again!
Guest favourite
Condo in Chicago
4.93 out of 5 average rating, 119 reviews

Urban Oasis | Great for Families w/ Kids

SophieRating, 5 stars2 days ago
Our group had a wonderful stay at Alex's place! He was so accommodating setting us up for our stay, allowing an early check in, getting parking passes and a crib set up prior. We appreciated his quick response times and thoughtful communication - it is apparent he wants his guests to have a relaxing and enjoyable stay. We recommend this place to anyone! 10/10.
Guest favourite
Condo in Chicago
4.91 out of 5 average rating, 103 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

DebRating, 5 stars1 day ago
Although I did have the address and some information about the entrance way, the lock box for the keys was a tad difficult to figure out. A call to him and his prompt response helped me out. Talking with him on the phone helped me understand where the free parking spaces were (in a gated area) and how to access them. The smart lock box on the door of the "apartment" was confusing to me but I'm of a different generation. Another call to him, again with a prompt response, helped me out. The only complaints would be that the jet tub in my bathroom wasn't able to be used due to the nozzle not working to fill the tub and there was only one box of facial tissues on the fireplace mantle. For people with allergies, a box in each bathroom would have been a plus. My brother and I enjoyed our stay even though it was a tad noisy due to street noise but ... that's a downtown stay, I suppose.
Top Guest favourite
Condo in Chicago
4.98 out of 5 average rating, 116 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

AndrewRating, 5 stars2 weeks ago
Under the category of actions speak louder than words, I have stayed at Allan's place about five times, and it remains my first choice when visiting Chicago.
Superhost
Condo in Chicago
4.86 out of 5 average rating, 148 reviews

Tri-Taylor/Medical Dist. near West Loop

BibiannaRating, 5 stars2 weeks ago
Ariel was helpful when we had questions or encountered issues. The house was in a quiet neighbourhood and a short uber ride away to downtown Chicago.
Guest favourite
Condo in Chicago
4.98 out of 5 average rating, 161 reviews

Spacious 4 Bedroom Condo

LindseyRating, 5 stars2 weeks ago
Adrian’s condo was perfect! We had the most incredible stay! Gorgeous design, comfortable beds, great bathrooms, felt very safe, amazing communication, etc! So impressed! We will definitely be back and will recommend to family and friends!

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