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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, 104 reviews

Lovely 2-bedroom apartment in Pilsen

AnaRating, 5 stars1 week ago
Good location and within a quiet neighborhood
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, 99 reviews

Spacious 1BR Garden Apt & Parking

BrianRating, 5 stars2 weeks ago
Lovely private garden, comfortable apartment, great selection of books for some quiet reading, and cool Hilma Af Klint poster
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 106 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

JillRating, 5 stars1 month ago
Good location and had everything we needed. Handy to have nearby stores within walking distance. Great place and would definitely stay again.
Guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 36 reviews

River North | Rooftop With In & Out Parking | 3

CameronRating, 5 stars1 week ago
Great location, clean, modern, cozy, and very helpful hosts. Highly recommend for a stay in Chicago.
Top Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 38 reviews

2 Room Apartment in Vintage Bldg

HollyRating, 5 stars2 weeks ago
Karen's place was cozy, clean, and convenient. It is located one block from the lake and one block from Michael's Pizza. She has warmly and beautifully decorated the space, so it is easy to immediately feel at home. It was a quick walk to the metro station, as we didn't have a car. I recommend going to Green Mill for a jazz show!
Superhost
Apartment in Glenview
4.86 out of 5 average rating, 28 reviews

1 Bedroom Apartment/free parking

DarrenRating, 5 stars1 month 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
4.92 out of 5 average rating, 38 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

AshleyRating, 5 stars1 month ago
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.
Guest favourite
Home in Chicago
4.88 out of 5 average rating, 49 reviews

CasaNova Modern City Living

KatieRating, 5 stars6 months ago
Lilly was prompt in her responses and very helpful. The place was well kept and clean. A quick Uber ride to downtown. Our group really enjoyed our stay!!
Guest favourite
Home in Chicago
4.97 out of 5 average rating, 29 reviews

Wrigley classic+trendy+2garage

JulieRating, 5 stars1 week ago
This is a great property. We had a fantastic stay in Chicago. It was so clean and just like the photos. Very spacious and ideal for families. Thank you.
Superhost
Home in Chicago
4.71 out of 5 average rating, 51 reviews

Animal House near Sox stadium

AnneRating, 5 stars2 days ago
We had a great stay at Miranda's. The apartment was just as advertised and had lots of items to use in the kitchen. Miranda gave great restaurant recommendations. We loved the maple lattes at Blind Owl and had an excellent dinner at TLP (Three Little Pigs). Bridgeport is a quiet neighborhood with easy access to downtown Chicago. If you are traveling with a pet this is the place to stay, I felt guilty I left my fur baby at home.
Superhost
Home in Chicago
4.86 out of 5 average rating, 99 reviews

Casa PLZN Location | Entire Home | Garage Parking

CecilioRating, 5 stars3 weeks ago
Great place near restaurants and cafes. Garage access is a plus. Train noise is noticeable at first but you get used to it and it's only noise as the house doesn't rumble when the train passes.
Top Guest favourite
Home in Worth
5 out of 5 average rating, 16 reviews

3 x Queen Beds + Pull Out Sofa Bed - No Stairs !

SawsanRating, 5 stars3 weeks ago
Amazing house and location. Great host. Highly recommend.
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 38 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars6 months ago
This is a great house to stay for a family or two couples. Out of several ABNBs, this one gets the award for most clean. There is a fairly new Italian restaurant, Il Girasole Trattoria, that is walk-able and delicious. You will not be disappointed with your stay.
Top Guest favourite
Home in Chicago Ridge
4.93 out of 5 average rating, 123 reviews

Quiet cul-de-sac with huge fenced in backyard

MichaelRating, 5 stars3 weeks ago
Absolutely loved staying here. Tom was an awesome host. He has very detailed instructions throughout the house for everything from connecting to the WiFi to how the individual tvs work. The couch in the living room is stupid comfortable and the master bedroom was cool and dark. 10/10 would stay here again

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, 111 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars1 week 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, 113 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

SearaRating, 5 stars1 week ago
Great place to stay! Quiet neighborhood and walkable distance from a few shops and food places. We enjoyed our stay very much!!
Top Guest favourite
Condo in Chicago
4.98 out of 5 average rating, 104 reviews

The Ramblers Inn, Northside NEW Reno w/parking!

SusanRating, 5 stars2 days ago
We were in town visiting our son for Easter and this place was exactly what we needed. Unbeknownst to me, my son lives in the building behind the Rambler Inn so it was so convenient. My daughter drove in from Ohio so the parking space was a bonus. The house was very spacious for the four of us and we were able to have family meals in the dining room. The hosts were great about communicating and we definitely plan on staying again in the future.
Guest favourite
Condo in Chicago
4.93 out of 5 average rating, 117 reviews

Urban Oasis | Great for Families w/ Kids

ParkerRating, 5 stars1 week ago
We had a very good stay for a friends wedding a few blocks away in Chicago. As it is very modern, cozy, and clean. Alex's response time is very quick to whatever may arise. We would highly recommend staying there. Thanks for the stay!
Superhost
Condo in Chicago
4.8 out of 5 average rating, 249 reviews

Logan Square Beauty with 2 Bedrooms W/parking

SarahRating, 5 stars5 days ago
We really enjoyed our three nights in Matt's roomy upstairs apartment. Great to have a space in his garage; the car stayed parked there while we took the blue line downtown each day. It was an easy 10 minute walk to the Logan Square station. If you're flying into or out of O'Hare, it would be convenient, since the airport is the last stop on the blue line.
Guest favourite
Condo in Chicago
4.91 out of 5 average rating, 100 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

KendraRating, 5 stars3 months ago
John’s place was clean and cozy. The kitchen was immaculate and we appreciated the nespresso machine and pods. The location was excellent, many food and drink choices right outside the door. It was amazing to have our own parking spot! There are a lot of stairs but that is expected in the city. I would definitely recommend this spot to my friends.
Top Guest favourite
Condo in Chicago
4.98 out of 5 average rating, 115 reviews

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

TylerRating, 5 stars2 weeks ago
This is my favorite place to stay in all of Chicago! I try to come up 1-2 times a year and checking to make sure this spot is available is the first thing I do when planning out my trip(s). The apartment is spacious, comfortable, and clean; central to a lot of fun neighborhoods, and right above (and across) from some of the best nightlife in the city. Allan is an awesome host, always available if something’s needed, and super communicative. I’m already looking forward to my next visit so I can stay here again!

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