Vacation rentals with outdoor seating in West Loop, Chicago

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Popular amenities for West Loop, Chicago outdoor seating rentals

House rentals with outdoor seating

Guest favorite
Home in Near West Side
4.85 out of 5 average rating, 41 reviews

The Banksy-King Bed-Firepit-Rooftop-United Center

AllenRating, 5 stars1 week ago
Very nice place with ample room for our 11 guests. Robert was quick to respond to questions. The back patio and rooftop deck are an added bonus. Walkable to the United Center and a few blocks from the Blue Line. Great stay.
Guest favorite
Home in Elmhurst
4.86 out of 5 average rating, 22 reviews

Enamored in Elmhurst

YvonneRating, 5 stars2 weeks ago
This home is in a beautiful neighborhood. It was very clean and the decor was simple yet stunning. There was plenty of linen and the kitchen was stocked well enough to cook an entire meal Mark was very responsive and provided clear instructions for check in and out. I would stay here again
Guest favorite
Home in Brookfield
4.92 out of 5 average rating, 86 reviews

Remodeled | Game room | Fire Pit | 5 Min to Zoo

TimothyRating, 5 stars3 days ago
This was our second stay and it as as wonderful as the first time.
Guest favorite
Home in Roscoe Village
4.92 out of 5 average rating, 279 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

BrigidRating, 5 stars4 days ago
We enjoyed preparing pizzas from scratch in the perfectly sized kitchen with our adult kids who live in Chicago and their friends. There was plenty of space to sit around the spacious kitchen island and talk while cooking. The whole experience was made even better by using the Wolf stove top and Bosch wall-mount oven, which produced perfectly crisp crust and tasty toppings. The neighborhood felt safe and peaceful while providing everything we needed within walking distance. Parking was also easy. We had no trouble finding a space in front of the house all 4 days we were there. As a special bonus, a new chocolate cafe opened a few days ago (Hotel Chocolat Velvetiser Cafe) and is just a short walk away! We had a great time in this lovely home.
Guest favorite
Home in Irving Park
4.96 out of 5 average rating, 28 reviews

Wrigley classic+trendy+2garage

JulieRating, 5 stars1 day 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 Bridgeport
4.69 out of 5 average rating, 49 reviews

Animal House near Sox stadium

KimRating, 5 stars1 week ago
Very nice home! Very nice host! Would definitely go again. Thank you so much for hosting us.
Superhost
Home in Illinois Medical District
4.87 out of 5 average rating, 97 reviews

Casa PLZN Location | Entire Home | Garage Parking

ZayuriRating, 5 stars3 weeks ago
The place was lovely, my family and I loved it. Very spacious and close to downtown Chicago.
Guest favorite
Home in Logan Square
4.95 out of 5 average rating, 38 reviews

Gorgeous and Luxurious 3 BR Home

SeanRating, 5 stars5 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.

Apartment rentals with outdoor seating

Guest favorite
Apartment in West Town
4.96 out of 5 average rating, 134 reviews

Bohemian Moto Inn

EliRating, 5 stars3 weeks ago
Nicole has a wonderful place. It is well located and connected to good public transit. It also has nice touches that you don’t normally see at Airbnbs. Would come back!
Superhost
Apartment in Lincoln Park
4.72 out of 5 average rating, 117 reviews

The Biddle House (#1)

SitaRating, 5 stars3 months ago
We really enjoyed staying at this place - it was clean and comfortable, and the location is fantastic. Elizabeth was very responsive and a great host. We would stay here again!
Guest favorite
Apartment in Near North Side
4.91 out of 5 average rating, 132 reviews

Modern 3BR with Private Rooftop & Free Parking

JohnRating, 5 stars1 month ago
We really enjoyed our stay. Song was responsive and helpful. The property was as advertised. It was very comfortable, clean and quiet. There is easy access to public transportation and downtown is also within walking distance. Check in and checkout were very simple/easy. We would stay here again and can recommend the property for families looking for a place to stay in Chicago.
Guest favorite
Apartment in Avondale
4.98 out of 5 average rating, 105 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.
Superhost
Apartment in East Rogers Park
4.89 out of 5 average rating, 166 reviews

Executive Apartment on Lake Michigan with parking

DebraRating, 5 stars2 weeks ago
This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!
Top guest favorite
Apartment in Lake View
5 out of 5 average rating, 110 reviews

Spacious 2 Bedroom in the heart of Lakeview!

SarahRating, 5 stars3 weeks ago
Beautiful boho, whimsical space, firm mattresses, all the comforts of home: extra blankets, pillows, towels, books and magazines. Took pictures of how pretty everything was, thinking I want my home to look like this. Toilet flush was tricky in the way of older homes. Super convenient, in a fun neighborhood and easy walk to public transportation, parking available. We had a great time.
Top guest favorite
Apartment in Roscoe Village
4.97 out of 5 average rating, 144 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

TerryRating, 5 stars1 week ago
Wonderful stay! From sitting on the front stool as weather was great for a couple of days to being able to walk everywhere we needed. Lara even left us some milk when we inquired about a market to visit. Close to shops, food and all of Roscoe Village- would highly recommend
Guest favorite
Apartment in Lincoln Park
4.93 out of 5 average rating, 504 reviews

Victorian Home in Old Town

AlexRating, 5 stars4 months ago
I really enjoyed my stay! I loved the art and decor of the space. I am a solo traveler and I felt safe being here. There are written instructions on the door and in the home that explain almost everything I needed. I felt safe in the neighborhood! I would get back late and felt safe doing so. There are multiple stores within walking distance so it was easy to grab food or any items I may have needed. I didn't have a car and found it very easy to get to everywhere I wanted to go. Shampoo/Conditioner/Body Wash was a pleasant surprise to have! Along with the teas and coffee items. The space was a great size and I had everything I needed. It was easy to come and go and check in was very easy. I would stay here again, Lynn was super responsive, helpful, and kind! The bedroom area doesn't get much light, but it wasn't an issue for me. Bed was comfy, home was beautiful, and I loved my stay. Thank you so much Lynn!

Condo rentals with outdoor seating

Guest favorite
Condo in Woodlawn
4.88 out of 5 average rating, 230 reviews

A Stones Throw from U Chicago South Campus!

NatalieRating, 5 stars2 weeks ago
Great stay at Luke’s place. Walkable to campus, is as described in the listing, snacks saved me after a long evening of travel and the fact there was coffee already there for the morning was lovely. These little thoughtful touches matter! Very grateful to have been able to experience Luke’s place! Thank you so very much Luke!
Guest favorite
Condo in Bridgeport
4.89 out of 5 average rating, 110 reviews

Convenient & Spacious 3BR Condo w/Free Parking

DanRating, 5 stars1 month ago
Great place in a quite neighborhood. Close to the convention center and really close to some awesome restaurants.
Guest favorite
Condo in West Town
4.92 out of 5 average rating, 112 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

SummerRating, 5 stars1 week ago
We had a lovely stay. It was very close to everywhere we needed to go.
Guest favorite
Condo in Pilsen Historic District
4.95 out of 5 average rating, 115 reviews

Urban Oasis | Great for Families w/ Kids

Charles DwyerRating, 5 stars5 days ago
Great spot to stay very clean a spacious space! Great and responsive host!
Guest favorite
Condo in Lincoln Park
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.
Guest favorite
Condo in Wrigleyville
4.84 out of 5 average rating, 425 reviews

Authentic Condo steps from Wrigley Field!

ChelseaRating, 5 stars5 days ago
What a great experience! If you’re looking to check out a game and be in Wrigleyville this is the place. We had such a blast and the place was exactly like the photos! Josh was always responsive and being able to walk to all the places we wanted to go made it even better! Thank you for your hospitality and making it possible to celebrate my birthday in Chicago!
Top guest favorite
Condo in Lake View
4.98 out of 5 average rating, 114 reviews

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

TylerRating, 5 stars1 week 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!
Guest favorite
Condo in West Town
4.98 out of 5 average rating, 158 reviews

Spacious 4 Bedroom Condo

Maria MagdalenaRating, 5 stars2 weeks ago
The place was very nice as anticipated from the photos and the description in the listing. Adrian was friendly and responsive. I would gladly return.

Quick stats about vacation rentals with outdoor seating in West Loop, Chicago

  • Total rentals

    160 properties

  • Nightly prices starting at

    $50 before taxes and fees

  • Total number of reviews

    6.5K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    100 properties allow pets

  • Rentals with a pool

    100 properties have a pool

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