
Vacation rentals with outdoor seating in West Loop, Chicago
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Top-rated outdoor seating rentals in West Loop, Chicago
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Popular amenities for West Loop, Chicago outdoor seating rentals
House rentals with outdoor seating

NEW! 3BR/2.5B Duplex in Noble Sq
Host is very accommodating and responsive. The place is nice and was in a great location. Only a short 10 minute drive that was a straight shot to Michigan Ave. The only thing we felt was slightly misleading was that we were under the impression that the 3rd bedroom with a couch was able to pull out and convert into a bed. Unfortunately, that wasn’t the case, so we ended up leveraging an air mattress we had packed as a contingency. Overall, we had an enjoyable stay and would recommend.

Flat in Lincoln Park 2-Flat Central to Everything
We stayed for a week with 2 children of 8 and 10. The place is larger than we expected; which is nice. The street and neighborhood are both really nice. Train is close; which is very handy to visit the city. Close to Lincoln park and many restaurants and shops. This place was very comfortable, private and quiet. Brian was also also very flexible with check in and check out times. Definitely recommended !

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.

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. (=

Private Logan Square Garden Apt
Had a lovely stay at Janice's place! It is located a short drive from Logan Square, which has restaurants, bars, and a blue line metro stop. There was also a bus stop just outside the neighborhood. Speaking of the neighborhood, it was very serene and private, with plenty of parking regardless of the time of day. The airbnb is a basement unit, so maybe something to keep in mind if you're on the taller side, but it was spacious, and there was minimal noise from the floor above. Shower had great water pressure! Bedroom was clean and comfortable. Janice was very communicative and clear instructions were given for checkin and checkout processes.

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
This place was amazing! My friends and I were scared about the parking at first but it was pretty easy. Instructions were really clear and the host was really amazing with their communications. The area that the home was located in felt safe and is pretty quiet. The home itself had great designs and decorations which made the home feel really cozy to me. I would definitely stay here again and I recommend it to others who are traveling to Chicago.

Retro Modern Bungalow | fire pit • free parking
We had a great stay at this place. The location is very nice. Get to be outside of downtown still while close enough to visit whenever you’d like. The retro vibes of the home itself is very cozy and unique. Will definitely book again if we ever come back.

Cozy/Spacious WFH Family Friendly w Permit Parking
Lovely place! Nathaniel was very responsive and accommodating to us while in Chicago! Made everything easy and created a homey space for us to enjoy. Would definitely stay again.
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!

*A Happy (City) Glamping- walk to train FREE park
So much fun! Had all the amenities I needed for the stay. The bed was comfortable and there was enough space to move around. Read the instruction book well and you will have a great stay.

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
We loved our stay! It was so clean and very close to public transit! We navigated the trains to and from Cicero into Chicago NP! We will definitely be back and we would definitely recommend staying at this Airbnb!!!

Logan’s Cozy Inn.
Great location with lots of nice bars and restaurants locally and easy access also to the CTA blue line to Downtown and O’Hare. Apartment was ideal and was just as described. Would recommend and if ever back in Chicago would look to stay here again.

Logan Square Garden Sanctuary
Tess’s place was exactly as described. Very clean and there were lots of little extra amenities that were appreciated. Seemed they thought of everything! Extra toothbrushes and disposable razors, Q-tips, cotton balls, snacks, water and more! Our only issue was spotty internet which might have been due to provider outages. Wasn’t too much of an issue for us as we were out exploring the city most of the day.

Colorful Bucktown Garden Apartment
Great stay. Home was as expected in the listing and very nice - but it was the location that made this stay perfect. It was so nice to be away from the hustle of downtown. You are in walking distance to many coffee shops, restaurants, bars and running paths. Would definitely stay here again.

✨Spacious Centrally Located West Loop Loft✨
Excellent place, near downtown, i highly recommend this airbnb. Host is great and always responsive. You don’t need to bring anything the airbnb has it all.

Cozy Neighborhood Escape | Near NU-Chicago-Beaches
Imani’s place worked out great for our last minute, one night stay in Evanston! The apartment is in a nice area, and we felt very safe with the added entry/exit security locks. There was always ample street parking and the space inside felt larger than photos depicted. All furnishings, appliances and decor felt upscale, looked new, and everything was very clean.
Condo rentals with outdoor seating

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Our stay in Evanston was great! The apartment is close to all of downtown Evanston, the Metra, and the L. Also easy access to NU. Everything was just as it says and the free underground parking is a HUGE plus!

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Wendy and Matt's place was comfortable and homey. The location was great, the apartment comfortable, and we had essential amenities. The building is mid-century modern and designed by famed architect Harry Weese that incorporates thoughtful references to Chicago architectural history throughout while still remaining visually cohesive. One minor issue is the stove, which is electric and somewhat underpowered. It's good enough for minor work like breakfast or heating leftovers but you may struggle producing more elaborate meals. It was a very minor quibble but worth noting for those culinarians wanting to prepare their own meals. The oven is decent but there is only one. Overall, my stay was excellent and I recommend Wendy and Matt's place wholeheartedly. They are excellent hosts as well.

Urban Oasis | Great for Families w/ Kids
Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!

Bold Ukrainian Village 2 Bedroom w/Garage Parking
Wonder 2 bedroom location. Good area for walking and close to downtown by public transport/Lyft.

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!

Luxurious River North 3BR/2BA- Free Onsite Parking
Great responsive host. The place was clean and check in was easy. They were very responsive and accommodating. The location was excellent and easy to navigate with plenty to do within walking distance.
Quick stats about vacation rentals with outdoor seating in West Loop, Chicago
Total rentals
160 properties
Nightly prices starting at
G$14,645 GYD before taxes and fees
Total number of reviews
6.7K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
100 properties have a pool
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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
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center