
Vacation rentals with a patio in Downtown Chicago
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Top-rated patio rentals in Downtown Chicago
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Apartment rentals with a patio

Lovely 2-bedroom apartment in Pilsen
Very quiet neighborhood, the house is an easy 7min walk to the pink line. Quick ride to Chicago downtown. There is a cute bakery within walkable distance as well as a few grocery stores within a mile. The place itself looked exactly like pictures, very clean.

Spacious! 3 bedroom apartment in Edgewater!
Spacious apartment that’s great for kids (child safety gate, pack and play, toys, baby bath tub, bassinet). Great location close to Loyola and the red line. Very walkable. Hosts were responsive and very accommodating.

Lovely 2bedroom 1bath Apt and outdoor seating.
10/10 - already booked again for a second trip

2 Room Apartment in Vintage Bldg
Karen’s place is well equipped with everything and great accessibility to the lake, transportation, restaurants and entertainment. Lovely historic building really gives the authentic Chicago experience. We were very comfortable there.

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
The living room was very comfortable and provided a great space for all our group to hangout after a wedding. The extra bedding and coffee was a nice plus!

1 Bedroom Apartment/free parking
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!

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home
Great location and wonderful hosts! We will definitely be staying here next time we come to Chicago.

Huge Sofa-King Bed-Retro-Private Deck-Downtown Pal
It was a great stay and very close to the train station which was a plus. A good ideal spot if you want to walk downtown to grab a bite. The place is quiet and perfect for a pair, me and my partner really enjoyed the stay. Thank you so much for having us!
House rentals with a patio

Family Friendly Duplex/9 min from MDW/Free Parking
Very comfortable place and nice and very responsive host! Definitely recommend this stay!

Cheerful two bedroom home with patio/deck
Beautiful home in a quiet neighborhood with responsive and helpful hosts.

Maywood Relaxation
We came for The Weeknd concert in the city, so we got ready there, then spent the night and morning in the house. It was a beautiful house and felt super peaceful and safe! The beds were insanely comfy and we all slept so well! So much space! Everything was just so homey and comfortable.

Casa PLZN Location | Entire Home | Garage Parking
We had a wonderful stay. The place was clean, comfortable, and had enough space for our larger group. It was really nice getting to use the garage parking space and the outdoor area is cozy. After day 1, we did have trouble getting into the place through the front door keypad, there was a battery issue. Thankfully there is access to the home through the back door/garage. Thanks for a great stay!

Cozy 4-Bedroom House with Patio
Went to Chicago for a family trip and this place was perfect. We had a lot of amenities that made it well worth booking an Airbnb versus a hotel room. The place was clean and everyone had their own space. There was a patio outside and the owner was very flexible for check in. We even had a few grocery items like eggs and milk to make our stay better. There was parking right in front, which made it easy to come in and out. This was by far one of the best stays we’ve had! We highly recommend and we’ll definitely be back.

Spacious Home in Chicago Suburbs
This was a great spot for our larger group to stay during our visit to Chicago! Many places to eat nearby and spacious enough for everyone. The spit floor plan was also great as it gave our group different common areas to hang out in as well! The host was very accommodating for a late check out as well! Would certainly stay again!

A Comfortable Stay While You are Away in Oak Park
The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.

The Sunshine Spot
We stayed for a week. The house was spacious and clean, and the neighborhood felt very safe. It was close to the mall and any store you'd ever need. Richard was very responsive and helpful! Washer & dryer were great to have for a longer stay. Wifi and smart tv were great. Also was glad there was even a lead in the backyard for our dog!
Condo rentals with a patio

Loft-Like Wicker Park Condo Steps from the Cta!
Tom’s place was exactly what we needed for a weekend in Wicker Park! The location was perfect to enjoy restaurants and stores, and the ease of access with the keypad was great for check-in and coming/going. The unit was very clean and spacious, and having a dedicated parking spot was amazing! Would definitely stay here again.

Convenient & Spacious 3BR Condo w/Free Parking
Loved this condo. We had 7 adults staying and felt comfortable. Having a dedicated parking space was super helpful and on street parking was easy. Please note this is a 3rd floor walk up so if stairs are a problem you need to consider if this works for you. Easy access to Midway airport and Chinatown were also great features.

Luxuriously bright 3-bedroom condo: The Treehouse
The police was exactly as pictured. All necessary amenities were included and available. Our host was very responsive a very child appropriate Airbnb great experience.

Urban Oasis | Great for Families w/ Kids
Great place to spend a few days with friends. Spacious, comfortable beds, and nice common space. a few good restaurants close by.

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!

Tri-Taylor/Medical Dist. near West Loop
Great stay! The place was clean, comfortable, and in a convenient location. The host was friendly and helpful. I’d definitely stay here again!

Wicker Park/Bucktown condo with large balcony
We enjoyed our time at this apartment! Nestled in the Bucktown neighborhood of the city, which is peaceful and surrounded by beautiful homes. Nearby Wicker Park and Logan Square have a lot to offer, as well as Lincoln Park (the neighborhood) not being too far away either. While the bedroom and bathroom are on the smaller side, that’s just city life and it is a perfect retreat for 1-2 people. It’s very stylish yet cozy with the decor and all updated appliances and bathroom. I would take note of the stairs for this unit in particular, as it’s on the second level but they were fine and the patio deck was nice! We really appreciated Lauren being accommodating to our late booking. We would definitely stay here again!
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
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- Lincoln Park Zoo
- Willis Tower
- Lincoln Park
- Wicker Park
- Illinois Beach State Park
- Flossmoor Golf Club
- Brookfield Zoo
- The 606
- Washington Park Zoo
- Moraine Hills State Park
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