Holiday rentals with a balcony in Chicago

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Popular amenities for Chicago Accommodation with a Balcony

Apartment rentals with a balcony

Guest favourite
Apartment in West Town
4.91 out of 5 average rating, 385 reviews

The Craftsman Gallery at OHC - No Cleaning Fee!

GlomikaRating, 5 stars3 weeks ago
Our stay was great, the place is accessible and close to a lot of tourist spots. Matthew accommodated our special early checkin request. Would definitely recommend this place.
Apartment in Lincoln Park
4.81 out of 5 average rating, 245 reviews

Perfect Lincoln Park Retreat - Walk to Depaul!

CarolRating, 5 stars4 days ago
This is a nice and convenient apartment to stay in for families visiting the local area. Garden apartment means there is not a lot of sun light as it is ground floor. Street parking a bit challenging because it was a graduation weekend but they do have larger lots within moderate walking distance. But regardless - this apartment met our needs. Nice walking neighborhood and found nice local restaurants. Close to DePaul.
Superhost
Apartment in Pilsen Historic District
4.82 out of 5 average rating, 498 reviews

Eclectic Artist Designed Sanctuary Heart of Pilsen

JaideepRating, 5 stars3 weeks ago
Daniel’s place is in the heart of Pilsen, and very close to Downtown, Hyde Park etc, with lots of public transport around. The place is spacious with a nice back facing balcony. Daniel was very communicative, and very kindly allowed us an early check in as we had a lot of luggage. Would highly recommend his place to anyone visiting Chicago!
Apartment in West Town
4.78 out of 5 average rating, 148 reviews

2 Cozy Bedrooms In a Hidden Wicker Park Gem!

BenRating, 5 stars1 month ago
Convenient spot right on the train and good bus access around the city. Grocery store a few blocks away and tons of good restaurants and bars within 15 min walk.
Superhost
Apartment in Wicker Park
4.76 out of 5 average rating, 72 reviews

Artsy Chicago Abode: Steps to Shops & Restaurants

ColinRating, 5 stars10 months ago
Had a nice stay. Did the trick as a place to sleep while exploring the city. Good location
Guest favourite
Apartment in East Rogers Park
4.82 out of 5 average rating, 11 reviews

3 Bed 3 Bath Lakefront Oasis, Parking Included

ShannonRating, 5 stars4 days ago
Appreciate the great communication and beautiful accommodations, perfect for our multigenerational group. Would definitely come back and everyone in my family felt the same way.
Guest favourite
Apartment in West Town
4.91 out of 5 average rating, 561 reviews

The Woodsman's Gallery at OHC - No Cleaning Fee!

GuilhermeRating, 5 stars2 weeks ago
Everything very good, large apartment, organized, clean. Attentive host.
Apartment in Lincoln Park
4.7 out of 5 average rating, 44 reviews

Huge Lincoln Park 6 Bed Duplex with Free Parking!

RaviRating, 5 stars7 months ago
This place is great for large parties. It’s close to bars, restaurants and the main strip of Lincoln Park. Being close to the hub of things means it’s a bit noisier. Not crazy or anything, but if you’re not use to city noise this can be surprising. The bedrooms are laid in a way that not every room is private (glass doors), shared spaces, etc. more of a heads up when you enter into the unit there’s a flight of stairs to get to the unit. Not a deal breaker, but we had someone in a walker which made it a bit more challenging. Would rent this space again!

Holiday House Rentals with a balcony

Guest favourite
Home in Lake View
4.94 out of 5 average rating, 339 reviews

The Roscoe House near Wrigley Field

VictorRating, 5 stars1 week ago
One of the nicest places near Chicago,
Guest favourite
Home in Lake View
4.94 out of 5 average rating, 18 reviews

6 Bedrooms In Beautiful Sheridan Park!

JeromeRating, 5 stars3 months ago
Had a great stay over St. Patrick’s day weekend. The apartments are in a very walkable area with great access to public transportation. Fenton was also very quick to communicate and gave clear instructions. 10/10 would recommend to anyone.
Top Guest favourite
Home in Wicker Park
4.97 out of 5 average rating, 36 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

JohnRating, 5 stars2 weeks ago
Great place and stay! Location is amazing!
Home in Near West Side
4.65 out of 5 average rating, 43 reviews

Newly Updated Vintage 6 Bedroom Single Family Home

KrisRating, 5 stars3 weeks ago
My stay at this property was exactly as I expected and more. It was as described and was very much a vintage beauty. We felt right at home and had a great time. It accommodated my large party and the icing on the cake was all the great restaurants. We will definitely stay again in the future.
Superhost
Home in Logan Square
4.92 out of 5 average rating, 142 reviews

Southwestern Escape in Logan Square, Sleeps 12

AmyRating, 5 stars5 months ago
My friends and I celebrated the new year in Chicago and were so grateful to find this place! Logan Square is a great neighborhood with plenty of coffee shops, bars, and restaurants. The apartment was easy to access and very clean. It was particularly clean for a place that people use for celebrations and parties! I really appreciated that. Bathrooms were roomy, great fixtures, and nice decor. Thank you for a wonderful stay! I’d happily book it again.
Home in Des Plaines
4.29 out of 5 average rating, 24 reviews

Spacious Retreat Near Convention Centers

Adil KhanRating, 5 stars1 month ago
Really nice home in a great location. Everything checked out. The only thing you need to worry about is that there’s just one restroom in the house. Apart from that everything was great!
Guest favourite
Home in Logan Square
4.95 out of 5 average rating, 152 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

AlexRating, 5 stars3 weeks ago
Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!
Superhost
Home in Lake View
4.87 out of 5 average rating, 131 reviews

Soak Up Mid-Century Style in Wrigleyville and Boystown

KatieRating, 5 stars4 days ago
Sometimes pictures don't tell the whole story. In this case, the photos of Matt's property didn't do the property justice! This is a gorgeous, beautifully appointed house - difficult to fully convey in photos. Absolutely stunning! From the living areas to the dining room to the kitchen to the bedrooms, it was all perfection - welcoming, clean and user-friendly. The house is located in a wonderful area - restaurants and bars easily within walking distance. Despite the busy-ness of the surrounding area, the house itself was blissfully quiet (a rare find in the heart of Chicago)! Matt was super responsive to the few questions I had - a wonderful host all around. 10/10 would recommend this house, and I can't wait for my next stay!

Holiday condos with a balcony

Guest favourite
Condo in West Town
4.92 out of 5 average rating, 37 reviews

Newly Designed 3bd In Heart of Ukrainian Village

TeriRating, 5 stars1 week ago
The host was excellent at communicating and very responsive! I greatly appreciated her flexibility. Our kids loved the park in the back yard.
Superhost
Condo in Lincoln Park
4.83 out of 5 average rating, 363 reviews

Chic and Charming Vintage Condominium in Lincoln Park

FojanRating, 5 stars1 day ago
We enjoyed our stay! First and foremost Colin was superb! Very responsive and respectful. Many pros about the place: loved the bright bedroom, walkable to many restaurants, neighborhood felt safe, we did not travel with young kids but kids bedroom could have been fun for young kids, the parking spot provided was a huge plus. cons were loud AC, mattress was not as comfortable as one would hope. Place could use some simple aesthetic up keep. Overall, we enjoyed our star and felt very comfortable! Thank you Colin for being above and beyond host :)
Condo in Near West Side
4.87 out of 5 average rating, 382 reviews

3 Bedroom Vintage Hideaway In Little Italy/uic

AlyssaRating, 5 stars1 month ago
We had a great time staying at Matt and Christy’s place. The neighborhood was quiet, providing space to rest after busy days. The apartment had a lot of charm and was a comforting place to return to. It took us about fourteen minutes to walk to the closest metro station, but overall was centrally located for our purposes. The hosts are helpful and were quick to respond when we needed additional supplies.
Guest favourite
Condo in Logan Square
4.81 out of 5 average rating, 287 reviews

Renovated 3br Duplex In Logan Square W/parking

OlgaRating, 5 stars1 week ago
We enjoyed a week of comfortable stay at Matt’s place! We were a family of 5 people and had enough space for everyone! We came for my daughter’s wedding and it was great to have lots of things/amenities that helped us prepare for the wedding! Garage spot was helpful! Backyard peaceful and we spent some time relaxing on the deck! Adorable cozy duplex with everything you need for the relaxed and comfortable stay! Matt was respectful, helpful and very responsive! Area is great as well! Thank you so much!!
Superhost
Condo in Chicago
4.83 out of 5 average rating, 170 reviews

Modern, Spacious 3br Apt Minutes to Downtown!

AnthonyRating, 5 stars3 weeks ago
A great host who responded promptly and was welcoming !
Condo in Wrigleyville
4.8 out of 5 average rating, 230 reviews

Can't Beat This 2min Walk to Wrigley!

AdelineRating, 5 stars5 days ago
the location you can't beat if you are coming to town for a Cubs game. Just down the street from Murphys Bleachers, a great rooftop where you can listen to the game, and lots of space within the place. when we didn't have the corrects sheets for the Murphy bed Kimberly sent them over as soon as she could. I'd stay here again.
Condo in Edgewater
4.87 out of 5 average rating, 157 reviews

Walk to Foster Beach! 3 Bed Andersonville Duplex

MaryRating, 5 stars1 week ago
Our stay could not have been better. We enjoyed all the gathering spots the house afforded — especially the outdoor dining area and the back deck seating area. We had the best time!
Superhost
Condo in Old Town
4.88 out of 5 average rating, 90 reviews

Spacious & Elegant Old Town Duplex

AmyRating, 5 stars2 weeks ago
This condo worked great for our family of 5 (3 teenagers). The location was ideal to the train and bus stops. We were able to easily walk to Old Town where we enjoyed Second City, Corcoran’s Pub and Jeni’s Ice Cream. We felt the condo was in a safe location. You can hear the L go by, but we didn’t mind it; reminded me we were in the city. We were able to secure a parking spot (SpotHero) right behind the condo which was ideal. Was it a bit pricey, yes…it’s Chicago, everything was expensive. Enjoyed our visit!

Quick stats about holiday rentals with a balcony in Chicago

  • Total rentals

    60 properties

  • Nightly prices starting at

    $62 AUD before taxes and fees

  • Total number of reviews

    13K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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  6. Rentals with a balcony