
Holiday rentals with a balcony in West Side
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Top-rated accommodation with a balcony in West Side
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Apartment rentals with a balcony

Perfect Lincoln Park Retreat - Walk to Depaul!
Catherine was a great host - incredibly responsive and her place had everything my husband and son needed for our stay! Great walkable location and clean unit. Will definitely be returning next time we’re in Chicago!

Eclectic Artist Designed Sanctuary Heart of Pilsen
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!

2 Cozy Bedrooms In a Hidden Wicker Park Gem!
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.

Chic Penthouse In Perfect Wrigleyville Location
Super cute place in a safe neighborhood. The owner's were super nice and communicated with us quickly. We had everything we needed!

Artsy Chicago Abode: Steps to Shops & Restaurants
Had a nice stay. Did the trick as a place to sleep while exploring the city. Good location

3 Bed 3 Bath Lakefront Oasis, Parking Included
Great stay. The property is tucked away and is away from all the city noise. It was very clean and everyone was really impressed. Thank you Sally for a great stay.
The Woodsman's Gallery at OHC - No Cleaning Fee!
Place was as described. Close to great local bars and restaurants and the train. Host was very responsive.

Huge Lincoln Park 6 Bed Duplex with Free Parking!
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

The Roscoe House near Wrigley Field
One of the nicest places near Chicago,

6 Bedrooms In Beautiful Sheridan Park!
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.

Newly Updated Vintage 6 Bedroom Single Family Home
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.

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl
Great place and stay! Location is amazing!
Southwestern Escape in Logan Square, Sleeps 12
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.

Spacious Retreat Near Convention Centers
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!

Soak Up Mid-Century Style in Wrigleyville and Boystown
My family and I really enjoyed staying here. It is in a really cute neighborhood and looks like the photos described. Very walkable to things. Everything we needed for our stay was in the house and accessible to us. It is mentioned in the listing that street parking is available but not reserved spaces. Since we knew this, we planned ahead and found parking in the neighborhood which I strongly recommend doing. The street parking was hard to come by on a weekend. Again, this was not an issue for us but do plan ahead. Matt was a great host and if we ever are in town for a cubs game, we would absolutely stay at this place again. It has so much character and they have very clearly maintained the space well. Also we appreciated how extremely clean everything was.

The Grand Kimball Lodge, Logan Square, Sleeps 20
One of the most you unique Airbnb locations I’ve ever stayed. Bob did an amazing job creating the space . Feels more like a home or something out of photo shoot than an Airbnb. Great space to bring a big group for the weekend. The wood burning sauna was great to have and he was nice enough to set it up for us .
Holiday condos with a balcony

Newly Designed 3bd In Heart of Ukrainian Village
The host was excellent at communicating and very responsive! I greatly appreciated her flexibility. Our kids loved the park in the back yard.

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.

3 Bedroom Vintage Hideaway In Little Italy/uic
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.
The Penthouse Gallery at OHC - No Cleaning Fee!
We loved this place! The vibe is amazing, the neighborhood is safe, and transportation is super close. The host is friendly and helpful…we would definitely stay here again.

Logan Square Beauty with 2 Bedrooms W/parking
Matt is a great host. Open, responsive and informative…everything you want really when on vacation

Can't Beat This 2min Walk to Wrigley!
Wonderful stay!!! We will be back!!!! Great location!!! We loved it!!!

Duplex Near the Beach! 3 Bedrooms In Andersonville
Fantastic!! we love this home and had a beautiful small family reunion here. It was just perfect. The location is wonderful with easy access to Lake Michigan and beautiful walks along the lake.

Spacious & Elegant Old Town Duplex
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!
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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
- Wicker Park
- Willis Tower
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
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