
Holiday rentals with a fireplace in South Side
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Top-rated Accommodation with Fireplace in South Side
Guests agree: these holiday homes with a fireplace are highly rated for location, cleanliness and more.
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Popular amenities for South Side Accommodation with Fireplace
Holiday House Rentals with a fireplace

Gold Coast Home|Rooftop |PoolTable |Parking |Beach
Great home and location. Safe neighborhood, walkable to restaurants, shopping, beach. Home was clutter free, clean and well maintained. Beds were comfortable and we had plenty of supplies for duration of stay (fresh towels, blankets, paper products, soap, shampoo, conditioner, etc.) Rooftop deck with nice view. Host was very responsive with any questions and communicated well. House was perfect size for our group of 6. We appreciate Rasheed making our stay perfect! Will stay here again in the future.

Chicago Home (1st floor) by Midway near Downtown
This was the perfect location just out of the city but a 15 minutes drive to solider field. The rooms were awesome for our group and we really enjoyed our time, would definitely stay again next time I am in Chicago

Modern Charming Home w/Pergola & games
The house was super clean and had everything we needed. Was great to shoot a game or 2 of pool after a long day of visiting family and friends. Very comfortable.

Warm bungalow in New City
Jd’s space was as described, very spacious and accommodating for larger parties. There were snacks, drinks, and towels/linens for use as well as washer and dryer. Jd was also very responsive and a great host. I’d say the biggest drawback was the very creaky floors, with only 3 people staying here, every movement on the main floor was heard. Maybe if we had a larger party, it may have filled up and not been too bad? General Chicago advice for anyone booking: - When considering, be aware that traffic can play a factor in getting from A to B. This is nothing against this specific place or host, just something to be aware of. - You are best off if you rent a car! Paid so much in Ubers and Lyfts in and out of the city. - The roads around this side of town are really bad. All that said, if you prepare correctly and have a large party, this was a very quaint and accommodating stay overall.

Cozy Modern Home w/Fireplace & Pond
The host was very nice and attentive. The place was very nice and clean. Great place to stay

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.

Cozy at The Walter
I thoroughly enjoyed my recent stay at this home. The home itself was filled with everything we could have needed and saved us from trips to the store when we needed something quickly. It also felt to me like it was nicer than the photos and felt extremely safe and comfortable. All in all I would 100 percent stay here again!

Historic Hyde Park Gray stone (upper)
Absolutely stellar stay! Kymi’s Airbnb in Chicago was everything we hoped for and more during our time at ASCO. The home was beautifully decorated, exceptionally comfortable, and stocked with everything we needed. My family felt incredibly safe and at ease the entire time. Kymi herself was a dream host—warm, responsive, and genuinely hospitable. She graciously allowed us to extend our stay and have a late checkout, all without hesitation or hassle. Her kindness and attentiveness made the experience even more special. I highly encourage anyone visiting Chicago to stay at her amazing home—you won’t regret it!
Apartment rentals with a fireplace

Modern 3BR with Private Rooftop & Free Parking
Song’s place was perfect for our family trip to Chicago!

Stunning Retro Apartment in Andersonville
This place absolutely perfect! We were back and forth from Navy Pier for a tournament. The apartment was the perfect escape from the noise. We would definitely stay here again if we come back to the city. I can’t recommend this apartment enough. The price, for Chicago, is totally worth it!! Host is very quick to respond. The distance from the Pier to the apartment is an easy, short drive.

Lovely, spacious 2bd, 1bath home w/free parking
Tiffany was friendly host and made sure to communicate with us to make our stay enjoyable. The place walkable distance to public transit and the neighborhood was safe enough to walk at night. It was clean and as pictured, there was coffee, utensils, plates, etc if you needed prepare food.

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!

Decompress on a Sophisticated Chaise at a Glamorous Hideaway
Simidas very sweet and hospitable. I didn’t need anything but felt cared for. Place is nicer than I thought usually you expect it to be smaller but was very spacious. Great area Felt safe Would come again.

South Loop 3Br/2Ba Condo with Balcony & Parking
Got lucky finding this place. Excellent experience. Great owner. Everything was neat, clean, and super easy. We will gladly be back. Great job!

Large sunny 3BR apt. in downtown Oak Park
This is a great spot in Oak Park for a larger group. Would definitely stay here again when coming to Chicago!

Private apartment with retro vibe
Antoinette was very accommodating and kind! The stay was very comfortable and homey.all instructions were clear and check-in/check-out was a breeze! We walked over to the bakery ahead suggested in the morning too and it was delicious.
Destinations to explore
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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