
Mansion holiday rentals in Chicago
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Top-rated mansion rentals in Chicago
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Popular amenities for Chicago mansion rentals
Luxury mansion rentals

ALOHA Penthouse in Wicker Park w/Backyard Patio
Great Airbnb for a bachelorette party! Tons of space, beds and a great location in Chicago even for a local group. The hosts were very easy to communicate with. I would recommend the space to anyone looking for an Airbnb for a large group!

Sophisticated, Historic & Comfy Flat near Wrigley!
Definitely a beautiful home in a great neighborhood. We loved Chicago and being able to stay in such a a lovely home.

Luxe SFH Bucktown Retreat with Garage Parking
The home was beautiful, clean, easily accessible and located in a great area. We had many options for restaurants within a few minutes drive. Easy access to downtown for exploring. Very comfortable amenities and well stocked kitchen. We would stay here again!

Spacious Five Bedroom Home in Trendy Chicago Neighborhood
Great experience at Casey’s place. The home is as well stocked with kitchen essentials and extras as any place that we have ever stayed. There were toys for the kids and the design of the place was awesome. We had a great stay and would definitely come back.

Luxury Penthouse Loft | Heart of Fulton Market
This apartment is fantastically located and has many great amenities. My college buddies and I did a weekend in Chicago (7 of us total) and this place was an awesome home base. Sleek, modern feel, plenty of room and a great location. Highly recommend!

Downtown Elegance ✨ Private Yard Parking
Alex was great at communicating and following up. We had some questions and she was responsive. Also goes beyond expectations on things like forgetting coats :0) - thank you! The location is great. Short walk to a Main Street of bars and restaurants, kid friendly too - happy campers pizza joint was a great reco! Also close to the brown line train station and not too far into town - we walked it with children and it was fine. House is really large, spacious. I know some have mentioned about hearing the train, but that is part of city living, it was more than fine. Enjoyed the stay, would recommend it and would go back again if visiting Chicago. Thanks Alex!

Game Room • Fire-pit • Basketball • Gym • Billiard
Extremely nice home. One of the rooms was smaller than expected, that being said, 4 bedrooms is very impressive. Only complaint is things that I had to repair. The towel holder kept falling down but once I tightened the screws it stopped falling. Also the blind that covering the sliding door to the backyard was broken. So if we wanted to go outside or take out the trash we had to move around the blinds. Besides that the home was very spacious with a very nice kitchen and bathrooms. The master bathroom even had a bidet, which was a nice surprise!

Large Remodeled Home in Lincoln Park, Sleeps 12!
Kelsey and Sean’s place was fantastic. Beautiful home that was clean, in a great location, and easy check-in/check-out process. Would 100% recommend to others.
Pet-friendly mansion rentals

Cozy Private & Spacious Duplex
We had a large group staying overnight for a memorial service the next day. They were extremely accommodating as we had family coming from multiple states. It was exactly as described and Craig responded quickly. Would highly recommend and would be happy to stay there again.

Spacious Row Home next to Transit w Garage
Tian’s row-house was spacious and comfortable! Great for large groups with kids. 4 bedrooms had doors on them, and the 2 extra sleeping spaces were not enclosed, so better for kids (bunk beds). Kitchen was well appointed, open to the dining and living rooms, making the open plan common space really spacious. We were a group of 11 people and there was plenty of room for all of us. The neighborhood was quiet at night, sleeping was never a problem, and the beds were comfortable… plenty of extra pillows, blankets, etc. The 2 and a half bathrooms were also large and roomy. We mostly used Uber to get to downtown Chicago, although there is a train stop nearby. It usually took about 20 minutes and cost around $30. This was economic for us since we didn’t want to rent a car and navigate independently. The price for this extra large property was great, given all the comfortable space we got! We had a wonderful stay there.

Rejuvenate: 4BR, fenced yard
The only thing I didn’t like was the smart lock due to having to download an app and creating an account , there is not an exterior pic of the place and the floor was to noise when walking, I would wake up in the middle of the night from my roommates waking up to the toilet or early in the morning . But everything else was perfect.

The Country Life! Entire House.
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.

Chicago's Bridgeport Huge 4 Story w/Garage Parking
Wonderful home! Plenty of space for our family, super responsive host, very clean, and very close to lots of things in Chicago.

Home in Unincorporated Addison. RV & Pet Friendly
We loved our stay at Javier’s place! It was perfect for a large group. So spacious, clean, and comfortable. The backyard was also great, if the weather had been better it would have been lovely to spend time out there. Javier was also very responsive and proactive.

4BDRM Gorgeous Apt Pilsen Private Prking Available
The hosts were very responsive. The place is in a great location and close to public transit. Would definitely stay there again

Elegant Haven: 4BR/3BA Retreat
Jamie and Erika were very helpful and the home was beautiful and clean. Easy access to everything in Elmhurst. IL
Mansion rentals with a pool

Pardizes Suites
Lisa was the best host I've ever had. The house was amazing. Definitely #1 against every other AIR BNB I've ever stayed at before. This house was comfortable, up to date (if not ahead of its time). The atmosphere was great. The beds were comfortable. There was so much to do in that home. I honestly will do my best to stay in this home again in the future. Outstanding job Lisa. See you soon!!! Rated 10 stars.......

Munster hide away
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.

Whole House With Hot Tub And Spacious Bedrooms
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again

Your favorite vacation spot
A nice quiet calm getaway perfect for friends or family

Beautiful 137 Year Old Farm Home (3night min)
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

Spacious Family Glenwood Estates Home w/ Hot Tub!
Loved this Airbnb! Didn’t want to leave.

Paradise 4BR w/ Pool & Games
We recently moved backed to the Chicagoland area from Texas. We needed a place to stay while our Chicago home was being renovated. Lily’s place was perfect. It had everything we needed for the duration of our extended stay. It was well appointed. Exceptionally clean. It had all the amenities necessary for our family to live comfortably and it was close to grocery stores, shopping, restaurants, and downtown Chicago. Highly recommend.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Lincoln Park
- Museum of Science and Industry
- Willis Tower
- Chicago History Museum
- Brookfield Zoo
- Flossmoor Golf Club
- Illinois Beach State Park
- Skokie Country Club
- Garfield Park Conservatory
- Chicago Cultural Center
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