Mansion vacation rentals in Chicago

Find and book unique mansions on Airbnb

Top-rated mansion rentals in Chicago

Guests agree: these mansions are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Schaumburg

4.97 out of 5 average rating, 104 reviews

Modern Spacious Quiet Home Near O'Hare -Deck&Yard

Amazing Modern Big 4 BR 2.5 BA "Aqua' House.Quiet street in the heart of Schaumburg.Upper level:Living Room-TV&Fireplace to cozy up w/h Family.Modern Open Eat-in Kitchen:Custom cabinets,SS Appliances,White Quartz Countertops,breakfast Island.Master suit:King bed&Modern Shower Bath&TV,2nd BR-two full beds,3rd BR-king bed&2nd Modern Tub Bath. Lower Level:Big Family Rom where kids can play,4th BR -king bed&Work Desk,Half bath&Laundry.Big deck&Yard to enjoy w/h family.We have other houses nearby.

Dec 6 – 13

R5,576 ZAR per night

Guest favorite

Townhouse in Pullman

4.86 out of 5 average rating, 43 reviews

Large Executive Row house in Historic Pullman

Charming well appointed home w/exquisite furnishings. Safe, family friendly neighborhood w/shopping nearby. Walking distance to train station. Private entrance w/large rooms & plenty of space to host larger groups. We have everything from soaps to seasonings. Top quality new beds mattresses & linens. Walk to Pullman National Monument with visitors center staffed by US Park Rangers that feature state of the art interactive exhibits that appeal to all ages. Guided walking tours available.

Nov 22 – 29

R2,419 ZAR per night

Guest favorite

Home in Chicago

4.98 out of 5 average rating, 132 reviews

Southwestern Penthouse TRES | Sleeps 12

Come feel the spirit of the Southwest in one of Chicago's best neighborhoods, Logan Square. Relax in a space with Native American Art and dine alfresco on the themed backyard terrace complete with a real wigwam and life-size horses. This gem is ideal for entertaining large Bachelorette groups, friends, and family. Have a larger group? Book both units in the building to sleep 24. Garage onsite parking may be available for 2 cars & our concierge will reach out to help with your every wish!

Jan 15 – 22

R8,045 ZAR per night

Guest favorite

Home in Chicago

4.86 out of 5 average rating, 130 reviews

Lake View | Wrigley Designer House w/Patio

Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

Sep 26 – Oct 3

R7,489 ZAR per night

Guest favorite

Home in Highland Park

4.9 out of 5 average rating, 125 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Jan 22 – 29

R21,388 ZAR per night

Superhost

Apartment in Chicago

4.88 out of 5 average rating, 73 reviews

4Br Gold Coast Duplex w Jacuzzi in the Bedroom!

• MESSAGE US for SPECIAL RATES • Best possible location! • Duplex w amazing set up and comfortable sleeping with King and Queen size beds • Fast Internet • 4K Roku HDTVs in ALL rooms! • Jacuzzi inside the King bedroom • Patio with outdoor furniture • Optional Valet parking in front of the building • Fully equipped kitchen w complimentary Coffee & Tea • Magnificent mile is only a 10 min walk • Oak street beach is a 5 min walk • Rush street restaurants and bars only 5 min walk

Feb 22 – Mar 1

R7,886 ZAR per night

Superhost

Apartment in Chicago

4.83 out of 5 average rating, 250 reviews

4BDRM Gorgeous Apt Pilsen Private Parking avail

7 rooms for large groups and families Sleeps 10 Pls have accurate guest count on reservation before check in Pricing does fluctuate with additional guests. Please note that all guests will be required to send photo ID. Fully functional kitchen & washer/dryer Walking distance to great food Steps to Pink Line CTA station 1.5 blocks, Cermak bus Close to Chinatown, West/South Loops street parking -permit only Beds-2 queen, 1 full, 2 twins (bunk), 2 lounge style couches

Feb 26 – Mar 5

R3,035 ZAR per night

Guest favorite

Apartment in Chicago

4.99 out of 5 average rating, 215 reviews

Modern 4BR 2BA Apt Near Downtown, Free Parking

Welcome to our thoughtfully designed 4 bedroom 2 bath first floor apartment located in the heart of Chicago’s Little Italy, in close proximity to Downtown Chicago ( two miles), West Loop, Greek Town, The Medical District and University of Illinois at Chicago Campuses. You will have no trouble reaching the hottest destinations in Chicago via foot, bike, Uber, cab, or train. Come be our guest! Please read our full listing description and house rules prior to booking.

Apr 1 – 8

R6,551 ZAR per night

Guest favorite

Condo in Chicago

5.0 out of 5 average rating, 99 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Dec 10 – 17

R8,202 ZAR per night

Superhost

Apartment in Chicago

4.88 out of 5 average rating, 49 reviews

Spacious, Artsy 4 BR/2 BA Apartment with Gameroom

Located in the heart of the West Side of Chicago, this spacious 4-bedroom apartment features a stunning indoor arcade and quality amenities. It's the perfect place to have a quick but comfortable 3-day vacation where you can get your arcade gaming fix. Or host a company getaway - meetings during the day and unwind with game night afterward! No drinking bashes though. We’re located on a homey, quiet, peaceful, safe Chicago block....let's keep it that way.

Jul 4 – 11

R3,599 ZAR per night

Guest favorite

Home in Chicago

4.83 out of 5 average rating, 138 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck!

Jan 20 – 27

R6,776 ZAR per night

Guest favorite

Home in Lombard

4.95 out of 5 average rating, 55 reviews

Imagine… 5 Brs/ Game Room

Welcome to "Imagine" - Your Dream Retreat in Lombard, Illinois! Bring the whole family to relax and gather with one another. The attached & heated two car garage is set up as a game room and the fully fenced yard is perfect for your furry friend. Escape to the picturesque charm of Lombard in this spacious and stylish 5-bedroom, 2-bathroom home. "Imagine" is the perfect blend of comfort, convenience, and modern luxury.

Nov 14 – 21

R5,257 ZAR per night