Mansion vacation rentals in Chicago

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Top-rated mansion rentals in Chicago

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Superhost

Home in Highland Park

4.91 out of 5 average rating, 109 reviews

Rejuvenate and Relax in the North Shore

Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a home away from home. With it's perfect location close to Lake Michigan, Chicago Botanical Garden, Ravinia, Naval Base, and Six Flags Great America to name a few, our family home is within reach to Chicago as well. If you feel very adventurous, just leave your car in garage, pick up a bike and ride the Lake Shore Bike trail all the way to downtown Chicago, enjoying the beautiful scenery. If you feel less adventures but still would like to enjoy beautiful scenery, you can do it by taking a train. Metra can get you downtown Chicago in less than 45 min. and the stop is within walking distance.

May 17 – 24

G$107,728 GYD per night

Guest favorite

Townhouse in Chicago

4.87 out of 5 average rating, 200 reviews

Prime Reviews a Duplex in Logan Square Chicago

Nestled in a quiet cul-de-sac in Logan Square, this is a serene oasis. Steps away from Milwaukee Ave's renowned restaurants, bars, Revolution Brewery, Stan Mansion, and The Whale, 606 trail, Blue Line to airports and downtown, as well as Bucktown and Wicker Park. Logan Square Public Library a block away. Enjoy a self-check-in process, free street parking, fully-equipped kitchen, 4 BR, 2 baths, and amenities like a washer, dryer, and yard. Please note, per Chicago regulations, no parties allowed.

Apr 12 – 19

G$48,013 GYD per night

Guest favorite

Home in Schaumburg

4.97 out of 5 average rating, 103 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.

Sep 16 – 23

G$69,244 GYD per night

Guest favorite

Townhouse in Chicago

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 20 – 27

G$26,819 GYD 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!

Feb 10 – 17

G$97,374 GYD 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

G$83,025 GYD per night

Superhost

Apartment in Chicago

4.86 out of 5 average rating, 154 reviews

*Comfortable & Spacious Home Close to Downtown*

Comfortable & Spacious beautifully furnished home! 4 large bedrooms, and 3 large bathrooms. Fully equipped kitchen. This is a 2200 sq ft of a home away from home with in unit laundry. Free parking! The home is a few blocks from Humboldt Park! Blocks to the train and other nearby transportation. Easy to get a Lyft/Uber from the unit. Walking distance to restaurants, cafes and bars! Free Street parking directly in front of the building, there is no permit or parking pass needed.

Jan 31 – Feb 7

G$56,168 GYD 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

Nov 9 – 16

G$40,690 GYD 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.

Jan 3 – 10

G$54,152 GYD 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.

Jun 30 – Jul 7

G$40,016 GYD per night

Guest favorite

Home in Chicago

4.82 out of 5 average rating, 137 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

G$75,114 GYD per night

Guest favorite

Home in Lombard

4.94 out of 5 average rating, 54 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.

Dec 16 – 23

G$58,004 GYD per night