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Mansion vacation rentals in Chicago

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Top-rated mansion rentals in Chicago

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

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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.

Oct. 23 – 30

$802 CAD per night

Guest favourite

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.

Feb. 17 – 24

$389 CAD per night

Guest favourite

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. 25 – Oct. 2

$551 CAD per night

Guest favourite

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. 21 – 28

$228 CAD per night

Guest favourite

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. 26 – Feb. 2

$785 CAD per night

Guest favourite

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. 25 – Oct. 2

$706 CAD per night

Guest favourite

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. 21 – 28

$1,713 CAD per night

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

$484 CAD per night

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

$306 CAD per night

Guest favourite

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. 17 – 24

$618 CAD per night

Guest favourite

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.

Jan. 7 – 14

$647 CAD per night

Guest favourite

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

$677 CAD per night

Vacation rentals for every style

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Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Chicago mansion rentals

Free parking on premises

Air conditioning

Luxury mansion rentals

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 235 reviews

Spacious 5-BR home next to transit! Great area!

Sep. 18 – 25

$1,095 CAD per night

Guest favourite

Condo in Chicago

4.98 out of 5 average rating, 123 reviews

Luxury 4 bedroom steps from Wrigley

Mar. 5 – 12

$1,401 CAD per night

Apartment in Chicago

4.86 out of 5 average rating, 166 reviews

Impeccable 5-Bed Wrigleville Beauty

Sep. 29 – Oct. 6

$1,489 CAD per night

Condo in Chicago

4.82 out of 5 average rating, 187 reviews

Chicago River West 4 Bedroom / 3 Bathroom

Jul. 8 – 15

$1,369 CAD per night

Home in Chicago

4.9 out of 5 average rating, 160 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Jul. 21 – 28

$1,681 CAD per night

Guest favourite

Townhouse in Chicago

4.97 out of 5 average rating, 122 reviews

*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*

Oct. 3 – 10

$1,077 CAD per night

Guest favourite

Home in Chicago

5.0 out of 5 average rating, 10 reviews

THE DAMEN - Ultra Luxe & Modern + Skyline Rooftop!

May 15 – 22

$1,482 CAD per night

Guest favourite

Home in Chicago

5.0 out of 5 average rating, 50 reviews

Architect's Family Friendly Oasis | 4bd/3ba I Luxe

Nov. 4 – 11

$1,918 CAD per night

Pet-friendly mansion rentals

Guest favourite

Apartment in Chicago

4.92 out of 5 average rating, 133 reviews

❤️ Lowest Rates! Spacious Duplex with Parking!

Jul. 10 – 17

$1,081 CAD per night

Apartment in Chicago

4.8 out of 5 average rating, 263 reviews

Sophisticated, Historic & Comfy Flat near Wrigley!

Feb. 9 – 16

$431 CAD per night

Condo in Chicago

4.79 out of 5 average rating, 107 reviews

Spacious Home, Incredible Lakeview Location

Jul. 15 – 22

$962 CAD per night

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 100 reviews

Luxury House 6BED/2.5BATH/4PARKING close to lake

Jan. 12 – 19

$721 CAD per night

Guest favourite

Home in Chicago

4.84 out of 5 average rating, 150 reviews

Downtown Elegance ✨ Private Yard Parking

Feb. 10 – 17

$799 CAD per night

Guest favourite

Home in Lombard

4.95 out of 5 average rating, 55 reviews

Imagine… 5 Brs/ Game Room

Dec. 16 – 23

$449 CAD per night

Guest favourite

Home in Chicago

5.0 out of 5 average rating, 20 reviews

4BD/4BTH - Entire Building+Garage - Wicker Park!

Jan. 11 – 18

$718 CAD per night

Guest favourite

Home in Elmhurst

4.88 out of 5 average rating, 8 reviews

Elegant Haven: 4BR/3BA Retreat

May 3 – 10

$478 CAD per night

Mansion rentals with a pool

Guest favourite

Home in Schaumburg

4.93 out of 5 average rating, 14 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Jan. 9 – 16

$987 CAD per night

Guest favourite

Home in Glen Ellyn

4.94 out of 5 average rating, 16 reviews

Glen Ellyn Home

May 5 – 12

$795 CAD per night

Guest favourite

Yurt in Homewood

4.97 out of 5 average rating, 74 reviews

Glamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus

Jan. 24 – 31

$489 CAD per night

Apartment in Chicago

5.0 out of 5 average rating, 4 reviews

Luxe 2-Level PH + Spa House Retreat! Pets Welcome

Oct. 23 – 30

$780 CAD per night

Apartment in Chicago

4.61 out of 5 average rating, 49 reviews

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

Mar. 24 – 31

$1,671 CAD per night

Apartment in Chicago

5.0 out of 5 average rating, 3 reviews

Cloud9 | Up to 15 ppl Millenium Park | The Jordan

Jan. 19 – 26

$1,775 CAD per night

Home in Schaumburg

New place to stay

Paradise 4BR w/ Pool & Games

Jun. 25 – Jul. 2

$621 CAD per night

Home in Chicago Heights

Olympia field -matteson IL- homewood, park forest

Jul. 5 – 12

$903 CAD per night

Destinations to explore