Mansion holiday rentals in Chicago

Beautiful Chicago Greystone

Experience the best of Chicago from this sprawling, private 4-bedroom condo. Located just 15 minutes west of the City Center, you’re perfectly positioned to explore the culinary scene of the West Loop, the lush Garfield Park Conservatory, and the energy of the United Center Transit: Steps from multiple bus lines, 2 blocks to the Blue Line, and 1 mile to the Pink Line Amenities: On-site laundry (available upon request) Local Experts: We live in the unit below and happy to give recommendations

NorthSide Chicago duplex 5-BD,2King size-free park

5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

H&H 1896 - Spacious, Fully Stocked, & Free Parking

Built in 1896, modern restoration, & featured on HermosaChi blog “Homes built before 1900”. The exterior of this private compound includes free driveway parking for up to 6 cars, beautiful backyard garden, pergola, fire pit, basketball court, & children’s swing set. The interior sleeps up to 21 guests, consists of modern aesthetics, moody hues, home theatre, exercise room & also a kids jungle gym. Located just 20 minutes from the heart of downtown Chicago, your private urban retreat awaits!

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

Escape into this Wicker Park Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Division St. - Close to every popular attraction that makes Chicago so great - Luxurious interior filled with natural light - Open-floor plan for entertaining! - City skyline views from top floor! - Fast WiFi (1,000 mbps) - Large attached garage! - Beautiful custom built-ins - Next to modern park and playground! - 10 minute walk from blue line (CTA L)

Large Remodeled Home in Lincoln Park, Sleeps 12!

Stay in this thoughtfully remodeled home in Lincoln Park. Sleeps 12 w/ complimentary access to 3 parking spots! Enjoy the spacious layout, massive bedrooms, 2 private decks, and front yard w/ a grill. You will be steps from the North & Clybourn Red Line station, Divvy stations, Starbucks, Binny's, Whole Foods, Trader Joe's, Alinea, Steppenwolf Theatre, and more! Our home is (conveniently!) located next to train tracks. If you are a light sleeper, this urban location might not be for you.

Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

Treat yourself to this Chicago getaway with 14 of your friends & family. Be inspired to create culinary delights in our celebrated 5 stars outdoor kitchen. Reboot & relax in each of our thoughtfully designed powered by SOLAR ENERGY throughout. After a memorable night in OR an adventurous night out you will ask yourselves, 'Why don't we do this more often?' 15 mins to Downtown, O’Hare airport, West Loop. 20 mins to Lakeview, Wrigleyville, Boystown, Logan Square, Bucktown & Wicker Park.

Comfy/Elegant Home by Wrigley, Garage Spot & Yard

This chiq duplex home near Wrigley Field is a hidden gem. It features 6 beds, a garage parking spot; and a fenced yard; with 5 bedrooms, 3 baths, a spacious living & dining area and fast gigabit internet. In an unbeatable location close to many popular attractions, this home is the perfect base for your Chicago adventures. 6 min drive to: -Wrigleville -Andersonville & Boystown -Montrose Beach -Uptown, Green Mill, Riviera / Aragon Theaters 15-20 min drive: Cloudgate, Downtown, Loop!

Modern+Spacious Inn Little Italy Near W Loop W/PKG

Welcome to our super clean and 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.

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.

The Chicago Game Room (Oak Park, IL)

There is no other rental like this in the Chicago area! Located in the first suburb west of Chicago, this 4-bedroom, two-level private apartment is brand new and ready for your group to enjoy. It features an amazing game room/living room with cathedral ceilings, skylights, gas fireplace, bar seating, pool table, shuffleboard/bowling table, dart board, four bedrooms + sleeper sofa, full kitchen, spa-like bathrooms, in-unit washer/dryer, and private deck. GUESTS = 8 MAX