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House holiday rentals in Chicago

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Top-rated house rentals in Chicago

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Home in Lake View

4.87 out of 5 average rating, 127 reviews

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

Guest favourite

Home in Wicker Park

4.92 out of 5 average rating, 255 reviews

Cool Quiet Coach House, Private Access + Patio

Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

Home in Highland Park

5 out of 5 average rating, 28 reviews

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

Home in Carol Stream

4.57 out of 5 average rating, 23 reviews

Amazing Summer Pool Awaits You!

Vacation, Staycation or Business, you will love your stay at this beautiful paradise with heated pool and tri-level entertainment deck equipped with grill and outside seating and gazebo! Semi-secluded backyard, walking distance to bike path, playground, skate park, walking trails, restaurants and even the gym! Relax on the magnificent deck while watching the sunset This home is pet free and smoke free. Pool is available May-Sept. WiFi is available throughout and Smart TV in the family room.

Guest favourite

Home in Elmhurst

4.81 out of 5 average rating, 16 reviews

Enamored in Elmhurst

Have fun with the whole family at this beautifully renovated house with and open floor plan, fully stocked kitchen, 4 bedrooms, 2 bathrooms with smart tv's in all the bedrooms and quick reliable wifi for all to enjoy. Home is located only minutes from the highways, enjoy the deck right off the living room and overlooking a private yard . House also has a fully finished basement with 2 of the bedrooms, a full bathroom and a theater room with a sectional sleeper sofa if more space is needed.

Guest favourite

Home in Wrigleyville

4.91 out of 5 average rating, 173 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Home in Oak Park

5 out of 5 average rating, 3 reviews

Down Town Oak Park LUXE Home, 3-Bedroom, 2-Bath

Enjoy the comfort & luxury of this cozy master suite in a beautiful property located in Oak Park's historic district. Just a few steps from iconic sites like the Frank Lloyd Wright Studio and the Ernest Hemingway Birthplace Museum, this contemporary oasis is within walking distance of Oak Park’s vibrant downtown and public transit. This special home is brand new and meticulously clean! it is close to everything, making it easy to plan your visit. Party is not allowed in the house.

Home in Homewood

4.91 out of 5 average rating, 119 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Guest favourite

Home in Avondale

5 out of 5 average rating, 9 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Guest favourite

Home in Schaumburg

4.96 out of 5 average rating, 48 reviews

Paradise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd

Welcome to this inviting 3-bedroom, 1.5-bathroom home in a very safe and quiet neighborhood. Enjoy the tranquility while being close to all shopping, restaurants, and entertainment options. The spacious interior includes a bright living area and a functional kitchen. Additionally, an indoor park nearby offers a great place for year-round recreation. This home combines comfort, convenience, and a prime location, perfect for families and individuals alike.

Guest favourite

Home in Naperville

4.87 out of 5 average rating, 128 reviews

Home away from home

Perfect location, walk/bike to downtown area/ High Speed Wifi throughout the house / 2 King size beds one Queen bed /Newly remodeled / Huge back yard / Brand new appliances / Space for your car in a garage or plenty of parking on long driveway/ Outside porch with seating / Pet friendly - no deposit or any other charge. This is my first house ever listed I will add to the describtion more, after people will notice more things, too many to list.

Guest favourite

Home in Addison

4.96 out of 5 average rating, 69 reviews

Home in Unincorporated Addison. RV & Pet Friendly

Your family will be close to everything when you stay at this centrally-located place. This house is extremely family friendly. It has 4 bedrooms and three baths. It has been recently remodeled inside and out. The yard is close to 3/4 acres and has a kids playground and firepit. The driveway is long and can park a long RV if needed. This is a quiet location. Fully Fenced in Yard with lights all around the house. Very safe location.

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Popular amenities for house rentals in Chicago

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in The Loop

5 out of 5 average rating, 6 reviews

Luxury Condo Downtown Chicago

Guest favourite

Home in Munster

5 out of 5 average rating, 10 reviews

Munster hide away

Home in Lockport

4.67 out of 5 average rating, 3 reviews

Hidden GEM OASIS in Chicagoland

Guest favourite

Home in Near South Side

4.79 out of 5 average rating, 34 reviews

2Bed+2Bath PentHouse in South Loop

Guest favourite

Home in Bloomingdale

4.95 out of 5 average rating, 40 reviews

Whole House with a Hot Tub!

Guest favourite

Home in Schaumburg

4.87 out of 5 average rating, 15 reviews

Schaumburg Oasis with a Pool and Hidden Garden

Home in Glenwood

4.8 out of 5 average rating, 54 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

Home in Oak Lawn

New place to stay

Heated Pool Oasis in Chicago!

Weekly house rentals

Guest favourite

Home in Roscoe Village

4.92 out of 5 average rating, 267 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Guest favourite

Home in Glen Ellyn

4.93 out of 5 average rating, 134 reviews

Home in Glen Ellyn

Guest favourite

Home in Lansing

4.82 out of 5 average rating, 110 reviews

Cozy at the Walter

Guest favourite

Home in Wicker Park

4.97 out of 5 average rating, 30 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

Guest favourite

Home in Avondale

4.86 out of 5 average rating, 220 reviews

The Avondale Guesthouse

Home in Whiting

4.84 out of 5 average rating, 146 reviews

The Spa of Downtown Whiting

Guest favourite

Home in Lake View

4.94 out of 5 average rating, 181 reviews

Wrigleyville Greystone

Guest favourite

Home in Justice

4.94 out of 5 average rating, 220 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

Private house rentals

Home in Oak Park

5 out of 5 average rating, 4 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 16 reviews

Warm bungalow in New City

Home in Bolingbrook

4.73 out of 5 average rating, 22 reviews

Serenity King|7 min -> Hwy & Mall|Backyard

Guest favourite

Home in Logan Square

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

Home in Austin

4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

Home in Blue Island

4.81 out of 5 average rating, 185 reviews

Warm and comfortable inviting Suburban home !

Guest favourite

Home in Chicago Ridge

4.94 out of 5 average rating, 110 reviews

Quiet cul-de-sac with huge fenced in backyard

Home in Near West Side

4.84 out of 5 average rating, 486 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

Quick stats about house rentals in Chicago

Total rentals
2K properties
Total number of reviews
83K reviews
Family-friendly rentals
1.1K properties are a good fit for families
Pet-friendly rentals
520 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
1.3K properties have a dedicated workspace

Destinations to explore