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House holiday rentals in Downtown Chicago

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Top-rated house rentals in Downtown Chicago

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Home in Chicago

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 Chicago

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 Chicago

4.7 out of 5 average rating, 10 reviews

Entire Home + Jaccuzi! Gem in Chicago 4BD/3BA

Welcome to our stunning getaway! This entire luxury home is designed to provide comfort & entertainment for your group of up to 8 guests; Indulge in the spacious entertainment area. The backyard is your private oasis, a beautifully landscaped space perfect for gatherings. With 4 lavish bedrooms, a fully equipped kitchen, & modern amenities throughout, your stay here promises both luxury and convenience. Our central location puts you just moments away from the city's finest attractions. Book now!

Guest favourite

Home in Chicago

5 out of 5 average rating, 13 reviews

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

Guest favourite

Home in Elmhurst

4.82 out of 5 average rating, 11 reviews

Premier 5BR/3BA Modern Retreat with King Suite!

Beautiful 5BR/3BA Retreat in a Chicagoland suburb! ☆ Newly renovated and stylish, this spacious home features a modern open layout, luxurious bedrooms, a gourmet kitchen, and elegant bathrooms. Explore the vibrant Chicagoland neighborhood with local shops and parks, then come home to relax in peace. Conveniently located in a prime area, quick drives from the airport and Oak Brook shopping mall. Ideal for families, groups, or anyone seeking comfort and convenience. Book now for a memorable stay!

Guest favourite

Home in Chicago

4.85 out of 5 average rating, 87 reviews

California Cottage/4br prime location Logan Square

Incredible location in Logan Square! Walking distance from dozens of restaurants, breweries, bars, nightlife, the square, the farmers’ market and much more. Free street parking in front. 2 blocks from 90/94 and close to the blue line train which goes to many of Chicago’s iconic neighborhoods, downtown, and directly to O’ Hare airport. Beautiful house with high ceilings on the 1st floor. Lovely kitchen with nice appliances. 2 cozy bedrooms upstairs. One with a queen and the other has 3 twins.

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 Chicago

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.

Guest favourite

Home in Chicago

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 Elmhurst

4.96 out of 5 average rating, 105 reviews

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

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 Downtown Chicago

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Chicago

5 out of 5 average rating, 6 reviews

Luxury Condo Downtown Chicago

Home in Des Plaines

New place to stay

Rosemont 4BD2BA house with Pool

Guest favourite

Home in Chicago

4.79 out of 5 average rating, 34 reviews

2Bed+2Bath PentHouse in South Loop

Home in Oak Lawn

New place to stay

Paradise in Real Life , Downtown’s Best Citylife

Home in Oak Lawn

New place to stay

Heated Pool Oasis in Chicago!

Guest favourite

Home in Schaumburg

4.96 out of 5 average rating, 27 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Weekly house rentals

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 32 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 16 reviews

Warm bungalow in New City

Guest favourite

Home in Chicago

4.92 out of 5 average rating, 266 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Home in Blue Island

4.81 out of 5 average rating, 185 reviews

Warm and comfortable inviting Suburban home !

Guest favourite

Home in Chicago

4.97 out of 5 average rating, 30 reviews

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

Guest favourite

Home in Chicago

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 Chicago

4.94 out of 5 average rating, 181 reviews

Wrigleyville Greystone

Private house rentals

Guest favourite

Home in Chicago

5 out of 5 average rating, 6 reviews

Pilsen Single family house

Guest favourite

Home in Des Plaines

5 out of 5 average rating, 9 reviews

Des Plaines Home

Guest favourite

Home in Chicago

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

Home in Chicago

4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

Home in Glenview

5 out of 5 average rating, 17 reviews

Delightful Cozy 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 Chicago

4.84 out of 5 average rating, 486 reviews

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

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 27 reviews

A serene haven perfect for the whole family!

Destinations to explore