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House vacation 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, 249 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

4.67 out of 5 average rating, 9 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, 11 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.

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

Guest favourite

Home in Chicago

4.84 out of 5 average rating, 83 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

4.92 out of 5 average rating, 12 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.

Home in Wilmette

4.72 out of 5 average rating, 65 reviews

Wilmette "Treetops" Getaway

This beautifully tucked away east Wilmette gem is a perfect short-term SFH family rental in between real estate or during renovation. Quick walk to the beach, Maple Park, and downtown Wilmette, this 2 bed / 2.5 bath home comes packed with charm. Large en-suite master, and 2nd bedroom with enough beds for 4 kids! Large front patio deck with spiral staircase up to the 2nd-floor deck, which can be used as outdoor office space during the warm months. Make "Treetops" your home away from home!

Guest favourite

Home in Chicago

4.91 out of 5 average rating, 172 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!

Guest favourite

Home in Glen Ellyn

5 out of 5 average rating, 10 reviews

Spacious Deck & Balcony, Game Area, Garage

Welcome to our spacious 5-bedroom, 3.5-bathroom home, perfect for families and groups. Enjoy relaxing on the deck with stairs, and unwind in one of the 6 comfortable beds (all kings and queens). The house features 4 smart TVs and access to an attached garage. Downstairs, the full basement offers a fun game area with ping pong and foosball, plus a sleeper sofa for extra guests. Access to nearby attractions and towns is very easy through direct main road access. Your ideal retreat awaits!

Guest favourite

Home in Schaumburg

4.96 out of 5 average rating, 47 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 Skokie

4.88 out of 5 average rating, 84 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

20 mins from popping downtown Chicago and tucked within one of the Northside’s finest tree-line streets—The Haus of Love: A modern wood burning fireplace, new hardwood floors, and a bright airy space greets you in this newly renovated Kosher inspired design Spacious Eat-In Kitchen w/ double everything. Separate Formal Dining. Wetbar. High End Quartz Countertops 3Bd 3.5Bath Master BD w/Heated Floors, 10-ft ceiling, skylights, and a huge 8-ft tub.

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Popular amenities for Downtown Chicago house rentals

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House rentals with a pool

Home in Glen Ellyn

New place to stay

Pardizes Suites

Guest favourite

Home in Glen Ellyn

4.94 out of 5 average rating, 18 reviews

Glen Ellyn Home

Guest favourite

Home in Chicago

4.81 out of 5 average rating, 31 reviews

2Bed+2Bath PentHouse in South Loop

Guest favourite

Home in Bloomingdale

4.95 out of 5 average rating, 37 reviews

Whole House with a Hot Tub!

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!

Weekly house rentals

Home in Chicago

4.93 out of 5 average rating, 27 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 258 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Guest favourite

Home in Glen Ellyn

4.92 out of 5 average rating, 131 reviews

Home in Glen Ellyn

Home in Western Springs

5 out of 5 average rating, 10 reviews

Western Springs/Furnished long term rental

Guest favourite

Home in Chicago

4.86 out of 5 average rating, 220 reviews

The Avondale Guesthouse

Home in Whiting

4.83 out of 5 average rating, 144 reviews

The Spa of Downtown Whiting

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 180 reviews

Wrigleyville Greystone

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 207 reviews

Paradise on the Park

Private house rentals

Guest favourite

Home in Chicago

4.94 out of 5 average rating, 16 reviews

Warm bungalow in New City

Guest favourite

Home in Chicago

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

Guest favourite

Home in Maywood

5 out of 5 average rating, 8 reviews

Near city 5 BR, 2bath, 2 living room private home

Guest favourite

Home in Chicago Ridge

4.93 out of 5 average rating, 106 reviews

Quiet cul-de-sac with huge fenced in backyard

Home in Palos Heights

4.92 out of 5 average rating, 13 reviews

Luxury Home Fenced In Yard Palos Heights 3BR/2BA

Home in Chicago

4.84 out of 5 average rating, 483 reviews

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

Guest favourite

Home in Chicago

4.92 out of 5 average rating, 26 reviews

A serene haven perfect for the whole family!

Guest favourite

Home in Prospect Heights

5 out of 5 average rating, 15 reviews

Upscale-5 Bed 4.5 Bath-3/4 Acre- 5400 sq ft

Destinations to explore