House holiday rentals in Downtown Chicago

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Top-rated house rentals in Downtown Chicago

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Guest favourite

Home in Chicago

4.96 out of 5 average rating, 316 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

House is perfectly located within walking distance of Pilsen's best attractions. Home is furnished and newly renovated with the idea of making your stay as comfortable as possible. Walking distance from Thalia Hall and many other great restaurants and coffee shops. For your convenience there is a "corner store" steps from the home where you can purchase food and beverage items. The whole apartment is professionally cleaned after every guest no matter how many days they have stayed. Fresh sheets and towels are provided for all guests as well. Walking distance from local favorites: Simone’s, Honky Tonk BBQ, Dusek's/Punch House/Thalia Hall, 5 Rabanitos, Furious Spoon, S.K.Y and HaiSous. Located 2 miles South West of Downtown Chicago. Extremely close to South Loop and West Loop. Amenities: - Washer and Dryer (located in unit) - Granite counter tops - All new appliances - Tiled bathroom - Central Heat/AC - Private back deck - Closet space All access, full kitchen, washer and drier in apartment. Private entrance with Keyless entry. Available at any time, happy to answer any questions you may have. Interaction will be dictated by guests. This is a vibrant family neighborhood with character, art, great food, and culture. Walk to amazing restaurants, bars, and coffee shops, including local favorites Simone’s, Honky Tonk BBQ, 5 Rabanitos, Furious Spoon, S.K.Y, and HaiSous. Close to major Chicago highways: I-190: Kennedy Expressway I-290: Eisenhower Expressway I-55: Stevenson Expressway I-90/94: Chicago Skyway, Dan Ryan Expressway, Kennedy Expressway, Jane Addams Memorial Tollway Public transit easily accessible: CTA Bus #8, 18, 60 CTA Trains: Blue, Pink and Orange Lines Divvy Bike Rental Station one block away Permit Parking $6-10 dollar Uber to Downtown

2–9 Feb

$192 SGD per night

Guest favourite

Home in Berwyn

4.91 out of 5 average rating, 241 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

17–24 Sep

$130 SGD per night

Guest favourite

Home in Roscoe Village

4.94 out of 5 average rating, 211 reviews

Modern Home RoscoeVillage/Wrigley Free St Parking

The entire first-floor unit of this house is located in a safe, clean, and quiet area of Roscoe Village/Lake View, surrounded by shops and restaurants. It's just a 5-minute walk to the Brown-line Paulina station, 5 miles to downtown Chicago by L or car, 20 minutes walking to Wrigley Field, and 3 miles to Fullerton or Montrose Beach. It has an open-concept gourmet kitchen, full laundry, fast-speed WIFI, and Roku Streaming, Marquee; complimentary Starbucks coffee beans for freshly brewed coffee.

9–16 Mar

$218 SGD per night

Guest favourite

Home in Chicago

4.98 out of 5 average rating, 206 reviews

Wrigleyville Southport Studio

This Wrigleyville studio is the best of urban living combined with a tranquil retreat. With vintage, mahogany paneled walls and a comfy king size bed this apartment has everything! Free coffee, tea, snacks and dedicated work space. The Southport Corridor is blocks away with restaurants, bars and shopping. Free street parking and 4 blocks to El/ Brown/Purple/ Red line trains. Wrigley Field, Metro and Vic is 4 blocks away. This garden studio is the perfect retreat in the heart of Chicago!

30 Oct – 6 Nov

$219 SGD per night

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 128 reviews

Chicago Riverhouse summer on our patio!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. Amazing chef’s kitchen! 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Chill private patio with illuminating sofa

31 Oct – 7 Nov

$479 SGD per night

Guest favourite

Home in Chicago

4.81 out of 5 average rating, 196 reviews

Spacious Luxury Townhouse - Old Town

Historic 3 bedroom home in Old Town! Comfortably sleeps 6, and access to 3 levels of living space. The massive rain shower in the master bath is my favorite part, but there's plenty of luxury here to enjoy. Plus, we're right in the heart of Old Town, just steps from all of the shops and restaurants on Wells Street, and a 5 minute walk to the Sedgwick Brown/Purple line stop - you can be in the Loop in 20 minutes! Book today! Early Check-Ins and Late Check-Outs are difficult to accommodate.

30 Mar – 6 Apr

$822 SGD per night

Guest favourite

Home in Forest Park

4.91 out of 5 average rating, 223 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

23–30 Jun

$213 SGD per night

Guest favourite

Home in Chicago

4.88 out of 5 average rating, 372 reviews

Pro Cleaned & Isolated West Loop Coach House

Our historic ivy-covered coach house has a private entrance and an airy queen bedroom. The newly renovated kitchen is outfitted with European-sized appliances - though you'll probably have no time to cook, since we're surrounded by the best restaurants Chicago has to offer. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea!. Early Check-Ins and Late Check-Outs are difficult to accommodate.

3–10 Jul

$499 SGD per night

Guest favourite

Home in Chicago

4.86 out of 5 average rating, 215 reviews

The Avondale Guesthouse

This is a private three bedroom house you will be reserving in the Avondale neighborhood with plenty of available free street parking. The residence sits on the intersection of Elston, Rockwell and Wellington. We are in the middle of it all. You can shoot into downtown quickly or be in Wrigleyville within minutes to watch the Cubs. You’ll love this place because of the neighborhood and privacy. The space has been crafted by a well experienced host. 15 minute drive to downtown.

13–20 Feb

$129 SGD per night

Guest favourite

Home in Chicago

4.97 out of 5 average rating, 318 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

15–20 Jan

$250 SGD per night

Superhost

Home in Pilsen Historic District

4.83 out of 5 average rating, 114 reviews

Exclusive and Spacious Pilsen Guest House

Trendy and spacious private home with two bedrooms each with a queen-sized bed. located in the Center of Pilsen neighborhood named "the most vibrant neighborhood in Chicago". Walking distance to 18th street where all bars and restaurant . This elegant and meticulously maintained interior is complemented by stylish furniture and art all for your pleasure. Bunk bed is available for bookings of 5 or 6 guests with extra fee and by coordination at booking

22–29 Mar

$289 SGD per night

Guest favourite

Home in Chicago

4.95 out of 5 average rating, 122 reviews

Cozy & Modern Chic Full House in Trendy Bridgeport

Kick back & relax in your home away from home in our modern & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on popular Morgan Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

21–28 Feb

$164 SGD per night