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House vacation rentals in Downtown Chicago

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Top-rated house rentals in Downtown Chicago

Guests agree: these houses are highly rated for location, cleanliness, and more.

Guest favorite
Home in Chicago
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
Dec 14 – 21
$124 per night
Guest favorite
Home in Chicago
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!
Jul 26 – Aug 2
$139 per night
Guest favorite
Home in Chicago
Chicago Riverhouse springtime stay comfy beds
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. Chef’s kitchen! 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relaxing private patio with illuminating sofa
May 3 – 10
$273 per night

Popular amenities for Downtown Chicago house rentals

House rentals with a pool

Guest favorite
Home in Highland Park
2-Acre Highland Park Retreat with Heated Pool ~ 5*
Apr 4 – 11
$805 per night
Guest favorite
Home in Chicago
⭐️ Mario's Pad ⭐️ Arcade, Spa, Pool.
Mar 21 – 26
$759 per night
Guest favorite
Home in Chicago
Luxury Cabin in Lakeview
Aug 18 – 25
$893 per night
Guest favorite
Home in Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
Jan 16 – 23
$361 per night
Guest favorite
Home in Glen Ellyn
Luxe Estate: Heated Pool/Hot Tub/Firepit + 4 Kings
Feb 3 – 10
$956 per night
Guest favorite
Home in Glen Ellyn
Glen Ellyn Home
May 23 – 30
$443 per night
Home in Chicago
2Bed+2Bath PentHouse in South Loop
Mar 2 – 9
$316 per night
Home in Carol Stream
Amazing Summer Pool Awaits You!
Jun 26 – Jul 3
$370 per night
Guest favorite
Home in Niles
Luxury Modern House Epic Master Bath & Pool Table
Jun 30 – Jul 7
$892 per night
Home in Chicago
Animal House
Feb 3 – 10
$90 per night
Home in Lisle
Welcoming, cozy, and a fur baby paradise.
May 4 – 11
$290 per night
Home in Riverwoods
Riverwoods Nature Retreat
Oct 22 – 29
$675 per night

Weekly house rentals

Guest favorite
Home in Chicago
Pro Cleaned & Isolated West Loop Coach House
Dec 7 – 14
$163 per night
Guest favorite
Home in Chicago
Division St Designer Home In Heart of Wicker Park
May 22 – 29
$410 per night
Guest favorite
Home in Berwyn
Private apartment with retro vibe
Jun 11 – 18
$84 per night
Guest favorite
Home in Chicago
Private 3rd Floor Apartment
Dec 3 – 10
$109 per night
Guest favorite
Home in Chicago
Greystone Haven in Logan Square
Jul 6 – 13
$216 per night
Guest favorite
Home in Chicago
The Avondale Guesthouse
Dec 8 – 15
$70 per night
Guest favorite
Home in Chicago
Historic Old Town, Fabulous 4 Bedroom Home
Sep 18 – 25
$368 per night
Guest favorite
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
May 9 – 16
$119 per night
Guest favorite
Home in Chicago
Cool Quiet Coach House W/ Private Access and Outdoor Space
Dec 12 – 19
$190 per night
Superhost
Home in Chicago
Lincoln Park - DePaul House w/Patio Free Parking
Apr 7 – 14
$212 per night
Guest favorite
Home in Chicago
Spacious Two Story Luxurious Home w/Outdoor Deck!
Nov 28 – Dec 5
$300 per night
Guest favorite
Home in Chicago
Superhost Wrigley/Lakeview Duplex 3BR/2.5BA
Oct 10 – 17
$446 per night

Private house rentals

Guest favorite
Home in Chicago
Huge Home * Yard * Parking * Best Location
Mar 8 – 15
$394 per night
Guest favorite
Home in Chicago
Lakeview Condo
Jan 31 – Feb 7
$86 per night
Guest favorite
Home in Chicago
Live Like a Local + Roomy home by Mexican Museum
Apr 7 – 14
$61 per night
Superhost
Home in Chicago
503LOFT | Top Floor 5 BED, 2 BA Downtown Loft
Feb 6 – 13
$224 per night
Guest favorite
Home in Chicago
Modern Lux Getaway w/ Hot Tub, Lrg Yard, Pet Fndly
Nov 16 – 23
$273 per night
Guest favorite
Home in Chicago
NEW! 3BR/2.5B Duplex in Noble Sq
Dec 25 – Jan 1
$341 per night
Guest favorite
Home in Berwyn
Retro Modern Bungalow | fire pit | free parking
Nov 5 – 12
$125 per night
Guest favorite
Home in Chicago
Victorian House in Heart of Rogers Park
Mar 3 – 10
$347 per night
Guest favorite
Home in Skokie
Culinary DREAM - Pizza Oven/BBQ/Smoker
Apr 6 – 13
$334 per night
Guest favorite
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
Oct 24 – 31
$195 per night
Superhost
Home in Chicago
Hyde Park Haven: Exquisite Airbnb
Apr 21 – 28
$360 per night
Guest favorite
Home in Chicago
Flat in Lincoln Park 2-Flat Central to Everything
Feb 1 – 8
$204 per night

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