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Our top choices for Chicago holiday homes

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is HK$5,234
HK$9,050 total
includes taxes & fees
12 Jun - 13 Jun
Modern 3BR Apartment Near North Ave Shops

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (83 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is HK$854
HK$1,611 total
includes taxes & fees
18 Jun - 19 Jun
Master qtr close to nature & easy urban facilities

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
South Evanston
10.0 out of 10, Exceptional, (37 reviews)
"Excellent property and host. Truly enjoyed our stay. "
United States
Shashi Y.
The price is HK$1,559
HK$2,625 total
includes taxes & fees
2 Jun - 3 Jun
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
9.8 out of 10, Exceptional, (68 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is HK$1,410
HK$2,533 total
includes taxes & fees
2 Jun - 3 Jun
✽ Charming Cottage ✽ close to College/Town/Station

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is HK$1,254
HK$4,995 total
includes taxes & fees
16 Jun - 17 Jun
Near Lake and Museum • Modern • Game Area

South Loop · 3 Kings · Steps from McCormick Place

South Loop · 3 Kings · Steps from McCormick Place
Near South Side
10.0 out of 10, Exceptional, (1 review)
"This apartment had all the amenities we needed for our 3 day stay in Chicago. It was much larger than I expected and high ceilings made it feel like we were in a loft. I’m happy we made the decision to stay here rather than at a hotel, where I would’ve had to listen to people talking in the hallway or doors being slammed all night. Here, it was quiet and the location was perfect. We were just about 12 minutes from downtown, which made it convenient to drive downtown when we needed to. "
United States
Markeisha W.
South Loop · 3 Kings · Steps from McCormick Place

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (27 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is HK$1,171
HK$2,367 total
includes taxes & fees
1 Jun - 2 Jun
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
10.0 out of 10, Exceptional, (1 review)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is HK$1,034
HK$1,719 total
includes taxes & fees
26 May - 27 May
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (62 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is HK$1,269
HK$2,680 total
includes taxes & fees
26 May - 27 May
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is HK$1,341
HK$3,388 total
includes taxes & fees
26 May - 27 May
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
10.0 out of 10, Exceptional, (1 review)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is HK$1,269
HK$1,633 total
includes taxes & fees
26 May - 27 May
Attractive Coach House Apartment for rent in Oak Park.

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (48 reviews)
"Great stay"
United States
Steve T.
The price is HK$1,410
HK$2,909 total
includes taxes & fees
26 May - 27 May
LUXE 3 BR, 2 BA + Hot Tub

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Lombard
9.6 out of 10, Exceptional, (18 reviews)
"Location was easy to find and good as a base for day trips to Chicago. "
United States
Brian H.
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Bensenville
10.0 out of 10, Exceptional, (1 review)
"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "
United States
Jacob F.
The price is HK$1,322
HK$4,416 total
includes taxes & fees
27 May - 28 May
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (31 reviews)
"Wonderful place to gather for our annual corporate operations retreat. A great place to disconnect and focus. "
United States
Jennifer A.
The price is HK$1,569
HK$4,272 total
includes taxes & fees
26 May - 27 May
Oak Park Victorian by FLW Studio

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Game Room

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Game Room
Brookfield
The price is HK$1,873
HK$3,931 total
includes taxes & fees
10 Jun - 11 Jun
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Game Room

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (2 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is HK$1,918
HK$3,245 total
includes taxes & fees
9 Jun - 10 Jun
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
North Chicago
7.6 out of 10, Good, (4 reviews)
"Rented this property for my sons navy graduation, Base was only 6 minutes from the home. Tons of places to eat and shop no more then 15 minutes away. The house was super cute, very clean. we flew in at 10am and without even having to ask the host reached out and let us know it was ready for check in a few hours early which was great. left some packaged up congrats grad decor that hopefully didnt get thrown out and the next navy fam can use. "
United States
Linda U.
The price is HK$1,379
HK$3,081 total
includes taxes & fees
26 May - 27 May
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
The price is HK$1,771
HK$4,889 total
includes taxes & fees
16 Jun - 17 Jun
Game Room • Fire-pit • Playground • Gym • Billiard

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Carol Stream
9.4 out of 10, Exceptional, (6 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is HK$1,631
HK$4,809 total
includes taxes & fees
7 Jun - 8 Jun
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chicago Hotel Reviews

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
248
Accommodation
818 Vacation Homes
Lowest Price
HK$1,611
Highest Price
HK$9,050

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