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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Chicago vacation homes

Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is AED 347
AED 881 total
includes taxes & fees
10 Mar - 11 Mar
A quiet stay while you are away
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (78 reviews)
"Nice , private and peaceful definitely will be back "
United States
BRANDEN J.
The price is AED 360
AED 713 total
includes taxes & fees
16 Mar - 17 Mar
Master qtr close to nature & easy urban facilities
Exterior detail

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (69 reviews)
"Really amazing place. Adorable house, plenty of space, conveniently located. Great linens on the beds & amenities in the bathroom. Owner was incredibly flexible and responsive and great to work here. Had three visitors from Europe and they absolutely loved the place and had a great time. Would 100% stay here again the next time we're in the area. "
United States
Erika H.
The price is AED 496
AED 1,207 total
includes taxes & fees
10 Mar - 11 Mar
Quaint Bungalow, near Great Lakes Naval Base
Fridge, microwave, oven, stovetop

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 place Great location "
United States
Josh W.
The price is AED 528
AED 1,453 total
includes taxes & fees
10 Mar - 11 Mar
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Smart TV

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, (21 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is AED 545
AED 1,110 total
includes taxes & fees
10 Mar - 11 Mar
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (59 reviews)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is AED 624
AED 1,133 total
includes taxes & fees
10 Mar - 11 Mar
✽ Charming Cottage ✽ close to College/Town/Station
Fridge, microwave, oven, stovetop

Newly remodeled Near Lake 4BR Hot Tub Navy Family home

Newly remodeled Near Lake 4BR Hot Tub Navy Family home
Gages Lake
10.0 out of 10, Exceptional, (4 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
The price is AED 555
AED 2,824 total
includes taxes & fees
10 Mar - 11 Mar
Newly remodeled Near Lake 4BR Hot Tub Navy Family home
Fridge, microwave, oven, stovetop

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

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (57 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is AED 588
AED 1,240 total
includes taxes & fees
15 Mar - 16 Mar
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Outdoor dining

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.4 out of 10, Exceptional, (23 reviews)
"Had a nice time. Great location!"
United States
Jinjer M.
The price is AED 405
AED 1,033 total
includes taxes & fees
12 Mar - 13 Mar
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Fridge, microwave, oven, stovetop

4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection
Schaumburg
8.4 out of 10, Very Good, (5 reviews)
"Home was perfect for us with two kids. Beds were comfortable and a nice quiet location."
United States
Randy G.
The price is AED 621
AED 1,822 total
includes taxes & fees
10 Mar - 11 Mar
4BR Near Woodfield Mall & Metra | LCP Collection
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (40 reviews)
"Great place to stay. Plenty of backyard space. "
United States
Terrence M.
The price is AED 404
AED 1,041 total
includes taxes & fees
25 Mar - 26 Mar
LUXE 3 BR, 2 BA + Hot Tub
Dining

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, (1 review)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is AED 859
AED 1,468 total
includes taxes & fees
31 Mar - 1 Apr
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"Finding a good 3 br or 4 br option in and around OP / RF is challenging and if this one is available, jump on it. Functional plan, easy parking, great location and responsive owners. "
United States
Lawrence P.
The price is AED 529
AED 1,737 total
includes taxes & fees
10 Mar - 11 Mar
Oak Park Victorian by FLW Studio
Interior

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, (17 reviews)
"This house was perfect for an intimate family and friends get together."
United States
Alyssa R.
The price is AED 432
AED 1,065 total
includes taxes & fees
10 Mar - 11 Mar
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
TV

Modern 4BR Retreat Near MDW | LCP Collection

Modern 4BR Retreat Near MDW | LCP Collection
Burbank
8.6 out of 10, Excellent, (7 reviews)
"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "
United States
Stephanie S.
The price is AED 676
AED 1,682 total
includes taxes & fees
10 Mar - 11 Mar
Modern 4BR Retreat Near MDW | LCP Collection
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14 reviews)
"The house was spotless and very comfortable for our needs. Best of all it was not far from our son’s home in River Forest which made going back and forth convenient."
United States
Beryl I.
The price is AED 826
AED 2,123 total
includes taxes & fees
12 Mar - 13 Mar
Vintage Urban Retreat
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is AED 336
AED 1,976 total
includes taxes & fees
6 Apr - 7 Apr
Near Lake and Museum • Modern • Game Area
Exterior

Near Chicago and O’Hare +Fenced yard +Game room+New Bath!

Near Chicago and O’Hare +Fenced yard +Game room+New Bath!
Schaumburg
9.6 out of 10, Exceptional, (33 reviews)
"We came from Florida to visit family. This house was exactly what we were looking for. Kids loved the game room. Beautiful backyard and comfortable beds. Will stay again. "
United States
Mary M.
The price is AED 818
AED 1,696 total
includes taxes & fees
17 Mar - 18 Mar
Near Chicago and O’Hare +Fenced yard +Game room+New Bath!
Smart TV

Enamored in Elmhurst

Enamored in Elmhurst
Elmhurst
10.0 out of 10, Exceptional, (16 reviews)
"Clean rooms, very helpful and friendly host, the house had everything we needed"
United States
Kaitlyn M.
The price is AED 867
AED 1,915 total
includes taxes & fees
10 Mar - 11 Mar
Enamored in Elmhurst
Living area

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
The price is AED 441
AED 775 total
includes taxes & fees
18 Mar - 19 Mar
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking
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

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

8/10 Good
"Clean room nice staff hotel needed some work. Pool was freezing, our door broke and kept locking us out. "
Richard 1-night trip
Posted 2 hours ago
Courtyard by Marriott Chicago Magnificent Mile