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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Chicago vacation homes

Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Apartment looked exactly like the photos, very clean, great location, and perfect for our quick stay! The check-in process was very easy and we had no issues. The host is very responsive to any questions or concerns. "
United States
Jessica S.
The price is AED 1,050
AED 2,389 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
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, (84 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is AED 426
AED 787 total
includes taxes & fees
5 Jul - 6 Jul
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, (72 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
The price is AED 496
AED 1,296 total
includes taxes & fees
5 Jul - 6 Jul
Quaint Bungalow, near Great Lakes Naval Base
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (51 reviews)
"Great stay"
United States
Steve T.
The price is AED 661
AED 1,352 total
includes taxes & fees
7 Jul - 8 Jul
LUXE 3 BR, 2 BA + Hot Tub
Exterior

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (69 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is AED 661
AED 1,148 total
includes taxes & fees
26 Jul - 27 Jul
✽ Charming Cottage ✽ close to College/Town/Station
Smart TV

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
9.0 out of 10, Wonderful, (2 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AED 503
AED 845 total
includes taxes & fees
12 Jul - 13 Jul
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
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 location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is AED 926
AED 1,957 total
includes taxes & fees
6 Jul - 7 Jul
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, (28 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is AED 545
AED 1,106 total
includes taxes & fees
13 Jul - 14 Jul
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Paper towels, dining tables

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
wheaton
10.0 out of 10, Exceptional, (1 review)
"Perfect house for our family trip. Plenty of space for everyone. "
United States
Kristine T.
The price is AED 1,014
AED 2,087 total
includes taxes & fees
6 Jul - 7 Jul
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
Living area

Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
7.0 out of 10, Good, (2 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is AED 595
AED 765 total
includes taxes & fees
1 Jul - 2 Jul
Attractive Coach House Apartment for rent in Oak Park.
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
9.6 out of 10, Exceptional, (29 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
The price is AED 737
AED 1,431 total
includes taxes & fees
2 Jul - 3 Jul
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Interior

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.
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
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
9.6 out of 10, Exceptional, (62 reviews)
"Our stay was very comfortable. Communication was fantastic and super timely. The kitchen was well stocked. The house was very clean and spacious. Would definitely stay there again!"
United States
Erin B.
The price is AED 702
AED 1,481 total
includes taxes & fees
15 Jul - 16 Jul
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Private kitchen

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (75 reviews)
"Spacious, clean, well appointed kitchen with air fryer, good location and communication, we would rent again. "
United States
Ann T.
The price is AED 876
AED 1,499 total
includes taxes & fees
6 Jul - 7 Jul
Your Next Vacation Home
Fridge, microwave, oven, stovetop

Modern Stylish Comfort Near Casino and Hwy

Modern Stylish Comfort Near Casino and Hwy
Homewood
10.0 out of 10, Exceptional, (1 review)
"Very clean..out side garbage needs to be picked up. Toilet seats were loose and under kitchen sink was wet. Could use a toaster and some basic condiments. "
United States
margaret
The price is AED 646
AED 1,647 total
includes taxes & fees
1 Jul - 2 Jul
Modern Stylish Comfort Near Casino and Hwy
Fridge, microwave, oven, stovetop

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Property was the perfect size for our group. Neighborhood was quiet. Street parking was available directly in front of the house. Great experience!!!!"
United States
Justin C.
The price is AED 580
AED 1,994 total
includes taxes & fees
9 Jul - 10 Jul
Game Room • Fire-pit • Playground • Gym • Billiard
Exterior

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 AED 740
AED 1,331 total
includes taxes & fees
21 Jul - 22 Jul
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Fridge, microwave, oven, stovetop

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 AED 1,125
AED 2,671 total
includes taxes & fees
22 Jul - 23 Jul
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Fridge, microwave, oven, stovetop

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
Libertyville
The price is AED 657
AED 2,467 total
includes taxes & fees
6 Jul - 7 Jul
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
3 bedrooms, iron/ironing board, WiFi, bed sheets

Lovely 3-bedroom house in Villa Park with WiFi and AC

Lovely 3-bedroom house in Villa Park with WiFi and AC
Villa Park
9.0 out of 10, Wonderful, (2 reviews)
"Location was great."
United States
Jessica F.
The price is AED 764
AED 1,790 total
includes taxes & fees
1 Jul - 2 Jul
Lovely 3-bedroom house in Villa Park with WiFi and AC
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

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"Great place to stay in the city"
Burt 1-night trip
Posted 3 hours ago
Congress Plaza Hotel