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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Chicago vacation homes

Interior

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (8 reviews)
"Excellent, clean, modern, fully furnished apartment in downtown Chicago that is a short car ride or walk to anything you need or want to visit. The neighborhood and building are very safe and the covered parking is well worth the extra expense. We loved the extra space to spread out and the skyline views were beautiful at night. The staff responded right away to any questions we had and even helped to accommodate us an extra night when an event kept us in town longer. The beds were comfortable...
United States
Kathryn
The price is CA $383
CA $888 total
includes taxes & fees
Jul 12 - Jul 13
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (16 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is CA $1,475
CA $2,438 total
includes taxes & fees
Jul 30 - Jul 31
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, (85 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is CA $165
CA $310 total
includes taxes & fees
Jul 23 - Jul 24
Master qtr close to nature & easy urban facilities
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, (29 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is CA $210
CA $431 total
includes taxes & fees
Jul 21 - Jul 22
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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 CA $191
CA $506 total
includes taxes & fees
Aug 2 - Aug 3
Quaint Bungalow, near Great Lakes Naval Base
Interior

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
10.0 out of 10, Exceptional, (1 review)
The price is CA $935
CA $1,677 total
includes taxes & fees
Jul 18 - Jul 19
Modern 3BR Apartment Near North Ave Shops
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 CA $255
CA $461 total
includes taxes & fees
Jul 26 - Jul 27
✽ Charming Cottage ✽ close to College/Town/Station
TV

4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
The price is CA $166
CA $814 total
includes taxes & fees
Jul 12 - Jul 13
4BR Retreat w/ Theater, Arcade, Gym and Firepit
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, (30 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 CA $277
CA $544 total
includes taxes & fees
Jul 14 - Jul 15
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.
The price is CA $257
CA $826 total
includes taxes & fees
Jul 14 - Jul 15
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Interior

Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
The price is CA $254
CA $514 total
includes taxes & fees
Aug 10 - Aug 11
Cozy Home by O'Hare + EV Plug
7 bedrooms, desk, iron/ironing board, travel crib

Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (2 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is CA $212
CA $1,089 total
includes taxes & fees
Jul 14 - Jul 15
Arcade • Theater • Gym • Office • Sleeps 15
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (53 reviews)
"Great stay"
United States
Steve T.
The price is CA $283
CA $564 total
includes taxes & fees
Jul 27 - Jul 28
LUXE 3 BR, 2 BA + Hot Tub
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 CA $153
CA $686 total
includes taxes & fees
Jul 14 - Jul 15
Game Room • Fire-pit • Playground • Gym • Billiard
Dining

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (2 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is CA $196
CA $1,259 total
includes taxes & fees
Jul 14 - Jul 15
Sleeps 18 • 8BR • Game Room • Gym • Theater
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 CA $283
CA $587 total
includes taxes & fees
Aug 9 - Aug 10
*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, (76 reviews)
"This place was just what we needed. Super close to Allstate Arena, lots of food options nearby. Neighborhood was quiet and seemed very safe. Beds were comfortable, kitchen was fully stocked, had everything we needed for our 1 night stay!"
United States
Nikki B.
The price is CA $283
CA $518 total
includes taxes & fees
Jul 14 - Jul 15
Your Next Vacation Home
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 CA $255
CA $331 total
includes taxes & fees
Jul 22 - Jul 23
Attractive Coach House Apartment for rent in Oak Park.
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 CA $421
CA $844 total
includes taxes & fees
Jul 14 - Jul 15
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
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 CA $364
CA $784 total
includes taxes & fees
Jul 14 - Jul 15
Modern Stylish Comfort Near Casino and Hwy
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Awesome stay!"
Tiffany Rene 3-night trip
Posted 3 hours ago
Hotel Riu Plaza Chicago

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
529
Accommodation
856 Vacation Homes
Lowest Price
CA $310
Highest Price
CA $2,438

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