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Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

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

Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
The price is CA $344
CA $490 total
includes taxes & fees
Jul 22 - Jul 23
Beautifully furnished one bedroom loft located in Chicago's South side suburb
Dining

Charming Farmhouse Fully Furnished Near Chicago and Metra

Charming Farmhouse Fully Furnished Near Chicago and Metra
Harvey
The price is CA $131
CA $246 total
includes taxes & fees
Jul 19 - Jul 20
Charming Farmhouse Fully Furnished Near Chicago and Metra
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 $599
CA $1,199 total
includes taxes & fees
Jul 21 - Jul 22
Modern 3BR Apartment Near North Ave Shops
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)
"It was great! Very quiet and clean."
United States
Tony G.
The price is CA $163
CA $305 total
includes taxes & fees
Jul 23 - Jul 24
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)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
The price is CA $190
CA $501 total
includes taxes & fees
Aug 2 - Aug 3
Quaint Bungalow, near Great Lakes Naval Base
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)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is CA $208
CA $427 total
includes taxes & fees
Jul 20 - Jul 21
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Exterior

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (69 reviews)
"2nd stay. Will stay again"
United States
Rusty D.
The price is CA $253
CA $457 total
includes taxes & fees
Jul 29 - Jul 30
✽ Charming Cottage ✽ close to College/Town/Station
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 $277
CA $1,163 total
includes taxes & fees
Jul 20 - Jul 21
Arcade • Theater • Gym • Office • Sleeps 15
3 bedrooms, iron/ironing board, travel crib, WiFi

3BR · Steps from McCormick · Balcony & Gym

3BR · Steps from McCormick · Balcony & Gym
Near South Side
9.8 out of 10, Exceptional, (6 reviews)
"Six of us made a trip to Chicago and stayed at this location. The place is very roomy with a full kitchen. There was public transportation nearby to get us ro everywhere we were going ( Field museum, Grant park, Navy pier)."
United States
Kathy
The price is CA $293
CA $769 total
includes taxes & fees
Jul 20 - Jul 21
3BR · Steps from McCormick · Balcony & Gym
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 $326
CA $1,425 total
includes taxes & fees
Jul 22 - Jul 23
Sleeps 18 • 8BR • Game Room • Gym • Theater
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.
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Interior

Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.6 out of 10, Exceptional, (15 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 $233
CA $488 total
includes taxes & fees
Aug 10 - Aug 11
Cozy Home by O'Hare + EV Plug
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 $237
CA $788 total
includes taxes & fees
Jul 19 - Jul 20
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
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 $253
CA $524 total
includes taxes & fees
Jul 27 - Jul 28
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (77 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 $289
CA $523 total
includes taxes & fees
Jul 22 - Jul 23
Your Next Vacation Home
Coffee/tea maker, fridge, microwave, oven

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 $216
CA $767 total
includes taxes & fees
Aug 11 - Aug 12
Game Room • Fire-pit • Playground • Gym • Billiard
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 $253
CA $328 total
includes taxes & fees
Jul 27 - Jul 28
Attractive Coach House Apartment for rent in Oak Park.
2 bedrooms, iron/ironing board, WiFi, bed sheets

Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is CA $242
CA $506 total
includes taxes & fees
Aug 4 - Aug 5
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Exterior

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

New Bath! Near Chicago and O’Hare +Fenced yard + Game room!
Schaumburg
9.6 out of 10, Exceptional, (35 reviews)
"Host was amazing, house was clean and easy to access! "
United States
Central A.
The price is CA $370
CA $728 total
includes taxes & fees
Jul 27 - Jul 28
New Bath! Near Chicago and O’Hare +Fenced yard + Game room!
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

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"This property and staff was amazing! We planned a small event for my daughters marriage proposal in one of their lounges as well as stayed in one of the rooms. The staff was so appreciatively attentive to our needs to pull off the proposal as a secret. My family felt they went above and beyond when they attended to us during our small event. Because of a plane delay we were scrambling to get things set up, they recognized that and stepped right in to help wherever they could including bringing much needed refreshing glasses of water since we were hot, scrambling and parched. Three families including my husband and I stayed at the Allegro. This hotel is iconic, historic and absolutely beautiful. Our room offered everything we needed: was clean and the mattress was great. All staff from doorman to check-out was very kind and helpful, including the Allegro Lounge with great service and drinks. If we have opportunity to stay in Chicago again we will be staying here."
Linda 3-night trip
Posted less than an hour ago
The Allegro Royal Sonesta Hotel Chicago Loop

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
492
Accommodation
857 Vacation Homes
Lowest Price
CA $246
Highest Price
CA $1,425

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