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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Chicago holiday homes

TV, offices

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
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, (80 reviews)
"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."
United States
Kyle M.
The price is HK$769
HK$1,545 total
includes taxes & fees
7 May - 8 May
Master qtr close to nature & easy urban facilities
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is HK$940
HK$4,566 total
includes taxes & fees
11 May - 12 May
Near Lake and Museum • Modern • Game Area
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 HK$1,058
HK$2,574 total
includes taxes & fees
6 May - 7 May
Quaint Bungalow, near Great Lakes Naval Base
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (45 reviews)
"Nice overall"
United States
Hell
The price is HK$1,567
HK$3,093 total
includes taxes & fees
25 May - 26 May
LUXE 3 BR, 2 BA + Hot Tub
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (64 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$1,332
HK$2,408 total
includes taxes & fees
11 May - 12 May
✽ Charming Cottage ✽ close to College/Town/Station
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
9.6 out of 10, Exceptional, (5 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is HK$1,022
HK$4,056 total
includes taxes & fees
6 May - 7 May
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
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, (23 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 HK$1,163
HK$2,351 total
includes taxes & fees
11 May - 12 May
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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 HK$1,168
HK$3,169 total
includes taxes & fees
5 May - 6 May
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Fridge, microwave, oven, stovetop

Navy Family home -Near Lake 4BR Hot Tub

Navy Family home -Near Lake 4BR Hot Tub
Gages Lake
10.0 out of 10, Exceptional, (11 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
The price is HK$1,755
HK$5,268 total
includes taxes & fees
11 May - 12 May
Navy Family home -Near Lake 4BR 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, (2 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is HK$1,438
HK$2,615 total
includes taxes & fees
12 May - 13 May
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
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, (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
Private kitchen

Spacious Deck & Balcony, Game Area, Garage

Spacious Deck & Balcony, Game Area, Garage
Glen Ellyn
9.6 out of 10, Exceptional, (23 reviews)
"Great place to stay. "
United States
Jason T.
The price is HK$1,843
HK$4,593 total
includes taxes & fees
5 May - 6 May
Spacious Deck & Balcony, Game Area, Garage
Fridge, microwave, oven, stovetop

Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn

Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn
Berwyn
10.0 out of 10, Exceptional, (3 reviews)
"We had an excellent stay. Our host was responsive & accommodated an extremely early check-in request for us. This helped tremendously. Instructions were clear to get in & the home was spacious & clean. The location was great & easily accessible to restaurants. We would stay here again. "
United States
Sarah H.
The price is HK$1,836
HK$2,986 total
includes taxes & fees
19 May - 20 May
Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn
Paper towels, dining tables

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
streamwood
10.0 out of 10, Exceptional, (2 reviews)
"Was nice would recommend staying with you folks"
United States
Richard W.
The price is HK$1,185
HK$2,935 total
includes taxes & fees
6 May - 7 May
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Smart TV, fireplace, offices

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
The price is HK$1,530
HK$3,598 total
includes taxes & fees
5 May - 6 May
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 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$1,410
HK$4,063 total
includes taxes & fees
5 May - 6 May
Oak Park Victorian by FLW Studio
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
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$940
HK$1,644 total
includes taxes & fees
11 May - 12 May
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
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 HK$1,755
HK$4,466 total
includes taxes & fees
5 May - 6 May
4BR Near Woodfield Mall & Metra | LCP Collection
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 HK$2,361
HK$4,686 total
includes taxes & fees
10 May - 11 May
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
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

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"."
Claudia 1-night trip
Posted 3 hours ago
Club Quarters Hotel, Central Loop, Chicago

Find out more about Chicago

Chicago Vacation Homes information

Number of reviews
335
Accommodation
818 Vacation Homes
Lowest Price
HK$1,545
Highest Price
HK$5,268

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