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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Chicago holiday homes

Interior

1. Great America Getaway | Sleeps 12 | Near Navy Base

Great America Getaway | Sleeps 12 | Near Navy Base
Gurnee
The price is HK$4,078
HK$7,656 total
includes taxes & fees
10 Aug - 11 Aug
Great America Getaway | Sleeps 12 | Near Navy Base
1 bedroom, Internet, bed sheets

2. Lombard 1BR & 1BH Suite Close to freeway & Mall

Lombard 1BR & 1BH Suite Close to freeway & Mall
Lombard
The price is HK$974
HK$1,199 total
includes taxes & fees
3 Aug - 4 Aug
Lombard 1BR & 1BH Suite Close to freeway & Mall
3 bedrooms, iron/ironing board, travel cot, WiFi

3. 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 HK$2,298
HK$5,158 total
includes taxes & fees
6 Aug - 7 Aug
3BR · Steps from McCormick · Balcony & Gym
Smart TV

4. 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, (30 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 HK$1,165
HK$2,362 total
includes taxes & fees
3 Aug - 4 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Exterior

5. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (70 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is HK$1,412
HK$2,527 total
includes taxes & fees
7 Aug - 8 Aug
✽ Charming Cottage ✽ close to College/Town/Station
Interior

6. Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center
Oak Park
9.8 out of 10, Exceptional, (19 reviews)
"Overall just great lovely area and chill place, rooms was great and I love the Roku tvs to sit back In chill!"
United States
Chantrice A.
The price is HK$1,765
HK$5,324 total
includes taxes & fees
5 Aug - 6 Aug
Chic 3bed 2bath Home with free parking close to United Center
TV

7. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (2 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is HK$1,437
HK$5,268 total
includes taxes & fees
3 Aug - 4 Aug
4BR Retreat w/ Theater, Arcade, Gym and Firepit
Exterior detail

8. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (32 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$2,549
HK$5,342 total
includes taxes & fees
4 Aug - 5 Aug
Oak Park Victorian by FLW Studio
Coffee/tea maker, fridge, microwave, oven

9. Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly

Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly
Westmont
10.0 out of 10, Exceptional, (3 reviews)
"Clean, Family friendly yes"
United States
ronald M.
The price is HK$2,556
HK$5,152 total
includes taxes & fees
10 Aug - 11 Aug
Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly
Outdoor dining

10. 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, (32 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 HK$1,103
HK$2,483 total
includes taxes & fees
4 Aug - 5 Aug
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
TV

11. Spacious and Inviting

Spacious and Inviting
Willowbrook
10.0 out of 10, Exceptional, (1 review)
"I had family in from the West Coast. I would recommend. Very well decorated and very cozy. Nice outside deck with plenty of seating and large yard! It was great to be able to have family over and visit. Communication was very good also! Thank you! "
United States
karin e.
The price is HK$3,269
HK$6,249 total
includes taxes & fees
3 Aug - 4 Aug
Spacious and Inviting
Coffee/tea maker, fridge, microwave, oven

12. Wonderful in Wood Dale, right by O’Hare airport!

Wonderful in Wood Dale, right by O’Hare airport!
Wood Dale
9.6 out of 10, Exceptional, (20 reviews)
"Very clean, comfortable home in a good location. This was a great place to stay while visiting Chicago. "
United States
Pelayo M.
The price is HK$2,274
HK$4,181 total
includes taxes & fees
4 Aug - 5 Aug
Wonderful in Wood Dale, right by O’Hare airport!
Exterior

13. 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, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is HK$1,405
HK$2,604 total
includes taxes & fees
1 Sept - 2 Sept
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Interior

14. Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (15 reviews)
"It was a very nice neighborhood, with many restaurants and retail establishments in proximity. We really enjoyed our stay and our host was an excellent when it comes to communication."
United States
Tim P.
The price is HK$1,608
HK$4,211 total
includes taxes & fees
4 Aug - 5 Aug
Vintage Urban Retreat
Microwave, oven, stovetop, dishwasher

15. Grand 5BR, 4.5BA Game Rm, Near O’Hare, & Down Town

Grand 5BR, 4.5BA Game Rm, Near O’Hare, & Down Town
Bensenville
10.0 out of 10, Exceptional, (3 reviews)
"Great property, and very responsive host!"
United States
Bridget M.
The price is HK$3,970
HK$8,471 total
includes taxes & fees
3 Aug - 4 Aug
Grand 5BR, 4.5BA Game Rm, Near O’Hare, & Down Town
Dining

16. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (53 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is HK$1,482
HK$2,978 total
includes taxes & fees
16 Aug - 17 Aug
LUXE 3 BR, 2 BA + Hot Tub
Coffee/tea maker, fridge, microwave, oven

17. 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, (2 reviews)
"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 HK$2,461
HK$5,759 total
includes taxes & fees
6 Aug - 7 Aug
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Coffee/tea maker, fridge, microwave, oven

18. Charming Retreat in Evanston Right Next to Beach

Charming Retreat in Evanston Right Next to Beach
South Evanston
8.2 out of 10, Very good, (10 reviews)
The price is HK$2,353
HK$4,019 total
includes taxes & fees
16 Aug - 17 Aug
Charming Retreat in Evanston Right Next to Beach
Coffee/tea maker, fridge, microwave, oven

19. *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, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
The price is HK$1,568
HK$3,223 total
includes taxes & fees
9 Aug - 10 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Coffee/tea maker, fridge, microwave, oven

20. Premier 9BR Art Deco manor with garage.

Premier 9BR Art Deco manor with garage.
Lakeview
7.4 out of 10, Good, (3 reviews)
"Check in seamless, property was clean and very well appointed, and hosts were responsive, professional and polite. Can’t ask for much more. "
United States
Joel D.
The price is HK$5,828
HK$17,421 total
includes taxes & fees
11 Aug - 12 Aug
Premier 9BR Art Deco manor with garage.
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Great location! Rooms were clean and nice. The elevator wait time was never long, which can be a problem in a high rise. Employees were always helpful and gave us plenty of water bottles from the front desk. Would definitely stay here again."
Lara 4-night trip
Posted less than an hour ago
Hilton Chicago/Magnificent Mile Suites

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