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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Chicago vacation homes

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 393
AED 748 total
includes taxes & fees
28 Jun - 29 Jun
Master qtr close to nature & easy urban facilities
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)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
The price is AED 1,227
AED 2,629 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Terrace/patio

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!

Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
South Evanston
9.8 out of 10, Exceptional, (39 reviews)
"Excellent property and host. Truly enjoyed our stay. "
United States
Shashi Y.
The price is AED 1,098
AED 1,702 total
includes taxes & fees
28 Jun - 29 Jun
Historic Coach House in Evanston One Block to Beach and Close to Town and NU!
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (68 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 1,176 total
includes taxes & fees
24 Jun - 25 Jun
✽ Charming Cottage ✽ close to College/Town/Station
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 1,312 total
includes taxes & fees
5 Jul - 6 Jul
Quaint Bungalow, near Great Lakes Naval Base
Smart TV, fireplace, books, video library

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie
10.0 out of 10, Exceptional, (37 reviews)
"Our host Craig did a great job of being available and the home worked perfectly for our visit with grandkids"
United States
Nancy S.
The price is AED 1,550
AED 3,018 total
includes taxes & fees
1 Jul - 2 Jul
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Private kitchen

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (75 reviews)
"This house was wonderful, it was clean, spacious, and had everything we needed. Thank you for being such a kind and welcoming host, we will definitely stay here again!"
United States
Michelle D.
The price is AED 873
AED 1,496 total
includes taxes & fees
6 Jul - 7 Jul
Your Next Vacation Home
Shower, jetted tub, hair dryer, towels

Spacious Deck & Balcony, Game Area, Garage

Spacious Deck & Balcony, Game Area, Garage
Glen Ellyn
9.6 out of 10, Exceptional, (25 reviews)
The price is AED 771
AED 2,032 total
includes taxes & fees
24 Jun - 25 Jun
Spacious Deck & Balcony, Game Area, Garage
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
6 Jul - 7 Jul
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Shower, hair dryer, shampoo

Navy retreat near Naval Base-Tiki Bar,Sauna,Games

Navy retreat near Naval Base-Tiki Bar,Sauna,Games
North Chicago
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay. I would definitely stay there again. "
United States
Chris G.
The price is AED 1,014
AED 2,586 total
includes taxes & fees
20 Jul - 21 Jul
Navy retreat near Naval Base-Tiki Bar,Sauna,Games
Interior

Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
North Chicago
7.6 out of 10, Good, (5 reviews)
"Rented this property for my sons navy graduation, Base was only 6 minutes from the home. Tons of places to eat and shop no more then 15 minutes away. The house was super cute, very clean. we flew in at 10am and without even having to ask the host reached out and let us know it was ready for check in a few hours early which was great. left some packaged up congrats grad decor that hopefully didnt get thrown out and the next navy fam can use. "
United States
Linda U.
The price is AED 790
AED 1,623 total
includes taxes & fees
12 Jul - 13 Jul
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
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 1,473 total
includes taxes & fees
9 Jul - 10 Jul
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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 552
AED 1,199 total
includes taxes & fees
24 Jun - 25 Jun
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Exterior detail

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.
Oak Park Victorian by FLW Studio
Exterior

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

Game room+ New Bath! Near Chicago and O’Hare +Fenced yard
Schaumburg
9.6 out of 10, Exceptional, (35 reviews)
"This is our second stay at the property. The place is clean, comfortable, and in a good location. I recommend it for families of six or fewer."
United States
David G.
Game room+ New Bath! Near Chicago and O’Hare +Fenced yard
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (50 reviews)
"Great stay"
United States
Steve T.
The price is AED 661
AED 1,352 total
includes taxes & fees
25 Jun - 26 Jun
LUXE 3 BR, 2 BA + Hot Tub
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
Interior

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, (18 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 AED 918
AED 2,636 total
includes taxes & fees
21 Jul - 22 Jul
Chic 3bed 2bath Home with free parking close to United Center
Fridge, microwave, oven, stovetop

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

Wonderful in Wood Dale, right by O’Hare airport!
Wood Dale
10.0 out of 10, Exceptional, (18 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 AED 1,120
AED 2,005 total
includes taxes & fees
8 Jul - 9 Jul
Wonderful in Wood Dale, right by O’Hare airport!
Interior

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 AED 1,240
AED 2,656 total
includes taxes & fees
7 Jul - 8 Jul
Vintage Urban Retreat
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Best location, great breakfast, clean room , friendly staff, the only thing missing is a fresh towel, that I was mentioned to employees to escalated to their manager"
soheila 3-night trip
Posted less than an hour ago
Hyatt Regency Chicago