Holiday Homes in Chicago

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chicago holiday homes

Holiday Home in Oak Park

A quiet stay while you are away
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is AU$348
includes taxes & fees
18 Mar - 19 Mar
A quiet stay while you are away
9.8 out of 10, Exceptional, (78 reviews)
"Nice , private and peaceful definitely will be back "
United States
BRANDEN J.
The price is AU$279
includes taxes & fees
19 Mar - 20 Mar
Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (69 reviews)
"Really amazing place. Adorable house, plenty of space, conveniently located. Great linens on the beds & amenities in the bathroom. Owner was incredibly flexible and responsive and great to work here. Had three visitors from Europe and they absolutely loved the place and had a great time. Would 100% stay here again the next time we're in the area. "
United States
Erika H.
The price is AU$468
includes taxes & fees
22 Mar - 23 Mar
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (59 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is AU$438
includes taxes & fees
30 Mar - 31 Mar
✽ Charming Cottage ✽ close to College/Town/Station

Holiday Home in Gages Lake

Navy Family home -Near Lake 4BR Hot Tub
10.0 out of 10, Exceptional, (4 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
The price is AU$1,053
includes taxes & fees
23 Mar - 24 Mar
Navy Family home -Near Lake 4BR Hot Tub
9.4 out of 10, Exceptional, (57 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is AU$471
includes taxes & fees
12 Apr - 13 Apr
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
The price is AU$575
includes taxes & fees
18 Mar - 19 Mar
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
8.0 out of 10, Very good, (21 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 AU$433
includes taxes & fees
23 Mar - 24 Mar
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Holiday Home in Elmhurst

LUXE 3 BR, 2 BA + Hot Tub
8.8 out of 10, Excellent, (40 reviews)
"Great place to stay. Plenty of backyard space. "
United States
Terrence M.
The price is AU$377
includes taxes & fees
26 Mar - 27 Mar
LUXE 3 BR, 2 BA + Hot Tub

Holiday Home in Oak Park

Vintage Urban Retreat
10.0 out of 10, Exceptional, (14 reviews)
"The house was spotless and very comfortable for our needs. Best of all it was not far from our son’s home in River Forest which made going back and forth convenient."
United States
Beryl I.
The price is AU$691
includes taxes & fees
18 Mar - 19 Mar
Vintage Urban Retreat

Holiday Home in Oak Park

Oak Park Victorian by FLW Studio
10.0 out of 10, Exceptional, (29 reviews)
"Finding a good 3 br or 4 br option in and around OP / RF is challenging and if this one is available, jump on it. Functional plan, easy parking, great location and responsive owners. "
United States
Lawrence P.
The price is AU$710
includes taxes & fees
18 Mar - 19 Mar
Oak Park Victorian by FLW Studio
9.6 out of 10, Exceptional, (24 reviews)
"Had a nice time. Great location!"
United States
Jinjer M.
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
The price is AU$752
includes taxes & fees
22 Mar - 23 Mar
Near Lake and Museum • Modern • Game Area

Holiday Home in Oakton

Your Next Vacation Home
9.4 out of 10, Exceptional, (67 reviews)
"We enjoyed our stay"
United States
Lukose K.
The price is AU$472
includes taxes & fees
18 Mar - 19 Mar
Your Next Vacation Home
9.6 out of 10, Exceptional, (17 reviews)
"Location was easy to find and good as a base for day trips to Chicago. "
United States
Brian H.
The price is AU$487
includes taxes & fees
18 Mar - 19 Mar
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
10.0 out of 10, Exceptional, (22 reviews)
"Nice clean home, easy check in processes close to the base. Perfect for our stay with kids. "
United States
Thomas D.
The price is AU$1,012
includes taxes & fees
23 Mar - 24 Mar
Navy retreat near Naval Base-Tiki Bar,Sauna,Games
The price is AU$279
includes taxes & fees
22 Mar - 23 Mar
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking
9.6 out of 10, Exceptional, (33 reviews)
"We came from Florida to visit family. This house was exactly what we were looking for. Kids loved the game room. Beautiful backyard and comfortable beds. Will stay again. "
United States
Mary M.
The price is AU$639
includes taxes & fees
19 Mar - 20 Mar
New Bath!Near Chicago and O’Hare +Fenced yard +Game room
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 AU$743
includes taxes & fees
18 Mar - 19 Mar
4BR Near Woodfield Mall & Metra | LCP Collection

Holiday Home in Des Plaines

Cozy Home by O'Hare + EV Plug
9.6 out of 10, Exceptional, (7 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 AU$508
includes taxes & fees
12 Apr - 13 Apr
Cozy Home by O'Hare + EV Plug
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chicago Hotel Reviews

Find out more about Chicago

Chicago Holiday Homes information

Number of reviews
600
Accommodation
822 Holiday Homes
Lowest Price
AU$279
Highest Price
AU$1,053

Explore a world of travel with Expedia