Book a Chicago Cottage

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Chicago

Wildwood Camper: Grill, Firepit & Pets OK
House (2 Bedrooms) | Floor plan

Wildwood Camper: Grill, Firepit & Pets OK

2.0 star property
The price is NZ$445
includes taxes & fees
4 Sept - 5 Sept
Wildwood Camper: Grill, Firepit & Pets OK
Salem Vacation Home w/ Dock: Steps to Paddock Lake
House (4 Bedrooms) | Interior

Salem Vacation Home w/ Dock: Steps to Paddock Lake

3.0 star property
The price is NZ$1,151
includes taxes & fees
24 Aug - 25 Aug
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Pet Friendly ($50) 2b/1b Cottage with large yard just off the lake!
Exterior

Pet Friendly ($50) 2b/1b Cottage with large yard just off the lake!

10.0 out of 10, Exceptional, (5)
"A pleasant and welcoming vibe near the lake. Very clean. Lots of special touches. Caring and attentive host. We would stay here again. "
The price is NZ$596
includes taxes & fees
26 Aug - 27 Aug
Pet Friendly ($50) 2b/1b Cottage with large yard just off the lake!
Spacious 3BR House With Firepit & Grill, Near Beach
Front of property

Spacious 3BR House With Firepit & Grill, Near Beach

2.0 star property
5.0 out of 10, (2)
"It is a beautiful residence. This is a relatively new residence, evidenced by all the brand new with tags furniture, lamps, appliances etc. No internet or cable, which was sort of a downer. Did not get the code until 15 minutes after check in time. No coffee or silverware. We only found one spoon. "
The price is NZ$709
includes taxes & fees
27 Aug - 28 Aug
Spacious 3BR House With Firepit & Grill, Near Beach
Cozy Cabin w/ Loft, Grill & Fire Pit
House (1 Bedroom) | Floor plan

Cozy Cabin w/ Loft, Grill & Fire Pit

2.0 star property
4.0 out of 10, (1)
"No curtains at all. Small window air conditioning that doesn't cool the whole cabin down. Sketchy ladder screwed into the wall to got to the loft. Any mobility issues beware. Wifi has no internet. Was there less than 30 minutes no reund offered. It is new and clean. "
The price is NZ$657
includes taxes & fees
14 Sept - 15 Sept
Cozy Cabin w/ Loft, Grill & Fire Pit
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
Sign in
Sign up, it's free

Top Chicago Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Very good experience! Thanks "
Michail 5-night trip
Posted 1 day ago
The Whitehall Hotel, BW Premier Collection

Frequently asked questions

What is there to do in Chicago near my cottage?
Chicago has enough activities and experiences to keep you going for weeks, beginning with Anna and Frederick Douglass Park. Grant Park, Marquette Park and Midway Plaisance are other popular attractions. If you're hanging around a while, Ernest Hemingway Museum and House and Bridgehouse and Chicago River Museum are great additions to your itinerary.