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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Chicago and around

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

Wildwood Camper: Grill, Firepit & Pets OK

2.0 star property
The price is €228
includes taxes & fees
18 Aug - 19 Aug
Wildwood Camper: Grill, Firepit & Pets OK
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 €354
includes taxes & fees
18 Aug - 19 Aug
Cozy Cabin w/ Loft, Grill & Fire Pit
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 €386
includes taxes & fees
19 Aug - 20 Aug
Spacious 3BR House With Firepit & Grill, Near Beach
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 €534
includes taxes & fees
20 Aug - 21 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, (4)
"This was a great spot to spend the night with our 2 Golden Retrievers. The house had everything you would find at your own home."
Pet Friendly ($50) 2b/1b Cottage with large yard just off the lake!
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

Freehand Chicago

Freehand Chicago

10/10 Excellent
"Super clean"
Anna 3-night trip
Posted 17 hours ago
Freehand Chicago

Frequently asked questions

Why book your cottage in Chicago with Expedia?
Expedia has some wonderful cottages in Chicago, so start packing for an unforgettable holiday on nature's doorstep. If you need to stick to a budget, click on how much you'd like to spend and your preferred property star rating. Or, make the most of our filters to search for cottages with free WiFi or a pool. We'll help you find the perfect fit whatever your style of travel or plans.
How can I find cheap cottages in Chicago?
An excellent way to compare cheap cottages in Chicago is with Expedia's user-friendly filter tool. Refine your search results by amenities, budget and star rating to take advantage of awesome bargains with only a few clicks.
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.