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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Chicago cottages

Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Cottage in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
The price is S$530
includes taxes & fees
1 Jan - 2 Jan, 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line
Interior
Salem Vacation Home w/ Dock: Steps to Paddock Lake

Cottage in Salem

Salem Vacation Home w/ Dock: Steps to Paddock Lake
3.0 star property
The price is S$836
includes taxes & fees
25 Dec - 26 Dec
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Interior
Fire Pit & Grill: Family Home on Fox River Trail!

Cottage in St. Charles

Fire Pit & Grill: Family Home on Fox River Trail!
3.0 star property
The price is S$694
includes taxes & fees
1 Jan - 2 Jan, 2026
Fire Pit & Grill: Family Home on Fox River Trail!
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

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

10/10 Excellent
"The staff were wonderful! The only thing I missed in the room was a desk."
Lillian 4-night trip
Posted 1 day ago
Silversmith Hotel Chicago Downtown

Find out more about Chicago

Chicago Cottages information

Number of reviews
Accommodation
24 Cottages
Lowest Price
S$530
Highest Price
S$836

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.

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