A river with a yellow boat, surrounded by tall buildings and a bridge.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chicago cottages

A two-story house with a front porch, a staircase leading to the second floor, and a well-maintained garden.

1. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is £359
includes taxes & fees
15 Oct - 16 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
A covered deck with a table and chairs, overlooking a body of water.

2. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem Vacation Home w/ Dock: Steps to Paddock Lake
3.0 star property
Salem
The price is £616
includes taxes & fees
17 Oct - 18 Oct
Salem Vacation Home w/ Dock: Steps to Paddock Lake
A residential area with a basketball hoop, stone steps, a red house, and a garage.

3. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (19 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is £148
includes taxes & fees
4 Oct - 5 Oct
Little Fox Cottage - A Cozy Riverview Getaway
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"The hotel was a very convenient location from downtown and Lake Michigan. Definitely one of the better breakfasts I've had recently and the pricing sits just right for the amenities and convenience this hotel offers"
Sudeep 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Chicago

Chicago Cottages information

Number of reviews
19
Accommodation
27 Cottages
Lowest Price
£148
Highest Price
£616

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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