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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 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 HK$1,897
HK$3,722 total
includes taxes & fees
9 Nov - 10 Nov
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 HK$1,278
HK$6,396 total
includes taxes & fees
9 Nov - 10 Nov
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
9.8 out of 10, Exceptional, (20 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is HK$952
HK$1,491 total
includes taxes & fees
16 Nov - 17 Nov
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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Chicago and related destinations

Towering skyscrapers frame the stunning Millennium Park where 'The Bean' reflects the city's vibrant energy. Cruise along the Chicago River for spectacular architecture views or catch a Cubs game at historic Wrigley Field.

See all hotels in Chicago
A river with a yellow boat, surrounded by tall buildings and a bridge.

Top reviews in Chicago

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
Downtown Chicago

10/10 Excellent

very good hotel and nearby the shopping area
Hong Kong SAR China
Kwok Tai
Reviewed March 7, 2025
Hotel Riu Plaza 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.