Search Chicago Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 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 S$609
includes taxes & fees
22 Nov - 23 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 S$1,046
includes taxes & fees
10 Nov - 11 Nov
Salem Vacation Home w/ Dock: Steps to Paddock 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.
View all properties

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

A hotel entrance with a modern facade, large windows, and a sign indicating it is a 64th floor building.
L7 CHICAGO by LOTTE HOTELS

L7 CHICAGO by LOTTE HOTELS

L7 CHICAGO by LOTTE HOTELS
Downtown Chicago

10/10 Excellent

A very nice property with an excellent location. The Korean restaurant on the ground floor was a pleasant surprise and served very tasty food. The only downside was that one of the two lifts was out of service for the entire four nights of my stay, which led to longer wait times and was somewhat frustrating.
Singapore
Sungwon
Reviewed June 21, 2026
L7 CHICAGO by LOTTE HOTELS

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.