City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day

Search Cottages in Chicago

  • 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

Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Chicago cottages

House (4 Bedrooms) | Interior

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 AED 466
AED 2,959 total
includes taxes & fees
22 Jun - 23 Jun
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Property grounds

Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (18 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is AED 678
AED 1,006 total
includes taxes & fees
23 Jun - 24 Jun
Little Fox Cottage - A Cozy Riverview Getaway
Beach nearby, sun loungers, beach towels

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Miller Beach
10.0 out of 10, Exceptional, (51 reviews)
"Had a great stay and robin was super helpful and friendly! Great location close to lake"
United States
Weylin W.
The price is AED 2,314
AED 3,900 total
includes taxes & fees
18 Jul - 19 Jul
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chicago Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Allowed us to check in early and store bags which was so helpful!"
Anthony 1-night trip
Posted less than an hour ago
Congress Plaza Hotel

Frequently asked questions

Why book your cottage in Chicago with Expedia?
Expedia has some wonderful cottages in Chicago, so start packing for an unforgettable vacation 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.