Chicago Cottages

Q: 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.

Q: 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.

Q: 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.

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

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Our top choices for Chicago cottages

Classic Forest Park Foursquare < 1 Mi to Blue Line

Forest Park

RM1,726 total

includes taxes & fees

14 Feb - 15 Feb

Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem

RM2,643 total

includes taxes & fees

15 Jan - 16 Jan

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Top Chicago Hotel Reviews

River Hotel

10/10 Excellent

"Very good service"

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