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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Chicago

Wildwood Camper: Grill, Firepit & Pets OK
Floor plan

Wildwood Camper: Grill, Firepit & Pets OK

2.0 star property
The price is S$343
includes taxes & fees
1 Sept - 2 Sept
Wildwood Camper: Grill, Firepit & Pets OK
Cozy Cabin w/ Loft, Grill & Fire Pit
Floor plan

Cozy Cabin w/ Loft, Grill & Fire Pit

2.0 star property
4.0 out of 10, (1)
"No curtains at all. Small window air conditioning that doesn't cool the whole cabin down. Sketchy ladder screwed into the wall to got to the loft. Any mobility issues beware. Wifi has no internet. Was there less than 30 minutes no reund offered. It is new and clean. "
The price is S$532
includes taxes & fees
28 Aug - 29 Aug
Cozy Cabin w/ Loft, Grill & Fire Pit
Spacious 3BR House With Firepit & Grill, Near Beach
Front of property

Spacious 3BR House With Firepit & Grill, Near Beach

2.0 star property
5.0 out of 10, (2)
"It is a beautiful residence. This is a relatively new residence, evidenced by all the brand new with tags furniture, lamps, appliances etc. No internet or cable, which was sort of a downer. Did not get the code until 15 minutes after check in time. No coffee or silverware. We only found one spoon. "
The price is S$580
includes taxes & fees
1 Sept - 2 Sept
Spacious 3BR House With Firepit & Grill, Near Beach
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Interior

Salem Vacation Home w/ Dock: Steps to Paddock Lake

3.0 star property
The price is S$802
includes taxes & fees
20 Aug - 21 Aug
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.
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Top Chicago Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"The breakfast buffet was nice, with plenty of options for us vegetarians. The king bed was very comfortable. We slept well. The Internet access was good. A few times my access dropped, but that happened only infrequently. Our only suggestion is to make it a secure system (with a password required) instead of an open system, to improve the security. I wouldn’t want anybody’s information stolen by unknowingly exposing credit card or password information to potential eavesdroppers. It was easy to get cabs and Ubers to and from the hotel. There are also bus routes nearby and El stops within easy walking distance."
Anonymous traveller 4-night trip
Posted 7 hours ago
The Whitehall Hotel, BW Premier Collection

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.