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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured Cottages in Chicago

2 Mi to Northwestern: Updated Home w/ Game Room!
Interior

2 Mi to Northwestern: Updated Home w/ Game Room!

3.0 star property
2 Mi to Northwestern: Updated Home w/ Game Room!
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
TV, fireplace, books

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

3.0 star property
10.0 out of 10, Exceptional, (1)
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Interior

Home w/ Fenced Yard: 13 Mi to Downtown Chicago!

3.0 star property
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Cozy Westmont Home: Walk to Metra Station!
Outdoor dining

Cozy Westmont Home: Walk to Metra Station!

3.0 star property
2.0 out of 10, (1)
"Very upset with the communication of this rental. I booked this rental for a weekend getaway with the family. I received an email a couple of days ahead of the booking reminding me of my trip and that I was all set. Then on check in day, I realized that I needed the check in information. I sent a message through the app to the renter. The response was "it may take a few days for the property to get back with you" so I called the number on the response. The operator then tried to look up my...
Cozy Westmont Home: Walk to Metra Station!
Des Plaines Vacation Rental w/ Spacious Backyard!
Private kitchen

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Interior

8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

3.0 star property
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Private kitchen

Home w/ Office + Yard: 25 Mi to Downtown Chicago!

3.0 star property
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Fireplace

Classic Oak Park Home, 11 Mi to Downtown Chicago!

3.0 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Family-friendly Villa Park Home: 16 Mi to Chicago!
Private kitchen

Family-friendly Villa Park Home: 16 Mi to Chicago!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We recently had the pleasure of staying at this fantastic home with our large family, and I can't recommend it enough! From the moment we arrived, we were greeted by a clean and pleasant neighborhood that immediately put us at ease. The home itself was incredibly roomy, accommodating all of us comfortably. It was spotless and had a warm, welcoming atmosphere that made it feel like a home away from home. We appreciated the thoughtful touches that the owners provided, which added to our overall...
Family-friendly Villa Park Home: 16 Mi to Chicago!
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!
Exterior

Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
"So cozy. Feels like staying in a guest house with the whole place to yourself! "
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!
Peaceful Warrenville Home: 1 Mi to Herrick Lake!
Interior

Peaceful Warrenville Home: 1 Mi to Herrick Lake!

3.0 star property
Peaceful Warrenville Home: 1 Mi to Herrick Lake!
Glendale Heights Home With Office and Backyard!
Interior

Glendale Heights Home With Office and Backyard!

3.0 star property
6.0 out of 10, (1)
Glendale Heights Home With Office and Backyard!
Country Club Hills Home: Walk to Rec Center!
TV, books

Country Club Hills Home: Walk to Rec Center!

3.0 star property
Country Club Hills Home: Walk to Rec Center!
Spacious Family Glenwood Estates Home w/ Hot Tub!
Interior

Spacious Family Glenwood Estates Home w/ Hot Tub!

3.0 star property
Spacious Family Glenwood Estates Home w/ Hot Tub!
Charming Illinois Retreat w/ Hot Tub, Deck & Grill
Private kitchen

Charming Illinois Retreat w/ Hot Tub, Deck & Grill

3.0 star property
Charming Illinois Retreat w/ Hot Tub, Deck & Grill
Pet-friendly Bartlett Farmhouse w/ Deck!
Interior

Pet-friendly Bartlett Farmhouse w/ Deck!

3.0 star property
Pet-friendly Bartlett Farmhouse w/ Deck!
Homewood Home ~ 1 Mi to Metra Station!
Private kitchen

Homewood Home ~ 1 Mi to Metra Station!

3.0 star property
Homewood Home ~ 1 Mi to Metra Station!
Lakefront Prospect Heights Home: Ice Fish On-site
Interior

Lakefront Prospect Heights Home: Ice Fish On-site

3.0 star property
Lakefront Prospect Heights Home: Ice Fish On-site
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
Interior

13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

3.0 star property
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
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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Other property types in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (695)
"Amazing and clean experience I highly recommend "
The price is S$237
includes taxes & fees
12 Mar - 13 Mar
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (447)
"Amazing space - I'll be requesting the same one in the summer :) Spacious and clean! Absolutely loved the view of Willis Tower from our room. Excellent stay!"
The price is S$147
includes taxes & fees
1 Apr - 2 Apr
Sonder South Wabash
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (146)
"⭐️⭐️⭐️⭐️⭐️ Had a fantastic stay at Sonder Chicago West Loop during my business trip! The location was perfect for meetings, and I loved having the extra space. The studio felt more like an apartment—super clean, spacious, and well-appointed with stylish decor. The kitchen was fully stocked and well-maintained, making the stay even more comfortable. The reception area was great for getting work done before check-in, and the luggage room lockers were a huge plus. The app-based entry system was...
The price is S$197
includes taxes & fees
1 Apr - 2 Apr
Sonder The Burnham Apartments
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.

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.