Search Cottages in Chicago

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Compare 29 Cottages in Chicago with updated reviews, rates, and availability.

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!

“The cottage” 2 bedrooms cozy and private home

9.6 out of 10, Exceptional, (5)
"6 girls in one house, everyone had a bed or couch to sleep on, clean and convenient "
“The cottage” 2 bedrooms cozy and private home

Country Club Hills Home: Walk to Rec Center!

3.0 star property
Country Club Hills Home: Walk to Rec Center!

Classic Oak Park Home, 11 Mi to Downtown Chicago!

3.0 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!

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!

Glendale Heights Home With Office and Backyard!

3.0 star property
6.0 out of 10, (1)
Glendale Heights Home With Office and Backyard!

Des Plaines Vacation Rental w/ Spacious Backyard!

3.0 star property
Des Plaines Vacation Rental w/ Spacious Backyard!

Peaceful Warrenville Home: 1 Mi to Herrick Lake!

3.0 star property
Peaceful Warrenville Home: 1 Mi to Herrick Lake!

Charming Oak Park Retreat w/ Fenced Backyard!

3.0 star property
Charming Oak Park Retreat w/ Fenced Backyard!

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!

Spacious Family Glenwood Estates Home w/ Hot Tub!

3.0 star property
Spacious Family Glenwood Estates Home w/ Hot Tub!

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen

13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

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

Homewood Home ~ 1 Mi to Metra Station!

3.0 star property
Homewood Home ~ 1 Mi to Metra Station!

Pet-friendly Bartlett Farmhouse w/ Deck!

3.0 star property
Pet-friendly Bartlett Farmhouse w/ Deck!

Lakefront Home w/ Deck & Grill in Prospect Heights

3.0 star property
Lakefront Home w/ Deck & Grill in Prospect Heights

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

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

Charming Illinois Retreat w/ Hot Tub, Deck & Grill

3.0 star property
Charming Illinois Retreat w/ Hot Tub, Deck & Grill

Chicago Home w/ Spacious Yard: 14 Mi to Dtwn

3.0 star property
Chicago Home w/ Spacious Yard: 14 Mi to Dtwn

Glen Ellyn Home: Walk to Downtown Dining & Shops!

3.0 star property
Glen Ellyn Home: Walk to Downtown Dining & Shops!
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

4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is SAR 405
SAR 585 total
includes taxes & fees
24 Nov - 25 Nov
Sentral Michigan Avenue

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is SAR 211
SAR 247 total
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"This property was in a good location - walked to Shedd Aquarium, Soldier Field, and good restaurants on South Michigan. Asked a few questions via text with prompt responses. No complaints with this clean property exactly as advertised."
The price is SAR 453
SAR 532 total
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash
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?
Booking a cottage in Chicago is as simple as working out your travel dates and picking an ideal place for outdoor relaxation and recreation. From upmarket retreats to affordable properties and cottages that include perks like a pool, Expedia has something for all traveler styles. As for irresistible deals? We have them too!
How can I find cheap cottages in Chicago?
With Expedia’s convenient filter tool, booking cheap cottages in Chicago is easy. To find accommodations that are very pocket friendly, narrow your search by star rating, budget and amenities.