Search Cottages in Chicago

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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

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

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

3.0 star property
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
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!
“The cottage” 2 bedrooms cozy and private home
Room

“The cottage” 2 bedrooms cozy and private home

9.4 out of 10, Exceptional, (6)
"We were at this location for 13 days while visiting family. It was just what we needed for our stay. Clean and functional, enough amenities for a long stay "
“The cottage” 2 bedrooms cozy and private home
Country Club Hills Home: Walk to Rec Center!
Living area

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!
Living area

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!
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!
Glendale Heights Home With Office and Backyard!
Exterior

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!
Living area

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!
Living area

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

3.0 star property
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!
Peaceful Warrenville Home: 1 Mi to Herrick Lake!
Dining

Peaceful Warrenville Home: 1 Mi to Herrick Lake!

3.0 star property
Peaceful Warrenville Home: 1 Mi to Herrick Lake!
Family-friendly Villa Park Home: 16 Mi to Chicago!
Living area

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!
Living area

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
Living area

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
Living area

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!
Living area

Homewood Home ~ 1 Mi to Metra Station!

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

Pet-friendly Bartlett Farmhouse w/ Deck!

3.0 star property
Pet-friendly Bartlett Farmhouse w/ Deck!
Lakefront Home w/ Deck & Grill in Prospect Heights
Living area

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!
Dining

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
Living area

Charming Illinois Retreat w/ Hot Tub, Deck & Grill

3.0 star property
Charming Illinois Retreat w/ Hot Tub, Deck & Grill
Glen Ellyn Home: Walk to Downtown Dining & Shops!
Living area

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.
Don't see what you're looking for?
See all available properties in Chicago
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chicago

Sentral Michigan Avenue
Garden

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (624)
"I have stayed at this property 3 times now and every time has been amazing. They have become the only place I will stay at in the city. The location is great with a parking garage around the corner at is very cheap. You get so many more amenities than a hotel and is an overall great experience. I highly recommend."
The price is AED 403
AED 581 total
includes taxes & fees
23 Dec - 24 Dec
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
Front of property

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (342)
"The property location was great. The room was very spacious. The only knock was there was not a tv in the bedroom."
Kasa Magnificent Mile Chicago
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (407)
"Outstanding accommodations! Will choose this property again for my travels."
The price is AED 456
AED 536 total
includes taxes & fees
12 Jan - 13 January 2025
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.