Compare Chicago Cottage Rentals

Featured Chicago Cottages

Pet-friendly Abode, 2 Mi to Dtwn Evanston!

Guests of this cottage have access to free WiFi in public areas. You can take advantage of free parking if you drive.

Kitchen

Pet friendly

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

At this cottage, guests have access to free WiFi in public areas. If you drive, take advantage of free parking.

Kitchen

Pet friendly

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

This cottage features free WiFi in public areas and a garden. You can put free parking to good use if you drive. This smoke-free cottage also has barbecue grills.

Kitchen

Washer

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

This cottage features free WiFi in public areas and an arcade/game room. Free parking is included with your stay.

Kitchen

Washer

Game Nights, Bbqs & Family Fun: Chicago Area Hub

This cottage features free WiFi in public areas and barbecue grills. A stay here includes free parking.

Kitchen

Washer

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

This cottage features free WiFi in public areas and barbecue grills. Free parking is available if you drive.

Kitchen

Parking included

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

At this cottage, guests have access to free WiFi in public areas. You can put free parking to good use if you drive.

Kitchen

Washer

The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!

This cottage offers a water park, a gym, and laundry facilities. Other amenities at this family-friendly cottage include barbecue grills and a garden.

Kitchen

Washer

Classic Oak Park Home, 11 Mi to Downtown Chicago!

This cottage features free WiFi in public areas and barbecue grills. If you drive, put free parking to good use.

Kitchen

Washer

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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.

Chicago Beach Accommodation

Sheraton Grand Chicago Riverwalk

301 E North Water St Chicago IL

$175 nightly

$205 total

Dec 21 - Dec 22

Total with taxes and fees

8.4/10 Very Good! (1,565 reviews)

Hotel Options in Chicago

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

$94 nightly

$111 total

Dec 18 - Dec 19

Total with taxes and fees

8.4/10 Very Good! (5,366 reviews)

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

$106 nightly

$124 total

Dec 15 - Dec 16

Total with taxes and fees

8.8/10 Excellent! (3,435 reviews)

Silversmith Hotel Chicago Downtown

10 S Wabash Ave Chicago IL

$127 nightly

$149 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

9.2/10 Wonderful! (2,096 reviews)

Cottages

Book a cottage in Chicago
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Chicago. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Chicago better.

Cottage apartments in Chicago range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Chicago
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Chicago and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Chicago cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Chicago. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Chicago Cottages essential information

Accommodation	29 Cottages
Lowest Price	$111
Highest Price	$205
Popular accommodation	Pet-friendly Abode, 2 Mi to Dtwn Evanston!, 6 Mi to Naval Base: Spacious Waukegan Home w/ Yard, Home w/ Fenced Yard: 13 Mi to Downtown Chicago!, 2 Mi to Northwestern: Updated Home w/ Game Room!, Game Nights, Bbqs & Family Fun: Chicago Area Hub, Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!, Home w/ Office + Yard: 25 Mi to Downtown Chicago!, The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!, Classic Oak Park Home, 11 Mi to Downtown Chicago!