Compare Chicago Cottage Rentals

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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

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

Parking included

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

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

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

Guests of this cottage enjoy features like free WiFi in public areas. Free parking is available if you drive.

Kitchen

Parking included

Cozy Westmont Home: Walk to Metra Station!

Guests staying at this cottage enjoy free WiFi in public areas, an arcade/game room, and barbecue grills. You can put free parking to good use if you drive.

Kitchen

Washer

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 a garden and barbecue grills.

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

$225 nightly

$264 total

Nov 9 - Nov 10

Total with taxes and fees

8.4/10 Very Good! (1,536 reviews)

Hotel Options in Chicago

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

$145 nightly

$170 total

Nov 2 - Nov 3

Total with taxes and fees

7.8/10 Good! (9,473 reviews)

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

$114 nightly

$134 total

Nov 16 - Nov 17

Total with taxes and fees

8.8/10 Excellent! (3,133 reviews)

Freehand Chicago

19 East Ohio Street, Chicago, IL

$95 nightly

$112 total

Nov 10 - Nov 11

Total with taxes and fees

7.8/10 Good! (2,494 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	28 Cottages
Lowest Price	$112
Highest Price	$264
Popular accommodation	Pet-friendly Abode, 2 Mi to Dtwn Evanston!, 6 Mi to Naval Base: Spacious Waukegan Home w/ Yard, Game Nights, Bbqs & Family Fun: Chicago Area Hub, 2 Mi to Northwestern: Updated Home w/ Game Room!, Classic Oak Park Home, 11 Mi to Downtown Chicago!, Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!, Cozy Westmont Home: Walk to Metra Station!, Home w/ Office + Yard: 25 Mi to Downtown Chicago!, The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!