Compare Chicago Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Chicago Cottages

Don't see what you're looking for?
See all available properties in Chicago
View all properties
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

    Sheraton Grand Chicago Riverwalk

    301 E North Water St, Chicago, IL
    $225 nightly
    The price is $264 total per night from Nov 9 to Nov 10
    $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

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago, IL
    $145 nightly
    The price is $170 total per night from Nov 2 to Nov 3
    $170 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.8/10 Good! (9,473 reviews)
    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl, Chicago, IL
    $114 nightly
    The price is $134 total per night from Nov 16 to Nov 17
    $134 total
    Nov 16 - Nov 17
    Total with taxes and fees
    8.8/10 Excellent! (3,133 reviews)
    Freehand Chicago

    Freehand Chicago

    19 East Ohio Street, Chicago, IL
    $95 nightly
    The price is $112 total per night from Nov 10 to Nov 11
    $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!

Explore More Ways to Travel with Travelocity