Compare Chicago Cottage Rentals

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, 60611
    The price is $195 per night from Apr 2 to Apr 3
    $195
    per night
    Apr 2 - Apr 3
    8.4/10 Very Good! (1,004 reviews)

Hotel Options in Chicago

    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago, IL, 60605
    The price is $139 per night from Apr 2 to Apr 3
    $139
    per night
    Apr 2 - Apr 3
    7.4/10 Good! (3,861 reviews)
    Aloft Chicago Mag Mile, a Marriott Hotel

    Aloft Chicago Mag Mile, a Marriott Hotel

    243 E. Ontario, Chicago, IL, 60611
    The price is $116 per night from Apr 3 to Apr 4
    $116
    per night
    Apr 3 - Apr 4
    8.4/10 Very Good! (1,390 reviews)
    River Hotel

    River Hotel

    75 East Wacker Drive, Chicago, IL, 60601
    The price is $125 per night from Apr 2 to Apr 3
    $125
    per night
    Apr 2 - Apr 3
    8.6/10 Excellent! (1,501 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.