Compare Southwest Side Cottage Rentals

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Featured Cottages in Southwest Side

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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.

Hotel Options in Southwest Side

    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl Chicago IL
    $81 nightly
    The price is $95 total per night from Jan 5 to Jan 6
    $95 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (3,467 reviews)
    Silversmith Hotel Chicago Downtown

    Silversmith Hotel Chicago Downtown

    10 S Wabash Ave Chicago IL
    $127 nightly
    The price is $149 total per night from Jan 4 to Jan 5
    $149 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (2,133 reviews)
    Palmer House a Hilton Hotel

    Palmer House a Hilton Hotel

    17 E Monroe St Chicago IL
    $134 nightly
    The price is $153 total per night from Dec 30 to Dec 31
    $153 total
    Dec 30 - Dec 31
    Total with taxes and fees
    8.4/10 Very Good! (2,123 reviews)

Cottages

Book a cottage in Southwest Side
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Southwest Side. 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 Southwest Side better.

Cottage apartments in Southwest Side 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 Southwest Side
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 Southwest Side 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 Southwest Side 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 Southwest Side. 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.

Southwest Side Cottages essential information

Accommodation
14 Cottages
Lowest Price
$95
Highest Price
$153
Popular accommodation
Pet-friendly Abode, 2 Mi to Dtwn Evanston!, 3 Mi to Hard Rock Casino: Charming Home in Gary!, 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, 4 Mi to Lake Michigan: East Chicago Home w/ Grill, Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!, Home w/ Office + Yard: 25 Mi to Downtown Chicago!, Classic Oak Park Home, 11 Mi to Downtown Chicago!

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