Southwest Side Apartments

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Featured Apartments 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
    $89 nightly
    The price is $105 total per night from Jan 5 to Jan 6
    $105 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (3,504 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
    $140 nightly
    The price is $160 total per night from Dec 28 to Dec 29
    $160 total
    Dec 28 - Dec 29
    Total with taxes and fees
    8.4/10 Very Good! (2,123 reviews)

Apartments

Book apartments in Southwest Side

Find your home-away-from-home when you book your next stay at an apartment in Southwest Side. Apartments are ideal for families, groups of friends and even solo travelers. More space, more options and more freedom—apartments are short-term digs that feel like a long-term arrangement. From one-bedroom apartments to three bedrooms or more, Orbitz has an incredible selection to choose from. It’s never been easier to live like a local in Southwest Side. 

Apartments for everyone in Southwest Side
Family apartments in Southwest Side have plenty of room for everyone. You’ll find multiple bedrooms, laundry facilities and furnished living rooms, so you can have movie nights just like at home. Plus, hotels with kitchens cut down on time spent finding kid-friendly restaurants. Spend that time making memories instead.

Friends are the family you choose, but you don’t need to be too close this vacation. Luckily, you can book apartments even your pickiest pal will love. This getaway with the girls or guys doesn’t have to break the bank, either. Cheap apartments in Southwest Side are just a click away. When it comes time to split the bill, no one will bail.

If you want the finer things in life, we’ll help you find luxury apartments in Southwest Side faster than you can say “thousand thread count sheets.” Get your best sleep ever, then wake up with a freshly brewed espresso and a full breakfast. It’s just like home, only much, much better.

Whether you’re a bargain hunter or a luxury lover, kitchens and kitchenettes are one of the most important features of short-term apartments in Southwest Side. It’s simple, really: Cooking your own meals is downright convenient. Even if you’re not a five-star chef, late-night snacks and morning mimosas get a whole lot easier when you’ve got a fully stocked kitchen to play with.

Southwest Side Apartments essential information

Accommodation
703 Apartments
Lowest Price
$105
Highest Price
$183
Popular accommodation
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