Compare Chicago Condo 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 Condo Rentals

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 Accommodation Oceanfront

    The Blackstone, Autograph Collection

    The Blackstone, Autograph Collection

    636 S Michigan Ave, Chicago, IL
    $219 nightly
    The price is $257 total per night from Aug 7 to Aug 8
    $257 total
    Aug 7 - Aug 8
    Total includes taxes and fees
    9/10 Wonderful! (1,000 reviews)
    Fairmont Chicago at Millennium Park

    Fairmont Chicago at Millennium Park

    200 North Columbus Drive, Chicago, IL
    $254 nightly
    The price is $298 total per night from Aug 8 to Aug 9
    $298 total
    Aug 8 - Aug 9
    Total includes taxes and fees
    8.6/10 Excellent! (1,797 reviews)
    Sheraton Grand Chicago Riverwalk

    Sheraton Grand Chicago Riverwalk

    301 E North Water St, Chicago, IL
    $275 nightly
    The price is $322 total per night from Aug 12 to Aug 13
    $322 total
    Aug 12 - Aug 13
    Total includes taxes and fees
    8.2/10 Very Good! (1,380 reviews)
    Waterfront Hotel and Marina

    Waterfront Hotel and Marina

    3309 North Chapel Hill Road, Johnsburg, McHenry, IL
    $89 nightly
    The price is $99 total per night from Jul 23 to Jul 24
    $99 total
    Jul 23 - Jul 24
    Total includes taxes and fees
    8/10 Very Good! (419 reviews)

Hotel Options in Chicago

    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago, IL
    $179 nightly
    The price is $210 total per night from Jul 27 to Jul 28
    $210 total
    Jul 27 - Jul 28
    Total includes taxes and fees
    7.8/10 Good! (8,936 reviews)
    InterContinental Chicago Magnificent Mile by IHG

    InterContinental Chicago Magnificent Mile by IHG

    505 N Michigan Ave, Chicago, IL
    $235 nightly
    The price is $271 total per night from Aug 10 to Aug 11
    $271 total
    Aug 10 - Aug 11
    Total includes taxes and fees
    9/10 Wonderful! (2,001 reviews)
    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl, Chicago, IL
    $162 nightly
    The price is $191 total per night from Aug 10 to Aug 11
    $191 total
    Aug 10 - Aug 11
    Total includes taxes and fees
    8.8/10 Excellent! (2,428 reviews)

Luxury Condos

Find luxury condos in Chicago
Get your vacation off to a fabulous start by booking a luxury condo in Chicago. They’re a great option if you want to pamper yourself a little more than usual on your next getaway. Plus, they give you a unique opportunity to see the city the way a local would. You’re not in a hotel—you’re home. Condominiums come in all shapes and sizes, and with Orbitz on your side, you’ll find exactly the right one for your trip.

Stay in a Chicago condo
Vacation condo rentals are a nice alternative to hotels with perks such as multiple bedrooms, living rooms, balconies, laundry facilities, Wi-Fi access and espresso machines. And don’t underestimate the power of the full kitchen in your condo: whipping up midnight snacks is a breeze, and hey, making a meal on your own without worrying about ordering in or going out to eat is just plain convenient. You might also have a pool, a gym and a hot tub on the property or close by.  

Exploring Chicago will be a breeze with a downtown condo as your home base. You’ll be close to the top sights, and within walking distance of great restaurants, shopping, and bars. Got leftovers? Put them in your fridge. Remember, you’re living like a local now.

Chicago Condo Rentals essential information

Accommodation
337 Condo Rentals
Lowest Price
$99
Highest Price
$355
Popular accommodation
Huge Projector and Designated Workspace - Near Wrigley!, Experience Chicago living near United Center, The Chic Urban Oasis Near the Lake!, Modern Living 1BR in Warrenville, Spacious 4BRCondo near Wrigley/Dtwn +FreeParking, Downtown Mich Ave #7| Park View Penthouse +gym, Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover, Urban Chicago Escape ~ 1 Mi to Local Beaches!, Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.