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Featured Chicago Condo Rentals

Equipped Suite Near the Heart of Chicago Free Shuttle + Complimentary Breakfast
Equipped Suite Near the Heart of Chicago Free Shuttle + Complimentary Breakfast
Oakbrook Terrace, IL
This condo is a smoke-free condo building.
Free Breakfast Buffet! Free Shuttle! Only 2 Miles From Oakbrook Center!
Free Breakfast Buffet! Free Shuttle! Only 2 Miles From Oakbrook Center!
Oakbrook Terrace, IL
This condo is a smoke-free condo building.
Great for Business Travelers! Free Breakfast, Pool & Hot Tub Access!
Great for Business Travelers! Free Breakfast, Pool & Hot Tub Access!
Lincolnshire, IL
Guests staying at this condo enjoy features like an indoor pool.

Chicago Accommodation Oceanfront

The Blackstone, Autograph Collection
The Blackstone, Autograph Collection
4.0 out of 5.0 636 S Michigan Ave, Chicago, IL
$175
4.5/5 (82 reviews)

Elegant, very excellent location. Clean, breakfast very good and included.

Reviewed on Feb 15, 2020
The Blackstone, Autograph Collection features a fitness center, free WiFi in public areas, and conference space. Front-desk staff can answer questions 24/7, ...
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5.0 200 North Columbus Drive, Chicago, IL
$229
4.4/5 (42 reviews)

It was beautiful and the room was great. Checking in out quick and easy

Reviewed on Dec 18, 2019
Guests staying at Fairmont Chicago at Millennium Park enjoy access to a full-service spa, a 24-hour health club, and a steam room. For transportation, you can ...
Sheraton Grand Chicago
Sheraton Grand Chicago
4.0 out of 5.0 301 E North Water St, Chicago, IL
4.0/5 (88 reviews)

All was good except they mixed up my room with my son's reservation. He checked in at 1am and I had to go down and straighten it out. I was still up as we had an engagement party for him that went late, but that was annoying. But all was resolved with no problems.

Reviewed on Jan 4, 2020
Guests of Sheraton Grand Chicago have access to an indoor pool, a 24-hour fitness center, and free WiFi in public areas. Valet parking is offered for USD 73 ...
Waterfront Hotel and Marina
Waterfront Hotel and Marina
2.0 out of 5.0 3309 North Chapel Hill Road, Johnsburg, McHenry, IL
$78
3.6/5 (12 reviews)

The scenery is beautiful its after hour ergo i cant speak on the services or amenities

Reviewed on Nov 1, 2019
Waterfront Hotel and Marina offers a marina, express check-out, and a terrace. You can put free parking to good use if you drive. Friendly staff can provide ...
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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.

Hotel Options in Chicago

See all 1,941 Properties in Chicago
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.