Cook County Vacation 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

Cook County Vacation Rentals

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE Chicago IL
Free Cancellation
Reserve now, pay when you stay
$203 nightly
The price is $238 total per night
$238 total
Jul 1 - Jul 2
Total with taxes and fees
Guests staying at Sentral Michigan Avenue enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Valet parking is offered for USD 77 per night. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and luggage storage. Additional amenities include meeting rooms, a 24-hour business center, and a meeting room.
Pool
Kitchen
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Guests staying at Kasa Magnificent Mile Chicago enjoy a gym, free WiFi in public areas, and a convenience store. Self parking is available for USD 51.00 per day. Front-desk staff can help with luggage storage, and provide local restaurant recommendations.
Kitchen
Washer
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
1140 North Wells Street Chicago IL
$272 nightly
The price is $319 total per night
$319 total
Jun 29 - Jun 30
Total with taxes and fees
At Level Chicago – Old Town, guests have access to a 24-hour gym, a sauna, and a rooftop terrace. Self parking is offered for USD 68.30 per night. The front desk is staffed 24/7 to help with dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this family-friendly aparthotel include free WiFi in public areas, a 24-hour business center, and a seasonal outdoor pool.
Pool
Kitchen
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4 out of 5
1431 W Taylor St Chicago IL
The Neighborhood Hotel-Little Italy features free WiFi in public areas and laundry facilities. Staff members can answer questions about accommodations, and also provide luggage storage.
Kitchen
Pet friendly
Kasa South Loop Chicago

Kasa South Loop Chicago

4 out of 5
900 S Clark Street Chicago IL
At Kasa South Loop Chicago, guests have access to a gym, a rooftop terrace, and free WiFi in public areas. Self parking is available for USD 32 per night. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a business center, an arcade/game room, and a terrace.
Kitchen
Washer
The Gem Museum Suites

The Gem Museum Suites

3.5 out of 5
1555 Oak Avenue Evanston IL
Free Cancellation
Reserve now, pay when you stay
$162 nightly
The price is $186 total per night
$186 total
Jun 21 - Jun 22
Total with taxes and fees
Guests of The Gem Museum Suites enjoy features like a 24-hour gym, free WiFi in public areas, and a terrace. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include laundry facilities, a banquet hall, and a garden.
Wrigleyville Suites

Wrigleyville Suites

2 out of 5
3727 N Clifton Ave Chicago IL
$267 nightly
The price is $313 total per night
$313 total
Jul 7 - Jul 8
Total with taxes and fees
Guests staying at Wrigleyville Suites enjoy free WiFi in public areas, laundry facilities, and a garden.
Free WiFi
Air conditioning
Kasa River North Chicago

Kasa River North Chicago

4 out of 5
808 N Wells St Chicago IL
Guests of Kasa River North Chicago enjoy a gym, a rooftop terrace, and a 24-hour business center. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include a seasonal outdoor pool, express check-out, and a communal living room.
Pool
Kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2 out of 5
3030 S Lyman St Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi and air conditioning. Popular attractions Soldier Field and United Center are located nearby.
LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View

Chicago IL
$552 nightly
The price is $652 total per night
$652 total
Jun 18 - Jun 19
Total with taxes and fees
Guests staying at this apartment enjoy features like a gym.
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

Chicago Illinois
This vacation home offers a water park, a gym, and laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
Charming Wrigleyville Home Close to the Cubs!

Charming Wrigleyville Home Close to the Cubs!

Chicago IL
At this apartment, guests have access to features like laundry facilities. This smoke-free apartment building also has barbecue grills.
King Comfort apartment, Quiet, Clean, AC & WiFi

King Comfort apartment, Quiet, Clean, AC & WiFi

Chicago IL
This vacation home is a smoke-free vacation home.
LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio

Chicago IL
$238 nightly
The price is $281 total per night
$281 total
Jun 21 - Jun 22
Total with taxes and fees
Guests staying at this apartment enjoy features like a gym.
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

Chicago IL
Free offsite parking is available if you drive.
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Chicago IL
At this apartment, guests have access to features like laundry facilities.
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

Chicago IL
Guests staying at this vacation home enjoy free WiFi in public areas and laundry facilities.
McCormick 2BR with Skyline View Near Soldier Field & Museum Campus

McCormick 2BR with Skyline View Near Soldier Field & Museum Campus

Chicago IL
This apartment features a gym and laundry facilities.
Don't see what you're looking for?
See all available properties in Cook County
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.

Hotel Options in Cook County

    Hyatt Regency O'Hare Chicago

    Hyatt Regency O'Hare Chicago

    9300 Bryn Mawr Ave Rosemont IL
    $135 nightly
    The price is $154 total per night from Jun 28 to Jun 29
    $154 total
    Jun 28 - Jun 29
    Total with taxes and fees
    8.8/10 Excellent! (2,681 reviews)
    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue Chicago IL
    $136 nightly
    The price is $162 total per night from Jun 29 to Jun 30
    $162 total
    Jun 29 - Jun 30
    Total with taxes and fees
    8/10 Very Good! (10,292 reviews)
    The Chicago Hotel Collection - Magnificent Mile

    The Chicago Hotel Collection - Magnificent Mile

    166 E Superior Street Chicago IL
    $162 nightly
    The price is $192 total per night from Jul 1 to Jul 2
    $192 total
    Jul 1 - Jul 2
    Total with taxes and fees
    7.8/10 Good! (1,596 reviews)

Orbitz makes it easy to find vacation rentals in Cook County 

🏠 What is the best price for a Cook County vacation rental?


Cook County rentals range between $154 and $652 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Cook County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Cook County getaway. Orbitz filters your search results so you can find the best Cook County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Cook County vacation rentals with Orbitz?


You may be able to cancel or amend your Cook County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Cook County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Cook County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Cook County?


When you book a Cook County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Cook County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Cook County—with plenty of hidden gems. We also have plenty of inventory in Cook County main cities and near popular attraction spots.


🏠 Why should I book my Cook County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Cook County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


More to Explore