Chicago Vacation Rentals

Welcome to the legendary ‘Windy City’ and home to the blues and jazz- Chicago, Illinois, United States. Located in the Midwest USA in the State of Illinois, Chicago is the largest city and is home to nearly 2.7 million residents, making it the third largest city in the United States. Get ready for a vacation packed with things to do as Chicago offers a Mecca of world class entertainment and activities. Owner Direct offers visitor the best selection of vacation rentals and accommodations to suite every budget and taste. Whatever your holiday lists contains, Chicago will definitely deliver to all types of travelers.

Chicago is a cross-cultural city having over 77 distinct neighbourhoods which singularly identify with specific ethnic backgrounds. Visitors will definitely want to take the time to research the varying quadrants of the city as each side offers vibrant hot spots and unique history.

Famous for being The Best Sports City in the United States by The Sporting News in 1993, 2006 and 2010, Chicago offers teams in the MLB, NHL, NFL and NBA. Sport Fans will want to plan around specific games when booking a vacation rental in Chicago as there are so many choices of games to attend.

Another main attraction to Chicago is for tourists to visit beautiful Lincoln Park where you will find The Lincoln Park Zoo, Chicago History Museum, Peggy Notebaert Nature Museum and the stunning Lincoln Park Conservatory. Another highlight, which attracts more than 8 million people each year is The Navy Pier, located just east of Streeterville it is home to the 150 foot tall Ferris Wheel. The Navy Pier is approximately 3,000 ft long and offers unique retail stores, restaurants, museums, exhibition halls and auditoriums.

Upscale shopping can be found along the Magnificent Mile and State Street, where thousands of restaurants, as well as Chicago's stunning and historic architecture can be found. Some of the famous local culinary favorites that should be enjoyed while visiting Chicago are deep dish pizza, a Chicago style hot dog and the Italian beef sandwich. Chicago is also home to a world famous orchestra, and award winning theatre productions. With one of the most vibrant theatre scenes in the U.S, Chicago offers an exhilarating mix of award-winning Broadway shows, critically-acclaimed regional plays and thought-provoking storefront/fringe performances.

Chicago is a city of world-class status and unsurpassed beauty. However visitors should plan on the weather when visiting. Chicago is classified within the humid continental climate zone, and experiences four distinct seasons. Summers are warm and humid and Chicago winters are cold, snowy, and windy. However spring and fall are generally mild seasons with low humidity. Therefore make sure you are weather prepared when visiting and booking a vacation rental and accommodation in this world class city.

No matter what type of vacation accommodations and lodging you are looking for, you will find it at Owner Direct Vacation Rentals ... including villa rentals, private condo rentals, suites, etc.

Chicago last minute travel deals or discounts on vacation rentals will be highlighted in red if available. Start your search for the perfect vacation rental and condo rental accommodation in Chicago now. Just enter your travel dates, number of travelers, and click 'search' for a list of accommodation options.

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5 Vacation Rentals

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  • Presidential Towers one Bedroom

    Presidential Towers one

    Presidential Towers: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 5
    • #224256
    avg $142 USD/night Credit Card Paypal Pet Friendly
    The minimum stay is 31 nights. This top West Loop location will allow you to walk to work, enjoy stunning views from home, and have the luxury of restaurants, nightlife, museums and shopping at your doorstep. The building features a BBQ deck and free WiFi lounge. There is an FFC Gym (paid membership) and a 24 hour Wal-Mart inside the building. Easy access to Chicago transportation ("El"/CTA/Metra/Amtrak/Bus/Highway). The apartments are furnished with all the comforts of home so all you need to bring is a bag of clothes and maybe a few groceries.
  • Presidential Towers Studio Apartment

    Presidential Towers Studio

    Presidential Towers: Apartment
    • 1 BA
    • Sleeps 4
    • #224254
    avg $104 USD/night Credit Card Paypal Pet Friendly
    The minimum stay is 31 nights. This top West Loop location will allow you to walk to work, enjoy stunning views from home, and have the luxury of restaurants, nightlife, museums and shopping at your doorstep. The building features a BBQ deck and free WiFi lounge. There is an FFC Gym (paid membership) and a 24 hour Wal-Mart inside the building. Easy access to Chicago transportation ("El"/CTA/Metra/Amtrak/Bus/Highway). The apartment is furnished with all the comforts of home so all you need to bring is a bag of clothes and maybe a few groceries.
  • Luxury one Bedroom Rental

    Luxury one Bedroom Rental

    The Loop: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 6
    • #224241
    avg $168 USD/night Credit Card Paypal Pet Friendly
    The minimum stay is 31 nights. This luxury building is close to work and offers top of the line amenities including an all-inclusive apartment. The LEED certified building offers a 24/7 door/security person, complimentary coffee/tea, 24/7 fitness center (cardio and weights), sauna, billiards table, poker table, entertainment room, board games, library, indoor and outdoor fireplace, business center (computers and printing), sky room (can be rented for parties), heated pool, outdoor grills, green dry cleaning and a dog run. Your apartment is equipped with all the comforts of home including stainless steel appliances (fridge, freezer, dishwasher, oven, stove top, garbage disposal), washer and dryer, flat screen TV, 140 cable channels, high-speed internet and a telephone with nationwide calling. All utilities are included including electricity, central heating/cooling, gas and water. We stock your kitchen with baking/cooking dishes and utensils, a coffee machine, teapot, and dishes. Your unit also includes all the linens and towels you will need in addition to a vacuum, hair dryer, iron and artwork. Dog friendly units are available upon request.
  • Luxury Jr. One Bedroom Rental

    Luxury Jr. One Bedroom

    The Loop: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 5
    • #224239
    avg $130 USD/night Credit Card Paypal Pet Friendly
    The minimum stay is 31 nights. This luxury building is close to work and offers top of the line amenities including an all-inclusive apartment. The LEED certified building offers a 24/7 door/security person, complimentary coffee/tea, 24/7 fitness center (cardio and weights), sauna, billiards table, poker table, entertainment room, board games, library, indoor and outdoor fireplace, business center (computers and printing), sky room (can be rented for parties), heated pool, outdoor grills, green dry cleaning and a dog run. Your apartment is equipped with all the comforts of home including stainless steel appliances (fridge, freezer, dishwasher, oven, stove top, garbage disposal), washer and dryer, flat screen TV, 140 cable channels, high-speed internet and a telephone with nationwide calling. All utilities are included including electricity, central heating/cooling, gas and water. We stock your kitchen with baking/cooking dishes and utensils, a coffee machine, teapot, and dishes. Your unit also includes all the linens and towels you will need in addition to a vacuum, hair dryer, iron and artwork. Dog friendly units are available upon request.
  • Luxury Studio Apartment Rental

    Luxury Studio Apartment

    The Loop: Apartment
    • 1 BA
    • Sleeps 3
    • #224235
    avg $115 USD/night Credit Card Paypal Pet Friendly
    The minimum stay is 31 nights. This luxury building is close to work and offers top of the line amenities including an all-inclusive apartment. The LEED certified building offers a 24/7 door/security person, complimentary coffee/tea, 24/7 fitness center (cardio and weights), sauna, billiards table, poker table, entertainment room, board games, library, indoor and outdoor fireplace, business center (computers and printing), sky room (can be rented for parties), heated pool, outdoor grills, green dry cleaning and a dog run. Your apartment is equipped with all the comforts of home including stainless steel appliances (fridge, freezer, dishwasher, oven, stove top, garbage disposal), washer and dryer, flat screen TV, 140 cable channels, high-speed internet and a telephone with nationwide calling. All utilities are included including electricity, central heating/cooling, gas and water. We stock your kitchen with baking/cooking dishes and utensils, a coffee machine, teapot, and dishes. Your unit also includes all the linens and towels you will need in addition to a vacuum, hair dryer, iron and artwork. Dog friendly units are available upon request.

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