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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  • All-Inclusive Luxury Studio in Greek Town

    All-Inclusive Luxury

    Chicago: Apartment
    • 1 BA
    • Sleeps 3
    • #234228
    avg $140 USD/night Credit Card Paypal Pet Friendly
    This stunning location with unobstructed city views is walking distance to the loop (business district), theater, west loop (Randolph St. Restaurant row), public transportation and recreation. Our apartments are fully furnished to the smallest detail, so you only need your suitcase. If there is something that would make your stay more comfortable, just ask. We pride ourselves on delivering top customer satisfaction, each and every time. Guests will have access to the entire apartment. Your apartment will include custom wide plank flooring, stainless steel appliances, elegant white quartz countertops in the kitchen and bath, modern fixtures, oversized walk-in closets and full size washer and dryer. We will also provide you with all kitchenware, linens, television, wifi, telephone, heating/cooling, electricity and everything else you need to be comfortable. The building amenities include an expansive fitness center and outdoor yoga studio, 24,000 SF outdoor sundeck with fire pits and grills, heated outdoor pool and hot tub, game room with billiards and 60” TV, party room with chef’s kitchen, technology lounge with complimentary coffee, 24/7 market with food and beverage options, bike storage and more. We professionally clean each property before your arrival, including every kitchen item and every linen in the property to ensure your complete satisfaction. We deliver 24-hour maintenance service to ensure your apartment stays in top condition for your entire stay.
  • All-Inclusive River North Luxu Jr. One Bedroom

    All-Inclusive River North

    Chicago: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 5
    • #234226
    avg $163 USD/night Credit Card Paypal Pet Friendly
    This River North location is surrounded by award winning restaurants and nightlife. Walk to the loop (business district), theater, magnificent mile, public transportation and river walk. The apartment is 961 SF and finished with granite countertops, stainless steel appliances, hardwood floors and modern furniture. The building includes resort level amenities such as a pool with private cabanas, fitness center and business center. Our apartments are fully furnished to the smallest detail, so you only need your suitcase. If there is something that would make your stay more comfortable, just ask. We pride ourselves on delivering top customer satisfaction, each and every time. Your apartment will include wood flooring, stainless steel appliances, elegant granite countertops in the kitchen and bath, modern fixtures, separate tub and showers and full size washer and dryer. We will also provide you with all kitchenware, linens, television, wifi, telephone, heating/cooling, electricity and everything else you need to be comfortable. Contact our office for a full inventory list. Guests will have access to the entire apartment. The building amenities include an expansive fitness center and private yoga/Pilates studio, resident lounge and gourmet kitchen, business center (copy, fax, scan wifi), library and fireplace, sports lounge with billiards table, private theater, golf simulator, coffee bar, 22,000 SF rooftop deck with outdoor fireplace, fire pit and lounge areas, heated pool, private cabanas with TV, outdoor kitchen/grills/bar, outdoor movie theater, dog park and pet wash, attached parking garage (extra fee), bike room and so much more. We professionally clean each property before your arrival, including every kitchen item and every linen in the property to ensure your complete satisfaction. We deliver 24-hour maintenance service to ensure your apartment stays in top condition for your entire stay. River North is surrounded by The Loop (business), Streeterville (retail) and Gold Coast (architecture and night life). Easy access to all public transportation. River North is known for it's restaurants, nightlife and upscale hotels. All doors provide cab access. The Clark Bus is at your doorstep. Other bus routes and all CTA Train routes are a couple blocks away. Easy access to major highways. Contact our office for detailed directions.
  • All-Inclusive Chicago Loop Apartment with River Views, Gym and Pool

    All-Inclusive Chicago Loop

    Chicago: Apartment
    • 1 BA
    • Sleeps 2
    • #233474
    avg $147 USD/night Credit Card Paypal Pet Friendly
    Enjoy stunning river views from your apartment before walking to work from this centrally located loop apartment. In your free time enjoy Michigan Avenue for shopping, as well as museums, restaurants and nightlife at your doorstep. The train, taxis, and buses are all accessible on the same block for even more convenience. Your apartment will include floor to ceiling windows with views of the Chicago river, designer kitchen with quartz countertops, white marble mosaic tile backsplash, stainless steel appliances, custom wood-plank flooring, polished natural stone vanities and tri-view medicine cabinets, custom closets with organizers, full sized-washer and dryer and controlled heating/air. We will also provide you with all kitchenware, linens, television, wireless internet, telephone, heating/cooling, electricity and everything else you need to be comfortable. This doorman building features an expansive two level outdoor sundeck including fire pits, private kitchens, lounge area, seating and grills, the building also features an expansive health club with towel service, stunning terrace, indoor pool and spa with retractable wall opening to sundeck, tech=bar with free printing, screening room, billiards room with TV and custom music system, lounge with floor-to-ceiling windows and another outdoor terrace overlooking the cityscape, bike room, heated parking (extra cost) and more. We deliver top customer service, and simple policies to meet your needs. Our clients enjoy month to month rental terms with just a 14-day notice to vacate and have the option to pay rent with any major credit card. Property is ready for our clients to move-in with just a suitcase. 31 Night Minimum Stay.
  • Luxury all-Inclusive Furnished River North Apartment

    Luxury all-Inclusive

    Chicago: Apartment in a complex
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #233206
    avg $194 USD/night Credit Card Paypal
    This location is surrounded by award winning restaurants and nightlife. Walk to the loop (business district), theater, magnificent mile, public transportation and river walk. The apartment is finished with granite countertops, stainless steel appliances, hardwood floors and modern furniture. The building includes resort level amenities such as a pool with private cabanas, fitness center and business center. If there is something that would make your stay more comfortable, just ask. We pride ourselves on delivering top customer satisfaction, each and every time. The apartment has wood flooring, stainless steel appliances, elegant granite countertops in the kitchen and bath, modern fixtures, separate tub and shower and full size washer and dryer. We will also provide you with all kitchenware, linens, television, wifi, telephone, heating/cooling, electricity and everything else you need to be comfortable. The building amenities include an expansive fitness center and private yoga/pilates studio, resident lounge and gourmet kitchen, business center (copy, fax, scan wifi), library and fireplace, sports lounge with billiards table, private theater, golf simulator, coffee bar, 22,000 sq foot rooftop deck with outdoor fireplace, fire pit and lounge areas, heated pool, private cabanas with TV, outdoor kitchen/grills/bar, outdoor movie theater, dog park and pet wash, attached parking garage (extra fee), bike room and so much more. We deliver 24-hour maintenance service to ensure your apartment stays in top condition for your entire stay. This building is surrounded by The Loop (business), Streeterville (retail) and Gold Coast (architecture and night life). Easy access to all public transportation. The River North area is known for it's restaurants, nightlife and upscale hotels. All doors provide cab access. The Clark Bus is at your doorstep. Other bus routes and all CTA Train routes are a couple blocks away. Easy access to major highways.
  • Luxury one Bedroom Rental

    Luxury one Bedroom Rental

    Chicago: The Loop: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 6
    • #224241
    avg $174 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

    Chicago: The Loop: Apartment
    • 1 BDR
    • 1 BA
    • Sleeps 5
    • #224239
    avg $147 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

    Chicago: The Loop: Apartment
    • 1 BA
    • Sleeps 3
    • #224235
    avg $135 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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1.250.469.9543