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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Chicago Vacation Activities

5 Vacation Rentals

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  • Modern Luxury one Bedroom

    Chicago: Apartment
    1 BDR • 1 BA • Sleeps 5 • #239117
    110 to 198 USD/night Credit Card Pet Friendly
    Modern. Clean. All-Inclusive. Enjoy stunning city and Chicago River views from floor to ceiling windows while having the luxury of premiere shopping, dining, and big city attractions at your doorstep. This spacious apartment includes a 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, in-unit washer and dryer and controlled heating/air. This 24-hour doorman building features an expansive two level outdoor sundeck including fire pits, private kitchens, lounge area, seating and grills, 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 and a bike room. Arrive with just your suitcase and we handle everything else for you. Your automated monthly payment includes all furnishings, linens, kitchen and household items, high speed wireless Internet, unlimited calling nationwide, all utilities, cable TV with flat screen TV/s, access to all amenities, 24-hour maintenance and 24-hour customer service. We offer month to month contracts with a 31 night minimum and a 14 day notice to vacate. Parking and maid service are available, and apartment prices depend on your dates of stay. Book today to start your Chicago experience!
  • Luxury Furnished all

    Chicago: Apartment
    1 BA • Sleeps 5 • #239119
    94 to 182 USD/night Credit Card Paypal Pet Friendly
    Modern. Clean. All-Inclusive. Enjoy stunning city and Chicago River views from floor to ceiling windows while having the luxury of premiere shopping, dining, and big city attractions at your doorstep. This spacious apartment includes a 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, in-unit washer and dryer and controlled heating/air. This 24-hour doorman building features an expansive two level outdoor sundeck including fire pits, private kitchens, lounge area, seating and grills, 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 and a bike room. Arrive with just your suitcase and we handle everything else for you. Your automated monthly payment includes all furnishings, linens, kitchen and household items, high speed wireless Internet, unlimited calling nationwide, all utilities, cable TV with flat screen TV/s, access to all amenities, 24-hour maintenance and 24-hour customer service. We offer month to month contracts with a 31 night minimum and a 14 day notice to vacate. Parking and maid service are available, and apartment prices depend on your dates of stay. Book today to start your Chicago experience!
  • All-Inclusive Chicago Loop

    Chicago: Apartment
    1 BA • Sleeps 2 • #233474
    82 to 170 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.
  • Loop Randolph Tower Studio

    Chicago: Apartment
    1 BA • Sleeps 2 • #250510
    97 to 170 USD/night Credit Card Pet Friendly
    Randolph Tower Studio apartment is located in the theater district of the loop. Enjoy stunning views of the city 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. Modern. Clean. All-Inclusive. Enjoy stunning city views from floor to ceiling windows while having the luxury of premiere shopping, dining, and big city attractions at your doorstep. This spacious apartment with 9 ft. Ceilings includes a designer kitchen with granite countertops and kitchen islands, King Bed, stainless steel appliances, custom wood-plank flooring, custom closets with shelving and a wall mounted shoe rack in-unit storage, individually controlled heating/cooling and in-unit washer and dryer. This 24-hour doorman building is a historic landmark. The building amenities include an expansive lounge area, bike storage, business center and conference room, concierge service, dry cleaning/laundry service, hot tub and indoor pool, on-site restaurant and pet facilities. Arrive with just your suitcase and we handle everything else for you. Your automated monthly payment includes all furnishings, linens, kitchen and household items, high speed wireless Internet, all utilities, cable TV with flat screen TV/s, access to all amenities, 24-hour maintenance and 24-hour customer service. We offer month to month contracts with a 31 night minimum and a 14 day notice to vacate. Parking and maid service are available, and apartment prices depend on your dates of stay. Book today to start your Chicago experience!
  • Convenient to the

    Chicago: Vacation Rental
    2 BDR • 2 BA • Sleeps 6 • #245073
    117 to 234 USD/night Credit Card
    Convenient to the North/Clybourn Red Line station, this 2BR condo is a 15-minute drive to Willis Tower, Millennium Park, Wrigley Field, and downtown Chicago. Enjoy the outdoor kitchen, covered living area, and rooftop patio with a skyline view. Sleeps 6.. Just a 5-minute walk from the North/Clybourn Red Line station, this beautifully decorated 2BR/2BA Lincoln Park condo is the perfect home base for an exciting Windy City vacation. The three-level property boasts two comfy living areas, a rooftop patio with a skyline view, and a spacious deck outfitted with heat lamps, TVs, and an outdoor kitchen. The city’s most popular sites are easily accessible, including Wrigley Field (2.5 mi), Willis Tower (3.5 mi), Millennium Park (4 mi), and downtown (5 mi). LIVING AREAS High ceilings and a wall of windows create an inviting main living area. Four can relax comfortably on the sofa in front of the 60” flat screen TV. A second living area in the upstairs loft offers a large sectional sofa that converts to a pull-out bed. Sit back and enjoy the 60” flat screen TV, surround sound speakers, and access to the outdoor kitchen and deck. KITCHEN & DINING Beautiful wood cabinets, granite countertops, and a suite of stainless steel appliances - including a side-by-side refrigerator, dual sinks, and a dishwasher - outfit the well-appointed kitchen. Serve casual meals at the kitchen counter with seating for four, or enjoy alfresco dining on the second-floor deck with seating for nine. BEDROOMS & BATHS This property sleeps a total of six between two bedrooms and a sleeper sofa in the second living area. The master bedroom has a king-size bed, 55” flat screen TV, and access to a small private balcony. The convenient en-suite bath includes a double vanity, jetted tub, and walk-in shower. Two can sleep comfortably in the second bedroom, outfitted with a queen-size bed and plenty of closet space. A second bathroom has a walk-in shower. OUTDOOR AREAS The second-floor deck is a perfect spot to gather with your group; it’s partially covered and decorated with two sofas, two wall-mounted TVs, and a fire pit. Use the grill to cook your favorite meals, keep your beverages cold in the mini fridge, and dine outdoors. There’s a table for six and nearby bar seating for an additional three. A spiral staircase leads to the rooftop deck, where you’ll find seating for seven, a 46” flat screen TV, and a beautiful view of the Chicago skyline. There is also a small balcony off the master bedroom. EXTRA AMENITIES Guest amenities include complimentary Wi-Fi, a DVD player, washer/dryer, and garage parking for one vehicle. Additional paid parking is available nearby. THE LOCATION With a prime location, this comfortable condo makes exploring easy. Walk 3 minutes for coffee and shopping at North & Sheffield Commons. Enjoy a night of improv at the iO Theater, just a 5-minute walk from home, or treat yourself to upscale dining at Alinea before catching a show at the Steppenwolf Theater, both just an 8-minute walk away. Or walk a minute farther to catch the latest movie release at ArcLight Cinema. Drive 10 minutes to the north end of Lakeshore Drive -- the start of a 15-mile-stretch of scenic urban parkway. Attractions include North Avenue Beach, the Chicago History Museum, and the Lincoln Park Zoo & Conservatory on the north end, and Soldier Field & Museum, Adler Planetarium, and Navy Pier on the south end. Easily access your vacation home with a keyless secure door code; no need for an in-person key exchange. Your rental will be professionally cleaned and ready for you to enjoy. You can expect all the comforts of a fine hotel, including shampoo, soaps, paper products, towels, and linens. Your home will include a HomeDroid tablet (electronic guest directory) providing specific home details, local suggestions, Wi-Fi access, and TV instructions. If you need anything before, during, or after your stay, our 24/7 local team is always ready to help!

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