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Chicago Vacation Rentals

This section features the following homes, villas, cabins, cottages or condos listed below. Please click on the description to view any of the Chicago rentals you see listed for more information. Vacation rentals in Chicago, illinois are added and updated every week, so please bookmark us and visit again. Be sure to check out Beverly Shores, Indiana (36 miles) for additional vacation rental choices. (Notice a problem with our distances? Report it here.)

Photo's available Pets? please inquire Swimming pool Jacuzzi Availability Calendar
Min Rate Max Rate Per Property Type Beds Baths Pets Pool Jacuzzi
Sort By  ->
Type Bed Bath Sleeps Rates or Community Property Name
 Studio 0 1 2 $100-$600 USD/wk Downtown Chicago w/ Rooftop Deck ~~ $100/night!
 Condo 1 1 2 $1000-$1400 USD/wk Luxurious Modern 1 bedroom Apt - 1250 sq ft
 Condo 1 1 2 $1800-$2750 USD/mth Lake Shore Drive - finest address and views in Chgo
 Apartment 1 1 2 $450-$600 USD/wk Pratt Shore
 Condo 1 1 3 $1200-$1600 USD/wk Mag Mile Condo
 Apartment 1 1 3 $1200-$1400 USD/wk Modern Luxury in the Heart of Downtown
 Condo 1 1 4 $950-$1100 USD/wk Museums,Parks,Lake Michigan,McCormick Place and More
 Condo 1 1 4 $950-$1100 USD/wk Jul 28 - Aug 4 availble in Downtown Chicago
 Condo 1 1 4 $700-$1000 USD/wk ** April Special ** Modern Printers Row Condo Downtown
 Condo 1 1 4 $750-$750 USD/wk Great Price ($125/nt) for Beautiful Downtown Condo
 House 1 1 4 $1000-$1050 USD/wk The Suite on Magnolia
 Apartment 1 1 4 $150-$2400 USD/mth Beautiful 1 bedroom apartment, 1 bathroom, internet
 Condo 1 1 4 $150-$1100 USD/wk Riverview Bedroom w/ Breathtaking View in Downtown Chicago!
 Apartment 1 1 4 $850-$1100 USD/wk Trendy Lincoln Park/DePaul Designer Apartment Sleeps 1-4
 Condo 1 1 4 $1400-$1750 USD/wk Last Days In JULY only $150! Magnificent Mile One BR
 Condo 1 1 5 $1050-$1400 USD/wk Beautiful Chicago Loft For Rent!
 Apartment 2 1 4 $1050-$1400 USD/wk The Shoreham - Beautiful Apartment near Millenium Park
 Condo 2 1 4 $200-$1400 USD/wk Gold Coast (Michigan Ave. area) Lux. 2 BR Condo Daily/wkly
 Condo 2 1 4 $1500-$2000 USD/wk Mag Mile Heart of Chicago Stays!!! Check out Discounts!!
 Condo 2 1 5 $1400-$1600 USD/wk By Millennium Park, McCormick Place in Downtown Chicago
 Condo 2 1 6 $1600-$1800 USD/wk The Buckingham
 House 2 1 6 $2000-$6000 USD/wk Private beach & lake front property in Chicago suburbs
 Condo 2 2 4 $1800-$1800 USD/wk Condo on Chicago's Gold Coast Steps from Michigan Avenue
 Apartment 2 2 4 $1250-$1500 USD/wk Great City Views, 45th Floor / 2 Bedroom unit with Balcony!
 Condo 2 2 4 $1500-$1750 USD/wk Premier Gold Coast Location! Every Room Overlooks Lake!
 Condo 2 2 6 $1000-$2000 USD/wk Steps from Michigan Ave... In the heart of Chicago
 Condo 2 2 7 $1800-$2500 USD/wk Heart of Chicago
 Condo 2 6 $350-$1800 USD/wk Six Acres of Serenity on the River in the Heart of the City
 Duplex 2 6 $900-$1450 USD/wk Condo close to downtown with terrace and rooftop
 Condo 2 6 $250-$1600 USD/wk Downtown Rooftop Penthouse w/ 2 Decks
 House 2 8 $1300-$1900 USD/wk Oak Park Townhome
 Apartment 3 1 5 $1200-$1750 USD/wk Wicker Park Apartment
 Condo 3 1 6 $1300-$1500 USD/wk Pet & Child friendly~Gorgeous Chicago Vacation Home!
 Apartment 3 1 8 $1750-$2450 USD/wk Family Friendly - Designer Chicago Apartment
 Townhome 3 7 $250-$1500 USD/wk Spacious 4 floor Townhouse, Perfect Location!
 House 3 8 $1950-$2350 USD/wk Lake Michigan Beachfront Cottage
 Coachhome 3 10 $2400-$2750 USD/wk Beautiful China Doll Coach House
 House 3 7 $1250-$1550 USD/wk 1714 West Ainslie
 House 4 10 $2700-$2700 USD/wk Modern 4 Level Home. Minutes from Downtown
 House 5 3 14 $400-$3000 USD/wk chicago lake vacation home less than 1 hr from downtown Chic
 House 5 18 $4800-$5500 USD/wk Luxury Home Near Downtown Chicago
Found 41 properties

Chicago, Illinois Vacation Rentals and Tourism

It’s impossible to return home from a Chicago vacation without feeling a lot more enlightened and cultured. The world-famous city in Illinois has open arms for everybody, no matter their age, background, or lifestyle. So no matter who you are or where you're from, Chicago vacation rentals are right up your alley.

The exquisite jazz and blues clubs will delight music lovers. Wrigley Field will thrill those who enjoy America’s favorite pastime, baseball. Kids (and their parents too) will lose track of time at the attraction-filled Navy Pier and Lincoln Park Zoo. Museum hoppers won’t ever run out of things to do, which will likely include a tour of the Art Institute of Chicago. And everybody will be intrigued by the many historical and architectural landmarks, like the famous Sears Tower. Don’t forget to spend at least one day in Millennium Park, which offers up adventure year-round (in the winter, you can ice skate). Also, Michigan Lake is always fun when it’s sunny out.

If a Chicago vacation house doesn’t sound appealing to you by now, then perhaps you’re concerned about how affordable your getaway will be! Fortunately, thanks to the many Chicago vacation rentals found here, you can definitely find cheap accommodations. Whether it’s a Chicago weekly condo rental or one-night accommodation you’re interested in, you can find it right here. And in fact, although dining out in Chicago is an unforgettable experience in itself, you still have the option to save money and dine in because your Chicago luxury condo rental will surely have a kitchen. You certainly can’t say the same for a hotel.

Chicago vacation apartments are extremely popular as they allow tourists to really enjoy the vibrant local culture of the city. Don’t hide away in a resort hotel; instead stay in one of the cozy Chicago condo rentals found here! There’s a reason people keep coming back to this rich and exciting city, so why don’t you experience it for yourself by booking one of the Chicago vacation apartments or houses listed here?

Sights and tours to see

Wrigley Field
Navy Pier
Lincoln Park Zoo
Art Institute of Chicago
Sears Tower
Millennium Park
Michigan Lake