Chicago - We currently have 13 Chicago vacation homes, condos and villas listed on this page!

Vacation Homes in Chicago Have a Lot to Offer

Chicago is the largest city in Illinois and the third most populated in the entire nation. As you might expect from a city with hundreds of years of history and nearly three million current residents, there is a wealth of activities and attractions available to those staying in Chicago vacation rentals. In an average year, Chicago attracts more than 30 million visitors from inside the United States alone; together, such tourists spend almost $12 billion per year in the city.

One of Chicago's great claims to fame is its shopping district. The "Magnificent Mile," well named for its hundreds of stores, provides upscale shopping for the discriminating traveler. The Chicago Cultural Center, which dates from the late 1800s was once the city's public library but now serves as the central Visitor Information center. Here, tourists can see a 38-foot wide dome made of Tiffany glass in the heyday of Chicago's glory days.

Each year, the Taste of Chicago festival attracts restaurateurs and gourmets to the city, long famed for its thousands of fine restaurants. A popular attraction all year long is the Art Institute of Chicago, along with Grant Park, which features the Buckingham Fountain, first installed in 1927. Winter visitors will be delighted to enjoy the outdoor ice rink in Millennium Park, which also hosts the Cloud Gate sculpture, famed for its reflections. Also in the park are two tall sculptures of glass. Known as the Crown Fountain, the towers display not just water effects but also LED imagery literally representing the "face" of Chicago.

Sort results by:
  • Chicago, Illinois
    Chicago Private Yacht Charters is a dream come true-exhilarating cruise experience along Lake Michigan with incredible views of the Chicago Skyline.
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    4 2 Yacht
    $1200 - $2500 $0 - $0 $0 - $0
  • Chicago, Illinois
    A newly decorated bed and breakfast located conviently on Chicago's North Side.
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    5 5 B&B
    $0 - $0 $99 - $179 $0 - $0
  • Chicago, Illinois
    China Doll offers three self-contained apartment suites with private entrances. Designed as productivity havens for the business traveler, they also contain superb personal comfort features.
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    2 1 B&B
    $225 - $375 $0 - $0 $0 - $0
  • Chicago, Illinois
    This unit is ideal for family and friends! With three bedrooms, 2 full baths and 2 half baths, a full kitchen, dining room, living room, fully equipped office, and a washer and dryer, it almost feels like you are at hom...
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 3 House
    $325 - $525 $0 - $0 $0 - $0
  • Chicago, Illinois
    Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck with poolside service, premier gym, wireless internet lounge, and much more. Overlooking 1,200 acres of gloriou...
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    1 1 Apartment
    $195 - $225 $1250 - $1400 $3000 - $3500
  • Chicago, Illinois
    For short- or long-term stays, we offer furnished apartments in the desirable Gold Coast and Michigan Ave districts of downtown Chicago. WWW.CHICAGOCORPORATE.COM
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    1 1 Apartment
    $125 - $250 $700 - $1500 $1750 - $3500
  • Chicago, Illinois
    Antiques, Wifi, AC, cable, sundeck. Elizabeth's Place: livingrm,formal diningrm, gourmand kitchen, sleep up to 6 in 3 bedrms. Alice's Annex sleeps up to 5 w bedrm, sleeper sofa and sleeping nook, W&D. Kristina's Suite: s...
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 1 Apartment
    $0 - $0 $0 - $0 $1500 - $2202
  • Chicago, Illinois
    1. *Alice's Annex*, 1.5 bedroom /1 bath sleeps up to 5 2. *Elizabeth's Place* 3 bedroom / 1 bath, up to 6 3. *Bella's Duplex*, 4 bedroom / 2 bath, up to 8 Bella's may be divided to sleep 2 or 4
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    8 4 Apartment
    $1 - $1 $1 - $1 $1 - $1
  • Chicago, Illinois
    Modern 4-story 2,500 sq. ft. townhome in historic downtown Oak Park and short train ride to downtown Chicago. Home has 3 full bedrooms, 2.5 baths, 1st floor sitting area, dining room, living room, kitchen and 2 car attac...
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 3 House
    $215 - $350 $1500 - $2100 $3300 - $4250
  • Chicago, Illinois
    Situated between Lake Michigan, Michigan Ave, Millennium Park and the Chicago River, discover Lakeshore East – a sophisticated, luxurious urban oasis located in Chicago’s newest neighborhood. Posh and luxurious interiors...
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    1 1 Apartment
    $190 - $225 $1250 - $1500 $3300 - $3600
  • Chicago, Illinois
    Spacious residences feature lux finishes including dramatic windows with panoramic views, stainless steel & black appliances, full granite kitchens with paneled wood cabinetry, gas cooking, in-home washer and dryers and ...
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    1 1 Condo
    $195 - $225 $1354 - $1500 $3000 - $3500
  • Chicago, Illinois
    5 bedrooms Back Patio Large Yard Brinks Alarm System 3 floors Grocery Service Transportation Service Free Tour and Concert Tickets with a Weekly Stay Daily Maid Service
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    5 2 House
    $200 - $300 $1600 - $2100 $4500 - $10000
  • Chicago, Illinois
    This 109 year old restored Victorian Home is located four short blocks from fabulous Lake Shore Drive and Chicago's gay Hollywood Beach, and offers all the comforts of home. North of Boystown and east of the gay nightlif...
    Call Owner For Payment Details
    Bedrooms Bathrooms Rental type Pet friendly Daily Rate Weekly Rate Monthly Rate
    3 2 B&B
    $0 - $0 $99 - $179 $0 - $0










Looking for vacation rentals near to Chicago ?

Michigan City Vacation Rentals By Owner  New Buffalo Vacation Rental By Owner  Kankakee Vacation Home Rentals  Twin Lakes Vacation Homes  Stevensville Vacation Home Rentals  Saint Joseph Condo Rentals  Benton Harbor Rental Vacation Homes  lake geneva Vacation Rentals  Delavan Vacation By Owner  
Learn More About
Chicago
Below you will find writings from other Chicago vacation rental owners about the area they know best! It's a great way to learn first hand about the Chicago region and all that it has to offer!

If you are a registered vacation rental property owner on VacationRentalDirect.com and want to tell everyone about the Chicago area and additional exposure for your listing, please login here and click on 'Edit Your Listing!'

 

Lakeview / Wrigleville Area of Chicago

Posted by Kate Goldenberg on Monday, December 01, 2008
 
The North side residential area of Chicago is well-established area of the city with large amount of local restaurants, boutique shops, galleries, bars, clubs, theaters. The Southport corridor is an area with stylish European markets and cafes, movie theaters and eclectic restaurants. Wrigley is a section in the heart of the Lakeview area. The very east end of Lakeview is the lakefront - Public Park managed and maintained by the city of Chicago. The park goes along the lake front (lake Michigan is so large it feels like an ocean or sea). The park area by the Lakeview neighborhood has golf course, many open free tennis courts, bike trails, and bike rental, open space with beautiful Chicago skyline. The yacht club at the Belmont harbor is filled with boats - large and small. It is a great pleasure walking by the lake and being in one of the most beautiful recreation areas in the world, and at the same time feel the vibrant modern city near by. The skyline view is unbeatable!