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Chicago Vacation Rentals
VacationRentalDirect.com has found 14 Chicago Vacation Rentals that match your search criteria. Your results can be sorted by price, bedrooms, type of unit and whether the unit is pet friendly or not. All Chicago cottages, homes and vacation rentals are presented by their respective owners or managers.
Please click on the photos or links below to view the property details, then contact the owner directly (via the phone number or property inquiry button on each listing).
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Chicago, Illinois
Each fully-furnished apartment includes 2 bedrooms, 2 bathrooms, living room, dining room and kitchen. Brick patio (& grill during warmer months) in the backyard is available for use by all guests. Parking spots are av...
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| Apartment | 2 | 2 | Yes | $1610 to $1855 |
Chicago, Illinois
Choose Elizabeth's Place with its formal diningroom and gourmand's kitchen to sleep 5 in 3 bedrooms, or Alice's Annex to sleep 5 in a bedroom, sleeper sofa and nook. Kristina's Suite sleeps two, full bed. Fine antiques b...
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| Apartment | 5 | 3 | No | $900 to $2000 |
Chicago, Illinois
Historic inn from 1886 furnished with 19th century antiques and artwork; then finsihed with 21st century WiFi and central air conditioning.
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| House | 4 | 4 | No | $800 to $2000 |
Chicago, Illinois
A newly decorated bed and breakfast located conviently on Chicago's North Side.
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| B&B | 5 | 5 | No | $99 to $179 |
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.
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| B&B | 2 | 1 | Yes | $1575 to $2800 |
Chicago, Illinois
In Chicago's Lincoln Park neighborhood, China Doll Country offers three complete self-contained apartment suites with private entrances. Unlike a Bed and Breakfast, there are no shared facilities.
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| B&B | 2 | 1 | Yes | $1365 to $2275 |
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¡¯re at hom...
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| House | 3 | 3 | Yes | $2625 to $3115 |
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...
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| House | 3 | 3 | No | $1500 to $2100 |
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...
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| Condo | 1 | 1 | No | $1250 to $1400 |
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...
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| Apartment | 1 | 1 | No | $1250 to $1500 |
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 ...
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| Condo | 1 | 1 | No | $1354 to $1500 |
Chicago, Illinois
Beautiful Victorian in the heart of Lincoln Park, one of Chicago's most desirable neighborhoods. Close to Park, cafes & restaurants and DePaul University. Hardwood floors, rehabbed condominium.
Features 3 "independen...
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| Apartment | 3 | 1 | No | $1200 to $1750 |
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
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| House | 5 | 2 | Yes | $1600 to $2100 |
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...
| Type: | Bedrooms | Bathrooms | Pet Friendly | Weekly Rate |
|---|---|---|---|---|
| B&B | 3 | 2 | No | $99 to $179 |
Learn More About Chicago
Chicago has a lot to offer all visitors to the area. 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!'