Chicago, Illinois Vacation Rentals
Found 59 Vacation Homes by Owner in Chicago, Illinois. Click on a property below to fill out an inquiry to book a Chicago, Illinois Villa, Apartment or Condo.
The average price for a rental in Chicago, Illinois listed on VILLASPY is 303 USD per night. The lowest price for a vacation rental in Chicago, Illinois is 100 USD per night, and the highest price we found for a Chicago, Illinois villa is 849 USD per night.
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3br - Beautiful Chicago Vacation Condo
Price: 190 USD per Night
Listing ID: 17->United States->Illinois->Chicagoland->Chicago
beautiful 3 bed, 2 bath condo with hardwood floors throughout, granite counters, 42" custom cabinetry, stainless steel appliances, crown molding, mable baths, glass vessel sinks, exposed brick, front balcony, and more! one parking space included.family...More
2br - Beautiful Getaway Vacation Condo
Price: 130 USD per Night
Listing ID: 21->United States->Illinois->Chicagoland->Chicago
stylish and affordable at the same time. this is what you will find in this beautifully furnished 2 bedroom/2bath vacation condo near lake michigan. this condo is all brand new. it has 2 queen beds, 2 full baths with shower and jacuzzi tub. kitchen has...More
3br - Rent a luxurious Condo in Chicago!
Price: 185 USD per Night
Listing ID: 30->United States->Illinois->Chicagoland->Chicago
rent a luxurious condo! gorgeous three story building with all the elegant charm. you are guaranteed that you will not regret this visit. this place has: great deck, cherry hardwood floors, jacuzzi tub , granite counter tops, stainless steel appliances,...More
4br - Aug. Special: Make Offer!! 4BR- Luxurious Home
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Listing ID: 51->United States->Illinois->Chicagoland->Chicago
sleek, new home.... features include: italian cabinetry and faucets, professional grade stainless steel apps, thick granite, exotic hardwood throughout, custom floating staircases, extensive use of imported tiles and mosaics, designer faux paint...More
5br - Beautiful Classic Brownstone Home- Northside
Price: 479 USD per Night
Listing ID: 64->United States->Illinois->Chicagoland->Chicago
enjoy this newly completed high- end renovation of a classic brownstone home with 5 spacious bedrooms, 3 full baths and home theater equipped living rooms. this beautiful home is located on a quiet, tree lined street on the northside of chicago. located...More
6br - Furnished apartments or individual guestrooms in
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Listing ID: 449->United States->Illinois->Chicagoland->Chicago
choose from complete apartments in an 1891 home or individual guestrooms in an 1886 mansion, both in the heart of downtown chicago's most upscale neighborhood. many city attractions right out our doors and we're one or two blocks from transportation...More
1br - 55th Floor 1 Bedroom Penthouse - Chicago Luxury
Price: 235 USD per Night
Listing ID: 721->United States->Illinois->Chicagoland->Chicago
this stylish, completely renovated condominium offers spectacular views from the 55th floor of the chicago skyline and lakeshore. it contains one bedroom with queen beds plus queen sized sleeper sofa in the living room , one full bath, and can comfortably...More
4br - The Biddle House - Located In Historic Old Town
Price: 225 USD per Night
Listing ID: 911->United States->Illinois->Chicagoland->Chicago
there are two fully furnished apartments available at the biddle house. each has two bedrooms, one bathroom, a fully equipped kitchen, dining room and living room. continental breakfast fixings are provided. the apartments include the following amenities...More
10br - Spacious meets Luxury & Location
Price: 600 USD per Night
Listing ID: 1767->United States->Illinois->Chicagoland->Chicago
treat your self to this brand new rental! finally a place that can accommodate large groups, while offering modern luxury. if you like nothing but the best, here it is. youre right in lincoln park so close to lake michigan, the zoo, just south of...More
1br - Sp Suites - near Michigan Ave. BEST LOCATION !!!
Price: 100 USD per Night
Listing ID: 1857->United States->Illinois->Chicagoland->Chicago
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 glorious lincoln park greenery and...More
2br - Millennium Park 2 bedrooms, 2 baths, near Michigan
Price: 220 USD per Night
Listing ID: 1858->United States->Illinois->Chicagoland->Chicago
these vacation rentals are situated in the new east side, chicagos newest neighborhood, a prime area of downtown chicago. cutting edge architecture, designer shopping boutiques, world renowned restaurants, and a nightlife second to none make the...More
2br - Aug Special: Make Offer! 2BR Walk to Mag Mile!
Price: 399 USD per Night
Listing ID: 1985->United States->Illinois->Chicagoland->Chicago
beautiful, 2 bdrm, 2 bath, condo with 10 ft floor to ceiling windows and a balcony with views of the city and the lake. complete with brazilian cherry hardwood floors, bosch appliances, washer/dryer in unit, and huge closets. includes indoor pool,...More
6br - Aug. Special:Make Offer! 6BR in Lincoln Park #245
Price: 849 USD per Night
Listing ID: 2056->United States->Illinois->Chicagoland->Chicago
this new 6- bedroom will blow you away. the interior is decked with contemporary and traditional finishes. the location is by far the best asset. steps from lincoln park's finest shopping & restaurants! this home is definitely a must- see!*exclusions:...More
3br - Aug. Special:Make Offer! 3BR Duplex Downtown #338
Price: 449 USD per Night
Listing ID: 2057->United States->Illinois->Chicagoland->Chicago
top floor duplex penthouse with spectular views of the city. river and park. 3200sqft of pure luxury w/top of the line kitchen, great room & seperate dining room. automation system throughout, custom built- ins and beautiful custom wet bar. top floor...More
2br - Aug. Special: Make Offer! 2BR Amazing Condo
Price: 259 USD per Night
Listing ID: 2062->United States->Illinois->Chicagoland->Chicago
featuring a modern contemporary feel, the chicago apartments offers dramatic finishes including tiled entries, granite islands and cherry cabinetry, with captivating views from the floor- to- ceiling windows, balconies and bay windows. amenities abound...More
2br - 2BR/2BA FURNISHED DOWNTOWN CONDO
Price: 189 USD per Night
Listing ID: 2109->United States->Illinois->Chicagoland->Chicago
42th floor, overlooking city, lake michigan and the chicago river. fully furnished 2 bedroom/2 bath. building amenities include work- out room, swimming pool, hot tub, parking, dry cleaners on- site, food market on- site. ...More
3br - Huge 4 Floor 2000 sq ft Chicago Luxury Townhouse
Price: 249 USD per Night
Listing ID: 2110->United States->Illinois->Chicagoland->Chicago
chicago's bed & breakfast and hotel alternative:this large 2000 sq ft property features amazing chicago skyline views on a private rooftop deck. the 1st floor has an attached garage and den with a large pull out sofa, complete home office and bathroom....More
2br - Aug. Special:Make Offer! Condo on Mag Mile #352
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Listing ID: 2199->United States->Illinois->Chicagoland->Chicago
2br + den(1 king, 1 queen and murphy bed) located 2 blocks from shopping and restaurants. walking distance to all downtown attractions. ...More
4br - Aug.Special: Make Offer!Casa Bella 4 BR Luxurious
Price: 399 USD per Night
Listing ID: 2257->United States->Illinois->Chicagoland->Chicago
see chicago like a star! oversized 4 bedroom home. this home has it all... hardwood floors, premium stainless appliances, master bath whirlpool, steam shower with body jets, rooftop garage deck, and more. in addition to vacationing luxuriously...More
2br - Aug. Special: Make Offer! Urban Loft 2BR+ Den #349
Price: 514 USD per Night
Listing ID: 2319->United States->Illinois->Chicagoland->Chicago
gorgeous, modern, and spacious are just a few words that best descibe this 2br with den in chicago's beautiful streeterville! (den includes queen sized bed) ...More
1br - Gorgeous 1BR - Condo Mag Mile #246
Price: 199 USD per Night
Listing ID: 2329->United States->Illinois->Chicagoland->Chicago
this gorgeous 1 bedroom has charm written all over it. located in the heart of chicago this beautifully furnished condo is determined to impress. the neighborhood alone offers a striking cityscape that sweeps from the john hancock center to navy pier....More
4br - Aug. Special:Make Offer! 5BR Downtown Mansion #371
Price: 1 USD per Night
Listing ID: 2596->United States->Illinois->Chicagoland->Chicago
gorgeous design single family on a double wide lot provides the perfect urban home! exquisite attention to detail is evident throughout this sun- splashed home extra wide entertainment & living space: fabulous custom eat- in kitchen has too many details...More
2br - Writers' Retreat Homey in Lakeview/Wrigleyville
Price: 150 USD per Night
Listing ID: 2706->United States->Illinois->Chicagoland->Chicago
writers' retreat is an immaculate two bedroom apartment less than a mile from wrigley field, home of the chicago cubs. located in a charming four unit building in a quiet, historic, residential chicago neighborhood. it is just down the street from...More
2br - Aug. Special: Make Offer! Sleek 2BR Downtown #283
Price: 279 USD per Night
Listing ID: 2806->United States->Illinois->Chicagoland->Chicago
this 2 bedroom modern condo has style and sleek written all over it - from the exterior to the interior! located in downtown chicago, this condo is equipped with the finest and rarest kitchen appliances and cabinetry. it is located downtown and is within...More
4br - Aug. Special: Make Offer! 4BR Downtown Home #142
Price: 499 USD per Night
Listing ID: 2807->United States->Illinois->Chicagoland->Chicago
fantastic contemporary home with a 2+ attached garage & fenced yard in a fantastic location. smart wiring throughout. gourmet kitchen with bosch & fisher paykel appliances. wall of windows with se exposure allows natural light & exceptional skyline views,...More
3br - Great Deal near Downtown & McCormick Place
Price: 130 USD per Night
Listing ID: 2899->United States->Illinois->Chicagoland->Chicago
close to downtown & mccormick place. 15 min by car or cab or 2- 3 train stops from everything that chicago has to offer.this is an amazing rental at a great price. we have two comfortable and convenient apartments with many luxurious features that...More
1br - Beautiful Executive APT.
Price: 150 USD per Night
Listing ID: 3170->United States->Illinois->Chicagoland->Chicago
thank you for your interest in our vacation condo in chicago. our apartment is very close to the lake and wrigley field, in a secure building and is well maintained. new kitchen and bathroom: hardwood floors throughout. easy transportation by taxi,...More
5br - Rent a Mansion in Chicago!
Price: 550 USD per Night
Listing ID: 3249->United States->Illinois->Chicagoland->Chicago
rent a mansion in wrigleyville! gorgeous four story home with all the elegant charm imaginable. you are guaranteed to not regret this visit. you name it, this place has it! great decks, party basement, a sun room, steam room, 4 fireplaces and more!...More
2br - Stylish, Hip & Nicely Decorated - STUDIOS
Price: 120 USD per Night
Listing ID: 3797->United States->Illinois->Chicagoland->Chicago
this is a 2 bedroom, 2 bathrooms, vintage building that has been rehabbed. this chicago vacation rental apartment is located on kedzie blvd in chicago, near the blue line. the apartment has washer/dryer in unit, stainless steal appliance, granite...More
1br - Large Executive Studio( Wrigley Field)
Price: 100 USD per Night
Listing ID: 4171->United States->Illinois->Chicagoland->Chicago
the property in our garden apartment has been fully remodeled and was recently converted into two units separated by a door with a double- sided lock for privacy:the unit has a private entrance accessed off the street.there is a full kitchen with...More
2br - Aug. Special: Make offer! 2BR Fulton River #178
Price: 199 USD per Night
Listing ID: 4236->United States->Illinois->Chicagoland->Chicago
step outside and you'll find yourself in chicago's hottest emerging neighborhoodthe trendy fulton river district embracing 10 square blocks bounded by the chicago river and the city's wholesale markets. in the mood for eclectic, five- star dining?...More
1br - Downtown condo above Chicago River - Gorgeous View
Price: 125 USD per Night
Listing ID: 4494->United States->Illinois->Chicagoland->Chicago
the riverview suite features:- 1 bedroom & 1 bath (sleeps 2~5 guests), kitchen, living room, make up area.- breathtaking views to chicago river, sears tower, and city view.- rooftop sun deck and barbeque is available for guests (two floors...More
2br - China Doll Guest House
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Listing ID: 4831->United States->Illinois->Chicagoland->Chicago
in chicago's lincoln park neighborhood, china doll offers complete self- contained apartment suites with private entrances. unlike a bed & breakfast, there are no shared facilities.china doll owns 3 buildings with a total of 6 apartments plus a...More
4br - August Special: Make Offer! Luxor Chalet 4BR #10
Price: 399 USD per Night
Listing ID: 4927->United States->Illinois->Chicagoland->Chicago
this property is within minutes to downtown chicago and lies next to all major highway intersections. it is situated next to the white sox stadium (u.s. cellular field). it contains all amenities, including direct tv with all movie channels, free wi-...More
2br - This penthouse puts you in the heart of it all!
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Listing ID: 5024->United States->Illinois->Chicagoland->Chicago
these units have recently been renovated and includes hard wood floors, granite countertops, stainless steel appliances and georgus marble bathrooms. the high rise is just steps from michigan avenue and will sleep up to 6 people. restaurants, cafes,...More
2br - 2bd/2ba Location! Location! Navy Pier Mag Mile!
Price: 200 USD per Night
Listing ID: 5089->United States->Illinois->Chicagoland->Chicago
**location **location **location! ***can't beat it! ***views views views! breathtaking lake and city views!!*** looks like hawii up there!***set in the heart of downtown chicago, our chicago apt is ideally placed for visitors to experience all...More
2br - The Villa Verdone - 2 Bedroom - Magnificent Mile
Price: 300 USD per Night
Listing ID: 5561->United States->Illinois->Chicagoland->Chicago
in the magnificent gold coast neighborhood of chicago is this stunning 1890s vintage georgian, only 1/2 block from oak beach, chicagos premier restaurants and nightlife on rush street and one block to the fabulous magnificent mile. situated...More
2br - Downtown Rooftop Penthouse+2Decks
Price: 195 USD per Night
Listing ID: 5757->United States->Illinois->Chicagoland->Chicago
the penthouse features:- 2 bedrooms & 2.5 bath (sleeps 2~7 guests), 1400 sf living space & 800 sf rooftop decks- two spacious decks w/ views to city, lake and garden.- master suite features walk- in closet, office area and its own private deck-...More
6br - Aug. Special: Make Offer!6BR Wrigley Mansion #138
Price: 1 USD per Night
Listing ID: 5866->United States->Illinois->Chicagoland->Chicago
whether you are looking for luxury, comfort, or just sheer quality - you will get it all from this beautifully furnished 6 bedroom home. boasting a space of 7, 000 sq. feet, it gets even better with the details: chef's kitchen with british aga stove...More
3br - Serene Setting, Urban Location near lake/downtown
Price: 175 USD per Night
Listing ID: 5893->United States->Illinois->Chicagoland->Chicago
we have 2 great options - tasteful and fully furnished three bedroom and two bedroom condos in chicago's desired edgewater neighborhood with parking included. bright, with understated elegance. both sun- filled apartments feature low voc paint, hardwood...More
7br - Aug. Special: Make Offer! 7BR In Lincoln Park #275
Price: 849 USD per Night
Listing ID: 5965->United States->Illinois->Chicagoland->Chicago
*exclusions: elite chicago rentals reserves the right to change prices without notice. promotional prices are valid between october 1, 2009 through march 31, 2010 and exclude heavily traveled weeks (ie. thanksgiving, christmas & new years, high...More
4br - Aug. Special: Make Offer!Bershire Manor-4 BR Home
Price: 749 USD per Night
Listing ID: 6017->United States->Illinois->Chicagoland->Chicago
amazing 4br home less than 1.5 miles from shopping on mag mile. close to the l train and expressway. amenities throughout the home, pool table, family room, modern kitchenoutdoor deck and yard. ...More
3br - Aug. Special: Make Offer!3BR In Wrigley Field #187
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Listing ID: 6242->United States->Illinois->Chicagoland->Chicago
this is an amazing graystone home in historic wrigley neighborhood. the house has been completely revamped to meet all the contemporary standards of today. aside from its spacious attribute, the house is decked with beautiful hardwood floors, new appliances...More
2br - Aug. Special: Make Offer!2BR Incredible Views #228
Price: 259 USD per Night
Listing ID: 6329->United States->Illinois->Chicagoland->Chicago
beautifully designed and furnished 2 bedroom 2 bath located on michigan avenue. this high rise condominium is next to several world- class restaurants. the list and variety of electric, upscale restaurants and stores is immense! numerous designer boutiques...More
2br - Beautiful Furnished Condo
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Listing ID: 6379->United States->Illinois->Chicagoland->Chicago
corporate rental or vacation condo beautiful furnished lake michigan view, condo 1st bedroom with queen size bed, 2nd bedroom has a pull- out sofa which sleep 2 and 2 bathrooms. great location: 1 block from navy pier, millennium park, and michigan...More
3br - 3bd/2.5ba **W**O**W** Heart of Downtown**Stunning
Price: 250 USD per Night
Listing ID: 6638->United States->Illinois->Chicagoland->Chicago
walk to everything downtown! enjoy stunning views of the city skyline and grant park! one of few 3bd/2.5ba units right in the middle of downtown chicago. very affordable! ***walk to everything***yes, these are the views!***breathtaking...More
1br - Millennium Park Furnished Residences
Price: 145 USD per Night
Listing ID: 7034->United States->Illinois->Chicagoland->Chicago
these vacation rentals are located in the new east side, a mixed- use neighborhood east of michigan avenue that includes apartments, homes, businesses and retailers surrounded by magnificent parks that are framed by the chicago river to the north, ...More
3br - Corporate or Vacation Rental
Price: 169 USD per Night
Listing ID: 7054->United States->Illinois->Chicagoland->Chicago
features 3 "independent" self catering units in the same building with fully functional kitchens. coffee, tea, snacks, toiletries and all linen provided.unit 1 - high 1st floor:3 bedrooms with a king size bed in master bedroom, 2 twin beds in...More
3br - The Maud House Of Lincoln Park - DePaul/3 Bedroom
Price: 165 USD per Night
Listing ID: 7191->United States->Illinois->Chicagoland->Chicago
located in the heart of lincoln park, the maud house offers the warmth of a classic bed and breakfast, in an ideal location for visits to depaul university, the magnificent mile, wrigley field and all the attractions that the city of chicago has to...More
4br - Teri's Chicago Guest Houses * Wrigleyville*
Price: 399 USD per Night
Listing ID: 8084->United States->Illinois->Chicagoland->Chicago
chicago guest house on lakewood avenue1 stately graystone with 3 separate apartments*1st fl wrigley suite 4bdrm/ 2bth (featured)*2nd fl shoreline suite 3bdrm / 2bth*3rd fl lakeview suite 3bdrm / 2bathsavor the warmth and charm of our historic...More
More Listings in Chicagoland, Illinois
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3br - THE CONVENIENCE OF HOME AWAY FROM HOME.
Price: 200 USD per Night
Listing ID: 8232->United States->Illinois->Chicagoland->Chicago
this beautiful, spacious third floor walk- up, 3 bedroom, 1 bathroom accomodation is conveniently located walking distance from restaurants, shopping, transportation, night life, the beach, chicago museum, churches, lincoln park zoo, the chicago...More
4br - Downtown Mansion - Rent one room or the whole inn!
Price: 150 USD per Night
Listing ID: 8343->United States->Illinois->Chicagoland->Chicago
the hansen house mansion was designed in 1886 by a prominent architect, harald m. hansen for his own family, and it now a historically significent building, as it has all its original victorian detail - - giannini and hilgart stained glass windows,...More
2br - Great Deal near Downtown & McCormick Place
Price: 130 USD per Night
Listing ID: 9008->United States->Illinois->Chicagoland->Chicago
close to downtown & mccormick place. 15 min by car or cab or 2- 3 train stops from everything that chicago has to offer.this apartment has two bedrooms that each have queen beds and there is a jennifer brand sleeper sofa in the living room that is...More
3br - Relax in an Affordable, Clean & Attractive Space!
Price: 130 USD per Night
Listing ID: 9114->United States->Illinois->Chicagoland->Chicago
surburban park forest - furnished 3bed & 1bth stainless refrigerator, stove & wall ovenhardwood floors, central air, fenced yard & deck.parking included ...More
2br - Convenient, Comfy Home Away from Home
Price: 140 USD per Night
Listing ID: 9917->United States->Illinois->Chicagoland->Chicago
irving loft is a two bedroom upper apartment situated in a convenient location for both car and public transportation, very accessible to and from o'hare, michigan avenue, the loop and lake shore attractions. irving loft is close to major streets and...More
1br - City style fully furnished condo in historic bldg
Price: 169 USD per Night
Listing ID: 9939->United States->Illinois->Chicagoland->Chicago
newly built fully furnished loft style condo located just one block north of mccromick place convention center in downtown chicago! one block from the wheeler mansion, the glessner house and clarke house museum.new historic condo is ideal for conventioneers...More
4br - Spacious 4 Bedroom In The Heart Of Lincoln Park
Price: 275 USD per Night
Listing ID: 10021->United States->Illinois->Chicagoland->Chicago
this stylish 3rd floor, four bedroom apartment has one king size bed and three queen size beds, one full bathroom and a second shower and sink in one of the bedrooms. it makes a wonderful choice for larger parties needing space for up to 8 guests (and...More
4br - Beautiful 4 Bedroom Vacation House
Price: 400 USD per Night
Listing ID: 11446->United States->Illinois->Chicagoland->Chicago
coming to chicago with the family and want to feel safe? our north side / northwest side vacation rentals location is the safest place to stay! from the moment you arrive you'll feel at home... no hustle and bustle or hassle here, located in a neighborhood...More
1br - Penthouse Views! - Edgewater Condo Rentals
Price: 150 USD per Night
Listing ID: 11263->United States->Illinois->Chicagoland->Chicago
do you want to visit chicago? you can rent furnished luxury condos with penthouse views of downtown chicago and the lake from the 48th floors and higher. choose between a lovely studio on the 48th floor facing city and lake, or a breathtaking 1 bedroom...More