Vacation Rentals in Chicago, Illinois

50 Properties Available

Perfect Spot for Unwinding! 4 Classy Units, Lake View, Pool, Pet-friendly Private vacation home
Perfect Spot for Unwinding! 4 Classy Units, Lake View, Pool, Pet-friendly
$3858 / night
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Vintage Chicago Gem: The Rockwell Retreat\n Apartment
Vintage Chicago Gem: The Rockwell Retreat\n
$3482 / night
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2 Connecting Suites at a 5? Hotel Private vacation home
2 Connecting Suites at a 5? Hotel
$3040 / night
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:: The Wolcott :: Modern Elegance at Its Finest Private vacation home
:: The Wolcott :: Modern Elegance at Its Finest
$2981 / night
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LUX Dtown Penthouses 9bd/9ba Sleep 25+Parking Apartment
LUX Dtown Penthouses 9bd/9ba Sleep 25+Parking
$2935 / night
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870 bldg - 3 Separate Suites in same building Apartment
870 bldg - 3 Separate Suites in same building
$2933 / night
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Unwind In Our Haven of Tranquility! 3 Lake View Suites, Pool, Pets Allowed Private vacation home
Unwind In Our Haven of Tranquility! 3 Lake View Suites, Pool, Pets Allowed
$2891 / night
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Perfect 5-bedroom estate in vibrant Chicago. Private vacation home
Perfect 5-bedroom estate in vibrant Chicago.
$2420 / night
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Luxury Lincoln Park Gem with Gourmet Kitchen & City Views Apartment
Luxury Lincoln Park Gem with Gourmet Kitchen & City Views
$2108 / night
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Unwind & Indulge In Our Oasis! 4 Relaxing Units, Rooftop Pool, Pets Allowed Private vacation home
Unwind & Indulge In Our Oasis! 4 Relaxing Units, Rooftop Pool, Pets Allowed
$2081 / night
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Spacious family size home with indoor pool Private vacation home
Spacious family size home with indoor pool
$2000 / night
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A Place To Unwind, Unplug, & Recharge! 2 Convenient Units Near Oak Street Beach Private vacation home
A Place To Unwind, Unplug, & Recharge! 2 Convenient Units Near Oak Street Beach
$1927 / night
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A Place To Reconnect! 4 Convenient Units, Rooftop Pool, Near Oak Street Beach Private vacation home
A Place To Reconnect! 4 Convenient Units, Rooftop Pool, Near Oak Street Beach
$1920 / night
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Downtown Mich Ave - 6 Penthouses, Sleep 25 Condo
Downtown Mich Ave - 6 Penthouses, Sleep 25
$1876 / night
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Spacious Penthouse Trio + Skyline Views for Groups Apartment
Spacious Penthouse Trio + Skyline Views for Groups
$1721 / night
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2 Connecting Suites at a 4.5? Hotel Hotel
2 Connecting Suites at a 4.5? Hotel
$1660 / night
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The Orleans - Floor 2 Private roof deck Patio! Apartment
The Orleans - Floor 2 Private roof deck Patio!
$1603 / night
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Escape To A World of Refined Indulgence! 3 Relaxing Units, Pool, Pets Allowed Private vacation home
Escape To A World of Refined Indulgence! 3 Relaxing Units, Pool, Pets Allowed
$1552 / night
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The Orleans Floor 3 Private rooftop deck! Apartment
The Orleans Floor 3 Private rooftop deck!
$1449 / night
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Unique Luxury Fulton Market Penthouse - Sleeps 32 Apartment
Unique Luxury Fulton Market Penthouse - Sleeps 32
$1413 / night
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Sophisticated Urban Escape, 4 Cozy Units, Near Water Tower Chicago! Private vacation home
Sophisticated Urban Escape, 4 Cozy Units, Near Water Tower Chicago!
$1399 / night
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Downtown Penthouse 5bd VIEWS | Parking, Gym Apartment
Downtown Penthouse 5bd VIEWS | Parking, Gym
$1367 / night
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DTown Penthouse - 4bd\/4ba +Parking, Gym, Pool, Gym, Private Patio Condo
DTown Penthouse - 4bd\/4ba +Parking, Gym, Pool, Gym, Private Patio
$1356 / night
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McCormick Place luxurious 5 bed\/3 bath HUGE Suite for groups Apartment
McCormick Place luxurious 5 bed\/3 bath HUGE Suite for groups
$1349 / night
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Luxury Loft Collection COMBO 901/902 | Terrace Apartment
Luxury Loft Collection COMBO 901/902 | Terrace
$1345 / night
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Your Tranquil Oasis! 3 Comfortable Units, Pet-friendly Property w\/ Rooftop Pool Private vacation home
Your Tranquil Oasis! 3 Comfortable Units, Pet-friendly Property w\/ Rooftop Pool
$1338 / night
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McCormick Place luxurious 5 bed\/3 bath HUGE Suite for groups Apartment
McCormick Place luxurious 5 bed\/3 bath HUGE Suite for groups
$1313 / night
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Sonder Onterie | Three-Bedroom Apartment Apartment
Sonder Onterie | Three-Bedroom Apartment
$1282 / night
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McCormick Place Luxurious 5 bed\/3 bath HUGE Suite for groups Apartment
McCormick Place Luxurious 5 bed\/3 bath HUGE Suite for groups
$1277 / night
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Whole house in Boystown Private vacation home
Whole house in Boystown
$1249 / night
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Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago Apart-hotel
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
$1238 / night
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Grand 5,500 sq ft Pilsen home, 5BR, sleeps 11, near downtown Private vacation home
Grand 5,500 sq ft Pilsen home, 5BR, sleeps 11, near downtown
$1234 / night
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ENTIRE BUILDING-Walk to Lincoln Park or The Beach! Private vacation home
ENTIRE BUILDING-Walk to Lincoln Park or The Beach!
$1233 / night
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3 Tranquil Eco-friendly Rooms, Stylish Decor, Near River North Hotspots Private vacation home
3 Tranquil Eco-friendly Rooms, Stylish Decor, Near River North Hotspots
$1189 / night
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\"Holy Cow\"! 4bed 4bath Duplex Penthouse w\/ 3,000 sqft Private Roof-Deck! Apartment
\"Holy Cow\"! 4bed 4bath Duplex Penthouse w\/ 3,000 sqft Private Roof-Deck!
$1182 / night
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Luxurious McCormick Place 6 bed\/3 bath Suite for groups with optional parking Apartment
Luxurious McCormick Place 6 bed\/3 bath Suite for groups with optional parking
$1148 / night
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Steps to Fulton Market Downtown 4 bedroom Entire Home Sleeps 11 with City Views Private vacation home
Steps to Fulton Market Downtown 4 bedroom Entire Home Sleeps 11 with City Views
$1134 / night
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Central Chic: 3 Plush Units, Near Chicago Museum of Contemporary Art! Private vacation home
Central Chic: 3 Plush Units, Near Chicago Museum of Contemporary Art!
$1050 / night
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Haven in The Heart of Chicago! 2 Relaxing Units, Rooftop Pool, Pets Allowed Private vacation home
Haven in The Heart of Chicago! 2 Relaxing Units, Rooftop Pool, Pets Allowed
$1036 / night
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Stylish Wicker Park Home with Garage Private vacation home
Stylish Wicker Park Home with Garage
$1034 / night
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Prime location Historic Chicago Townhouse Private vacation home
Prime location Historic Chicago Townhouse
$1016 / night
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2 Connecting Suites at a 4? Hotel Private vacation home
2 Connecting Suites at a 4? Hotel
$1015 / night
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Lovely 4 Bedroom Spot located in Charming Old Town Apartment
Lovely 4 Bedroom Spot located in Charming Old Town
$1012 / night
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A Place You'll Surely Enjoy! Terrace, Pet-friendly Property w\/ Rooftop Pool Private vacation home
A Place You'll Surely Enjoy! Terrace, Pet-friendly Property w\/ Rooftop Pool
$1009 / night
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Gold Coast Pristine 5BR - 3.5BA - Patio - Parking Private vacation home
Gold Coast Pristine 5BR - 3.5BA - Patio - Parking
$986 / night
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Best Place to Unwind! Lake View, Rooftop Pool, Pet-friendly Property Private vacation home
Best Place to Unwind! Lake View, Rooftop Pool, Pet-friendly Property
$964 / night
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53\/54th Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Balcony Apart-hotel
53\/54th Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Balcony
$956 / night
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Lincoln Park Mega Space 2 Parking Spaces Sleeps 20 by AllSet Turnover Condo
Lincoln Park Mega Space 2 Parking Spaces Sleeps 20 by AllSet Turnover
$929 / night
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Your Unforgettable Stay Awaits! City View, Rooftop Pool, Near Oak Street Beach Private vacation home
Your Unforgettable Stay Awaits! City View, Rooftop Pool, Near Oak Street Beach
$924 / night
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Indulge In Contemporary Comfort! 2 Family-friendly Units, Rooftop Pool Private vacation home
Indulge In Contemporary Comfort! 2 Family-friendly Units, Rooftop Pool
$918 / night
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