Cook Area Rentals
From $437 per night (USD)VRBO
Bright & Modern 3BR/1BA in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Prime Logan Square Locale! Steps away from premier restaurants, cafes, the square, and abundant entertainment options. C ...
From $437 per night (USD)VRBO
From $203 per night (USD)VRBO
Explore the City: Sleek 2BR Gem in North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the historic charm of North Side Chicago at our cozy residence. Tucked away in a quiet neighborhood with tree-l ...
From $203 per night (USD)VRBO
From $427 per night (USD)VRBO
Chic Studio with WiFi and AC in Beautiful Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Greatly situated in Logan Square! Just a stone's throw away from excellent restaurants, cafes, the square itself, and an ...
From $427 per night (USD)VRBO
From $685 per night (USD)Expedia
Spacious 4-bedroom Apartment In Lakeview Near Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
About this property Spacious Accommodations: Chic & Cozy 4BR Apt In Lakeview Near Wrigley Field offers a spacious apartm ...
From $685 per night (USD)Expedia
From $392 per night (USD)VRBO
Spacious 4BR Home. Your Cozy Home Away from Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Spacious & Stylish 4-Bedroom Retreat | Perfect for Families & Groups Welcome to your perfect Chicago getaway! This bea ...
From $392 per night (USD)VRBO
From $162 per night (USD)Expedia
Clean Safe Chicago Basement Apartment Washer Dryer Near Transit to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
A Chic & Tranquil Gem! Escape the hustle and bustle in our modern and serene basement apartment. This beautifully design ...
From $162 per night (USD)Expedia
From $2611 per night (USD)VRBO
Modern- Smart Home in Wicker Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come enjoy and relax in this calm, modern, stylish space located in Wicker Park. This plant filled oasis in the city i ...
From $2611 per night (USD)VRBO
From $122 per night (USD)Expedia
1 Mi to Garfield Park Conservatory: Modern Apt!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Dedicated Workspace | 6 Mi to Downtown Chicago Get ready to explore top Chicago attractions when you retreat to this br ...
From $122 per night (USD)Expedia
From $138 per night (USD)VRBO
Vintage 1-br apartment with AC, WiFi in charming, safe, quiet Berwyn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy the quiet and safety of Berwyn, IL, in a Mid-Century-styled, PRIVATE 1-bedroom apt in a classic, brick, 1929 2-fla ...
From $138 per night (USD)VRBO
From $182 per night (USD)Expedia
Modern 3BR/2BA Retreat with Deck, Grill, and 2GB Speed WiFi in Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Visiting Chicago for work, a game or a concert? Reside at this stylish sanctuary in Albany Park to complete your experie ...
From $182 per night (USD)Expedia
From $174 per night (USD)VRBO
Peaceful One Bedroom Home near Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: This peaceful one-bedroom home in Forest Park, IL, offers a serene retreat with convenient access to Chicago. L ...
From $174 per night (USD)VRBO
From $211 per night (USD)Expedia
Stylish 4BR/2BA Apartment with Office, Deck, Grill, and 2GB WiFi in Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Visiting Chicago for work, a game or a concert? Reside at this stylish sanctuary in Albany Park to complete your experie ...
From $211 per night (USD)Expedia
From $612 per night (USD)VRBO
Stylish 3BR Apt Near Wrigley Field & Lincoln Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in Chicago at this superb apartment. With 3 bedrooms including 1 full bed and 2 queen beds, thi ...
From $612 per night (USD)VRBO
From $325 per night (USD)VRBO
Spacious 2BR Family-Friendly Stay, 4 Queen Beds + 2 Baths, Parking & Laundry.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Relax and unwind in this cozy Evanston retreat. This spacious 2-bedroom apartment features 4 queen beds (2 in each room) ...
From $325 per night (USD)VRBO
From $1052 per night (USD)VRBO
7BR Apartment City Escape Near Cubs + Laundry Ready
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 16
Lakeview blends charm, excitement, and history—perfect for baseball fans and city lovers alike. Wrigley Field, home of t ...
From $1052 per night (USD)VRBO
From $167 per night (USD)Expedia
Cozy studio in Andersonville Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This newly constructed studio offers a stylish, modern space just steps from Clark Street—home to some of the best resta ...
From $167 per night (USD)Expedia
From $124 per night (USD)VRBO
Modern Condo - Lux Upgraded Unit - No Pet Fees!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kick back and relax in this beautifully designed, top 1% reviewed 1-bedroom condo. This open-floor-plan Owner’s Unit off ...
From $124 per night (USD)VRBO
From $187 per night (USD)VRBO
Amazing Location 3BR Gem in Logan Square w Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Prime location in Logan Square! Steps away from numerous top-tier restaurants, cafes, the square itself, and a plethora ...
From $187 per night (USD)VRBO
From $119 per night (USD)VRBO
Charming 2-bed Garden condo in beautiful Chicago + WiFi, AC, & private parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Your cozy getaway awaits in Chicago at this enchanting condo. With 2 welcoming bedrooms featuring queen beds and 2 seren ...
From $119 per night (USD)VRBO
From $526 per night (USD)VRBO
Best Place to Unwind! 2 Family and Dog Friendly Units! Walk to Millennium Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $526 per night (USD)VRBO
From $665 per night (USD)VRBO
Relax & Explore! 3 King Units, Steps from Riverfront, Pet-Friendly Property!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $665 per night (USD)VRBO
From $1052 per night (USD)VRBO
Four Cozy Queen Rooms! Perfect for Family & Friends, Pets Are Welcome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $1052 per night (USD)VRBO
From $789 per night (USD)VRBO
3 Comfortable Units! Pet-friendly Property! Near Riverwalk & Chicago Attractions
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $789 per night (USD)VRBO
From $443 per night (USD)VRBO
Look No Further! 2 Stylish King Units! Pet-Friendly, Walk to Riverwalk & Dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Guests will find an array of attractions within easy reach of the hotel’s convenient location. Visit the iconic Magnific ...
From $443 per night (USD)VRBO
From $437 per night (USD)VRBO
McCormick Cozy 3Bedroom with Optional Parking for 8 guests
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
• MESSAGE US for SPECIAL RATES • State street location • Minutes walk to McCormick Convention Center • 4K Roku HDTVs in ...
From $437 per night (USD)VRBO
From $207 per night (USD)Expedia
NEW Private West Loop 1br with Backyard near Green Line and CTA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This place is a true hidden gem. I’ve lived in Chicago for over two decades and travel often, so when I designed this sp ...
From $207 per night (USD)Expedia
From $258 per night (USD)VRBO
NEW! Vintage 3 Bed Condo in Chicagolands Trendy Berwyn by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this lovely three-bedroom hidden gem in Berwyn, just minutes away from Chicago and everything the city has to ...
From $258 per night (USD)VRBO
From $227 per night (USD)Expedia
NEW! 3 Bed Vintage Condo in Chicagolands Trendy Berwyn by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Start your adventures in this lovely three-bedroom hidden gem in Berwyn, just minutes away from Chicago and everything ...
From $227 per night (USD)Expedia
From $194 per night (USD)VRBO
Luxurious 3 Bedroom Apartment in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Your cozy getaway awaits in Chicago at this fabulous house. With 3 bedrooms including 2 queen beds and 1 sofa bed, this ...
From $194 per night (USD)VRBO
From $1307 per night (USD)VRBO
Great Relaxing Overnight Stay! 4 Units with City View, Pets Are Welcome!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1307 per night (USD)VRBO
From $251 per night (USD)VRBO
Serene 3-bedroom apartment in Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to our stunning retreat, perfect for families or friends seeking a stylish getaway. This beautifully designed un ...
From $251 per night (USD)VRBO
From $569 per night (USD)Expedia
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Modern Elegance Meets Historic Charm! Stunning 4-bed, 3.5-bath fully renovated home in the heart of the historic GAP dis ...
From $569 per night (USD)Expedia
From $160 per night (USD)VRBO
2 Mi to Wind Creek Casino: Quaint Homewood Haven
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Dog Friendly w/ Fee | Close to Golf, Dining & Shopping | 30 Mi to Chicago Whether you're visiting loved ones, hitting t ...
From $160 per night (USD)VRBO
From $156 per night (USD)Expedia
Your Perfect Schaumburg Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Have fun with the whole family at this beautifully remodeled home that offers a perfect blend of luxury and convenience. ...
From $156 per night (USD)Expedia
From $163 per night (USD)VRBO
New Listing /20% Discount 32+/ Fast Wi-Fi / 1 Parking Spot!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Highly sought-after North Center / St. Ben's Location -1 Garage Spot INCLUDED!! - Fully furnished unit with everything ...
From $163 per night (USD)VRBO
From $444 per night (USD)Expedia
Ideal Spot Just Minutes from O’Hare Airport | LCP Collection
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience a welcoming blend of comfort and ease in this inviting 3-bedroom getaway, conveniently situated only ...
From $444 per night (USD)Expedia
From $420 per night (USD)VRBO
3-bedroom apartment in Chicago Medical District, 5 mins from United Center
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Chicago at this 3-bedroom apartment. Each bedroom features a cozy queen bed, perfect for a good nigh ...
From $420 per night (USD)VRBO
From $431 per night (USD)Expedia
Spacious 3BR in South Loop Near McCormick - Optional Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The State Suite — a modern, artfully designed 3-bedroom, 2-bath apartment perfect for everyone! Just minutes ...
From $431 per night (USD)Expedia
From $107 per night (USD)VRBO
Charming 2-bedroom apartment in Roscoe Village/Free Washer/Dryer/WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bedroom, 1-bath home in Roscoe Village offers full-size beds in each bedroom, sleek vinyl flooring throughout, fr ...
From $107 per night (USD)VRBO
From $397 per night (USD)Expedia
Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This 5-bedroom bungalow in Berwyn is perfect for your escape to a tranquil setting. With 3 queen beds and 2 futons, gues ...
From $397 per night (USD)Expedia
From $66 per night (USD)VRBO
The Chicago Hotel Collection, Standard Double Queen with City Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $66 per night (USD)VRBO
From $103 per night (USD)VRBO
2 Bedroom Furnished Apartment with W/D Heart of Logan Square by Blueline train
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Home sits on private safe sought-after street block. This fully furnished 2-bedroom 1 bath apartment has a recently reno ...
From $103 per night (USD)VRBO
From $598 per night (USD)VRBO
Luxury Designer Penthouse NW | Pool | Gold Coast
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center o ...
From $598 per night (USD)VRBO
From $308 per night (USD)VRBO
Cozy 3BR with Parking Easy Access Lake Shore Dr
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Discover the hidden gems and welcoming atmosphere of Chicago's West Ridge neighborhood when you stay at this centrally-l ...
From $308 per night (USD)VRBO
From $194 per night (USD)VRBO
Chicago Chic: 2BR-1BA apartment in marvelous Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to your cozy urban retreat nestled in the heart of Chicago's vibrant near West Side. This charming 2-bedroom, 1- ...
From $194 per night (USD)VRBO
From $157 per night (USD)Expedia
Blueground | Greektown, bbq, gym, nr Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $157 per night (USD)Expedia
From $150 per night (USD)VRBO
Blueground | Greektown, bbq, gym, nr Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Greektown. It’ll be easy to simply show up and start li ...
From $150 per night (USD)VRBO
From $391 per night (USD)Expedia
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your cozy getaway awaits in Chicago at this condo. With 3 bedrooms featuring a king, queen, and full bed, this tranquil ...
From $391 per night (USD)Expedia
From $232 per night (USD)VRBO
2BR <10mins O’Hare &Transit Newly Furnished Modern
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your home away from home! This stylish 2BR offers comfort and convenience, offering you a relaxing retreat wh ...
From $232 per night (USD)VRBO
From $1510 per night (USD)VRBO
Luxury Designer Penthouse Combo | NW | Gold Coast
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 20
Summary: NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy the combination of your own 2 side-by-side private penthouses ...
From $1510 per night (USD)VRBO
From $1383 per night (USD)VRBO
Making The Best Memories Along The Way! 4 Units with City View, Pets Are Welcome
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1383 per night (USD)VRBO
From $694 per night (USD)VRBO
Better Choice for your Vacation! 2 Relaxing Units with City View, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $694 per night (USD)VRBO
From $1040 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 3 Relaxing Units, Pets Are Welcome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $1040 per night (USD)VRBO
From $654 per night (USD)VRBO
A Place You'll Surely Enjoy! 2 Relaxing Units with City View, Pet-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $654 per night (USD)VRBO
From $980 per night (USD)VRBO
Come Create Memories w/ Fun-filled Adventures at this Paradise! 3 Relaxing Units
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located Downtown near Chicago River, enjoy bars & restaurants all by walking distance. For sports fans, Soldier Field, W ...
From $980 per night (USD)VRBO
From $163 per night (USD)VRBO
Better Choice for your Vacation! Short Walk to River North Spots, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $163 per night (USD)VRBO
From $169 per night (USD)VRBO
Everything You Need For The Perfect Vacation! Pet-friendly Property, King Room!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nestled in the hip River North area of downtown Chicago, this property offers guests a great location near shops, restau ...
From $169 per night (USD)VRBO
From $87 per night (USD)Expedia
Blueground | Gold Coast, AC, nr Hancock Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $87 per night (USD)Expedia
From $370 per night (USD)VRBO
The Chicago Hotel Collection Magnificent Mile, 3 Standard King Rooms
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $370 per night (USD)VRBO
From $212 per night (USD)VRBO
Sleek Downtown Retreat by Chicago’s Mag Mile @ The Chicago Hotel Collection
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $212 per night (USD)VRBO
From $134 per night (USD)VRBO
The Chicago Hotel Collection, Mag Mile, Deluxe Double Queen - Premium Option
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $134 per night (USD)VRBO
From $66 per night (USD)VRBO
Upscale City Center Stay | Prime Locale | City Views | Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $66 per night (USD)VRBO
From $243 per night (USD)VRBO
Beautiful 4 bedroom 2 bath pet friendly Chicago brick bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy your stay at this Chicago style brick bungalow. Well cleaned updated 4 bedroom 2 bath. Near shopping, the universi ...
From $243 per night (USD)VRBO
From $339 per night (USD)VRBO
Charming 3-bedroom house in Streamwood with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your home away from home in Streamwood, IL! This warm and well-appointed 3-bedroom, 1-bath home is ideal for ...
From $339 per night (USD)VRBO
From $148 per night (USD)VRBO
Prime Location Wicker Park Studio Close to Shops & Dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Modern Comforts: Prime Wicker Park Studio, close to shops & dining in Chicago, offers a comfortable apartment with free ...
From $148 per night (USD)VRBO
From $395 per night (USD)VRBO
Spacious 4-bedroom house in amazing Des Plaines with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
This Des Plaines house boasts 4 inviting bedrooms, including 1 king bed, 2 queen beds, 1 bunk bed, and 1 futon. With 2 b ...
From $395 per night (USD)VRBO
From $331 per night (USD)VRBO
Family Haven-Prime location ideal for long stays
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
WELCOME to our inviting retreat❗️❗️ "Discover a haven of comfort and convenience in the heart of Streamwood, perfect fo ...
From $331 per night (USD)VRBO
From $681 per night (USD)Expedia
Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space 1 FREE Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Nestled in the heart of Chicago, this charming apartment boasts 2 cozy bedrooms with queen beds, perfect for a small gro ...
From $681 per night (USD)Expedia
From $108 per night (USD)VRBO
Charming 1-bedroom apartment with WiFi, AC in Glenview, great school district
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover this 1-bedroom gem in Glenview. This pleasant apartment offers WiFi, coin laundry, and more for your convenienc ...
From $108 per night (USD)VRBO
From $283 per night (USD)Expedia
Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Your Chicago adventure begins at this delightful 3-bedroom condo. With 3 queen beds, 2 futons, and 3 bathrooms featuring ...
From $283 per night (USD)Expedia
From $348 per night (USD)VRBO
Spacious apartment in awesome Chicago with WiFi, AC- 4 Bedrooms
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to Kam Suites, your ideal retreat in Chicago! This spacious apartment comfortably sleeps ten guests, with one co ...
From $348 per night (USD)VRBO
From $447 per night (USD)VRBO
Charming Hinsdale Home with Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover this marvelous 4-bedroom gem in Hinsdale. This cool house features 3 queen beds, WiFi, AC, a washing machine, h ...
From $447 per night (USD)VRBO
From $487 per night (USD)VRBO
\"Spacious 2BR Retreat with Office, Stunning Backyard & Grill in Hanover Park\"
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to The Hanover Hideaway, a stylish 2-bedroom retreat in Hanover Park that offers the perfect mix of comfort, con ...
From $487 per night (USD)VRBO
From $225 per night (USD)Expedia
The Family Retreat, The Family Retreat Oasis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A spacious 4-bedroom, 2-bathroom house ideal for larger groups or families. Situated just outside Chicago, in Calumet Ci ...
From $225 per night (USD)Expedia
From $409 per night (USD)VRBO
Charming 2-bedroom apartment in fabulous Westchester with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Your home away from home in Westchester with 2 bedrooms. This awesome apartment features 1 full bed, 1 bunk bed, a cozy ...
From $409 per night (USD)VRBO
From $221 per night (USD)Expedia
Clean home in quiet neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Relax alone or with family at this peaceful place in very quiet neighborhood. Single family house with 1600 sq ft ,it ha ...
From $221 per night (USD)Expedia
From $421 per night (USD)VRBO
The Urban Family Retreat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to your ideal getaway located on the vibrant southeast side of Chicago. This spacious property comfortably sleep ...
From $421 per night (USD)VRBO
From $320 per night (USD)Expedia
Blueground | South Loop, pool & gym, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy South Loop furnished one bedroom apartme ...
From $320 per night (USD)Expedia
From $326 per night (USD)VRBO
Blueground | South Loop, pool & gym, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop with high floor views over the city. It’ll b ...
From $326 per night (USD)VRBO
From $124 per night (USD)Expedia
Blueground | Fulton Market, gym & AC, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Fulton Market District with views over the city. It’ll ...
From $124 per night (USD)Expedia
From $528 per night (USD)VRBO
Elegant Escape by Downtown Burr Ridge with an easy access to Chicago Landmarks
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Nestled just 0.5 miles from Walker Park and the Edgewood Valley Country Club, this stunning home offers the perfect blen ...
From $528 per night (USD)VRBO
From $422 per night (USD)Expedia
Spacious 3-bedroom apartment near downtown, FREE PARKING
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to you home away from home! This bright and cozy space is perfectly located in Tri-Taylor neighborhood just 10mi ...
From $422 per night (USD)Expedia
From $138 per night (USD)VRBO
Enjoyable 3-bedroom apartment with WiFi in vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this lovely 3-bedroom gem in Chicago. This apartment boasts 3 full beds, perfect for a group getaway. With heat ...
From $138 per night (USD)VRBO
From $357 per night (USD)Expedia
Remodeled Charming Home,Backyard w/Pergola,Pool/Ping Pong Game Room, Homewood IL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
➜ Fully remodeled 3 beds, 2 bath home with modern finishes ➜ Spacious backyard with, pergola, seating areas, and outdoor ...
From $357 per night (USD)Expedia
From $187 per night (USD)VRBO
Charming 2-bed.apt in Franklin Park, AC, WiFi, O'Hare, free parking, W/D in unit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Make yourself at home in this remodeled 2-bedroom, second floor Franklin Park retreat. This amazing apartment features 1 ...
From $187 per night (USD)VRBO
From $228 per night (USD)Expedia
Suite Success • Business Class Living • Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your extended-stay retreat in the heart of Chicago’s South Loop. Whether you’re here for work, relocating to ...
From $228 per night (USD)Expedia
From $283 per night (USD)VRBO
Penthouse Paradise •Executive Elegance • Elevated Amenities • Sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience Elevated Urban Luxury in Chicago’s South Loop: Welcome to your home away from home—a sprawling, sun-drenched ...
From $283 per night (USD)VRBO
From $1156 per night (USD)Expedia
Luxury 5BR Family Getaway – Heated Pool, Hot Tub, Fire pit, Game Room,
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Step into this upscale residence with a touch of castle-like charm, featuring a massive heated 40-ft pool, outdoor hot t ...
From $1156 per night (USD)Expedia
From $224 per night (USD)VRBO
Relax & Unwind in This Comfortable 3BR Unit\n
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your home away from home! This beautifully kept 3-bedroom upstairs unit offers comfort, privacy, and plenty o ...
From $224 per night (USD)VRBO
From $954 per night (USD)VRBO
Luxe Home 20 min from Downtown Chicago ,heated indoor pool, Spa bath, tree house
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Exceptional house in a quiet neighborhood, walking distance to Emily Oaks and Skokie Water Park, shopping, subway, and o ...
From $954 per night (USD)VRBO
From $186 per night (USD)VRBO
Charming 2-bedroom apartment in fabulous Chicago with WiFi, Game Space
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your perfect Chicago getaway! A stylish & spacious Chicago stay perfect for families, friends, couples & busi ...
From $186 per night (USD)VRBO
From $123 per night (USD)Expedia
TOP PICK: Solo/Group, Private Rooms, Free Coffee!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $123 per night (USD)Expedia
From $125 per night (USD)VRBO
Free Coffee & Private Room - Traveler's Favorite!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $125 per night (USD)VRBO
From $123 per night (USD)Expedia
Traveler’s Favorite: Private Room Near Attractions
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $123 per night (USD)Expedia
From $124 per night (USD)VRBO
Clean & Modern • Central Location • Free Coffee!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $124 per night (USD)VRBO
From $125 per night (USD)Expedia
Secure, Quiet, Solo Traveler's Fave, Free Coffee!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $125 per night (USD)Expedia
From $124 per night (USD)VRBO
Morning Brew & Museum Views • Downtown Solo Stay
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $124 per night (USD)VRBO
From $126 per night (USD)Expedia
Best Private Room in Downtown | Free Coffee
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $126 per night (USD)Expedia
From $125 per night (USD)VRBO
Budget-Friendly Stay and Free Coffee | Downtown
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $125 per night (USD)VRBO
From $125 per night (USD)Expedia
All Ease Private Stay |Traveler's Top Fave!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Welcome to your perfectly located home base in the heart of Chicago! Just 16 km from Midway International Airport and wa ...
From $125 per night (USD)Expedia