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  • Charming 6BD Retreat - Steps Away from Wrigley
    From $636 per night (USD)

    VRBO

    Charming 6BD Retreat - Steps Away from Wrigley

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    13

    Welcome to our *NEW* charming and spacious 6BD home—perfect for large groups seeking comfort and convenience. Just a few ...

    From $636 per night (USD)

    VRBO

    Details
  • Logan Square SRO Hotel Room 209
    From $72 per night (USD)

    VRBO

    Logan Square SRO Hotel Room 209

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Fully furnished private hotel room in a perfect Logan Square location! This room shares a bathroom with one other room a ...

    From $72 per night (USD)

    VRBO

    Details
  • Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
    From $1589 per night (USD)

    VRBO

    Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    26

    Welcome to Waveland Chicago 100 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...

    From $1589 per night (USD)

    VRBO

    Details
  • 2BR • Newly Furnished Modern Apt • Near O'Hare
    From $381 per night (USD)

    Expedia

    2BR • Newly Furnished Modern Apt • Near O'Hare

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to Potawatomie Chicago 201 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪ ...

    From $381 per night (USD)

    Expedia

    Details
  • Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
    From $397 per night (USD)

    VRBO

    Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Welcome to Drummond Chicago 233 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...

    From $397 per night (USD)

    VRBO

    Details
  • Walk to the Beach • Private Office • 5BR
    From $516 per night (USD)

    Expedia

    Walk to the Beach • Private Office • 5BR

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    13

    Welcome to Columbia Chicago 655 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...

    From $516 per night (USD)

    Expedia

    Details
  • Private Workspace •  Sleeps4 • Modern Stylish Stay
    From $255 per night (USD)

    VRBO

    Private Workspace • Sleeps4 • Modern Stylish Stay

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Waveland Chicago 568 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...

    From $255 per night (USD)

    VRBO

    Details
  • Modern Condo • Safe Chicago Stay Near O’Hare
    From $328 per night (USD)

    Expedia

    Modern Condo • Safe Chicago Stay Near O’Hare

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to River Chicago 442 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...

    From $328 per night (USD)

    Expedia

    Details
  • Top Rated Condo •King Bed • Safe Historic Location
    From $142 per night (USD)

    VRBO

    Top Rated Condo •King Bed • Safe Historic Location

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to 78th Elmwood Park 453 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...

    From $142 per night (USD)

    VRBO

    Details
  • Top Rated Condo • 65” TV • Family-friendly 2BR
    From $83 per night (USD)

    Expedia

    Top Rated Condo • 65” TV • Family-friendly 2BR

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to 78th Elmwood Park 417 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...

    From $83 per night (USD)

    Expedia

    Details
  • 2BR Fitness Pad • Private Gym • Sleeps 7
    From $278 per night (USD)

    VRBO

    2BR Fitness Pad • Private Gym • Sleeps 7

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Welcome to Waveland Chicago 268 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...

    From $278 per night (USD)

    VRBO

    Details
  • Game Room • Fire-pit • Playground • Gym • Billiard
    From $446 per night (USD)

    Expedia

    Game Room • Fire-pit • Playground • Gym • Billiard

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Kilpatrick Chicago 600 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...

    From $446 per night (USD)

    Expedia

    Details
  • King Sleep Number Bed • Prime Location
    From $91 per night (USD)

    VRBO

    King Sleep Number Bed • Prime Location

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Welcome to 78th Elmwood Park 241 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...

    From $91 per night (USD)

    VRBO

    Details
  • Sleeps 7 •  Huge Projector •  Designated Workspace
    From $313 per night (USD)

    Expedia

    Sleeps 7 • Huge Projector • Designated Workspace

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Welcome to Waveland Chicago 845 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...

    From $313 per night (USD)

    Expedia

    Details
  • Sleeps 18 • 7BR • Gym • Game Room • Theater
    From $921 per night (USD)

    VRBO

    Sleeps 18 • 7BR • Gym • Game Room • Theater

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    18

    Welcome to Waller Chicago 344 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Not ...

    From $921 per night (USD)

    VRBO

    Details
  • 2BR Traveler's Favorite • Modern and Clean
    From $395 per night (USD)

    Expedia

    2BR Traveler's Favorite • Modern and Clean

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to Drummond Chicago 839 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...

    From $395 per night (USD)

    Expedia

    Details
  • Mins from O'Hare • Safe Location • Private Parking
    From $287 per night (USD)

    VRBO

    Mins from O'Hare • Safe Location • Private Parking

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to River Chicago 490 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ Note ...

    From $287 per night (USD)

    VRBO

    Details
  • Sleeps 4 • New Modern 1BR • Private Workspace
    From $295 per night (USD)

    Expedia

    Sleeps 4 • New Modern 1BR • Private Workspace

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Waveland Chicago 513 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...

    From $295 per night (USD)

    Expedia

    Details
  • King Bed Studio | 60\ HDTV | Safe | Close to Metra
    From $102 per night (USD)

    VRBO

    King Bed Studio | 60\" HDTV | Safe | Close to Metra

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to 78th Elmwood Park 478 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ ...

    From $102 per night (USD)

    VRBO

    Details
  • 2BR w/ Workspace - Coffee Bar - Near Transit
    From $486 per night (USD)

    Expedia

    2BR w/ Workspace - Coffee Bar - Near Transit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to Drummond Chicago 523 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. ▪️ N ...

    From $486 per night (USD)

    Expedia

    Details
  • Designer Retreat 2BR w Cowboy Pool, Fire Pit  & Free Parking
    From $749 per night (USD)

    VRBO

    Designer Retreat 2BR w Cowboy Pool, Fire Pit & Free Parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your home away from home in the heart of Bridgeport, Chicago; a centrally located, artistic neighborhood in a ...

    From $749 per night (USD)

    VRBO

    Details
  • Blueground | Chicago Loop, rooftop, nr Millennium Park
    From $103 per night (USD)

    VRBO

    Blueground | Chicago Loop, rooftop, nr Millennium Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this lovely The Loop furnished one bedroom apartme ...

    From $103 per night (USD)

    VRBO

    Details
  • Spacious Bronzeville Apartment
    From $1116 per night (USD)

    VRBO

    Spacious Bronzeville Apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Come enjoy a comfortable and spacious apartment in the Bronzeville neighborhood. Walking distance from IIT and College o ...

    From $1116 per night (USD)

    VRBO

    Details
  • Modern 2BR, Private Elevator, Near United Center and Secure Parking
    From $202 per night (USD)

    Expedia

    Modern 2BR, Private Elevator, Near United Center and Secure Parking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience elevated city living in this modern 2-bedroom, 2-bath condo in Chicago’s Near West Side. A private elevator o ...

    From $202 per night (USD)

    Expedia

    Details
  • Blueground | South Loop, view, nr Grant Park
    From $97 per night (USD)

    VRBO

    Blueground | South Loop, view, nr Grant Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this comfortable South Loop furnished studio apart ...

    From $97 per night (USD)

    VRBO

    Details
  • Sleeps 12/Free parking+20 min to DT Chicago
    From $499 per night (USD)

    Expedia

    Sleeps 12/Free parking+20 min to DT Chicago

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Ideal for families or groups. This listing is for 2 apartments in the same building: 1. First floor apartment has no s ...

    From $499 per night (USD)

    Expedia

    Details
  • Modern 3BR Near Downtown & Free Parking
    From $482 per night (USD)

    VRBO

    Modern 3BR Near Downtown & Free Parking

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    People say there is no place like home… but this unit was designed to feel even better. From comfort to style, every det ...

    From $482 per night (USD)

    VRBO

    Details
  • 29th Floor 2BR Grant Park Suite with Balcony, Gym
    From $311 per night (USD)

    Expedia

    29th Floor 2BR Grant Park Suite with Balcony, Gym

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Stay in a luxury 2BR 2BA high-rise in downtown Chicago near Grant Park, Millennium Park, and the Lakefront. Sleeps 8 wit ...

    From $311 per night (USD)

    Expedia

    Details
  • Chicago 3BR Loyola - 10 Min Walk to Beaches & CTA
    From $186 per night (USD)

    VRBO

    Chicago 3BR Loyola - 10 Min Walk to Beaches & CTA

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Located in Chicago’s Edgewater area near Loyola University and the lakefront, this spacious 3BR stay places you close to ...

    From $186 per night (USD)

    VRBO

    Details
  • Chicago 3BR Retreat 10 Min Access to Downtown
    From $234 per night (USD)

    Expedia

    Chicago 3BR Retreat 10 Min Access to Downtown

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Experience Chicago from this bright retreat in Humboldt Park. Ideally located for exploring Chicago, the accommodation o ...

    From $234 per night (USD)

    Expedia

    Details
  • Walk to Wrigley! Spacious 3BR in the Heart of Chicago
    From $307 per night (USD)

    VRBO

    Walk to Wrigley! Spacious 3BR in the Heart of Chicago

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    1 mile to Wrigley! Bright and inviting 3-bedroom, 1-bath apartment in Chicago’s Edgewater neighborhood—sleeps up to 7 gu ...

    From $307 per night (USD)

    VRBO

    Details
  • Flexhome Wicker Park • Stylish 2BR • Sleeps 6
    From $151 per night (USD)

    Expedia

    Flexhome Wicker Park • Stylish 2BR • Sleeps 6

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Perched in the heart of Wicker Park, this charming 3rd-floor apartment is your perfect Chicago base. Whether you`re sipp ...

    From $151 per night (USD)

    Expedia

    Details
  • Blueground | Chicago Loop, pool, nr Millennium Park
    From $117 per night (USD)

    VRBO

    Blueground | Chicago Loop, pool, nr Millennium Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this pretty The Loop furnished one bedroom apartme ...

    From $117 per night (USD)

    VRBO

    Details
  • Private Romantic Retreat for Two • Luxury Escape
    From $217 per night (USD)

    VRBO

    Private Romantic Retreat for Two • Luxury Escape

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Escape the ordinary and step into a curated romantic retreat designed exclusively for adult couples (25+). This is more ...

    From $217 per night (USD)

    VRBO

    Details
  • Luxury Designer Apartment 802| Gold Coast/Old Town
    From $297 per night (USD)

    VRBO

    Luxury Designer Apartment 802| Gold Coast/Old Town

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Summary: NEW APARTMENT IN THE HEART OF GOLD COAST and OLD TOWN! Enjoy your own luxury apartment in Chicago's Gold Co ...

    From $297 per night (USD)

    VRBO

    Details
  • NEW! Charming Andersonville Coach House | 3BR/2.5BA
    From $537 per night (USD)

    VRBO

    NEW! Charming Andersonville Coach House | 3BR/2.5BA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    **Hosting 32+ Night Reservations** Tucked away on a quiet tree-lined street, this spacious two-story private coa ...

    From $537 per night (USD)

    VRBO

    Details
  • River North / Mag Mile, Lake and City Views, 43rd Floor Condo, Parking Included!
    From $186 per night (USD)

    VRBO

    River North / Mag Mile, Lake and City Views, 43rd Floor Condo, Parking Included!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    In this breathtaking NE corner apartment at Huron and Wabash, every window frames the mesmerizing Chicago Skyline and La ...

    From $186 per night (USD)

    VRBO

    Details
  • Stay near Wrigley Field! Spacious 3BD Penthouse!
    From $282 per night (USD)

    VRBO

    Stay near Wrigley Field! Spacious 3BD Penthouse!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Welcome to your spacious Lakeview retreat just steps from Wrigley Field! Catch a Cubs game, explore the neighb ...

    From $282 per night (USD)

    VRBO

    Details
  • Lakeview 3BD 2BA Penthouse near Wrigley Field!
    From $280 per night (USD)

    VRBO

    Lakeview 3BD 2BA Penthouse near Wrigley Field!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Experience the best of Chicago from this modern 3-bed, 2-bath Lakeview retreat, just steps from Wrigley Field, ...

    From $280 per night (USD)

    VRBO

    Details
  • Luxury Designer Apartment 1202|Gold Coast/Old Town
    From $308 per night (USD)

    Expedia

    Luxury Designer Apartment 1202|Gold Coast/Old Town

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Summary: NEW APARTMENT IN THE HEART OF GOLD COAST and OLD TOWN! Enjoy your own apartment in Chicago's Gold Coast and ...

    From $308 per night (USD)

    Expedia

    Details
  • Downtown Chicago Stay with Free In & Out Parking 1
    From $617 per night (USD)

    VRBO

    Downtown Chicago Stay with Free In & Out Parking 1

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Summary: 🏙️ For 4 Bedroom / 2 Bathroom Unit Enjoy a stylish experience at this centrally-located place! ✨🏙️ Exp ...

    From $617 per night (USD)

    VRBO

    Details
  • Downtown Chicago Stay with Free In & Out Parking 5
    From $584 per night (USD)

    Expedia

    Downtown Chicago Stay with Free In & Out Parking 5

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Summary: 🏙️ 3 Bedroom / 2 Bathroom Version Enjoy a stylish stay in the heart of downtown Chicago! ✨🌆 Modern 848 ...

    From $584 per night (USD)

    Expedia

    Details
  • Downtown Chicago Stay with Free In & Out Parking 3
    From $632 per night (USD)

    VRBO

    Downtown Chicago Stay with Free In & Out Parking 3

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Summary: 🏙️ 3 Bedroom / 2 Bathroom Version Enjoy a stylish stay in the heart of downtown Chicago! ✨🌆 Modern 848 ...

    From $632 per night (USD)

    VRBO

    Details
  • Stylish 2-Bedroom Condo – Easy Drive to Downtown Chicago & Midway Airport
    From $231 per night (USD)

    Expedia

    Stylish 2-Bedroom Condo – Easy Drive to Downtown Chicago & Midway Airport

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Overview: Welcome to your perfect home-base in the Chicago area! This beautifully styled 2-bedroom, 1-bathroom condo is ...

    From $231 per night (USD)

    Expedia

    Details
  • Giant 5-Bedroom Home w/ Pool Table, 15 Min to Wrigley & Downtown
    From $718 per night (USD)

    VRBO

    Giant 5-Bedroom Home w/ Pool Table, 15 Min to Wrigley & Downtown

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Bring the whole crew to this spacious Irving Park home packed w/fun! Shoot pool, kick back with smart TVs in almost ever ...

    From $718 per night (USD)

    VRBO

    Details
  • Landing | Beautiful 2BD, Gym, Rooftop Lounge
    From $162 per night (USD)

    Expedia

    Landing | Beautiful 2BD, Gym, Rooftop Lounge

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Stay luxe in the Loop. Located in the heart of Chicago’s vibrant West Loop, Luxe on Madison is your home for a flexible ...

    From $162 per night (USD)

    Expedia

    Details
  • Landing | Stylish 1BD, Clubhouse, Pool
    From $145 per night (USD)

    VRBO

    Landing | Stylish 1BD, Clubhouse, Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Soak up the best of River North at NEXT. Our fully-furnished homes are perfect for monthly or extended stays, featuring ...

    From $145 per night (USD)

    VRBO

    Details
  • Chicago Gem: Wrigley - Lakefront - Red Line Train
    From $296 per night (USD)

    Expedia

    Chicago Gem: Wrigley - Lakefront - Red Line Train

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Discover the perfect blend of city excitement and neighborhood charm in this spacious 2-bedroom, 1-bath condo located in ...

    From $296 per night (USD)

    Expedia

    Details
  • Compatible: 3BR-2BT Ranch with Finished Basement!
    From $440 per night (USD)

    VRBO

    Compatible: 3BR-2BT Ranch with Finished Basement!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Located in La Grange Park, enjoy what this 3-bedroom house has to offer. Each bedroom features a comfy king bed, perfect ...

    From $440 per night (USD)

    VRBO

    Details
  • 29th Floor 2BR Suite with Balcony and Gym
    From $295 per night (USD)

    Expedia

    29th Floor 2BR Suite with Balcony and Gym

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Stay in a luxury 2BR 2BA high-rise in downtown Chicago near Grant Park, Millennium Park, and the Lakefront. Sleeps 8 wit ...

    From $295 per night (USD)

    Expedia

    Details
  • Landing | Beautiful 2BD, Pool, Gym
    From $227 per night (USD)

    VRBO

    Landing | Beautiful 2BD, Pool, Gym

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in Schaumburg’s vibrant Veridian campus, Element at Veridian puts you minutes from Woodfield Mall, top dining sp ...

    From $227 per night (USD)

    VRBO

    Details
  • Pristine Apartment with Free Street Parking
    From $499 per night (USD)

    Expedia

    Pristine Apartment with Free Street Parking

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    The Fully Renovated Urban Retreat on Chicago Avenue Welcome to your beautifully renovated and pristine 3-bedroom upper-l ...

    From $499 per night (USD)

    Expedia

    Details
  • Blueground | Little Italy, pool, nr UIC
    From $90 per night (USD)

    VRBO

    Blueground | Little Italy, pool, nr UIC

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this pretty one bedroom Blueground apartment. You’ll love coming h ...

    From $90 per night (USD)

    VRBO

    Details
  • Modern Garden Apartment w/ New Kitchen + Bathroom
    From $137 per night (USD)

    VRBO

    Modern Garden Apartment w/ New Kitchen + Bathroom

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our newly renovated garden apartment in Irving Park! This private-entry unit features 2 cozy bedrooms, a bran ...

    From $137 per night (USD)

    VRBO

    Details
  • Westloop Spacious 4 bdrm Duplex with parking & workout area
    From $438 per night (USD)

    VRBO

    Westloop Spacious 4 bdrm Duplex with parking & workout area

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Centrally located duplex-down, ideal for families and groups of up to 10. Features 4 bedrooms (2 King, 2 Queen), 3 full ...

    From $438 per night (USD)

    VRBO

    Details
  • Cozy 2-bedroom apartment in peaceful Chicago with central A/C system
    From $186 per night (USD)

    Expedia

    Cozy 2-bedroom apartment in peaceful Chicago with central A/C system

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to this beautiful apartment in Chicago. Guests will find two comfortable bedrooms, each featuring a queen bed, p ...

    From $186 per night (USD)

    Expedia

    Details
  • Blueground | West Town, balcony, nr Chicago River
    From $160 per night (USD)

    VRBO

    Blueground | West Town, balcony, nr Chicago River

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Show up and start living from day one in Chicago with this spacious two bedroom Blueground apartment. You’ll love coming ...

    From $160 per night (USD)

    VRBO

    Details
  • Blueground | West Town, view, nr Chicago River
    From $147 per night (USD)

    VRBO

    Blueground | West Town, view, nr Chicago River

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Show up and start living from day one in Chicago with this stylish two bedroom Blueground apartment. You’ll love coming ...

    From $147 per night (USD)

    VRBO

    Details
  • 6BR Apt • Workspace • Near Lakefront + Red Line
    From $511 per night (USD)

    VRBO

    6BR Apt • Workspace • Near Lakefront + Red Line

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    12

    Welcome to Columbia Chicago 654 by EscapeStays, the name guests can easily remember when planning their stay. Note: Bef ...

    From $511 per night (USD)

    VRBO

    Details
  • Terrific 1 bedroom apartment to ''Stay, Unwind. Enjoy.''
    From $132 per night (USD)

    Expedia

    Terrific 1 bedroom apartment to ''Stay, Unwind. Enjoy.''

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Your Chicago adventure begins at this 1-bedroom apartment. Inside, guests find a welcoming space featuring a king bed an ...

    From $132 per night (USD)

    Expedia

    Details
  • Newly remodeled 3-bedroom house in delightful Harvey, near new Wind Creek casino
    From $540 per night (USD)

    VRBO

    Newly remodeled 3-bedroom house in delightful Harvey, near new Wind Creek casino

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Newly remodeled 3 bedroom in Harvey, this marvelous house offers a comfortable retreat for guests. With three spacious b ...

    From $540 per night (USD)

    VRBO

    Details
  • Two bedroom  in United States of America, Chicago
    From $201 per night (USD)

    Expedia

    Two bedroom in United States of America, Chicago

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Bright, newly renovated, and finished like a designer condo, this modern 2-bedroom is built for exploring Chicago in com ...

    From $201 per night (USD)

    Expedia

    Details
  • Spacious 4-bedroom apartment in fantastic Chicago with AC
    From $452 per night (USD)

    VRBO

    Spacious 4-bedroom apartment in fantastic Chicago with AC

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Your cozy getaway awaits in Chicago at this charming apartment. With four spacious bedrooms featuring three queen beds a ...

    From $452 per night (USD)

    VRBO

    Details
  • Cozy 1-bedroom garden apartment in W Lakeview/Wrigley/Roscoe Village/Fast WIFI
    From $101 per night (USD)

    VRBO

    Cozy 1-bedroom garden apartment in W Lakeview/Wrigley/Roscoe Village/Fast WIFI

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Bright 1BR & 1 Bath in Prime Lakeview — great for long stays, remote work, or city trips! What You’ll Love: • Fast WiFi ...

    From $101 per night (USD)

    VRBO

    Details
  • Modern Edgewater Apartment: 2BD 2BA with Parking!
    From $252 per night (USD)

    VRBO

    Modern Edgewater Apartment: 2BD 2BA with Parking!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Experience the charm of Chicago's Edgewater neighborhood from this modern retreat just steps from the Granvill ...

    From $252 per night (USD)

    VRBO

    Details
  • Blueground | Chicago Loop, pool, nr Millennium Park
    From $141 per night (USD)

    VRBO

    Blueground | Chicago Loop, pool, nr Millennium Park

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the best of Chicago, with this two bedroom apartment in The Loop. It’ll be easy to simply show up and start liv ...

    From $141 per night (USD)

    VRBO

    Details
  • Peaceful 3-bedroom apartment in charming Chicago Chinatown
    From $294 per night (USD)

    VRBO

    Peaceful 3-bedroom apartment in charming Chicago Chinatown

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    This 3-bedroom apartment is perfect for your escape to Chicago. Inside, guests find a wonderful mix of comfort with a qu ...

    From $294 per night (USD)

    VRBO

    Details
  • Penthouse Designer Loft 4W | GoldCoast/River North
    From $420 per night (USD)

    Expedia

    Penthouse Designer Loft 4W | GoldCoast/River North

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Summary: BRAND NEW APARTMENT IN THE HEART OF RIVER NORTH & GOLD COAST! Enjoy your designer styled unit located in Ch ...

    From $420 per night (USD)

    Expedia

    Details
  • Spacious West Loop Retreat  UnitedCenter & Dining
    From $379 per night (USD)

    VRBO

    Spacious West Loop Retreat UnitedCenter & Dining

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Bright and spacious top-floor condo in a 2-unit building, on a quiet and safe residential street. Perfect for couples, ...

    From $379 per night (USD)

    VRBO

    Details
  • Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
    From $343 per night (USD)

    Expedia

    Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    About This Space Welcome to your home away from home! This private 2-bedroom coach house offers all the comforts of home ...

    From $343 per night (USD)

    Expedia

    Details
  • Humboldt Hideaway! Spacious 3BR/1BA Apartment in the Heart of Humboldt Park
    From $315 per night (USD)

    VRBO

    Humboldt Hideaway! Spacious 3BR/1BA Apartment in the Heart of Humboldt Park

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to the Humboldt Hideaway! This spacious 3-bedroom, 1-bath apartment in vibrant Humboldt Park comfortably sleeps ...

    From $315 per night (USD)

    VRBO

    Details
  • Cozy 1-bedroom apartment in beautiful West Loop, in-unit laundry + pet friendly
    From $151 per night (USD)

    VRBO

    Cozy 1-bedroom apartment in beautiful West Loop, in-unit laundry + pet friendly

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Cozy up in this serene space in one of Chicago's most beautiful neighborhoods, the West Loop. This superb one-bedroom is ...

    From $151 per night (USD)

    VRBO

    Details
  • Your Own Private Spa Near Chicago • Barrel Sauna + Saltwater Hot Tub • Sleeps 10
    From $407 per night (USD)

    VRBO

    Your Own Private Spa Near Chicago • Barrel Sauna + Saltwater Hot Tub • Sleeps 10

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Relax in your private spa stay in Arlington Heights. This remodeled home features a 6-person European barrel sauna with ...

    From $407 per night (USD)

    VRBO

    Details
  • Blueground | Fulton Market District, pool, nr Park
    From $120 per night (USD)

    VRBO

    Blueground | Fulton Market District, pool, nr Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in Fulton Market District. It’ll be easy to simply show up ...

    From $120 per night (USD)

    VRBO

    Details
  • Luxury 4BR 4-Story Chicago Villa |Prime Gold Coast
    From $642 per night (USD)

    VRBO

    Luxury 4BR 4-Story Chicago Villa |Prime Gold Coast

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to your Chicago stay in the heart of the Gold Coast - a spacious, architect-designed townhome perfect for relaxi ...

    From $642 per night (USD)

    VRBO

    Details
  • Designer 3BR with Resort Amenities and Balcony
    From $533 per night (USD)

    Expedia

    Designer 3BR with Resort Amenities and Balcony

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Experience iconic Chicago with a stay at a high-end and spacious 3BR apartment right in downtown with a large ...

    From $533 per night (USD)

    Expedia

    Details
  • Feel at Home while Exploring Chicago!
    From $148 per night (USD)

    VRBO

    Feel at Home while Exploring Chicago!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Stay comfortably in Chicago at this 2-bedroom apartment. The space features one queen bed and one twin bed, plus a cozy ...

    From $148 per night (USD)

    VRBO

    Details
  • Cozy Chicago Retreat Near All The Action
    From $170 per night (USD)

    Expedia

    Cozy Chicago Retreat Near All The Action

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Discover this 1-bedroom 2-flat in Chicago. The upper level space features a terrific bedroom with two Queen beds, a dinn ...

    From $170 per night (USD)

    Expedia

    Details
  • Stunning Evanston Retreat Near Northwestern University
    From $436 per night (USD)

    VRBO

    Stunning Evanston Retreat Near Northwestern University

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to this beautifully renovated Evanston brick home, just 10 minutes from Northwestern University and 30 minutes f ...

    From $436 per night (USD)

    VRBO

    Details
  • Sleek Avondale Condo Spa Bath King Bed +Queen bed +Garage
    From $394 per night (USD)

    VRBO

    Sleek Avondale Condo Spa Bath King Bed +Queen bed +Garage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Modern meets mmm-hmm in this 2BR Avondale gem. King & queen beds? Check. Spa bath with rain shower & jets? Oh yes. Strea ...

    From $394 per night (USD)

    VRBO

    Details
  • 2-BR central Oak Park flat+near FLW homes+near trains to Chicago+pets ok+parking
    From $279 per night (USD)

    VRBO

    2-BR central Oak Park flat+near FLW homes+near trains to Chicago+pets ok+parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Historic Oak Park Retreat Near Frank Lloyd Wright & Downtown Chicago with parking. This full-floor apartment occupies an ...

    From $279 per night (USD)

    VRBO

    Details
  • Stylish 2-bedroom Retreat Near UChicago & Close to Downtown
    From $116 per night (USD)

    Expedia

    Stylish 2-bedroom Retreat Near UChicago & Close to Downtown

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Consider this apartment your home away from home while you visit Chicago. This fabulous space features two cozy bedrooms ...

    From $116 per night (USD)

    Expedia

    Details
  • Patio • Workspace • Dog Friendly • Free Street Parking • Train Access
    From $420 per night (USD)

    VRBO

    Patio • Workspace • Dog Friendly • Free Street Parking • Train Access

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    You'll fall in love with this garden apartment that offers easy access to both the O'Hare airport & the heart of Chicago ...

    From $420 per night (USD)

    VRBO

    Details
  • Fabulous hotel suites in Chicago , 3 miles from United Center
    From $248 per night (USD)

    Expedia

    Fabulous hotel suites in Chicago , 3 miles from United Center

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Unwind in Chicago at this perfect hotel suite. Guests enjoy a comfortable stay with one bathroom and climate control tha ...

    From $248 per night (USD)

    Expedia

    Details
  • Cul de sac jacuzzi home
    From $307 per night (USD)

    VRBO

    Cul de sac jacuzzi home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Your Country Club Hills adventure begins at this 3-bedroom house. Inside, guests find two twin beds and one queen bed, p ...

    From $307 per night (USD)

    VRBO

    Details
  • Chic Luxe Spa Retreat - Light Filled+King Bed+Garage
    From $348 per night (USD)

    VRBO

    Chic Luxe Spa Retreat - Light Filled+King Bed+Garage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Experience top-floor luxury in this fully remodeled Avondale condo. Soak in the spa-style bath, bask in natural light fr ...

    From $348 per night (USD)

    VRBO

    Details
  • Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday
    From $983 per night (USD)

    VRBO

    Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    17

    After two years of carefully restoring and renovating this beautiful home from the inside out, we’re excited to finally ...

    From $983 per night (USD)

    VRBO

    Details
  • New Luxury 3BR - Steps to Downtown and Metra
    From $531 per night (USD)

    VRBO

    New Luxury 3BR - Steps to Downtown and Metra

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Brand-new, light-filled 3-bedroom apartment in the heart of Brookfield, thoughtfully designed for comfort and style. Fea ...

    From $531 per night (USD)

    VRBO

    Details
  • Edgewater Gem by the Lake! 2BR with Parking & Gym
    From $230 per night (USD)

    VRBO

    Edgewater Gem by the Lake! 2BR with Parking & Gym

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Escape to Chicago's charming Edgewater neighborhood, where mornings begin with a stroll along the lakefront an ...

    From $230 per night (USD)

    VRBO

    Details
  • Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking
    From $239 per night (USD)

    VRBO

    Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Experience your ideal Chicago escape with this modern retreat in Edgewater. Start your morning with coffee bef ...

    From $239 per night (USD)

    VRBO

    Details
  • 3BR Retreat Perfect for Professionals and Families in South Shore/ Chicago
    From $348 per night (USD)

    VRBO

    3BR Retreat Perfect for Professionals and Families in South Shore/ Chicago

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to your home away from home! This fully renovated 3-bedroom, 2-bathroom apartment offers modern comfort in the h ...

    From $348 per night (USD)

    VRBO

    Details
  • Fabulous 5-bedroom, 6 beds, 3 bath house near Ohare in Prospect Heights
    From $663 per night (USD)

    Expedia

    Fabulous 5-bedroom, 6 beds, 3 bath house near Ohare in Prospect Heights

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    This unique place has a style of its own. It's spacious with 5 bedrooms, 3 full bathrooms, single family home that is in ...

    From $663 per night (USD)

    Expedia

    Details
  • Spacious 4-bedroom Home - Walk to Lake Michigan, Beaches, NU Campus, and more!
    From $1722 per night (USD)

    VRBO

    Spacious 4-bedroom Home - Walk to Lake Michigan, Beaches, NU Campus, and more!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Shack on Judson | Walk to Northwestern, Lake Michigan, Downtown Evanston and more Welcome to Shack on Judson, a spaciou ...

    From $1722 per night (USD)

    VRBO

    Details
  • Peaceful King+Queen - 2BR+2BA - WFH Apt - Near: Northwestern-Chicago-Beach
    From $268 per night (USD)

    Expedia

    Peaceful King+Queen - 2BR+2BA - WFH Apt - Near: Northwestern-Chicago-Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy this beautiful, newly renovated 2-bedroom 2-bathroom apartment in Evanston’s arts district. Walk to shops, cafes, ...

    From $268 per night (USD)

    Expedia

    Details
  • Downtown Chicago Stay with Free In & Out Parking-2
    From $519 per night (USD)

    VRBO

    Downtown Chicago Stay with Free In & Out Parking-2

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Summary: 🏙️ For 4 Bedroom / 2 Bathroom Unit Enjoy a stylish experience at this centrally-located place! ✨🏙️ Exp ...

    From $519 per night (USD)

    VRBO

    Details
  • 3-bedroom apartment in adorable Chicago with AC for your stay
    From $360 per night (USD)

    Expedia

    3-bedroom apartment in adorable Chicago with AC for your stay

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Discover the beauty of Chicago from this 3-bedroom apartment. The fabulous space features one king bed and two queen bed ...

    From $360 per night (USD)

    Expedia

    Details
  • Inviting & Serene: A Book Lover’s Haven
    From $321 per night (USD)

    VRBO

    Inviting & Serene: A Book Lover’s Haven

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to our newly updated 3-bedroom, 2-bath home! Thoughtfully designed to create a restful, welcoming atmosphere. En ...

    From $321 per night (USD)

    VRBO

    Details
  •  The Langley Luxe Modern style unit
    From $174 per night (USD)

    Expedia

    The Langley Luxe Modern style unit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The Langley Luxe Chicago is waiting for you at this 2-bedroom apartment. Inside, guests find two queen beds that promise ...

    From $174 per night (USD)

    Expedia

    Details
  • Studio King Hotel Suite – Sports Illustrated Resorts Chicago, Downtown Loop
    From $202 per night (USD)

    VRBO

    Studio King Hotel Suite – Sports Illustrated Resorts Chicago, Downtown Loop

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience the vibrant heart of downtown Chicago at the Sports Illustrated Resorts Chicago – Studio King in the Loop. Th ...

    From $202 per night (USD)

    VRBO

    Details
  • Studio Hotel Suite: 2 Dbl Beds-Sports Illustrated Resorts Chicago, Downtown Loop
    From $224 per night (USD)

    VRBO

    Studio Hotel Suite: 2 Dbl Beds-Sports Illustrated Resorts Chicago, Downtown Loop

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stay in the heart of downtown Chicago at the Sports Illustrated Resorts Chicago Studio with 2 beds – Sleeps 4. This mode ...

    From $224 per night (USD)

    VRBO

    Details