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Results: 48 Rentals

  • Angie & Mike's Nest!
    From $115 per night (USD)

    VRBO

    Angie & Mike's Nest!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Newly renovated three bedroom & 1 bath apartment with stainless steel appliances. The space The apartment is in the se ...

    From $115 per night (USD)

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  • *Comfortable & Spacious Home Close to Downtown*
    From $346 per night (USD)

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    *Comfortable & Spacious Home Close to Downtown*

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    We are Airbnb Superhosts and have been on the platform since 2016. This is a Comfortable & Spacious beautifully furnish ...

    From $346 per night (USD)

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  • Newly Renovated Apartment! 10 Minutes From Dowtown And The Beach!
    From $179 per night (USD)

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    Newly Renovated Apartment! 10 Minutes From Dowtown And The Beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Experience the charm of our newly renovated Wicker Park Airbnb, nestled in the heart of Chicago. This stylish, cozy retr ...

    From $179 per night (USD)

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  • Wicker Park Duplex: 10 Min to Downtown
    From $438 per night (USD)

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    Wicker Park Duplex: 10 Min to Downtown

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Experience luxury in our 2 bedroom (3 bed) duplex down, spread over 2 levels, our home offers over 1800+ sq ft of room. ...

    From $438 per night (USD)

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  • Wicker Parks, Designers Dream, on-trend 2 Bdrm
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    Wicker Parks, Designers Dream, on-trend 2 Bdrm

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    About this space Wicker Parks, Designers Dream is just that. As a facet of Red Robin Rentals property portfolio, you are ...

    Click For Pricing

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  • Cozy West Loop Apartment w\/Private Patio
    From $159 per night (USD)

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    Cozy West Loop Apartment w\/Private Patio

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Welcome to this stunning West Town Apartment, located close enough to all the attractions Chicago has to offer ...

    From $159 per night (USD)

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  • Family Fun Escape: With 2 Free Parking Spaces!
    From $275 per night (USD)

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    Family Fun Escape: With 2 Free Parking Spaces!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    14

    Summary: As soon as you step inside, you'll be struck by the open floor plan and sleek design. The living room is the pe ...

    From $275 per night (USD)

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    Details
  • Family Fun Haven: Luxurious Retreat for all Ages
    From $324 per night (USD)

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    Family Fun Haven: Luxurious Retreat for all Ages

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Welcome to this stunning West Town Apartment, located close enough to all the attractions Chicago has to offer ...

    From $324 per night (USD)

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    Details
  • Chic 4-Bedroom Haven: Designer's Dream Home
    From $393 per night (USD)

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    Chic 4-Bedroom Haven: Designer's Dream Home

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Welcome to our Chic 4-Bedroom Haven in the heart of Ukrainian Village, Chicago! This meticulously curated home ...

    From $393 per night (USD)

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  • Contemporary, elegantly styled spacious apartment with a lot to offer!!!!
    From $152 per night (USD)

    VRBO

    Contemporary, elegantly styled spacious apartment with a lot to offer!!!!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    4

    Well-styled living! Beautiful spacious apartment with a lot to offer - an original piece of Chicago's history! Walk into ...

    From $152 per night (USD)

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  • NEW LUXURY PENTHOUSE CONDO
    From $283 per night (USD)

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    NEW LUXURY PENTHOUSE CONDO

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    9

    OVERVIEW: This is a spacious penthouse condo with an amazing city skyline view on private rooftop terrace. Comfortably s ...

    From $283 per night (USD)

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  • NEW LUXURY CONDO WITH PATIO DECK
    From $200 per night (USD)

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    NEW LUXURY CONDO WITH PATIO DECK

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    5

    OVERVIEW: This is a high end first floor condo that comfortably sleeps 5 persons. Luxury bathrooms. Fully equipped chef’ ...

    From $200 per night (USD)

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  • Smart Home in Logan Square by the 606 Trail
    From $450 per night (USD)

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    Smart Home in Logan Square by the 606 Trail

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This property is a smart home with 3 bedrooms and 2 1/2 bathrooms, with a garage for a small to medium size SUV, which c ...

    From $450 per night (USD)

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  • Beautiful 1st floor apartment.
    From $212 per night (USD)

    VRBO

    Beautiful 1st floor apartment.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    We have the spot you would love. Perfect for a cozy get away. Our unit is central to the city and has easy access to do ...

    From $212 per night (USD)

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  • Entire Below Level Studio w\/ Private Sauna
    From $186 per night (USD)

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    Entire Below Level Studio w\/ Private Sauna

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Centrally located between Logan Sq., Bucktown, Wicker Park & Ukrainian Village. Easily jump on the 606 walk/bike path or ...

    From $186 per night (USD)

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  • Beautiful 7 Bed, 3.5 Bath
    From $515 per night (USD)

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    Beautiful 7 Bed, 3.5 Bath

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Experience the ultimate comfort and style during your stay at this perfectly located 4-bedroom, 3.5-bathroom home. In th ...

    From $515 per night (USD)

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  • NEW 5BR Home * West Bucktown * 12 Guests * Garage
    From $379 per night (USD)

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    NEW 5BR Home * West Bucktown * 12 Guests * Garage

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Modern, single-family home in the heart of Bucktown. Our custom 5 bedroom home is at the intersection of luxury and comf ...

    From $379 per night (USD)

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  • NEW Contemporary Home - 5BR\/3.5BA+office+garage
    From $297 per night (USD)

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    NEW Contemporary Home - 5BR\/3.5BA+office+garage

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    13

    This NEW gut rehab 4 bedroom + office, single family home with garage parking right in the center of Humboldt Park and U ...

    From $297 per night (USD)

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  • Steel and Sky At The Mine of Diamonds
    From $386 per night (USD)

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    Steel and Sky At The Mine of Diamonds

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    One of a kind design blends light, steel, brick and wood and pairs it with a fully landscaped, leafy side lot for all re ...

    From $386 per night (USD)

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  • Spacious & Modern 4BR\/1BA Suite Near Downtown and Night-Life
    From $199 per night (USD)

    VRBO

    Spacious & Modern 4BR\/1BA Suite Near Downtown and Night-Life

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to our beautifully renovated four bedroom, one bathroom apartment located in the trendy Humboldt Park/Wicker Par ...

    From $199 per night (USD)

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  • Cozy Spacious Logan Square\/Wicker Park 2BR Apt
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    Cozy Spacious Logan Square\/Wicker Park 2BR Apt

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This newly remodeled, cozy, boho- styled apartment has everything you need for your visit to Chicago. The space is conve ...

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  • Light Filled, bright and close to downtown
    From $118 per night (USD)

    VRBO

    Light Filled, bright and close to downtown

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Beautiful and light filled second floor two bedroom/1 bath apartment that has been recently renovated located a block aw ...

    From $118 per night (USD)

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  • Charming 3bd Duplex Down in Central Logan Square by RedAwning
    From $431 per night (USD)

    VRBO

    Charming 3bd Duplex Down in Central Logan Square by RedAwning

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your home away from home in the heart of Logan Square! My 3bed duplex down offers the perfect blend of comfor ...

    From $431 per night (USD)

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  • Stunning modern Luxury home with 3 outdoor spaces. Minutes from downtown Chicago
    From $795 per night (USD)

    VRBO

    Stunning modern Luxury home with 3 outdoor spaces. Minutes from downtown Chicago

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to our one-of-a-kind home! Situated across from Smith Park tennis courts and a short walk from Wicker Park and U ...

    From $795 per night (USD)

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  • 3 Bedroom FREE parking Chicago - Wicker Park Tulum Inspired apartment
    From $192 per night (USD)

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    3 Bedroom FREE parking Chicago - Wicker Park Tulum Inspired apartment

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Who says you can’t bring Tulum to Chicago? Enjoy the most vibrant bohemian vibes in Wicker Park while you enjoy the rel ...

    From $192 per night (USD)

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    Details
  • Steps from 606 bike trail near Logan Square and near CTA trains
    From $80 per night (USD)

    VRBO

    Steps from 606 bike trail near Logan Square and near CTA trains

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Artsy, fun hood and everything you need is very walkable. It is a biker's paradise w/ short transit to downtown Chicago. ...

    From $80 per night (USD)

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    Details
  • SUNNY 2 BEDROOM IN HUMBOLDT PARK
    From $85 per night (USD)

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    SUNNY 2 BEDROOM IN HUMBOLDT PARK

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Sunny & comfortable 2 bedroom with an office in Humboldt park. Pet friendly. Washer/dryer/dishwasher in unit. High speed ...

    From $85 per night (USD)

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  • Entire 2 bedroom with Office & Deck!
    From $149 per night (USD)

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    Entire 2 bedroom with Office & Deck!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome! This gorgeous spacious top floor unit of a 3 flat provides ample daylight and easy access to many of Chicago’s ...

    From $149 per night (USD)

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  • Luxe Spacious SFH in Bucktown w\/Secure Parking
    From $602 per night (USD)

    VRBO

    Luxe Spacious SFH in Bucktown w\/Secure Parking

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Stunning newly renovated and decorated SFH in Bucktown. Massive 5 bedroom 3.5 half bath home perfect for large families ...

    From $602 per night (USD)

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  • City Living at its Best: Stylish 2BR Getaway
    From $210 per night (USD)

    VRBO

    City Living at its Best: Stylish 2BR Getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Whether you're a solo traveler or a couple seeking a charming and budget-friendly stay in the city center, our delightfu ...

    From $210 per night (USD)

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    Details
  • Wicker Park. 3-Level Home. 12Beds.10min walk to Train. Rooftop+Spa Bath+Garage.
    From $733 per night (USD)

    VRBO

    Wicker Park. 3-Level Home. 12Beds.10min walk to Train. Rooftop+Spa Bath+Garage.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    20

    An ideal retreat for special occasions in Wicker Park. This spacious home is a celebration of contrasts. An eclectic sty ...

    From $733 per night (USD)

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  • 5BR\/5BA Architectural Estate-Theatre, Gym, Rooftop
    From $1115 per night (USD)

    VRBO

    5BR\/5BA Architectural Estate-Theatre, Gym, Rooftop

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    16

    Summary: Indulge in the epitome of luxury with this exquisite 5-bedroom, 5-bathroom architectural masterpiece spanning 4 ...

    From $1115 per night (USD)

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    Details
  • Winter SPECIAL, family & pet friendly! Visit me December '23-February '24!!!!
    From $166 per night (USD)

    VRBO

    Winter SPECIAL, family & pet friendly! Visit me December '23-February '24!!!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Well-styled living! Beautiful spacious apartment with a lot to offer - an original piece of Chicago's history! Walk into ...

    From $166 per night (USD)

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    Details
  • Cozy Vintage Chicago Apartment near Downtown
    From $128 per night (USD)

    VRBO

    Cozy Vintage Chicago Apartment near Downtown

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This is your launching pad to see the city! It is a vintage apartment with your own private entrance and space. It is wi ...

    From $128 per night (USD)

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    Details
  • Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
    From $350 per night (USD)

    VRBO

    Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    HOT HOT HUMBOLDT PARK WEST BUCKTOWN! This comfortable and welcoming, NEWLY CONSTRUCTED 5 bedroom duplex condo (2 units c ...

    From $350 per night (USD)

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  • Bright, Spacious 2 BR w\/ Private Rooftop Deck - Skyline Views!
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    Bright, Spacious 2 BR w\/ Private Rooftop Deck - Skyline Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to your urban oasis! Centrally located, experience all that Ukrainian Village and the adjacent neighborhoods hav ...

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  • A Gem on Crystal Street
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    A Gem on Crystal Street

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This stylish apartment is located in Central Humboldt Park — close to other popular neighborhoods like Logan Square, Buc ...

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  • Urban Fab!
    From $397 per night (USD)

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    Urban Fab!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Free garage parking!!! Fabulous and expansive! 4 bedroom and 3 full bathroom apartment set in trendy Humboldt Park. The ...

    From $397 per night (USD)

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  • PET FRIENDLY! Beautiful Bucktown Home Offers Room for All by RedAwning
    From $388 per night (USD)

    VRBO

    PET FRIENDLY! Beautiful Bucktown Home Offers Room for All by RedAwning

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Our single family home in the heart of Bucktown is the perfect spot for groups to stretch out with 3 bedrooms, a spaciou ...

    From $388 per night (USD)

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  • 5 BR \/ 3.5 BA Newly Built Home in Logan Square!
    From $362 per night (USD)

    VRBO

    5 BR \/ 3.5 BA Newly Built Home in Logan Square!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Stay with us at our newly renovated home and enjoy Logan Square's popular dining scene, vibe, and great location. You'll ...

    From $362 per night (USD)

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  • Beautiful 5BR\/3.5BA Home - West Town - w\/garage!
    From $510 per night (USD)

    VRBO

    Beautiful 5BR\/3.5BA Home - West Town - w\/garage!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    $486 night $486 per night 4.72 · 39 reviews CHECK-IN Add date CHECKOUT Add date GUESTS 1 guest Check availability Re ...

    From $510 per night (USD)

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  • Spacious and Sleek 4BD\/2.5BA - Logan Square!
    From $407 per night (USD)

    VRBO

    Spacious and Sleek 4BD\/2.5BA - Logan Square!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    This sleek and modern 3 bedroom / 4 queen beds / 2.5 bathroom condo is spacious and beautifully decorated with high end ...

    From $407 per night (USD)

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    Details
  • Modern & centrally located apartment with free parking.
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    Modern & centrally located apartment with free parking.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Our apartment is cozy & situated in the most sought out area in Chicago. We are centrally located near Wicker Park, Buck ...

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  • ? Lovely 3-bedroom Condo With Free Parking ?
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    ? Lovely 3-bedroom Condo With Free Parking ?

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    INTRODUCTION: A spacious 3-bedroom apartment in a hot neighborhood. Short Uber ride to Downtown Chicago. Plenty of resta ...

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  • 🦋 Garden 1BR Condo W\/ Free Parking & Comfy Queen Bed 🦋
    From $119 per night (USD)

    VRBO

    🦋 Garden 1BR Condo W\/ Free Parking & Comfy Queen Bed 🦋

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    INTRODUCTION: A charming 1-bedroom apartment in a hot neighborhood. Perfect for a couple's-getaway or a small family of ...

    From $119 per night (USD)

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  • 🦋Boho Chic 2BR Condo, Queen Bed With Free Parking 🦋
    From $188 per night (USD)

    VRBO

    🦋Boho Chic 2BR Condo, Queen Bed With Free Parking 🦋

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    INTRODUCTION: Newly remodeled spacious 2br/1.5ba apartment with modern finishes, smart tech & security, in a hip, centra ...

    From $188 per night (USD)

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  • Stay in “STYLE” Apartment, close to CHI downtown
    From $181 per night (USD)

    VRBO

    Stay in “STYLE” Apartment, close to CHI downtown

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This is a stylish two bedroom unit with all the modern touches and amenities one could ask for. Inside the space you wil ...

    From $181 per night (USD)

    VRBO

    Details
  • Luxe SFH Bucktown Retreat with Garage Parking
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    VRBO

    Luxe SFH Bucktown Retreat with Garage Parking

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Indulge in the perfect retreat for large groups in this newly renovated single-family home, featuring beautiful design a ...

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    Details