World's Fair Bison Rentals
From $164 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 $164 per night (USD)VRBO
From $600 per night (USD)VRBO
*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 $600 per night (USD)VRBO
From $231 per night (USD)VRBO
Luxury Chicago 2 Story Condo: 10 Mins 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 $231 per night (USD)VRBO
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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 ...
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Bucktown Apartment near all amazing restaurants, shops and bar\/lounges
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Recently renovated apartment in a two-story building. Sits right above our family-owned and operated chicken restaurant. ...
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From $554 per night (USD)Expedia
Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop, 2car Garage
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 16
Luxurious Modern Retreat with 1000 sqft Rooftop Welcome to the Monticello - our stunning modern new construction, desig ...
From $554 per night (USD)Expedia
From $362 per night (USD)VRBO
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Bee's Knees - a blast from the past with a hollywood-glam twist. This 4 BR home is the perfect getaway for a ...
From $362 per night (USD)VRBO
From $151 per night (USD)Expedia
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer\/Dryer
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Unwind in Chicago at this lovely newly renovated home! Nestled in the heart of West Town, this amazing property offers a ...
From $151 per night (USD)Expedia
From $156 per night (USD)VRBO
~Exquisite 2-BR Residence| Top Notch Amenities ~
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to our Chic 2-Bedroom Haven in Ukrainian Village, Chicago! This stunning modern unit offers high-end am ...
From $156 per night (USD)VRBO
From $667 per night (USD)Expedia
8 beds. Wicker Park Spacious Guest House wi\/Spa Bath, Fireplace, 1 Grg Spot.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 13
Escape to a superb 3-bedroom guest house in Wicker Park. This enjoyable retreat is a Unwind, relax, and enjoy everything ...
From $667 per night (USD)Expedia
From $106 per night (USD)VRBO
Apt w\/ Deck ~ 6 Mi to Downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Urban Neighborhood | WFH Friendly | Washer/Dryer Your next long-term stay awaits at this 2-bed, 1-bath Chicago vacation ...
From $106 per night (USD)VRBO
From $541 per night (USD)Expedia
Family Fun Escape: With 2 Free Parking Spaces!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
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 $541 per night (USD)Expedia
From $275 per night (USD)VRBO
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 $275 per night (USD)VRBO
From $216 per night (USD)VRBO
SPRING Special, April-May '24! Contemporary, elegantly styled spacious flat!!!!
- 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 $216 per night (USD)VRBO
From $328 per night (USD)VRBO
NEW LUXURY PENTHOUSE CONDO
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
OVERVIEW: This is a spacious penthouse condo with an amazing city skyline view on private rooftop terrace. Comfortably s ...
From $328 per night (USD)VRBO
From $276 per night (USD)Expedia
NEW LUXURY CONDO WITH PATIO DECK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
OVERVIEW: This is a high end first floor condo that comfortably sleeps 5 persons. Luxury bathrooms. Fully equipped chef’ ...
From $276 per night (USD)Expedia
From $548 per night (USD)VRBO
Smart Home in Logan Square by the 606 Trail
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $548 per night (USD)VRBO
From $179 per night (USD)Expedia
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 $179 per night (USD)Expedia
From $188 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 $188 per night (USD)VRBO
From $160 per night (USD)Expedia
Brand New 3B-2BA Unit,4 miles from Downtown Chicago with WiFi, AC, Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the beauty of Chicago from this 3-bedroom apartment. This superb property offers a serene escape with a queen b ...
From $160 per night (USD)Expedia
From $224 per night (USD)VRBO
Spacious 3-bedroom apartment in lovely CHICAGO Ukranian VILLAGE w\/laundry
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Newly redesigned first floor unit with a sleek, minimalist approach. Equipped with brand new appliances, comfy beds, str ...
From $224 per night (USD)VRBO
From $249 per night (USD)Expedia
Logan Square! Renovated Vintage! Gorgeous Kitchen & Bath-private back deck!\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Steps to the 606 walking/riding trail, close to restaurants and nightlife. The place is beautiful. Tall ceilings, restor ...
From $249 per night (USD)Expedia
From $323 per night (USD)VRBO
Modern 2BR APT -- West Town -- Tons to do-- Central Location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come experience Chicago from our modern neighborhood apartment where 5 vibrant West Town neighborhoods meet: Wicker Park ...
From $323 per night (USD)VRBO
From $720 per night (USD)VRBO
Beautiful 4 Bedroom, 3.5 Bath
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Experience the ultimate comfort and style during your stay at this perfectly located 4-bedroom, 3.5-bathroom home. In th ...
From $720 per night (USD)VRBO
From $510 per night (USD)VRBO
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 $510 per night (USD)VRBO
From $418 per night (USD)Expedia
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 $418 per night (USD)Expedia
From $1090 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 $1090 per night (USD)VRBO
From $380 per night (USD)Expedia
West Town walk-up, Pets OK, 90 Walk Score, Holds 6, 1,500ft², W\/D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
• 1,500ft² / 140m² • Walk Score 90, walk to everything • Biker's paradise • Fully stocked kitchen • Safe neighborhood • ...
From $380 per night (USD)Expedia
From $123 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 $123 per night (USD)VRBO
From $220 per night (USD)Expedia
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 $220 per night (USD)Expedia
From $526 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 $526 per night (USD)VRBO
From $627 per night (USD)Expedia
Chic Mid-Century House Perfect Getaway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Our chic, cozy and spacious coach house is the perfect getaway! It has four bedrooms (with three queen beds & four twin ...
From $627 per night (USD)Expedia
From $590 per night (USD)VRBO
5BR\/4BA Architectural Estate-Theatre, Gym, Rooftop
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: Indulge in the epitome of luxury with this exquisite 5-bedroom, 4-bathroom architectural masterpiece spanning 4 ...
From $590 per night (USD)VRBO
From $275 per night (USD)VRBO
WINTER SPECIAL, family & pet friendly! Visit me November-December '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 $275 per night (USD)VRBO
From $133 per night (USD)VRBO
Cozy Vintage Chicago Apartment near Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $133 per night (USD)VRBO
From $390 per night (USD)Expedia
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 $390 per night (USD)Expedia
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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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From $360 per night (USD)Expedia
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 $360 per night (USD)Expedia
From $353 per night (USD)VRBO
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 $353 per night (USD)VRBO
From $303 per night (USD)Expedia
Charming and Recently Renovated - You Will Love This Humboldt Park Area Home by AllSet Turnover
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our newly gut-renovated 4 bedroom condo is in a classic Chicago building and has high-end features throughout. We're ide ...
From $303 per night (USD)Expedia
From $270 per night (USD)VRBO
PET FRIENDLY! Beautiful Bucktown Home Offers Room for All by AllSet Turnover
- 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 $270 per night (USD)VRBO
From $295 per night (USD)Expedia
Go Out or Stay In... This Property Has Everything You Need for a Perfect Visit - Just Steps from Humboldt Park by AllSet Turnover
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Get a taste for the Chicago high life in this stylish condo, with exposed brickwork, mocha-stained hardwood flooring and ...
From $295 per night (USD)Expedia
From $466 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 $466 per night (USD)VRBO
From $310 per night (USD)Expedia
Lovely 3-bedroom Condo With Free Parking King Bed
- 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 ...
From $310 per night (USD)Expedia
From $201 per night (USD)VRBO
Garden 1BR Condo W\/ Free Parking & Comfy Double Bed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
INTRODUCTION: A charming 1-bedroom apartment in a hot neighborhood. Perfect for a couple's-getaway. Short Uber ride to D ...
From $201 per night (USD)VRBO
From $309 per night (USD)Expedia
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 $309 per night (USD)Expedia
From $217 per night (USD)VRBO
Stay in “STYLE” Apartment, close to CHI downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $217 per night (USD)VRBO
From $456 per night (USD)Expedia
Luxe SFH Bucktown Retreat with Garage Parking
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Indulge in the perfect retreat for large groups in this newly renovated single-family home, featuring beautiful design a ...
From $456 per night (USD)Expedia