Richard Clark Park Rentals
- From $135 per night (USD)
VRBO
Great Chicago getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful furnished 2nd floor apartment. 2 bedroom, 1 bath. Large and spacious, with hardwood floors throughout. Nice ki ...
From $135 per night (USD)VRBO
- From $186 per night (USD)
VRBO
Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Vil ...
From $186 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Beautiful Spa Like Suite on the North side!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a quiet, tree-lined street in the North Center/Lakeview neighborhood, the featured space is a beautiful studi ...
From $225 per night (USD)VRBO
- From $194 per night (USD)
VRBO
The Avondale Guesthouse
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This is a private three bedroom house you will be reserving in the Avondale neighborhood. Plenty of available free stree ...
From $194 per night (USD)VRBO
- From $180 per night (USD)
VRBO
MODERN-SLEEK-BRIGHT Avondale Apartment...Ideal Northside Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This well appointed 2 bedroom and 1.5 bathroom apartment is the ideal place to stay in Chicago’s Northside. It’s perfec ...
From $180 per night (USD)VRBO
- From $186 per night (USD)
VRBO
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roscoe Village Inn offers charming vacation rental homes in Chicago's trendy Roscoe Village neighborhood 5 miles north o ...
From $186 per night (USD)VRBO
- From $1075 per night (USD)
VRBO
Stylish 6 Bedroom Home in Trendy Logan Square!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Our stylish and newly-built home in Logan Square has all of the space a family or group of friends traveling together ne ...
From $1075 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Gorgeous Home Near Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern design of a historic Chicago row house in one of the "cities best" neighborhoods. This home was totally redesigne ...
From $600 per night (USD)VRBO
- From $435 per night (USD)
VRBO
Modern 4 Bedroom Apt Next to Park&Pool | Lakeview
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Ready to stay in MODERN Chicago? Our NEWLY FINISHED 2-level masterpiece has IMPECCABLE DESIGN, 4 bedrooms, IN-U ...
From $435 per night (USD)VRBO
- From $71 per night (USD)
VRBO
North-Side of Chicago near Wrigley + 90\/94 + CTA Addison Blue Line Station
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Retro style 1 bedroom apartment available in the Irving Park neighborhood off of Addison Street. This is a private attic ...
From $71 per night (USD)VRBO
- From $527 per night (USD)
VRBO
Gather Together & WFH in Piece of Chicago History
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
‘The Wellington’ was created for those looking to gather in a piece of Chicago history. This thoughtfully refurbished 19 ...
From $527 per night (USD)VRBO
- From $191 per night (USD)
VRBO
Spacious 3 bedroom in ideal Roscoe village location
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Come stay in our beautiful vintage updated spacious, and comfortably furnished 3 bedroom, 1 bath, private city apartment ...
From $191 per night (USD)VRBO
- From $872 per night (USD)
VRBO
Home Near Wrigley *Free Parking & Pet Friendly!*
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Located in the vibrant neighborhood of North Center, this stunning home offers the perfect blend of relaxation and enter ...
From $872 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your getaway location in the heart of the Roscoe Village neighborhood of Chicago! A short walk to Wrigley Fie ...
From $300 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you're traveling for business or pleasure, with family, friends or solo, this comfortable 2-bedroom in a classic ...
From $225 per night (USD)VRBO
- From $325 per night (USD)
VRBO
4\/2 Home + Foosball Table | Near Wrigley
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to this four bedroom, two bathroom apartment located in the neighborhood of Lakeview. The location is f ...
From $325 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Your 1BR Homey Haven in Vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the allure of urban living at its finest with a warm invitation to our exquisitely renovated one-bedroom apartm ...
From $239 per night (USD)VRBO
- From $634 per night (USD)
VRBO
Gorgeous NEW 5 BDR\/ 4BA in Logan Square w\/Parking!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
In desirable LOGAN SQUARE - 10 minutes from Downtown Chicago, steps away from the new Restaurant Row on Diversey Avenue! ...
From $634 per night (USD)VRBO
- From $238 per night (USD)
VRBO
Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A gorgeous, spacious and relaxing 2 bedroom, 1 bathroom in Logan Square - one of Chicago's hottest neighborhoods. While ...
From $238 per night (USD)VRBO
- From $153 per night (USD)
VRBO
Spacious & Modern Family Friendly North Center Apt - Solar-Powered
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Newly renovated, modern kitchen and bath, comfortable beds, and solar-powered. Great location in a safe neighborhood, Je ...
From $153 per night (USD)VRBO
- From $488 per night (USD)
VRBO
3BR Comfy & Bright Apartment Fully Furnished
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover your home away from home in our inviting 3-bedroom apartment, where comfort and brightness create the perfect r ...
From $488 per night (USD)VRBO
- From $166 per night (USD)
VRBO
North-Side of Chicago \/ Irving Park \/ 3 Miles to Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Check out my quirky basement apartment in Irving Park. The property is right off of Addison Street. Free parking and clo ...
From $166 per night (USD)VRBO
- From $194 per night (USD)
VRBO
Roscoe Village Unit \/ Close to Addison Train Station - 5 min \/ Near Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our unit is located in one of the best neighborhoods in Chicago. We are in the heart of Roscoe Village and walking dista ...
From $194 per night (USD)VRBO
- From $218 per night (USD)
VRBO
Charming 1BR Apt in North Center Near Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our chic one-bedroom home, the perfect place to start your city adventures. This fully furnished apartment in ...
From $218 per night (USD)VRBO
- From $280 per night (USD)
VRBO
Family Friendly - Wonderful Neighborhood - Perfect Layout for all Groups - Even Pets Welcome! by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Our 4 bedroom Irving Park duplex is ideal to spend time in Chicago - Neighborly street, friendly people and plenty to do ...
From $280 per night (USD)VRBO
- From $234 per night (USD)
VRBO
Roscoe Village Coach House is Full of Light and Luxury... and an EPIC Master Suite! by RedAwning
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
**Hosting 32+ Night Reservations** Coach house in Roscoe Village gets the most fantastic light! The master suite encomp ...
From $234 per night (USD)VRBO
- From $198 per night (USD)
VRBO
Designed with You in Mind - This Property Offers Everything You Need to Work and Play in Chi-Town by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
**Now hosting 32+ nights!** Professionally-designed apartment surrounded by some of the best restaurants in the city (i ...
From $198 per night (USD)VRBO
- From $283 per night (USD)
VRBO
Charming Garden Apartment - Perfect for a Family Getaway by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The quintessential Chicago two-bedroom garden apartment - close to Wrigley Field! Ours gets beautiful light through the ...
From $283 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Logan Blvd Luxury! Enjoy the Well-Equipped Kitchen and Prime Location by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
From our beautifully updated unit on historical Logan Blvd, you can walk to the farmer's market on Sundays, then cook yo ...
From $350 per night (USD)VRBO
- From $255 per night (USD)
VRBO
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our Roscoe Village two-bedroom condo is a spacious converted storefront that can accommodate up to six people - which is ...
From $255 per night (USD)VRBO
- From $681 per night (USD)
VRBO
Stunning \/ Spacious 6BD Home + garage - Bucktown!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
About this space NEW HOME/NEWLY FURNISHED! This 5 br home is centrally located to Chicago's best areas; Wicker Park, Log ...
From $681 per night (USD)VRBO
- From $185 per night (USD)
VRBO
Decorated 1BR Apt, Natural Light, Comfy King Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We have a stunning newly remodeled one-bedroom apartment located in the vibrant St. Ben's area of Chicago. The place is ...
From $185 per night (USD)VRBO
- From $512 per night (USD)
VRBO
Beautiful 5BR Reunion Home near O'Hare and Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy this spacious and tastefully updated home in the perfect location to experience Chicago. Professionally designed a ...
From $512 per night (USD)VRBO
- From $227 per night (USD)
VRBO
Light and bright 3BD duplex in Avondale, Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ahh, the calm colors and neutral tones in this main & upper level, 3 bedroom / 2 bath duplex is just what you need to re ...
From $227 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Beautiful Apartment Just Steps to Great Live Music Venues and World Famous Chicago Nightlife by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Indulge in the charm of Roscoe Village with our beautifully designed 3-bed condo. Elegant yet cozy, it offers modern com ...
From $400 per night (USD)VRBO
- From $818 per night (USD)
VRBO
Luxury Home near Wrigley, Boystown & Andersonville
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This luxury property is perfect for family and group trips. The first floor consists of a beautiful living room, chef's ...
From $818 per night (USD)VRBO
- From $357 per night (USD)
VRBO
Avondale Condo Near Classic Bars, Eateries, and More! by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Come stay at our newly updated home in the heart of Chicago's Avondale neighborhood! Full of character and fun design to ...
From $357 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Beautiful Roscoe Village\/Hamlin Park 4 bed 3 bath.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious 4 bed 3 bath pet friendly duplex up lives like a house with everything you need and want. Great neighborhood pa ...
From $550 per night (USD)VRBO
- From $272 per night (USD)
VRBO
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Look no further - Read our reviews! Ideal for a Chicago Get-Away, business trip, or to visit family & friends! This com ...
From $272 per night (USD)VRBO
- Click For Pricing
VRBO
Modern Northside Chicago Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Great location in Avondale/Logan Square neighborhood. Rooftop deck with city views and convenient location to public tra ...
Click For PricingVRBO
- From $796 per night (USD)
VRBO
Eddy House, Roscoe Village Hideaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Steps away from Roscoe Village dining & shopping and a short train to the Mag Mile. Enjoy the best Chicago has to offer ...
From $796 per night (USD)VRBO
- From $126 per night (USD)
VRBO
Beautiful & Chic Loft on the River! Excellent location & has everything you need
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
I'm new to VRBO ! This Very Stylish & Affordable Loft is Fully Furnished on the River w/ Nature Views. You will be imp ...
From $126 per night (USD)VRBO
- From $269 per night (USD)
VRBO
home sweet home chicago - garage parking & downtown in 20m
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Chicago!! Enjoy a slice of the city with your own private apartment in the Avondale neighborhood. Perfectly ...
From $269 per night (USD)VRBO
- From $273 per night (USD)
VRBO
Cozy Garden Unit Located in North Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
My home is located on a charming tree-lined street in the North Center/Lakeview neighborhood. The featured space is a qu ...
From $273 per night (USD)VRBO
- From $750 per night (USD)
VRBO
Amazing City Get Away. Perfect for Entertaining!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to this beautiful hidden gem in the Logan Square neighborhood. Our guests love this place because of the lofted ...
From $750 per night (USD)VRBO
- Click For Pricing
VRBO
Perfect 4 Bedroom + 2 Bath unit on 2 separate floors, Free parking, CUBS
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy Chicago in this lovely and very spacious home! Entire 2 floors of space for guests to enjoy! 4 total bedrooms with ...
Click For PricingVRBO
- From $500 per night (USD)
VRBO
Charming 3-BR House in Logan Sq
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Discover this exquisite treasure nestled in the heart of Logan Square. Guests adore this residence for its 2-level, glas ...
From $500 per night (USD)VRBO
- From $235 per night (USD)
VRBO
Cozy, Bright and a Great Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Centrally located in Logan Square, this beautiful bright and airy space is overlooking one of the coolest streets in Chi ...
From $235 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Fully restored 1900's 2-Flat on Chicago’s family friendly quiet North Side.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
When I renovated this building my dream was to maintain the look and feel of a 1911 city farmhouse building's charm but ...
From $375 per night (USD)VRBO
- Click For Pricing
VRBO
Chicago Private apt Near Wrigley Field & Logan
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Welcome!! The property is a Chicago 2 Flat house, with all the amenities that you need. Sleeps 10 with tight accommodati ...
Click For PricingVRBO
- Click For Pricing
VRBO
Lovely Private Coach House in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our charming and stylish house nestled in the heart of Logan Square, Chicago! A perfect blend of urban excite ...
Click For PricingVRBO
- From $95 per night (USD)
VRBO
Cozy apartment near downtown
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Cozy studio apartment near downtown (about 10-15 minutes), 24-30 minutes to O’Hare and Midway airports. Very close to su ...
From $95 per night (USD)VRBO
- From $351 per night (USD)
VRBO
1 Garage Spot Included - Near Brown Line - NEW Listing - Hestia Apt -Northcenter
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
-1 Garage Spot INCLUDED!!!! - Fully furnished unit with everything you'll need for your stay. - Third-floor rear unit ...
From $351 per night (USD)VRBO
- From $263 per night (USD)
VRBO
3 Bdrm 2 Bath House Sleeps 8-10 in Chicago 2.5 miles to Wrigley w\/ 2 car garage.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Come park in our two car garage off the alley and make your way into our Victorian home that can sleep up to 10. Enjoy ...
From $263 per night (USD)VRBO
- From $178 per night (USD)
VRBO
Homey 1BR Apartment in Irving Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the epitome of urban living in our fully furnished 1-bedroom apartment. This gem features a well-equipped kitch ...
From $178 per night (USD)VRBO
- From $170 per night (USD)
VRBO
Private Coach House! Close to transport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Logan Square, known for its hip atmosphere, tree-lined streets, and diverse dinin ...
From $170 per night (USD)VRBO
- From $130 per night (USD)
VRBO
Spacious, private, 1 BR apt!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
About this space Clean and charming 1bed/1ba unit in highly sought after neighborhood Irving Park, Chicago! New furnitur ...
From $130 per night (USD)VRBO
- From $1146 per night (USD)
VRBO
Huge & Luxurious Logan Sq home,2 car garage,PRIVATE rooftop deck,great location!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Look no further than our newly renovated house in Logan Square! Start your adventure in Chicago from this prime location ...
From $1146 per night (USD)VRBO
- From $223 per night (USD)
VRBO
Cozy 2 Bedroom Home Near Downtown & Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our cozy Vrbo in the vibrant city of Chicago. Situated conveniently between O’Hare airport and downtown. Our ...
From $223 per night (USD)VRBO
- From $238 per night (USD)
VRBO
Luxury Meets Chic at Urban 2BR\/2BA Condo in Roscoe Village
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Luxury meets urban chic in this gorgeous, recently renovated Roscoe Village condo! Walk in to find soaring 12' ceilings ...
From $238 per night (USD)VRBO
- From $394 per night (USD)
VRBO
Stylish 3BD 2BA Apt Near Wrigley w\/ Parking x3
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a neighborhood feel within a big city. Welcome to our centrally located 3 bedroom, 2 bathroom apartment on a quiet ...
From $394 per night (USD)VRBO
- From $844 per night (USD)
VRBO
New Rehab with Car Charging!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
About this space Enjoy this stylish apartment with two levels of living space! A full gut rehab finished late 2023 provi ...
From $844 per night (USD)VRBO
- From $107 per night (USD)
VRBO
Chicago Wrigley Roscoe Village Lakeview Luxury Flat Free Parking\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Top rated bright first floor in top rated Roscoe Village. High speed internet+ work area. Bose music & Smart TV. Very sp ...
From $107 per night (USD)VRBO
- From $595 per night (USD)
VRBO
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Spacious 8-bedroom townhome withThis newly renovated and styled 8 bedroom in Avondale is ready to host you! Two units ha ...
From $595 per night (USD)VRBO
- From $151 per night (USD)
VRBO
Bright 3BR APT close to O'hare and 15 minutes to City center + O'Hare
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Centrally located, this sunny and compact second floor apartment is the perfect home base for your next Chicago trip! Pr ...
From $151 per night (USD)VRBO
- From $612 per night (USD)
VRBO
Stunning, Enormous Single-Family Home
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
This is one of the largest and most beautifully finished, urban vacation homes you will find! With five large bedrooms ...
From $612 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Unique Chicago Penthouse Loft - Amazing Deal & Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ideal for a Chicago Get-Away, business trip, or to visit family & friends! This comfortable 3rd-floor Penthouse Loft (no ...
From $400 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Avondale Oasis Beautiful + Bright Condo\nLogan Square\/Avondale
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Owned and designed by a gracious and helpful host who has 15+ years of experience in the interior design industry, this ...
From $175 per night (USD)VRBO
- Click For Pricing
VRBO
Flexhome Avondale 3BR Private Home S1 - READ INFO
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The space: Enjoy seamless living in this 2-story single-family home featuring direct access, multiple workspaces, in-uni ...
Click For PricingVRBO