Uptown (Chicago) Rentals
From $1117 per night (USD)VRBO
Sensational 5 Bed beauty steps from Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
One of a kind, beautifully designed 5 bedroom 2 full bath and one half bath, two-level condo, in classic Chicago brick b ...
From $1117 per night (USD)VRBO
From $403 per night (USD)VRBO
Beautiful and Relaxing Wrigleyville Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Located across the street from Wrigley Field, this recently remodeled and thoughtfully decorated apartment provides a pe ...
From $403 per night (USD)VRBO
From $420 per night (USD)VRBO
Wrigleyville Condo 2 Blks from Lake & Train
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red lin ...
From $420 per night (USD)VRBO
From $469 per night (USD)VRBO
Wrigleyville Private Guesthouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New Guesthouse ideal for 6+guests 1 block from Southport brown line station, 1/2 mile from Wrigley Field & red line stat ...
From $469 per night (USD)VRBO
From $391 per night (USD)VRBO
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Discover Chicago's charm in this newly designed 2-bedroom condo! Located a few blocks away from the heart of Lincoln Sq ...
From $391 per night (USD)VRBO
From $481 per night (USD)Expedia
Cozy 2 bedroom apartment in Wrigleyville
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the heart of Wrigleyville, this 2 bedroom, 1.5 bathrooms in situated right on Clark St. This property comes w ...
From $481 per night (USD)Expedia
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Charming House in Lakeview - 1895. Walk to Wrigley
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
About this space Great city living in this bright, comfy, farmhouse style home. Perfect for entertaining with the whole ...
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From $421 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 $421 per night (USD)VRBO
From $423 per night (USD)VRBO
The Irving Park Hideaway – Prime Location w\/ Patio & Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
-1 Garage Spot INCLUDED!!!! - Fully furnished unit with everything you'll need for your stay. - Third-floor rear apar ...
From $423 per night (USD)VRBO
From $918 per night (USD)VRBO
The Wrigleyville Penthouse with Private Rooftop!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Steps from Wrigley Field, my 2 bed/2 bath + Den penthouse with a private rooftop is the perfect “home base” for your gro ...
From $918 per night (USD)VRBO
From $485 per night (USD)VRBO
Lovely 3 Bedroom condo near Wrigley!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
My charming 3-bedroom apartment has everything you need for your Chicago trip. The unit comes with washer/dryer in build ...
From $485 per night (USD)VRBO
From $344 per night (USD)Expedia
Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Our 2 bed garden apartment in Ravenswood will be the ideal home base for your stay! Located in one of Chicago's vibrant ...
From $344 per night (USD)Expedia
From $557 per night (USD)VRBO
Stylish Two Bedroom - A block from Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Come stay at this gorgeous, clean, renovated apartment in beautiful Lakeview/Wrigleyville. The unit is located on a beau ...
From $557 per night (USD)VRBO
From $501 per night (USD)Expedia
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
If you love Mid-Century Modern decor you will love this apartment. The light- filled main family room and sun porch is ...
From $501 per night (USD)Expedia
From $511 per night (USD)VRBO
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our charming three-bedroom duplex in Andersonville is steps to the beach, antique shopping, and so many food options - ...
From $511 per night (USD)VRBO
From $72 per night (USD)Expedia
Luxe Edgewater Studio w\/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach. with views over the city. It’ll be eas ...
From $72 per night (USD)Expedia
From $144 per night (USD)VRBO
Ideal Edgewater 1BR w\/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Edgewater Beach furnished one b ...
From $144 per night (USD)VRBO
From $774 per night (USD)Expedia
Luxury Wrigleyville condo steps from Wrigley
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
New construction property that has 4 bedrooms, one with king, two with queen beds, and one with a queen bed and bunk bed ...
From $774 per night (USD)Expedia
From $162 per night (USD)VRBO
Cute and Cozy 2 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy Classic decor in a spacious two bedroom one bathroom. Large eat-in kitchen and laundry in the basement! Tony's gro ...
From $162 per night (USD)VRBO
From $132 per night (USD)Expedia
Modern Edgewater 1BR w\/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach. with views over the city. It’ll be eas ...
From $132 per night (USD)Expedia
From $143 per night (USD)VRBO
Hip Edgewater Studio w\/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach. with views over the city. It’ll be eas ...
From $143 per night (USD)VRBO
From $134 per night (USD)Expedia
Ideal Lakeview 1BR w\/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $134 per night (USD)Expedia
From $345 per night (USD)VRBO
Warm|Cozy|Lovely|1BR|Lincoln Sq.|
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $345 per night (USD)VRBO
From $229 per night (USD)VRBO
Comfy Lincoln Square guest apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This unit, recently remodeled, is in the basement of our 127 year old Victorian home. It has its own separate entry thr ...
From $229 per night (USD)VRBO
From $132 per night (USD)VRBO
Cute, Cozy, Elegant Budlong Woods
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Book with us and enjoy classic charm and elegant décor located in the Budlong woods neighborhood. Experience a great nig ...
From $132 per night (USD)VRBO
From $142 per night (USD)Expedia
Trendy Lakeview 1BR w\/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Lake View East. with views over the city. It’ll be easy ...
From $142 per night (USD)Expedia
From $261 per night (USD)VRBO
Cute new Garden unit located between Andersonville and Lincoln Square , Chicago.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Large and quiet 1 bedroom 1 bathroom Garden unit located in a typical Chicago 2 flat building type. We are exactly betw ...
From $261 per night (USD)VRBO
From $204 per night (USD)Expedia
Comfy Garden Suite in Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A comfortable garden unit in a well cared for 3-flat, in a wonderful and safe neighborhood. Easy access to the lake fro ...
From $204 per night (USD)Expedia
From $1509 per night (USD)VRBO
The Wrigleyville Deluxe -Steps from Wrigley Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to The Wrigleyville Deluxe. Perfect for large groups. 2 full Kitchens. 3 full baths. Sleeps 10. 1 King bed. 4 ...
From $1509 per night (USD)VRBO
From $178 per night (USD)Expedia
Upscale Lakeview 2BR w\/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this charming two bedroom Blueground apartment. You’ll love coming ...
From $178 per night (USD)Expedia
From $221 per night (USD)VRBO
Modern Lakeview 2BR w\/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Lake View East. . It’ll be easy to simply show up and s ...
From $221 per night (USD)VRBO