Vacation rentals in North Side

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Top-rated vacation rentals in North Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private room in Chicago
#4 Historic Chicago Home - Private Single Bedroom
The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan - perfect for gatherings of any kind. We're in the heart of the Rogers Park, walking distance from many restaurants & shops, one block from Loyola Beach Park, and 5-15 mins walk to 2 different train / metro lines. Breakfast is self-serve & included with bagels, cream cheese, eggs, yogurt, cereal & fresh fruit. The home is run by friendly local folks who are happy to help during your stay.
$35 per night
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Rental unit in Chicago
Hip Chicago Apartment - FREE Parking Spot Included
You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run
$24 per night
Loft in Chicago
Grand Studio in the Heart of Lakeview!
NEW Listing: Artsy loft style studio in Lakeview; steps from the Belmont Red/Brown/Purple Lines. Quiet interior unit, high 15ft concrete ceilings, dishwasher, multi-view wall mounted TV, full size murphy bed, and walk in closet. Gorgeous Rooftop views. Close to Wrigley Field, Lakeshore Drive, Target, and Whole Foods. Twenty minute train ride to the loop.
$51 per night
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Other great vacation rentals in North Side

Rental unit in Chicago
Stylish mid-century modern apartment
$66 per night
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Rental unit in Chicago
Modern Uptown Apartment - Clean & Close to Train!
$36 per night
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Rental unit in Chicago
Short-Term Sublet Near Lake Michigan
$42 per night
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Rental unit in Chicago
Loyola University | Cosy Apartment
$70 per night
Private room in Chicago
#1 Historic Chicago Home - Private Queen Bedroom
$47 per night
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Rental unit in Chicago
Private unit with sauna in safe, pretty area!
$59 per night
Private room in Chicago
Comfy and convenient in Lincoln Square
$55 per night
Condo in Chicago
Gorgeous 1bd/1ba in the Heart of Logan Square
$89 per night
Condo in Chicago
Charming Lincoln Park Duplex Apartment
$91 per night
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Rental unit in Chicago
10% Winter Promo! Stylishly Furnished Studio Apt
$48 per night
Loft in Chicago
Industrial Style Chicago Loft with FREE parking
$45 per night
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Rental unit in Chicago
Modern Chicago Loft with a Complimentary Garage Spot
$45 per night
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