Family-friendly vacation rentals in Near North Side, Chicago

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Top-rated family-friendly rentals in Near North Side, Chicago

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Superhost

Rental unit in North Center

4.9 out of 5 average rating, 188 reviews

Spacious Vintage 3 BR in Chicago's NorthCenter!

Location, location, location! Vintage 3BR second floor Apartment only 10 Blocks from Wrigley Field & 2 miles from Lake Michigan. Bus stop in front, CTA Brownline train to loop a 5 minute walk, bus/CTA from OHare airport 1 block away. Washing machine and dryer in apartment. Neighborhood setting. Walk to restaurants, local breweries, Old Town School of Folk Music & theaters, ballgames, concerts, Trader Joe's, banks, boutiques . Divy bikes, CVS & Starbucks across the street. Garage option.

Guest favorite

Rental unit in Logan Square

4.96 out of 5 average rating, 414 reviews

King Bed, Huge Spa Shower, Dining Destination

This home was designed with love! Inspired by our favorite boutique hotels - nestled on a tree-lined street in Logan Square, a locals-only destination for brunch, coffee, craft beer and cocktails. Relax in the massive custom steam shower or catch up on HBO on the 50” WiFi TV. Luxe details throughout -premium espresso, memory foam beds and upgraded Italian linens, lots of outlets, and a fully-equipped kitchen. Easy parking, a rarity in the city. Central location- Quick walk to Blue Line Train

Guest favorite

Rental unit in Roscoe Village

4.9 out of 5 average rating, 399 reviews

Relax and Enjoy Chicago in an Updated and Private Apartment in Roscoe Village

We converted our garden unit into a great space for travelers, we updated everything with you in mind, features high end appliances, full kitchen, 1 king and 1 queen pullout, heated floors, and free wifi. There are only 2 beds. We also have a landscaped backyard and grill access if requested If you need anything please let me know ahead of time Roscoe Village is often thought of as a small town inside the big city. It is one mile west of Wrigley Field and two miles west of the lakefront.

Guest favorite

Rental unit in Roscoe Village

4.96 out of 5 average rating, 275 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Superhost

Rental unit in Logan Square

4.84 out of 5 average rating, 781 reviews

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

Superhost

Rental unit in Magnificent Mile

4.94 out of 5 average rating, 235 reviews

Urban Chic Apartment by the Magnificent Mile

Ideally located just half a block from Michigan Avenue, this bright and open 3rd floor apartment boasts thoughtfully appointed rooms for your comfort so will have everything you need to enjoy your stay in style! PLEASE NOTE: 3rd floor walk up (NO ELEVATOR) There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard in the living room but rarely, if ever, in the bedrooms.

Guest favorite

Condo in West Town

4.97 out of 5 average rating, 759 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Guest favorite

Rental unit in East Rogers Park

4.84 out of 5 average rating, 371 reviews

Cozy Garden Unit In Edgewater

Cozy vintage garden apartment, walking distance to University Loyola, trains, shopping and restaurants. Perfect for family or 2 adults and kids. Full-sized bed and sofa bed in living room. Spacious, clean, airy with six windows for natural light. Laundry in next room. Enclosed one car garage space included.