Family-friendly vacation rentals in Rogers Park, Chicago

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Top-rated family-friendly rentals in Rogers Park, Chicago

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

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Guest favorite

Rental unit in Edgewater

4.89 out of 5 average rating, 324 reviews

Edgewater escape, charming 2 BR, Rooftop Solar

Self check-in to a charming 2-BR+ liv/dining room, private entrance garden apartment, 3 blks to Red Line or Metra to downtown or Evanston, Skokie, theaters, restaurants, and parks. Edgewater has tree-lined streets, known as a quiet, safe, diverse & friendly neighborhood. Breakfast foods (coffee, tea, fruit, milk, cereal, bread, homemade jam) for starters. Has a microwave, small fridge, toaster oven & induction stovetop. Your stay reduces carbon emissions due to solar panels & heat/ac pumps.

Guest favorite

Rental unit in Edgewater

4.93 out of 5 average rating, 413 reviews

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Guest favorite

Rental unit in Evanston

4.94 out of 5 average rating, 133 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 18 min walk for trains to city, 5 min drive to lake. Wifi

Guest favorite

Rental unit in Edgewater

4.96 out of 5 average rating, 129 reviews

Edgewater, private, charming coach house 1 (of 2) Licensed by the City of Chicago 2209375

Our Edgewater coach house is a haven in the city. A ten minute walk to Hollywood Beach, a fifteen minute walk to fun Andersonville and a five minute walk to the 'L' train for direct downtown access, it is near to everything but feels far away from the busy city. Great restaurants are right around the corner, and Wholefoods is three blocks away. Managed 100% for guests, two independent units are superbly comfortable/ pristine. All essentials and more provided. Enjoy the city and relax at once.

Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 235 reviews

A guest suite centrally located, but so quiet...

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my guest suite w/private kitchen, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Guest favorite

Rental unit in East Rogers Park

4.98 out of 5 average rating, 132 reviews

Vintage Charm Near Lake

This is a 3 bedroom flat located on the 2nd floor of a historic brownstone, 1 block from the beach. Guests have easy access to the beach and lakefront parks, tennis courts, Loyola University and library, Starbucks and restaurants, Jazz club, tot-lot playground and movie theater, all within walking distance. This location has easy access to downtown or the North Shore and Northwestern University using the Red Line.

Guest favorite

Condo in East Rogers Park

4.99 out of 5 average rating, 278 reviews

Northside Chicago Favorite with parking!

Discover this recently renovated, 3-bedroom home offering free on-premises parking and a prime location. Only 3 blocks from Lake Michigan, convenient access to public transportation, express bus to downtown, Navy Pier, and Grant Park (9 miles), and the CTA Jarvis station just 3 blocks away. Close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). Perfect for couples, business travelers, and families.

Guest favorite

Rental unit in Andersonville

4.93 out of 5 average rating, 422 reviews

Andersonville Living

Sunny 3 Bedroom 1 Bath located in Andersonville right off Clark St. with its shopping, bars and restaurants. The apartment has vintage charm with original woodwork and floors as well as modern amenities such as the new kitchen and central AC. There is a large sunny back deck for sipping your morning coffee, wifi, cable and Amazon for your media needs.

Guest favorite

Rental unit in East Rogers Park

4.84 out of 5 average rating, 374 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.

Guest favorite

Guest suite in Lincoln Square

4.91 out of 5 average rating, 450 reviews

Cozy, Quiet, Garden Getaway!

Quiet 1BD garden apartment in Northcenter/Lincoln Square. 10 minutes to the el and Lincoln Square, one of the best neighborhoods in Chicago. Full kitchen, bathroom, cable and internet. Tree lined street close to two parks and a river walk. ****WE DO NOT RENT TO FILM CREWS****