Family-friendly holiday rentals in Chicago

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

LIVN Millennium Park Downtown Chicago 1 BR

Experience the best of Chicago from this stylish, newly renovated 1-bedroom at 19 S Wabash Ave. Perfectly located in the heart of downtown, you'll be steps away from iconic Millennium Park, the vibrant shops of Michigan Avenue, and a world of dining options. This 1 bedroom offers modern comfort with a fully equipped kitchen, including a refrigerator, dishwasher, and coffee maker, plus the convenience of an in-unit washer and dryer, making it ideal for both short getaways and extended stays. Enjo

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot/cool tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

【Central】- Eclectic Fun 1BR APT in Wicker Park

Located in the heart of Wicker Park! Just a 5-min walk from the CTA blue line Damen station. This bright second floor 1-bedroom, 1-bath apartment allows you to access EVERYTHING Chicago has to offer all within short walking distance, with great nightlife. Just walk downstairs, you will find trendy restaurants, cocktail bars, cozy coffee shops and a variety of shops in this popular neighborhood. Want to explore downtown? Uber/Lyft or Hop on the CTA "L" train to go anywhere in the city.

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

An elegant Chicago Northside Getaway

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Entire first floor in Lincoln Square!

First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!