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Kid-friendly holiday rentals in Wrigleyville, Chicago

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Wrigleyville, Chicago

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

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Guest suite in Lake View

4.85 out of 5 average rating, 239 reviews

Wrigleyville/Boystown/Entire Private Floor!

1000 sq ft-entire private floor & door access. The perfect Wrigleyville/Boystown/Lake location. Zip to downtown Chicago in minutes via cab or public transportation options. Our friendly neighborhood is packed with fun bars, fabulous restaurants, unique boutiques & great music venues. Enjoy pool, ping pong and pinball and our 65" 4K flat screen TV or a seat at the bar. A Queen bed, 2 single beds in the main room, steam shower and bathroom. We have a mini fridge, microwave, coffee and home gym.

Guest favourite

Rental unit in Roscoe Village

4.9 out of 5 average rating, 398 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.

Rental unit in Lake View

4.75 out of 5 average rating, 153 reviews

Steps from Wrigley Field - Sleeps 1-4 - Play Ball!

Located steps away from Wrigley Field. 5 min = 2 1/2 blocks. = 0.2 miles. Can you get any closer? This 2nd floor beautifully furnished unit sits comfortably in Wrigleyville and sleeps up to 6 guests. Need to work, play, maybe a little of both? Your Wrigleyville unit has the best of what you are looking for. On historic Addison Ave, you can hop, skip, and jump out the door to see a baseball game, concert, go to bars, restaurants, shops, coffee shops, and outdoor life! Let's Play Ball!

Guest favourite

Home in Lake View

4.98 out of 5 average rating, 233 reviews

Wrigleyville Southport Studio

This Wrigleyville studio is the best of urban living combined with a tranquil retreat. With vintage, mahogany paneled walls and a comfy king size bed this apartment has everything! Free coffee, tea, snacks and dedicated work space. The Southport Corridor is blocks away with restaurants, bars and shopping. Free street parking and 4 blocks to El/ Brown/Purple/ Red line trains. Wrigley Field, Metro and Vic is 4 blocks away. This garden studio is the perfect retreat in the heart of Chicago!

Guest favourite

Rental unit in Lake View

4.93 out of 5 average rating, 195 reviews

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

Welcome to our family-friendly & cozy 1-bedroom/1 bathroom apartment! We are walking distance from Wrigley Field, Montrose Beach, Andersonville restaurants, Green Mill Jazz Club, Riviera, Lincoln Square, Target and grocery. Close to Red, Purple & Brown CTA trains and 22, 78 bus lines to reach airports & top sights. Street parking is open & free (check signage!) We are a smoke-free home directly across from a school with playground in a very quiet & safe neighborhood: Ravenswood/Uptown.

Guest favourite

Rental unit in Lake View

4.97 out of 5 average rating, 274 reviews

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

Guest favourite

Loft in Lake View

4.95 out of 5 average rating, 460 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

Guest favourite

Rental unit in Lake View

4.97 out of 5 average rating, 359 reviews

Charming, Spacious 3BR Lakeview Apt Near Transit

This newly remodeled 3-bedroom unit with 1-bath apartment is perfect for both leisure & business travelers. Located on a safe, tree-lined street, in the Lakeview neighborhood, with a completely private entrance of it's own. We are just a 5 minute walk away from the CTA Irving Park Brown Line, which will get you downtown in less than 20min. We are also conveniently close to Wrigley Field, Lake Michigan, Bus Stops, and other great neighborhood shops, restaurants, and nightlife.

Guest favourite

Rental unit in Lake View

4.87 out of 5 average rating, 122 reviews

The Wrigley Escape - Sleeps 1-4

Located steps away from Wrigley Field. 5 min = 2 1/2 blocks. = 0.2 miles. Can you get any closer? This beautifully furnished unit sits comfortably in Wrigleyville and sleeps up to 4 guests. Need to work, play, maybe a little of both? Your Wrigleyville unit has the best of what you are looking for. On historic Addison Ave, you can hop, skip, and jump out the door to see a baseball game, concert, go to bars, restaurants, shops, coffee shops, and outdoor life ! Let's Play Ball!

Guest favourite

Rental unit in Lake View

4.97 out of 5 average rating, 145 reviews

Walk to Wrigley * Garage Parking* Peaceful Patio

Relax in our comfortable apartment after exploring Wrigley or visiting one of the many bars and restaurants nearby. The apartment boasts 3 bedrooms with large living spaces in the Kitchen, Living Room, and Dining Room. In the summer you can enjoy our beautiful backyard patio with the option to grill or relax before the Cubs game. If you feel like exploring more of Chicago, the brown line is a short 10 minute walk away and there are always Uber’s or Lyft’s available.

Guest favourite

Rental unit in Lake View

4.93 out of 5 average rating, 155 reviews

Quirky Quarters at Wrigley

I think you are just going to love my apartment. The space features wonderful large street level windows in the living room and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a ten minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. There is no parking available with the apartment.

Guest favourite

Rental unit in Lake View

4.87 out of 5 average rating, 275 reviews

WELCOME TO NANCY'S PAD!

BOOK TODAY!! `Located in the heart of Lakeview this fabulous flat has everything you want. We have taken the time and care to make your stay PERFECT! This comfy 2-bedroom and 1-bath apartment sleeps 6 with luxury pillow top mattresses and an Air Dream air mattress on the sofa bed. And the best part...we are family/kid oriented. Free laundry is available in the basement of this flat.

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Popular amenities for Wrigleyville, Chicago family-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Guest favourite

Home in Lake View

4.95 out of 5 average rating, 110 reviews

Entire house 1 City block from Wrigley Field!

Guest favourite

Home in Lake View

4.95 out of 5 average rating, 300 reviews

The Roscoe House near Wrigley Field

Guest favourite

Home in Roscoe Village

4.94 out of 5 average rating, 252 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Guest favourite

Home in Lake View

4.88 out of 5 average rating, 162 reviews

Lake View | Wrigley Designer House w/Patio

Guest favourite

Home in Wrigleyville

4.91 out of 5 average rating, 171 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Guest favourite

Home in Lake View

4.94 out of 5 average rating, 178 reviews

Wrigleyville Greystone

Guest favourite

Home in Jefferson Park

4.91 out of 5 average rating, 107 reviews

Chicago getaway for two!

Guest favourite

Home in Lake View

4.96 out of 5 average rating, 208 reviews

Charming 2BR on Quiet Street Close to the Action

Family-friendly apartment rentals

Guest favourite

Rental unit in Lincoln Square

4.96 out of 5 average rating, 352 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Guest favourite

Rental unit in Lake View

4.97 out of 5 average rating, 330 reviews

Lincoln Park/Lake View/Wrigley/Walk to El/Parking

Guest favourite

Rental unit in Lincoln Park

4.96 out of 5 average rating, 107 reviews

Elegant Depaul Apt on Jonquil Park

Guest favourite

Rental unit in Lake View

4.98 out of 5 average rating, 262 reviews

A Whimsical Fairy-tale Loft in Ravenswood Chicago

Guest favourite

Rental unit in Lincoln Square

4.93 out of 5 average rating, 109 reviews

Beautiful, sunny 2nd floor 3BR/1BA w free parking

Guest favourite

Rental unit in Andersonville

4.96 out of 5 average rating, 285 reviews

Sunny, Cozy, Colorful Andersonville

Guest favourite

Rental unit in Lake View

4.98 out of 5 average rating, 179 reviews

Modern vintage chic steps from Wrigley Field!

Guest favourite

Rental unit in Edgewater

4.93 out of 5 average rating, 410 reviews

Ravenswood Guest House Annex

Family-friendly apartment rentals

Guest favourite

Apartment in Wrigleyville

4.92 out of 5 average rating, 101 reviews

Spacious, Clean and Steps from Wrigley Field!

Guest favourite

Apartment in Lake View

4.98 out of 5 average rating, 132 reviews

HoIiday Decorated Designer’s Duplex 2bd 2bat

Guest favourite

Apartment in Lake View

4.99 out of 5 average rating, 128 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

Guest favourite

Apartment in Wrigleyville

4.82 out of 5 average rating, 335 reviews

Dream Condo steps from Wrigley Field!

Guest favourite

Apartment in Lincoln Square

4.97 out of 5 average rating, 374 reviews

Lincoln Square Gem!

Guest favourite

Apartment in Lake View

4.98 out of 5 average rating, 104 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Guest favourite

Apartment in Uptown

4.98 out of 5 average rating, 242 reviews

Near Lake Michigan & Wrigley Field

Guest favourite

Apartment in Wrigleyville

4.99 out of 5 average rating, 143 reviews

Luxury 4 bedroom steps from Wrigley

Quick stats about holiday rentals that are kid-friendly in Wrigleyville, Chicago

Total rentals
20 properties
Nightly prices starting at
$158 SGD before taxes and fees
Total number of reviews
990 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore