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Kid-friendly vacation rentals in Wicker Park, Chicago

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Wicker Park, Chicago

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

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Loft in West Town

4.86 out of 5 average rating, 628 reviews

West Town Traveler's Lodge

Come and stay at my gorgeous 2 bedroom 1 bath condo! It's in a wonderful neighborhood, and in an ideal location for hopping around the city. It's a perfect place to re-energize between big city adventures --> just a 7-10 min walk to the Division St Blue Line Station (3 stops to The Loop). Hardwood floors, granite counter tops, high ceilings, a large back patio, some cool furniture, and exposed brick await in this charming West Town loft. Easy access to both airports via public transit is a plus!

Guest favourite

Rental unit in Wicker Park

4.82 out of 5 average rating, 407 reviews

WESTERN AVE ARTISTS LOFTS- Park Free

FREE street PARKING. Walk to Wicker Park restaurants, bars & shopping. 10 MINUTE WALK to CTA Blue line TRAIN-Damen stop. Premium queen mattress ( small bedroom but a queen bed) & brand new sofa bed. Full kitchen & washer & dryer in apartment. Resident artists work on first floor of this historic former telephone repair and switching station. Very laid back vibe. EVERYONE is Welcome. All guests must be on the reservation for $total. Note $30 per night per guest charge AFTER 2 Guests ( 3&4)

Guest favourite

Rental unit in Logan Square

4.95 out of 5 average rating, 200 reviews

Tastefully designed 1500 Sq of Homeyness!

Newly rehabbed, charming 2 bd duplex down apartment in Bucktown. + Tastefully FURNISHED with comforts of home + FULLY EQUIPPED KITCHEN with Calphalon cookware, bakeware and serveware. + COMPLETE TURNOVER with every booking. + 2 minutes to the train station to get to/from O'hare and downtown. + By the entrance to the 606. Walk to vibrant nightlife, restaurants and shopping. + Free street parking. Permit provided Please be aware that you may hear construction noises between the times 8am-8pm.

Guest favourite

Rental unit in Wicker Park

4.96 out of 5 average rating, 119 reviews

Spacious Studio w/Balcony in Bucktown/Wicker Park

My place is in the heart of one of Chicago's Hottest and Hippest neighborhoods(Wicker Park/Bucktown) with everything you need or want within a short walk - Transportation(Blue Line Train) which is a direct shot to and from O'hare airport, Dining, Nightlife, High End boutique shopping. 15 minutes to the Magnificent Mile, Millennium Park, Wrigley Field. Perfect for couples, solo adventurers, and business travelers with Internet and Cable TV included. Sleeps 2 adults comfortably w/sleeper sofa.

Guest favourite

Rental unit in West Town

4.95 out of 5 average rating, 286 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Clean, stylish & comfy apartment, perfect for 1 or 2 adults. 2 guest maximum, no children. Close to public transit (bus), wonderful restaurants & bars, gift shops, boutiques, coffee shops, parks, museums & more. Ukrainian Village/Humboldt Park area. King size comfortable Tempurpedic mattress. Central heat, A/C. Nice kitchen, nice shower & tub. Free street parking. Relax in the comfort of the Turquoise Wonder! Enhanced cleaning protocols for COVID. Sorry, no laundry facilities available in unit.

Guest favourite

Rental unit in Wicker Park

4.95 out of 5 average rating, 293 reviews

Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!

Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.

Guest favourite

Rental unit in Wicker Park

4.95 out of 5 average rating, 131 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Guest favourite

Rental unit in Ukrainian Village

4.98 out of 5 average rating, 256 reviews

Ukrainian Village Garden Retreat

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

Rental unit in Wicker Park

4.9 out of 5 average rating, 123 reviews

Strictly Commercial Storefront: Humboldt, Bucktown

Enjoy a private entrance to your street-level storefront apartment at the intersection of Bucktown, Wicker Park, Humboldt Park and Logan Square neighborhoods. Easy access to transport. Rest in comfort and check out the 606 elevated trail, Humboldt Park, restaurants, shopping, and nightlife. Well-outfitted apartment features exposed brick, unique lighting, and lofted bedroom. Anthropologist? Watch the street scene through one way glass. You can see out, but your subjects can't see in.

Condo in West Town

4.87 out of 5 average rating, 126 reviews

Spacious Duplex in Great Location

This below-grade unit has everything you want! Nestled on a quiet tree-lined street public transport is close by and downtown is a quick car ride away. The condo has lots of space and all the amenities you can ask for - plenty of parking, a King sized bed with premium linens, a luxury memory foam mattress, walk-in closet to store all your things, double spa shower, and a coffee bar stocked with top shelf Nespresso coffee. This unit books up quickly, so grab it today!

Guest favourite

Home in Wicker Park

4.96 out of 5 average rating, 225 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Loft in Wicker Park

4.89 out of 5 average rating, 124 reviews

Entire Loft in Heart of Wicker Park with Parking

Entire floor in one of the coolest neighborhoods of Chicago. You will have access to whatever you desire right here, from it’s amazing abundance restaurants, shopping and cafes to walking the almost three mile walkway of the “606” and it’s rotating installations, observatory and relaxed vibe. At the end of your day you’ll love heading back to your wide open space with its retro inspired furnishings with just the right amount of modern amenities and comfort.

Vacation rentals for every style

Get the amount of space that is right for you.

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Wicker Park, Chicago kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Guest favourite

Home in Wicker Park

4.93 out of 5 average rating, 352 reviews

Amazing Penthouse Skyline Views!

Guest favourite

Home in Uptown

4.9 out of 5 average rating, 356 reviews

Private 3rd Floor Apartment

Guest favourite

Home in Lake View

4.98 out of 5 average rating, 233 reviews

Wrigleyville Southport Studio

Guest favourite

Home in West Town

4.96 out of 5 average rating, 108 reviews

Cozy/Spacious WFH Family Friendly w Permit Parking

Guest favourite

Home in Jefferson Park

4.9 out of 5 average rating, 110 reviews

Chicago getaway for two!

Guest favourite

Home in Oak Park

4.97 out of 5 average rating, 112 reviews

Clean, Cozy 1st Flr, 3 Beds, Kitchen, Free Parking

Home in Near West Side

4.85 out of 5 average rating, 480 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

Guest favourite

Home in Portage Park

4.98 out of 5 average rating, 187 reviews

The Evergreen House

Family-friendly apartment rentals

Guest favourite

Rental unit in Ukrainian Village

4.9 out of 5 average rating, 507 reviews

iKlektik House Chicago / Robin

Guest favourite

Rental unit in West Town

4.95 out of 5 average rating, 401 reviews

A Vintage Pink House in the Heart of Chicago

Guest favourite

Rental unit in Logan Square

4.9 out of 5 average rating, 379 reviews

Sunny Logan Square Artists' home

Rental unit in Wicker Park

4.88 out of 5 average rating, 138 reviews

Charming Two Bedroom in Wicker Park

Rental unit in Wicker Park

4.83 out of 5 average rating, 185 reviews

Ina's Beachwood Inn In the Heart of Wicker Park

Guest favourite

Rental unit in Logan Square

4.88 out of 5 average rating, 161 reviews

Bright and Cozy 1BR Apartment in Logan Square!

Rental unit in Wicker Park

4.95 out of 5 average rating, 132 reviews

Hip 3 BR in Heart of Historic Wicker Park!

Rental unit in Logan Square

4.8 out of 5 average rating, 288 reviews

Cozy 2BR Garden Apt, Steps from Train

Family-friendly condo rentals

Guest favourite

Condo in West Town

4.89 out of 5 average rating, 257 reviews

2 King Bed Condo Easy Downtown Free Street Parking

Guest favourite

Condo in West Town

4.92 out of 5 average rating, 102 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

Guest favourite

Condo in Lincoln Square

4.97 out of 5 average rating, 376 reviews

Lincoln Square Gem!

Guest favourite

Condo in West Town

4.96 out of 5 average rating, 106 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Condo in West Town

4.86 out of 5 average rating, 229 reviews

Bold Ukrainian Village 2 Bedroom w/Garage Parking

Guest favourite

Condo in West Town

4.97 out of 5 average rating, 155 reviews

Sunny Tri Level

Guest favourite

Condo in Ukrainian Village

4.93 out of 5 average rating, 110 reviews

Modern Chicago Movie Themed Apt

Guest favourite

Condo in Lincoln Park

4.95 out of 5 average rating, 472 reviews

Unique Lincoln Park Duplex Apt

Quick stats about vacation rentals that are kid-friendly in Wicker Park, Chicago

Total rentals
30 properties
Nightly prices starting at
$56 CAD before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

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