Family-friendly vacation rentals in Chicago Loop

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Top-rated family-friendly rentals in Chicago Loop

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Guest favorite

Rental unit in Lincoln Park

4.87 out of 5 average rating, 178 reviews

Chicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre

This East Lincoln Park condo is steps to the lakefront, restaurants, shopping, the Zoo, North Pond Nature Sanctuary, and more! Features 2 bedrooms, 2 desks, and a brand new marble bath & kitchen (plus a pack-in-play!). This dream location is across the street from the $22MM Morningstar mansion. Since the 1800s the term pied-à-terre (literally 'foot-to-the-ground') has meant a vacation or weekend home in the city. Whether your Chicago travel is leisure or business, you'll feel right at home. Experience Chicago like a local, in this incredible East Lincoln Park location. This renovated condo in a vintage building is the perfect launching pad for your stay in Chicago. 1st Bedroom This bedroom has a queen bed, desk, and desk chair. Please note that the bedroom "door" is a curtain. 2nd Bedroom The second bedroom has a queen bed, desk, and under-bed storage drawers. WIFI + Work We offer wifi throughout the apartment. Should you need to get work done during your visit, both bedrooms have desks. Kitchen The new white quartz kitchen is small but mighty! Features white quartz countertops, a marble backsplash, garbage disposal, a gas range, Bosch dishwasher, LG fridge, microwave, electric kettle and drip coffee maker. It is stocked with cooking essentials and utensils. If salt, pepper, oil or sugar run out during your stay you would be responsible for purchasing additional, if needed. Coffee and Tea We provide an electric tea kettle, 5-cup drip coffee machine and ground coffee. Feeling indulgent? The area has MANY coffee shops! Families For those traveling with youngsters, a pack-in-play and bedtime books are provided. The apartment's walk-in closet is large enough to set up the provided pack-in-play if you like. Note that the apartment's outlets have not been covered. Climate Control Each bedroom has a window AC unit in the summer. Radiators heat the home in the winter. Living and Dining Room The combo living/dining room has a wall-mount 2020 55” smart television and a small counter-height table. The sofa folds down into a bonus 3rd bed. If you plan to use the sofa as a sleeping space, kindly bring your own additional bedding. Laundry A coin-operated laundry room is located in the building. $0.75 to wash and $0.75 to dry. Pets Pets are considered on a case by case basis with a pet fee and *must* be given advanced authorization to be at the property *before* booking. A $250 fine will be assessed if any pets are found on the property without prior authorization. Parking Free street parking is available in the neighborhood. Although we don't have off-street parking, the hospital garage a 1/2 block away at 2515 N Clark St has paid parking ($6 for 3 hours, $10 for 7 hours, $15 for 24 hours). Pied-à-Terre My husband and I use this home as our own pied-à-terre. Accordingly, we put a lot of attention into the details that make us feel comfortable when traveling. Some of those details include high thread-count cotton and linen bedding, and high quality fixtures and appliances. We're always thrilled to see others enjoying the home just as much as we do! I would love to host you! Send me a message with any additional questions you may have. ♡ Heather FAQ's Q: Do you offer early check-in or late check-outs? A: We use this precious little time we have between guests to prepare the home following the CDC Cleaning Guidelines, as well as to complete any maintenance tasks, so your stay is uninterrupted. If you request an early check-in or late check-out, we will try to accommodate if possible but cannot confirm until a day or two ahead. If additional time is important, we recommend booking an additional night to your stay. Q: Do you allow luggage drop-off for early arrivals or late departures? A: We are unable to guarantee the availability of luggage drop-off, but will accommodate when possible. Q: Do you offer a cleaning service? A: Our cleaners can accommodate additional cleaning services for an added cost. Just ask us! Q: Is the home ADA accessible? A: The home is on a high first floor 12 steps up. Q: Can I book on behalf of a friend, family member or co-worker? A: While we would love to host whoever you are booking for, we do need them to book for themselves with their own account. For business trips or if you book travel for your company, Airbnb allows designated bookers at companies enrolled in Airbnb for Work to book trips on behalf of others. This is a fantastic neighborhood with an incredible amount of restaurant, shopping and entertainment options steps away! Street parking is available, no permit needed! No on-site parking. The building has a shared laundry room. The picturesque, affluent Lincoln Park neighborhood is a nature lover’s dream — manicured gardens, a hidden lily pond, historic homes, and tons of lakefront green space with sweeping city views. It also happens to be home to one of the country’s oldest free zoos and an acclaimed dining scene! PARKING • Free street parking is available in the neighborhood and a permit is *not* needed. Although we don't have off-street parking on the premises, the hospital garage a 1/2 block away at 2515 N Clark St has paid parking ($6 for 3 hours, $10 for 7 hours, $15 for 24 hours). BUS • Clark Street has a bustling bus schedule and the #22 Clark and #36 Broadway are very frequent. The #151 is a half block east on Stockton and will take you directly down Michigan Ave. On weekdays you can also grab the #156 LaSalle at that same stop. BIKE • We’re a biking city. Chicago has 303 miles of bike lanes and the second-highest percentage of commuters riding their bikes to work. Our bike share program is called Divvy. We have 3 dock stations within an approx. 4-minute walk of the apartment. The cost is $3.30 for a single 30 minute ride; $15 for a day pass of unlimited rides in a 24-hour period, up to 3 hours each. Passes can be purchased at the dock. TRAIN • The closest El station is the Fullerton Red, Purple and Brown Line station [13 min. walk]. TAXI • Uber/Lyft/Curb: These ride hailing apps are all easy to use and convenient! Although the maximum number of people you may have on your reservation is 5, the apartment is set up for 4 people. Please note that the blue sofa and dining table are apartment-sized (see photos). Four bath towels, two hand towels, and two wash cloths are provided. There is a laundry room on site should you require freshly washed towels during your stay. The blue sofa does fold down into a bonus 3rd bed. This has not been included in the listed number of beds because extra bedding is not provided for this 3rd bed.

Guest favorite

Rental unit in Wicker Park

4.97 out of 5 average rating, 260 reviews

Stylish First Flr. Studio. Best Location Division+Hermitage.

Clean! Private! Studio located in the popular Ukrainian Village. This quiet unit is located in a charming 19th century pink brick Victorian cottage. It is a great retreat from work or play when visiting Chicago. This welcoming space features modern amenities, stylish decor with unique artwork, tall ceilings and an inviting color palette. Hermitage House Studio a perfect home away from home with in unit laundry, cable with On Demand and green filled backyard patio perfect for sipping your morning coffee or tea. Need 2nd space same building? Check out airbnb.com/h/chicago-hermitage-loft2 This private –very hip studio apartment - completely renovated and newly decorated is set up like a posh hotel suite with all the amenities of home!! Used for guests only this cozy and modern first floor apartment is set in an 1892 vintage brick cottage with a beautiful outdoor rear patio on a quiet tree lined street! This richly colored designer decorated space with all original artwork has comfort in mind. It has plenty of seating including a comfortable leather sofa, a cool desk area and raised bar. Hardwood floors throughout living space, 9’ ceilings, washer/ dryer, central air and heating, hotel like bathroom with soaking tub and an in unit stacking washer/dryer. Modern white kitchen has granite countertops, quartz sink, gas stove-oven, dishwasher, garbage disposal , microwave. The kitchen has many fun gadgets like French press coffee maker, electric tea pot and more. Everything is available for you to use. The high counter with barstools separates the kitchen from the living/sleeping space. The relaxing bedroom area accommodates 2 with a queen pillow top Serta mattress, great lighting, beautiful Mediterranean blue curtains and storage end tables filled with additional blankets. A full aero bed can accommodate a third person if needed. There is a custom closet system with great storage for personals, shoes and folded clothing. Perfect for a couple or an Airbnb business user! Flat screen TV with cable and movie channels Fast Wi-Fi This unit is located in the quiet first floor rear of this building. The first floor rear patio is yours to enjoy! The upper level deck is private. This unit features a digital locks. You will be able to pick your own code before check-in. I am readily available but will respect your privacy unless you need me. I live in the building (Sometimes out of town) but always accessible by phone or internet if anything is needed but the place is yours to enjoy! Located just steps off bustling Division Street this neighborhood has it all without the fuss of downtown. Within walking distance there are restaurants with cuisines from around the world as well as comfort food. Nightlife options including live music and sports venues. There is boutique shopping, art galleries, a local gym and even a mini Target. This cozy Studio is quick walk from the Division St. Blue-Line train that will get you downtown or to O'hare Airport in minutes. Just two blocks to the Division Blue line running from O’Hare and downtown at the intersection of Division/Ashland/Milwaukee This is a great walking neighborhood but it is easily accessible to many buses, cabs, trains and even the new shared Divvy bike station just a block from the studio. If you choose to drive there is zoned parking permits available- 1 per day. I will happily provide directions to attractions, neighborhoods, great food, groceries, coffee and nightlife

Superhost

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 favorite

Guest suite in West Town

4.96 out of 5 average rating, 331 reviews

Secret Garden | Noble Square | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Guest favorite

Rental unit in Roscoe Village

4.9 out of 5 average rating, 400 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 Lincoln Park

4.96 out of 5 average rating, 408 reviews

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

Guest favorite

Rental unit in Logan Square

4.9 out of 5 average rating, 379 reviews

Sunny Logan Square Artists' home

2nd floor classic Chicago 2flat with lots of light. 3 bedrooms available, with 2 additional sofabeds. Great if you and family/group of friends are in town for an event and want to stay together. Grocery store 1.5 blocks away. Quiet street. Parking is decent. New bath has all marble walls, extra long/deep tub and rain shower. 1 mile walk to the Logan Square CTA Blue Line and Logan Square brunch/night-life. 5 min walk to Metra. Walk to 606 trail. Chicago Registration Number: R24000117459

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

Townhouse in Near West Side

4.87 out of 5 average rating, 316 reviews

CITY CONDO with GARAGE 7 min Walk to Train

Experienced Super-host offers private spacious & sunny condo 3 miles from Chicago "Loop" Lakefront and Museums. Large one bedroom with king size premium mattress, and full sized sofa-bed sleeps 4. 1 FREE garage PARKING wi-fi , washer & dryer. BUS to city center is across the street. 10 minute ride to city center. Walk to United Center Bulls/Blackhawk games /concerts and large international grocery store. Note- WE DO NOT HOST SMOKERS.

Guest favorite

Condo in West Town

4.97 out of 5 average rating, 760 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.