Family-friendly holiday rentals in Downtown Chicago

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Top-rated family-friendly rentals in Downtown Chicago

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Guest favourite

Rental unit in Chicago

4.87 out of 5 average rating, 175 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 favourite

Guest suite in Chicago

4.96 out of 5 average rating, 330 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.

Superhost

Apartment in Chicago

4.86 out of 5 average rating, 457 reviews

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed -> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

Superhost

Rental unit in Chicago

4.82 out of 5 average rating, 189 reviews

Your brand new Chicago suite (unit 1F)

Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.

Superhost

Rental unit in Chicago

4.79 out of 5 average rating, 277 reviews

Cozy Lincoln Park Nook with Free Street Parking!

This apartment is on the lower level of an updated 1880s Chicago frame home in Lincoln Park and includes its own separate, private entrance. - Fast internet! - Washer/Dryer (private, in-unit) - Free, plentiful street parking! (a rarity in Chicago) Just a few blocks west of DePaul University (0.5-1 mi), the apartment is located on a bustling main street with easy access to public transit (bus, train, & Metra) and a variety of bars and restaurants. Please note ceiling height is 7 ft!

Superhost

Rental unit in Chicago

4.84 out of 5 average rating, 780 reviews

Hip Chicago Apartment - FREE Parking Spot Included

You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run

Superhost

Rental unit in Chicago

4.94 out of 5 average rating, 233 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 favourite

Townhouse in Chicago

4.87 out of 5 average rating, 312 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.

Superhost

Rental unit in Chicago

4.81 out of 5 average rating, 206 reviews

In artistic Pilsen~Continental Breakfast~Near DWTN

Located in the artistic town of Pilsen; minutes away from downtown Chicago, Lake Shore drive, Shedd aquarium, United Center, UIC Pavilion and McCormick Place. Great and convenient location. Walking distance from CTA #60 bus-stop and pink line to downtown. Enjoy charming first floor, full kitchen, & bathroom. Also includes continental breakfast for first day of your stay and street parking with permit.

Guest favourite

Apartment in Chicago

4.97 out of 5 average rating, 756 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.