Chicago, IL

Voted by Conde Nast as the best big city in the U.S. for 5 straight years, there’s no shortage of fun adventures to be had! The award winning food scene is as diverse as the city itself. From classic Chicago dishes to globally inspired plates, you stomach is sure to be satisfied in this city. If Museums are more your speed you can meet the world’s largest dinosaur, step inside a whirling tornado, or admire world class art in the handful of gallerias throughout Chicago! And how could one forget the countless outdoor adventures that await visitors in the “city in a garden!” One can bike the Lakefront Trail, take a boat cruise on the Chicago River, or kayak alongside the scenic skyline, and let’s not forget “The Bean” in iconic Millennium Park!

What’s Popular in Chicago

Wrigley Field Home of Chicago Cubs in Chicago, IL.

Wrigley Field

Home of Chicago Cubs

Wrigley Field is the oldest National League ballpark and has been home to the Chicago Cubs since 1916. It is baseball’s quintessential old-school, neighborhood ballpark—designed by architect Zachary Taylor Davis. Wrigley Field’s ivy fence is a twisty, tangly ground-rule-double garden—where big hits play hide-and-seek with confused outfielders as runners round the bases. Go catch a game – PLAY BALL!

Chicago hotels and skyline

Chicago’s Millennium Park

Expression of the Chicago

The lakefront campus, located in the heart of downtown Chicago, is home to the iconic “The Bean”, fountains, gardens, events, public art, skating rinks, rock climbing (Maggie Daisey Park), and plenty of green space. Grab a seat or sprawl out on the Great Lawn with a picnic as you take in a music or film festival.

Chicago Riverwalk public space on the river.

Chicago Riverwalk restaurants and bars

Beautiful outdoor spaces

You can find public art, boat tours, kayak rentals, open green spaces and it’s also home to some of Chicago’s most scenic restaurants. Riverwalk establishments are seasonal, so check with individual businesses before heading out.

Magnificent Mile in Chicago, IL.

Chicago Riverwalk restaurants and bars

Beautiful outdoor spaces

You can find public art, boat tours, kayak rentals, open green spaces and it’s also home to some of Chicago’s most scenic restaurants. Riverwalk establishments are seasonal, so check with individual businesses before heading out.

Riverwalk by the Navy Pier in Chicago, IL.

Chicago Riverwalk restaurants and bars

Beautiful outdoor spaces

You can find public art, boat tours, kayak rentals, open green spaces and it’s also home to some of Chicago’s most scenic restaurants. Riverwalk establishments are seasonal, so check with individual businesses before heading out.

Destination SItters babysitter

Chicago Hotel Babysitting Service

Professional fully screened childcare

Visiting the Windy city with your child(ren)? Not a problem! Let’s help you get some time off our professional childcare providers are here to ensure your little ones are safe, always engaged, and well cared for! We come to your destination, whether at it’s your hotel, vacation rental, or Airbnb!

A Small Glimpse of Chicago

Destination Sitters Babysitting Reviews

I want to thank you for the chance to have an adult evening out on our trip. Rebecca was wonderful! A lot of people can be overwhelmed by our triplet boys- but she seemed comfortable right away. And our boys were at ease with her immediately as well. They all had a good night! You are lucky to have Rebecca. Please give her our kindest regards.

Sherri Simonetti

Love the ease of making the reservation. Simple, straight-forward price where it is only an hourly fee. No extra or “hidden” additional costs. Greatly appreciate Yvonne making the reservation with the same sitter (Lauren) for the day where Lauren came in the morning for 4 hours then return to the hotel in the evening for another 4 hours. This really helped my 2year old adjust easily with Lauren. Just wanted to add that Lauren Crites is fantastic! My 2-year old can have stranger anxiety where if I’m not there, she would not want to stay with a sitter. Let me just say, my daughter immediately adjusted with Lauren. There were no tears. I was able to easily leave her in the hands of Lauren without any worry. Lauren is very calm, flexible, easy-going, extremely attentive to my 2 year-old and would even interact/play with my 5year old (he didn’t feel left out) while at Camp Pelican. Thank you for making our visit enjoyable. Now I have a reason to return to the area again!

Julie Chen

Libbie was absolutely amazing with my son. He had such a great time, and I felt so comfortable leaving him with her.

Zena Gardner

I loved the initial customer service. Alex made sure to find the right sitter for our six-month-old twins. Maria was excellent. Our babies were fed, changed, and completely asleep when we returned. She also updated us with texts.

Jennifer Davis

Wow. I would do anything to have a sitter like Martha at home. She was beyond qualified, the kids absolutely loved her (which made it easy for us to be away, knowing they were so happy). She was kind and gentle and so loving to the kids. And so knowledgeable. It was such a comfort having her there!

Cathy Pandila

Extremely friendly and efficient service through the booking process.
Gabby was great – my daughter had a great time with her and was great
to have peace of mind while travelling in another country. Thank you :)

Amie Shaw

The convenience of booking and paying with a credit card (I don’t like carrying a lot of cash on vacation), the sitter did a great job with our son and he had a wonderful time and was talking about the fun he had for days.

Alan Lynn

What a great resource Destination Sitters’ provides, for parents like me who want the peace of mind of leaving the kids with a safe and responsible young adult, who is also so much fun that the kids are happy to go with them. It gave me a few hours to enjoy the La Costa resort in ways that I couldn’t do with the kids. They said their sitter was “awesome.” I felt confidence to leave them with him, and I got the rejuvenation I wanted from a few hours at the spa! I will definitely be calling you again!

Sharon Josepho
destination-sitter

Subscribe to our Newsletter

Get helpful tips and advice for traveling with kids.