David and Mom Rule Chicago at Hotel Allegro

We boarded the South Shore commuter train bound for Chicago Friday afternoon, both looking forward to a weekend getaway in this city we both love. We’d been to Chicago many times, but this was different. I was just the two of us,  my seven year-old son, David, and I.

Two hours later we arrived at Millennium Station. We emerged from underground to bright sunlight and the busy corner of Randolph and Michigan. Some people were standing around listening to a street performer sing, and the rest were busily on their way to somewhere. We joined the crowds moving along the sidewalk, and walked west towards Kimpton’s Hotel Allegro, our host for the weekend.

We checked into our beautiful room at Kimpton’s Hotel Allegro where Kid’s Rule this summer.

We found this special bag waiting for David.

David settled right in on the comfy bed to watch cartoons. I used the complimentary in-room WiFi to check my email.

After unpacking, we went down to the Allegro’s lobby for Kid’s Hour. David quickly made new friends, and had fun playing Wii and board games in the hotel “living room” while snacking on popcorn. I chatted with the other moms visiting the Allegro that weekend, and we were all treated to delicious food from the Allegro’s restaurant, 312.

David was tired out from all the excitement, so we headed back to our room to rest. He picked out a movie from the hotel’s on-demand choices, and relaxed under the covers.

Just when we wanted a bedtime snack, Room Service delivered chocolate chip cookies, milk, tea and a box of truffles.

They even brought us a bedtime story, Larry Gets Lost in Chicago. It was so thoughtful of the Allegro staff, and it really was the perfect way to end the night.

Chicago is a great place for a summer vacation with kids. The staff at Hotel Allegro sent us on outings around the city that showcased just that.

Saturday we lunched at The Plaza at Park Grill, an outdoor dining area at the gateway to Chicago’s Millennium Park. It has a great view of the park, the city and all the hustle and bustle on the street. The food was good and they offered a kid’s menu. If you’re feeling adventurous, you can even try a Chicago-style hot dog.

After lunch, Hotel Allegro sent us out on a scavenger hunt to visit five of Chicago’s top attractions. Visit all five, and you can redeem a prize at front desk.

David and I made our first stop at Crown Fountain at Millennium Park.

More than just a fountain, it’s an interactive work of art. If you’re a kid, it’s the most awesome splash pad ever. It’s also probably the only city fountain in American you can play in without being charged with trespassing. It was warm that day, and David was more than happy to get soaked.

The faces on two towers anchoring the fountain are displayed digitally. Water rushes over the towers, and occasionally it appears that the face are “spitting” water from their mouths.

Cloud Gate, or The Bean to locals, is the other popular public work of art on display at Millennium Park. It’s distorting, reflective surface fascinates young and old alike.

After a quick trip back to the hotel to fetch dry clothes for David, we walked the short distance to Willis Town, formerly known as the Sears Tower.  To me it will always be the Sears Tower, just as Macy’s will always be Marshall Field’s.

We took the high-speed elevator up to the observation deck of the tallest building in North America, and enjoyed the gorgeous views of the city and Lake Michigan. We also ventured out on to the SkyLedge, a glass box that extends out beyond the tower, giving you views up, down and on all sides. It made David a little nervous.

Back on ground level David sunk his teeth into his first taste of gooey, cheesy Chicago-style deep dish pizza.

He liked it. A lot.

Then we caught a cab to the Field Museum. You could spend all day in that place and still not see it all. In fact, we have spent all day there, and not seen it all. We only had about an hour this time, so we headed straight for Sue, the largest T-rex specimen every found.

David studied Sue for along time. He said he felt like she was going to reach out and grab him with her enormous jaws!

We checked out a few more exhibits in the Field Museum, then caught a cab back to the Allegro for dinner.

Dinner was at the Hotel Allegro’s award-winning Italian restaurant 312.

We dined on salad, pasta, fish and delicious desserts. Kid-friendly fare was also available. As a special treat, all the children visited the kitchen with Chef Luca where they made their own personal pizzas.

The next day, our last day in Chicago, Hotel Allegro took us on a trolley ride to Ed Debevic’s for lunch.

You don’t have to be in Chicago long before you realize the city has a sense of humor about its self, and Ed Debevic’s is proof of that. In this 50’s-style diner, waiters intentionally serve cheeseburgers with a side of sass and a chaser of sarcasm. While we were there they also put on an impromptu performance of YMCA.

Before we left town, the Hotel Allegro had one last exciting surprise for us. We went over to Navy Pier where we raced around Lake Michigan with the wind in our hair on the Seadog speed boat.

While on the the boat we learned the history of the city’s beautiful skyline. We didn’t have time to ride the famous Ferris wheel at Navy Pier.

Oh, well. Just one more reason to come back to Chicago. As if we need any more.

We rode back to Hotel Allegro on the trolley, the driver telling us more about the fascinating history of Chicago including the not-so-true tale of Mrs. O’Leary’s Cow and the Great Chicago Fire.

We said good-bye, packed up, and returned to Millennium Station to board the South Shore for home late Sunday afternoon. Worn out from all our sightseeing, David fell asleep, his head in my lap.

What fun it was to see the Windy City hand-in-hand with my oldest son.

More about Hotel Allegro:

– The Kid’s Rule Program runs through Labor Day at Hotel Allegro Chicago.

– Kid’s Hour every Friday and Saturday from 4-5 pm in the lobby. Kids can snack on popcorn and lemonade and play Wii and board games.

-Allegro’s FUNcierge will direct you to the best kid-friendly attractions in the city.

-Families can explore Chicago on a scavenger hunt that takes them to some of Chicago’s top attractions, and receive a prize for tweeting photos from all five destinations.

-Also take advantage of the Kimpton Kid’s Program offered at all Kimpton Hotels which includes a special children’s welcome amenity, a child-size animal print robe for loan or purchase and comment cards just for kids.

-Complimentary in-room WiFi is available to all members of the Kimpton In Touch Loyalty program. It’s free to sign up.

-Rooms have a gourmet honor bar with organic options and in-room safes.

-37 inch flat screen TV in all rooms

-On-site fitness center

-312 Chicago restaurant offers contemporary, authentic Italian cuisine using the freshest seasonal ingredients, under the direction of Executive Chef Luca Corazzina.

-Hotel Allegro, located in Chicago’s theater district, is just minutes from major attractions, parks and shopping with easy access to buses and trains.

-To book a stay at Hotel Allegro visit www.allegrochicago.com or call 312-236-0123

Disclosure: Kimpton Hotels and Hotel Allegro provided us with accommodations, meals, amenities, transportation, and admittance to attractions, however, all thoughts and opinions are my own.