Week Long Getaways, Weekend Away

Chicago: Our Kind of Town for a Perfect Family Trip


We love the Windy City of Chicago — Melissa just returned from a “grown up” trip last month where she stayed at chic new Hyatt Centric Hotel in the Loop and checked out some of our guest writer Randi Mazzella‘s top picks for families, including the Architecture Tours River Cruise and Millennium Park. She had a blast, and your family can, too, by following our comprehensive guide below:

Many years ago, Frank Sinatra sang, ”Chicago is my kind of town,” and this held true for my family of five one recent summer. We had only a few days and were brainstorming where to go for a quick vacation when my husband mentioned that he needed to be in Chicago for a meeting. At first my 16 year old balked that Chicago didn’t seem like much of a “vacation destination,” but it turned out that it was the perfect kind of town for a family trip.

Flying to Chicago takes a little under two hours from the Tri-State area, which gave us almost four full days to explore The Windy City. Sometimes I have trouble coming up with a good itinerary for my family because we have such a wide age gap (19, 16, and 10), but Chicago offered a wide variety of activities to choose from. The abundance of things to do indoors and outdoors in Chicago is incredible.

See the Sights by Boat, Bike or Foot


We began our trip with a boat cruise on the Chicago River. There are many boat tour operators and we chose to take the Architecture Tours River Cruise, which was geared toward families with kids ages 12 and up. This 90-minute tour gave us a good overview of the Chicago landscape. After our tour, we walked along the scenic River Walk and discovered Urban Kayaks. We signed up for a 60-minute intro to paddle—it was relatively simple and a total blast for all of us.


We also did a bike tour with Bobby’s Bike and Hike. They have several group tour options but we chose to do a private 2-hour tour so we could go at our own pace. After getting our bikes, our tour guide Matty led us to several cool spots in the city including Navy Pier, Millennium Park, Grant Park, and Lake Shore Drive (where several museums are located) and provided great information about Chicago at all of these locations.

Sporting Venues  

The timing of our trip allowed us to see two professional sporting events much to the delight of my 10-year-old sports fanatic son.


If you are a baseball fan, Chicago is home to both the White Sox and the Cubs. We went to a game at Wrigley Field, which is over 100 year old. Having gone to Yankee Stadium this summer as well, the juxtaposition of one the oldest and one of the newest baseball stadiums was pretty amazing – as were the Chicago hot dogs (served with grilled onions and freshly made relish.)

ChicagoThe last time I watched a Chicago Bears football game was on television when William “The Refrigerator” Perry played for them in the 1980s.  The Bears (or Da Bears) play at Soldier Field, the third smallest field in the NFL. Watching a pre-season game here was a lot of fun due to the relatively intimate setting and the fabulous fans singing the Bears fight song after every touchdown. Even though we are Jets fans we couldn’t help but join in on the chorus when it appeared on the jumbotron, “You’re the pride and joy of Illinois …”

Museums and More


Chicago has many wonderful family-friendly museums, plus an aquarium and a planetarium.. We spent an afternoon at the Art Institute, which is located by Millennium Park (home of “The Bean” and other larger than life public art). My 16-year old had just studied Magritte’s work in her art class and was thrilled that there was a special exhibition of his work going on. Even my son, who isn’t a big art fan, managed to find some works he thought were interesting, like a modern film exhibit on clowns (creepy!)

We also went to the Shedd Aquarium where the highlight was touching a stingray and learning “What Lives in Lake Michigan.” The Adler Planetarium, located walking distance from the aquarium, was also a must see. We caught two shows, including one called Cosmic Wonder about the star alignment.


If you are planning to go to a few museums consider purchasing a Chicago CityPASS, which provides visitors with admission to five of Chicago’s best attractions at a discounted price. The Field Museum and The Museum of Science and Industry are included and great places to visit with families.

In addition to museums, there are many other attractions in the city. The whole family enjoyed our morning at Navy Pier, located on the Lake Michigan shoreline, which hosts several amusement park rides, mini golf, and restaurants. (Insiders note: The 20-yr old, 150-foot ferris wheel here was dismantled in 2015 and a brand new 196 foot version will debut in 2016! )Visit the Skydeck in The Willis Tower, to see views of the city from the 1, 353 feet in the air.

Pizza Please!


No trip to Chicago would be complete without sampling the city’s deep-dish pizza. Our family remains lovers of Tri-state area pizza (let’s face it, what Chicago calls pizza is really more of a casserole) but we did enjoy the local legend twice during our stay.  Everyone disagrees on where the “best” Chicago pizza is but some good choices are Bacino’sLou Malnati’s, and Giordano’s.

Happy Travels!

This post originally ran on Baristakids.com

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