Chicago: The Kind of Town Perfect for a Family Trip


Many years ago, Frank Sinatra sang, ”Chicago is my kind of town” and this held true for my family of five this summer. We had only a few days and were brainstorming where to go for a quick summer 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 kind of town perfect for a family trip.

Flying to Chicago takes a little under two hours, 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 – especially in the summer time.

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. At first, I was nervous because I lack some coordination and feared falling into the river but 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 two-hour tour so we could go at our 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 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 1980’s.  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 museums, aquariums, and other places to visit. We went spent an afternoon at the Art Institute, which is located at The Loop on Michigan Avenue (by Millennium Park). My 16-year old had just studied Magritte’s work in her art class so she 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 my son 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 saw 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 — a ride on the 150-foot ferris wheel is highly recommended! 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.



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  1. Perhaps I should have just visited. Instead, I lived there for a year. What a nightmare!! As I’ve said over the years, the UGLIEST city ever. The people, I mean.


    If you’re used to the good looking folk around here, be prepared: Chicago is filled with “U-G-L-Y, YOU UGLY, YOU UGLY!!!”

    Compare this to say, Boston/Atlanta/LA/NYC where folks are GOOD LOOKIN’. In Chicago? No way. UGLY!

    So forgive me if I never go back. Though I did literally run into the Dali Lama on the street there. Other than that?


  2. Please…Chicago is the most beautiful city in the country. It is home to the first skyscraper, Second City,an amazing lakefront with beaches, friendly people, great sports, incredible food and it is CLEAN. It is a true midwestern town.

    The winters are awful and spring only lasts a few weeks, but the city is great.

    Prof-living there for a year must have meant you brought the level of attractiveness down a few pegs.

  3. Can totally understand how visiting a city and living in a city can leave two differnet impressions. As a visitor, it took me three trips to like Chicago, but I really like Chicago. Haven’t taken the kids yet, but thinking about it now.

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