Explore CHICAGO With Kids

Chicago native Dana Sara offers an insider’s guide to memorable kid-friendly entertainment for the entire family and stays at the grand 92-story Trump International Hotel & Tower Chicago.

Trump International Hotel & Tower Credit: ©Cesar Russ Photography

Chicago offers experiences that will make a lasting impression upon you and your children, creating memories that will last a lifetime.  A weekend in Chicago can open your family’s eyes to a not so distant past where imagination, creativity and perseverance were the values that turned a prairie into one of the world’s greatest cities.

Centered on The Chicago River, the former lifeline of this sprawling metropolis, the city’s neighborhoods are divided into the north, south, east and west “sides.”  Within each are “towns” where traditional cultures and flavors are uniquely preserved. Walking is the best way to get around (weather and time permitting) but public transportation is also convenient.  Be advised that parking is expensive, ($25-$35 a stop), so be prepared.

Lincoln Park Zoo during Holidays

Wrigley Field and Lincoln Park Zoo

On the north side, see the Cubs play at Wrigley Field, a good time in one of the few old ballparks left in the country and an easy “L” ride away.  The Lincoln Park Zoo, founded in 1868, is free 365 days a year.  Stroll through and imagine you are in a Monet painting with rolling greens, duck ponds, lovely structures and flower gardens from the adjacent botanical garden also hosting a butterfly exhibit.  Kids love the Farm-in-the Zoo, Story Time and Meet an Animal programs.   There are a few charming rides and a Festival of Lights in winter.

Wrigley Field

Chicago Grub

While on the north side enjoy a city signature—Chicago hot dog—steamed all beef dog with mustard, onion, relish and pickle on a poppyseed bun.  Though Chicago dogs are found all over the city, Weiners Circle or The Clark St. Dog on N. Clark are favorites.  For something exotic, Ethiopian food at Mama Desta’s Red Sea on N. Clark has been famil- owned for decades and offers a compelling menu, including flavorful lentils, indra and greens.

Navy Pier

Navy Pier

East of the river is Navy Pier, which extends out into Lake Michigan. During the summer, boat rides are available.  The 150-foot Ferris wheel, built for the 1893 World’s Fair, runs year round, weather permitting (bring an extra layer in the winter).  The Chicago Shakespeare Theater makes its home at the pier along with the Smith Museum of Stained Glass Windows.  Around the holidays, Winter WonderFest is full of attractions, rides, entertainment, a skating rink and New Year’s fireworks.

The Children’s Museum of Chicago


The Children’s Museum of Chicago at Navy Pier curates exhibits that encourage kids to think outside of the box. Children enjoy fantasy  play as they create a rocket, castle or train from household items, proving that an old box can provide more entertainment and critical thinking skills than a $300 device.  Explore a tree house, dinosaur bone excavation site, water world and view from a bug’s life or gaze at giant Lego recreations of the John Hancock and Sears Tower buildings.

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

On former dock 201, the innovative Trump International Hotel and Tower is built on a unique frame that allows the 92-story building to move with winds that can reach up to 60 mph, and is a a proprietary mix of concrete designed to expand and contract in 60-degree below zero winter weather or in the hot and humid days of summer. This modern marvel offers visitors an ideal location from which to explore the Windy City and is filled with luxurious touches including floor-to-ceiling windows, fully equipped kitchens (with Nespresso machines), and limestone finished bathrooms. Rates start at $395 per night and are available to book here.


Chicago Pizza

Up the river off Wabash is Pizzeria’s Uno and Pizzeria Due, established in 1943 (not to be confused with Uno’s Pizza or Uno’s Grill, both chains). Expect a wait, which may be nice time to talk to your family about your adventures around the city.  Due’s cheese is the real deal original Chicago style pizza, worth the wait and the calories. After, take a walk across the river towards State St. to get your blood flowing again. Visit The Daley Center and see Picasso’s untitled sculpture known as, “The Picasso.”  Around the holidays there is a Christkindlmarket featuring arts and crafts, German beers and brats, crepes and cider.

Chicago Theater

This area in “the loop” has many theaters with world-class shows.   The Goodman Theater—called “the leading regional theater in the nation’s most important theater city” by Time Magazine—is a cultural pillar of the city.  The New Stages festival is free and presents works from rising star playwrights, workshop productions and staged readings.  Among its season schedule, Dickens’ A Christmas Carol, is now in it’s 36th year, seen by over 1,000,000 visitors and called by The Chicago Sun-Times as “a present for the entire family.”  The production is outstanding for its music, staging, acting and the spirit of joy it brings.

Second City is famous for comedy; Steppenwolf is known for its cutting edge material and quality; while the queen of theater in Chicagoland is Joyce Piven of The Piven Theater Workshop, located north in Evanston for the past 40 years.  Piven offers brilliant works, plays, Story Theater and theater training for youth and adults.  This sacred theater group has produced a generation of known playwrights, directors and Hollywood stars.

Museum and Planetarium

Further south, past the loop, stand several world-class museums: The Art Institute of Chicago, Field Museum, Museum of Science and Industry, The Shed Aquarium and Adler Planetarium are each worthy of a visit.  Check for free days and group discounts.  South of the museums are The Bears, Chinatown, several Frank Lloyd Wright masterpieces, the best fried chicken at Harold’s Chicken and legendary blues at The Checkerboard Lounge.

Historic Architecture

Boat rides are available on the river, where you can see Chicago’s buildings of elegance and industry.  Historic architecture with ornate details, domes and columns stand along side clever contemporary towers awarded for simplicity and function. Enjoy a relaxing boat ride and view the Willis Tower (formerly named the Sears Tower), the tallest building in the United States, as well as the second tallest Trump International Hotel and Tower Chicago, followed by the John Hancock Center.

Chicago offers visitors a wealth of intriguing activties and is equally enjoyable for adults and children. A weekend stay here reminds us why the Blues Brothers said, “Baby don’t you wanna go, back to that same old place, sweet home Chicago.”

Latest posts by Dana Sara


  1. Doreen on May 20, 2013 at 2:06 am

    Although the cheaper hotels are purely utilitarian, there are higher end types too with rooms decorated in various themes, rotating beds, ceiling mirrors, jacuzzis,
    and bizarre lighting. Reservations are not necessary unless otherwise noted.
    It’s a place that has something to offer everyone, no matter what age, so you will want to allow plenty of time for your stay in this unique part of New Zealand.

  2. Brent on May 15, 2014 at 8:46 am


    Great site. Another idea to enjoy Chicago with the kids.

    Checkout new iphone app, 312Go.

    As you walk, bike, run around Chicago the guides will talk to you and tell you about the sights you are seeing, as you see them. Amazing content, very cool technology. Similar to a museum audio tour, but for the entire city. Fun & educational – great way to spend a day outdoors with your family.

    Free on itunes.

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