Your family will be blown away by a trip to the Windy City. With world-class museums, mesmerizing interactive street art, parks for days and miles of shoreline, the “Second City” will quickly become number one in your family vacations. With so much to do, you’ll want to consider some tips for visiting Chicago with kids to make your planning and decision-making much easier.
Airports & Transportation | Weather | Fun Activities | Safety | Kid-Friendly Hotels
Tackling Transportation While Visiting Chicago with Kids
You can rent a car in Chicago, but it’s gotten a lot more expensive to park a car in the city. It can be a lot easier and less expensive (not to mention the time savings of not searching for a parking spot) to get around via public transportation, your own two legs and even bicycles if the weather permits.
In Private Cars
Whether you are renting or riding in private cars while visiting Chicago with kids, it’s a good idea to know the seatbelt and car seat laws, as they may differ from the laws in your state. All drivers and passengers must be secured in either a seatbelt or a child safety seat. Children under 8 must ride in child safety seats. Children over 1 year old and at least 20 pounds may use a forward-facing child safety seat. If you are renting a car, you can look into bringing your own car seat versus renting one from the car rental company. Chances are you will save a lot of money by bringing your own. If you are driving, keep in mind that sometimes the fast route through the city streets is to go underground. Yes, many streets go underground, and the trains are often elevated.
In Taxi Cabs and Hired Cars
If you will be taking a commercial vehicle, such as a taxi, when visiting Chicago with kids, be aware that young children are not required to be restrained in a restraint device. They will, however, be much safer if they are strapped into an appropriate infant seat, regular car seat or booster. You can order a ride with a car seat.
*Please visit the Illinois DMV for official laws and regulations.
On Buses or Trains
Children do not need to be in car seats when traveling by these methods. The “L” is the elevated train in the city and some surrounding suburbs (it’s still called the “L” even if parts are subway trains and not elevated). The Metra is the commuter railroad that fans out into the suburbs via 11 different lines.
Chicago Airports
Chicago has two major airports — Chicago O’Hare and Midway. They are a similar distance from the city, so choose the one with the best airfare or that has your favorite airline flying there. Midway is the smaller airport, but both airports have train service to downtown.
It can be difficult traveling with little ones and luggage on a train — plus it could put you at risk for theft — so you might consider arranging a ride with a car service for airport transfer. It’s also easy to grab a taxi cab, Uber or Lyft (be sure to request a car seat if needed). These vehicle options will cost more than taking the train, but it can make your life a lot easier than managing strollers, luggage and small children on public transportation. Then, you can take the trains once your luggage is stowed at the hotel.
Prepare for the Weather When Visiting Chicago with Kids
Depending on the season of your trip, you may need to prepare for weather when you visit Chicago with kids. You’ll find the best weather in April, May, September and October when temperatures are pleasant but not too hot. June through August can be very hot and humid or really nice. You just never know what you’ll get. A summer day can bring a downpour of rain, high heat and thick humidity ... or make a perfect sunny day. The city is beautiful in the summer, with many flowers in bloom and beaches packed with swimmers and volleyball players, but the city can also be very crowded, as this is a popular time to visit.
November through March can bring biting winds and freezing temperatures that can possibly dip below 0 degrees Fahrenheit. If you are braving the Chicago winter, wear layers and bring protective clothing. Check the weather before your trip to see if you’ll be needing an umbrella or raincoat during your visit.
Read Up Before visiting Chicago with Kids
Before we visit a new city, we love to read books about the city or stories that take place there. It’s also fun to recognize a city from movies. It helps the tadpoles make connections and get excited for seeing their stories come to life. Read your young children "Good Night Chicago" before bed to get them excited for the sights they are about to see. Middle readers will delve solving crimes in the Thorne miniature rooms at the Art Institute of Chicago in "The Sixty-Eight Rooms" by Marianne Malone.
Middle school and high school readers may get into the "Divergence" series of books and/or movies, which take place in a future dystopian Chicago. One of our family favorite movies that has many iconic views of Chicago is "Ferris Bueller’s Day Off." One of Mommy Frog’s favorite novels based in Chicago is "The Time Traveler’s Wife," which got her excited for a trip to the Art Institute.
Fun Activities When Visiting Chicago with Kids
When visiting Chicago with kids, the hard part will be narrowing down what to do. From shopping along the Magnificent Mile and visiting museums, to playing at parks, beaches and hopping on architecture tours, you’ll find something to entertain each member of your family.
Visit the Tallest Buildings
You can get a bird’s-eye view of the city from observation decks at two of the tallest buildings in the city. Both Willis Tower (formerly Sears Tower) and the John Hancock Building have great views. The Hancock building’s observation deck on the 94th floor is called 360 Chicago. It features TILT, an enclosed platform that moves and tilts you out over Michigan Avenue. It is not quite as high as the Willis Tower Skydeck’s 103rd floor, but it has nice views of the lake and of the Willis Tower. The Willis Tower Skydeck has glass boxes that extend out over 4.3 feet from the Skydeck. These activities are not for someone with acrophobia — a fear of heights!
Take a Boat or Bus Tour
As amphibians, we frogs love exploring any city by both land and water, so the tadpoles are especially excited when we can hop on a relaxing boat tour. You can take architectural tours along the Chicago River or even go through the interesting Chicago Harbor Lock system and leave the river for Lake Michigan for a lake view of the city’s famous skyline. The Big Bus Chicago Hop-on Hop-off tour will get you about the land, with fun facts and 14 stops along the way.
Play in the Parks
Chicago has amazing parks that appeal to all family members. The parks are filled with interactive art such as “The Bean," fountains, playgrounds, bike trails, other recreation and amazing views. You can rent bikes and take a long family ride along the lake or through the city’s many parks. The phenomenal Maggie Dailey Park offers a skate ribbon that is multi-seasonal. You can rent roller blades and scooters in the warmer months or ice skates in winter, and yes, Mommy Frog checked that protective equipment is included. Maggie Dailey also has mini golf, a climbing wall, tennis courts and various themed equipment in its play garden. You’ll forget you are in a city. And good luck getting your kids to leave!
The good news is that you can lure the tadpoles to yet another park. The nearby Millennium Park is where to find the iconic Cloud Gate, which is much more commonly referred to as “The Bean.” This massive stainless steel structure’s reflective surface is mesmerizing. Your kids will want to explore it from every angle. There is another ice rink at the McCormick Tribune Ice Rink. In warmer months, there are free live performances, a summer film series, a summer music series and gardens. And the tadpoles love to cool off by splashing in the park’s Crown Fountain, a shallow reflecting pool with lit-up 50-foot towers on either end. If you cannot get enough of the art, hop into the nearby Art Institute of Chicago or Grant Park, where you will find the famous Buckingham Fountain (any “Married with Children” fans out there? Perhaps I am dating myself?).
You can explore the 18-miles of shoreline on bike paths and numerous parks by bicycle. We offer some tips for a family bike ride on the Chicago Lakefront Trail. If you want someone to show you around, take a Bike City Sights Tour.
Visit Museums
As mentioned, Chicago has great museums. There are hundreds of them. The hard part is that you cannot possibly visit them all in the same trip when visiting Chicago with kids. How to choose? You cannot go wrong with any of the following must-see museums along the lakefront:
- The Art Institute of Chicago
- The Museum of Science and Industry
- The Field Museum of Natural History (for dinosaur fanatics)
- The Shedd Aquarium
There are many more to choose from that are related to art, architecture, history, culture, science, art, nature, space, performing arts and libraries. The Adler Planetarium is within walking distance of the Shedd Aquarium and the Field Museum. There are two zoos: the free Lincoln Park Zoo (surrounded by more parks and bike trails) just north of the city and the Brookfield Zoo (a larger zoo in the suburbs).
Visit Navy Pier
Navy Pier is popular with visitors and a huge hit when visiting Chicago with kids. With its giant Ferris Wheel and Amazing Chicago Funhouse Maze attractions and art exhibits, it draws people in. You’ll find restaurants, cruises, gardens, the Chicago Shakespeare Theatre and IMAX theatre and the Chicago Children’s Museum.
Try the Local Food
Chicago is known for its deep-dish pizza, Italian beef sandwiches and Chicago-style hotdogs piled high with everything except ketchup. Polish sausages, Chicago mix popcorn and tamales also come to mind. Diet food does not. Whether you want a quick bite or some fine dining, be sure to indulge guilt-free in Chicago food.
Foodies will find themselves in a culinary coma in the West Loop/Randolph St area. The Little Goat Diner is a family-friendly (if your kids are open-minded eaters) diner brought to you by the same creative genius behind the fancier Girl & the Goat across the street. If you are in that part of town, be sure to stop off at Cone for some interesting ice cream desserts — we recommend Netflix and Chill popcorn ice cream with mini M&Ms. Mommy Frog has been known to make us take a cab ride to this ice cream shop with an Irish Pub feel just for her favorite ice cream not found anywhere else. You’ll need some motivation to walk, ride bikes or go skating later and here it is (in the form of excess calories to burn).
See a Sports Game
Chicago has many teams popular with sports fans. Depending on the season, you may be able to catch a Chicago Cubs (at the iconic Wrigley Field) or White Sox game, see the Chicago Bears play, catch a Bulls game or even experience a Blackhawks game.
Be Street Smart when Visiting Chicago with Kids
Chicago’s crime rate has been growing, but in most touristy areas you should be pretty safe. It's always good advice to play it smart and be vigilant when visiting Chicago with kids.
- Hold hands.
- Look both ways when crossing the streets — there are many one-way streets, meaning traffic could be coming from an unexpected direction.
- Use a crosswalk — no jaywalking!
- Do not assume cars will stop for you, even if you have the walk signal.
- Discuss a plan in case you become separated.
- Note your hotel address — you can pick up a business card when you check in.
- Keep valuables in a safe. Do not carry money or ID in a backpack.
- Ask for directions if you are not sure where to go.
- Know which train or bus line and stop to take before you board.
- Stay in well-populated areas at night.
- Keep valuables and cell phones safely stowed and out of sight, and keep the kids close to you whether you are on the street or using public transportation.
Kid-Friendly Chicago Hotels
When visiting Chicago with kids, you’ll want to choose a kid-friendly hotel in an area near your favorite attractions. Undercover Tourist is now booking discount hotel rooms in Chicago. You can get a jump on saving money on your family-friendly accommodations.
Here are a few suggestions for our favorite Chicago hotels near the action. The newly renovated Omni Chicago is an all-suites hotel along the Magnificent Mile. They have an American Doll package. It comes with free milk and cookies, a complimentary backpack filled with crayons and other fun items, rooftop sundecks and an indoor pool.
The Residence Inn Chicago Downtown/River North offers one- and two-bedroom apartments with a full kitchen. You can call ahead for grocery service. There’s an indoor pool, and you can borrow board games. With complimentary breakfast and happy hour, you can save a lot of money on food. The Four Seasons appeals to kids of all ages with make-your-own sundaes, a teen pizza-making class, a Kids Clubroom and more. The Embassy Suites has two locations in Chicago, offering a more budget-friendly hotel choice with plenty of room for a family, free cooked-to-order breakfast, a complimentary reception with drinks and snacks and a pool. Each location is in walking distance of family-friendly entertainment.
Chicago makes a great family vacation no matter how old your tadpoles are. With these tips for visiting Chicago with kids, you’ll be off to a great start in planning the perfect trip. Have tips for visiting Chicago with kids? Please share them in the comment section below.
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Keep hopping!
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