Attend Chicagos Holiday Events
With glowing city lights and an abundance of holiday decor, Chicago becomes a winter wonderland each December. To celebrate the holidays, the city hosts a multitude of events and activities including:
Pick up a cup of coffee or hot cocoa and experience the magic of the holidays in Chicago.
Spend The Day At Navy Pier
Its easy to see why families visit the iconic Navy Pier each year- there are so many things to do! How about a spin on the 150-foot Ferris wheel while taking in magnificent views of the Chicago skyline?
If you have young kids, head to the Chicago Childrens Museum for hands-on fun. If the weather is nice, take a sightseeing cruise on Lake Michigan from the pier. If you time it right, you can also enjoy an amazing fireworks show and attend one of the many free, family-friendly events that take place throughout the year.
Learn The True Stories Behind The Citys Mob Past
Immerse yourself in Chicagos criminal pastimes by embarking on a dedicated gangster tour through the citys scorned streets.
Walk in the footsteps of infamous criminals, stand in historic crime scenes, and discover what made gangsters like Al Capone and John Dillinger tick.
Send some extra shivers down your spine by combining it with a ghost tour!
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River Trail Nature Center
If your little kids act like animals, give them the chance to do so for real. At River Trail Nature Center, they can crawl in an eagles nest or a foxs den. Other fun onsite activities include making nature puppets or exploring one of this nature centers many trails. In the mood for something sweet? The sugar maples here are a pretty sight in summer and fall, and the annual maple syrup festival is a treat for all ages. Your trip to Chicago with kids just got a whole lot happening.
The grounds, trail, and bathrooms are open every day from 8 a.m. until 4 p.m. The exhibit buildings are closed, and drinking fountains are not available. Youll need to bring your own water bottle. Parking is limited to 50% and visitors are expected to wear a mask and follow social distancing guidelines during their visit.
Field Museum Of Natural History
We walked to the Field Museum from the RV park we were staying at and had a couple of hours to explore. We love how the museum pass gives us the opportunity to do this! Since we get in for free. There were a lot of really cool things to look at, but out of all the museums it was our least favorite.
It seemed like the kids felt the same way. We kind of quickly walked through all of the displays which did take a while since there are so many and it is a big museum.
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Chicago Family Vacation: Best Time To Visit
The best time to spend 3 days in Chicago is during the months of May, June, September, and October.
In other words, visit Chicago when the weather is mild during the late spring, early summer, and early fall.
Though Chicago in summer can be hot and humid, many are drawn to the area during this time. By doing so, you can take advantage of lake activities and outdoor events.
Chicagos vibrant downtown and amazing architecture, as well as its playful green space, create a welcoming atmosphere for the young and old alike.
Last, keep in mind that Chicago gets very busy with tourists over weekends and holidays.
We just so happened to visit Chicago in September over Labor Day weekend.
Though the sidewalks throughout the city were very crowded, the holiday weekend special events still made this a great time to visit.
Crowds or no crowds, Chicago with kids is a great experience, especially because many activities are free!
Feel The Wrigley Field Phenomenon At Gallagher Way
Around the corner from the Wrigley Field marquee, youll find this outdoor space that hosts free events to enjoy the ambiance of the Friendly Confines without paying to enter the ballpark. At Gallagher Way, you can enjoy free farmers markets, live music, movie nights, and other seasonal events such as Christkindlmarket. Some events are ticketed, so check the website in advance.
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Take A Minute To Appreciate The Architecture
Speaking of tall buildings, did you know that Chicago was home to the worlds first skyscraper? Over the years, the city has built up an impressive resume of tall buildings in a variety of architectural styles, which you can explore at the Chicago Architecture Center. Here, kids can marvel at an interactive scale model of the entire city. Next, head to the Chicago River to catch a ride on an architectural river cruise where docents will give an overview of the buildings that populate Chicagos skyline as you cruise through the city.
Visit A U Pick Apple Orchard
One of our favorite things to do in the fall is picking apples at one of the local orchards. Finding the best apples is an annual event in our house and one of our favorite places to go is Apple Holler in Wisconsin. The reason we travel so far is because they consistently have a large selection of apples available and after 13 years of visiting, it is officially a tradition.
There are plenty of other apple orchards in Chicago and the suburbs. You can find an apple orchard near you at PickYourOwn.org. Dont miss our tips for visiting apple orchards in Illinois where you can find some great apple recipes too!
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Where To Eat With Kids In Chicago
Just about all but the most exclusive restaurants will accommodate children without batting an eye, though for your familys own comfort you might find it best to have your doggie bags in hand by 6:30pm, when dinner crowds can make maneuvering strollers and high chairs awkward. Adventurous eaters will love slurping noodles beneath the pagodas of Chicago’s Chinatown and digging into enormous dosas amidst the sari shops and Indian candy stores of Devon Avenue: both neighborhoods offer a spoil of dining spots that are casual and easy on the wallet.
Certain restaurants go the extra mile to welcome little guests. Lincoln Parks retro RJ Grunts soothes post-zoo fatigue with kid-sized shakes and burgers along with a complimentary stroller valet, while over in hip Ukrainian Village, Quad Cities-style pizza spot Roots encourages tiny diners to play with their food, distributing dough balls to be squashed and stretched while dinners in the oven. Grown-up topping options like duck sausage and a lengthy Midwestern beer list will keep parents happy too.
Kids get the royal treatment each afternoon at the Drake Hotels Little Prince and Princess Tea, an elaborate spread of dainty nibbles served up in the hotels grand Palm Court. Fanciful decorations and carolers make holiday season visits here particularly magical. Parents and rugrats alike will be sweet on the inventive ice cream at West Towns Black Dog Gelato and the rich hot chocolate at Logan Squares Katherine Anne Confections.
Best Things To Do In Chicago With Kids: Fun Family Friendly Attractions
- Tanner Wilkes
Chicago is one of the largest cities in the United States and has a gamut of things to offer people of all age groups.
This is a family-friendly destination where you can enjoy museums, theater, boat rides and splendid architecture and history.
If you are traveling with family or a mixed age group of people, the following are the best things to do in Chicago with kids.
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Catch A Performance Of The Chicago Symphony Orchestra
As the Chicago Symphony Orchestra edges its way toward 13 decades of captivating performances, it solidifies its reputation as one of the worlds best.
With brass, percussion, string, and woodwind instruments, coordinated by renowned Italian conductor, Riccardo Muti, its quite literally music to our ears.
Performances regularly take place at the Symphony Center in the Loop area.
Snack Happy At These Fun Chicago Kid
Who said you cant have fun with your food? These Chicago-area eateries elevate dining to an attraction that kids of all ages will love. If you are in Chicago with kids, youre in for a treat. From the most appealing food tour to one of the most beautiful city skyline. You can host a momentous birthday party or go visit a museum of science. From a medieval adventure complete with jousting to the only kid-friendly, G-rated restaurant where waitresses dance on the tables that we know of, this list is loaded with as much fun as food.
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Hop Between Chicagos Rooftop Bars
After soaking in the views from Tonys Rooftop Bar at the Time Out Market, continue the rooftop adventures by hopping around some of Chicagos very best patios and terraces.
Try the Elderflower Collins cocktail and take in the sweeping panoramic vista at Z Bar sample a flight of local beers at the garden-themed Raised or sit around a fire pit at Offshore, the largest rooftop bar in the world.
Things To Do In Chicago With Kids Before They Grow Up
Chicago is home to so many incredible parks, playgrounds, museums, and things to do with kids that one childhood doesn’t seem like enough time to fit them all inthough who could blame you for trying? Winter, spring, summer, or fallthere are so many great things to do with kids in Chi-town. Whether it’s racing with your toddler through the sprinklers at Mary Bartelme Park, wowing your preschooler at the Field Museum, gliding with your grade-schooler on the skating ribbon at Maggie Daley Park, or taking in engineering marvels with your tween at the Chicago Architecture Center, take advantage of everything this beautiful city has to offer kids of all ages. We’re also big fans of FREE fun, so we included as much of that as possible.
Whether you’re a local or a visitor to the Windy City, we hope you can use this list to make some great new memories with your kids. Now I’m off to scarf some Chicago-style hot dogs at Portillo’s.
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Visit The Christmas Market
Christkindlmarket in Chicago is inspired by the famous German Christmas Market in Nuremberg. The market usually sets up around Thanksgiving and lasts up to Christmas Eve. There are many vendors selling Christmas gifts, holiday beverages, foods, and more at the holiday market.
You can pick up one of a kind, often handmade items such as eclectic Christmas ornaments, wooden toys, cuckoo clocks, jewelry, and clothes, as well as really cool Christmas gifts. Vendors also sell German sweet and savory delicacies as well as Gluhwein, the famous spiced holiday wine.
If you are spending a long weekend in Chicago, then read this 3-day Chi-town itinerary now!
Another Resource For Free Things
Lake Michigans Lakefront Trail, Lincoln Park Zoo, Millennium Park, Navy Pier, Garfield Park Conservatory and free walking tours from Chicago Greeters can take up a whole weekend for hardly any money! For more ideas on free things to do when you visit Chicago, visit Choose Chicago. Also, if youre on a road trip through the Midwest, check out these free things to do in Muskegon, Michigan.
Stop #: Giordanos Pizza
After boarding Big Bus Chicago at Stop #12, we rode continuously to Stop #4 at Millennium Park.
Here, we got off and headed for lunch at Giordanos Pizza .
After having a slice of their famous deep-dish pizza while on the Navy Pier, we fell in love. We couldnt leave our new favorite city without another round of this authentic Chicago-style pizza.
In fact, no Chicago family trip would be complete without eating this delicacy!
Plan to spend 1.5 hours at Giordanos as the pizza alone take 45 minutes to bake.
Embrace Your Inner Homer Simpson On An Original Donut Walking Tour
Chicagoans have long adored the donut. Taste the very best the city has to offer with a dedicated desert tour, stopping into a hand-picked selection of the Chicago Loops top donut shops.
The tastings are all included , while vegan, gluten-free, and nut-free options are also available.
For anyone with a sweet tooth, this tour should headline your bucket list of things to do in Chicago.
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Appreciate Jazz At The Green Mill
Known across the city for its eclectic jazz performances and poetry readings, The Green Mill is a Chicago treasure.
Its the oldest jazz club in the U.S., welcoming tourists since way back in 1907.
Celebrities and mobsters alike frequented this prohibition-era speakeasy over the years, and travelers continue to do so to this day.
Board The Iconic Tall Ship Windy
Modeled after a traditional Great Lakes trading ship, the Tall Ship Windy is as charming as it is historic.
The majestic 148-foot schooner sets sail from Navy Pier out to the calm waters of Lake Michigan, where spectacular views of the Chicago skyline await.
The trip isnt only picturesque, but interactive as well guests assist in raising the sails and sending out the commands to the crew.
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Grab Some Ice Cream At Original Rainbow Cone
This longstanding Chicago ice creamery hibernates in the winter, but in the summer theyre teeming with elated customers and ice cream fanatics.
Visit the Original Rainbow Cone, choose from cones, milkshakes, sundaes, or banana splits, then burn off the calories with a pleasant stroll through the parks of Dan Ryan Woods.
Attend A Chicago Bulls Game
Chicago loves its sports teams and there are plenty of games to watch even during winter. You can watch the Chicago Bears play football at Soldier Field from September till December or the Chicago Bulls play basketball at United Center throughout winter. For ice hockey, watch out for the Chicago Blackhawks and Chicago Wolves.
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Go See Some Live Music
Music venues around town have reopened for live events, with heavy hitters City Winery, Carols, , Rosas, Reggies, Green Mill, Montrose Saloon, Uncommon Ground, FitzGeralds, Kingston Mines, and Empty Bottle leading the charge. So what the hell are you waiting for? If youre looking for something with a more romantic vibe, check out the candlelight concert series from Fever and catch classical music in unique outposts like Stan Mansion and Salvage One. Pretty hard to screw up that date night.