Planning a city trip with kids can feel like navigating a maze. You envision architectural marvels and cultural experiences, while the kids might be dreaming of toy stores and treats. When we booked two days in Chicago with our children, fresh off a visit with friends in the States, we wondered if we were being overly ambitious. Would we be able to bridge the gap between their desire for the latest toys and our yearning to explore the urban landscape of Chicago?
The answer, we discovered, was food – and a whole lot more.
Before our trip, researching fun things to do in Chicago with kids opened our eyes to the city’s vibrant food scene. Chicago isn’t just a city; it’s a culinary destination with its own dedicated hashtags! We quickly realized our belts might need loosening after just 48 hours. Chicago-style hot dogs, deep-dish pizza, and an array of donut shops became essential stops on our itinerary.
However, Chicago offers far more than just delicious food. Zoos, iconic monuments, sprawling parks, diverse shopping, and much more await families ready to explore. Chicago became a highlight of our family trip to the States, and we believe it can be for your family too.
This itinerary for What To Do In Chicago with kids isn’t exhaustive – our visit was brief, but we aimed to blend the city’s must-see landmarks with kid-friendly activities. Chicago can captivate young minds for days! Here are our top recommendations, encompassing famous attractions and hidden gems, all punctuated with the best places to eat in Chicago.
Family Friendly Hotels In Chicago
BEST WESTERN RIVER NORTH HOTEL
Finding the right family-friendly hotel in Chicago means balancing location, amenities, and budget. After extensive research, we discovered the Best Western River North, a fantastic Chicago hotel in an ideal location. We were genuinely thrilled when we saw our room! Centrally located downtown, it’s a mere 5 to 10-minute walk from major attractions and close to numerous family-friendly restaurants.
The room was impressively spacious and stylish, comfortably accommodating our family of five with two double beds and a sofa bed. On-site parking is available for a small additional fee, and the hotel staff were exceptionally helpful throughout our stay.
The hotel also boasts a heated indoor swimming pool on the top floor, with a relaxed atmosphere regarding children swimming without direct adult supervision. Plus, thankfully, no mandatory swim caps!
Adjacent to the pool is an outdoor deck area offering stunning city views. It’s the perfect spot to unwind with a drink while the kids enjoy the pool. Traveling to Chicago with kids can be tiring, so this rooftop relaxation area became a major highlight for us.
Without a doubt, this is the best family hotel in Chicago, especially considering the fantastic room views.
Things To Do In Chicago With Kids
Day 1 In Chicago With Kids
A BIRDSEYE VIEW OF CHICAGO
Before diving into your two days in Chicago, getting a lay of the land is a great idea. Chicago is vast and visually stunning from above, which explains the popularity of the Willis Tower and its SkyDeck. While undoubtedly one of the cool things to do in Chicago, especially for the views, the $25 per person cost can add up quickly for a family. We opted for a different, budget-friendly perspective.
After a quintessential Chicago breakfast of coffee and a vanilla glazed donut topped with bacon at Do Rite Donuts on West Randolph Street, we began our day at the Richard J Daley Center, just across the street. This hidden gem offers equally impressive views, for free!
The Richard J Daley Center is Chicago’s official Civic Center and once held the title of Chicago’s tallest building. Entering the quiet lobby, you might initially feel unsure if you’re in the right place. However, a quick chat with the friendly security guard confirmed we were welcome to enjoy the view, and he was delighted we chose his building over the Willis Tower.
Security is present – you’ll need to pass through a metal detector (leave any prohibited items behind!). Camera batteries may need to be removed briefly, but phones are permitted.
Take the elevator to the 30th floor – the rapid ascent is a thrill for kids (and maybe a little for adults too!). At the top, you’ll share the space with lawyers and court attendees, who might be slightly amused by a family of five amidst their workday. However, Chicagoans are known for their friendliness and are happy to showcase their city.
The 180-degree view is breathtaking and expansive. Plus, you’ll have saved your family a significant amount of money while enjoying a unique Chicago experience.
The Richard Daley Center also features a charming courtyard, home to a massive Picasso sculpture that often goes unnoticed by the crowds. In-ground fountains nearby provide entertainment for kids while you appreciate this artistic landmark. This untitled 50-foot sculpture was a gift from Pablo Picasso to the city in 1967 and has appeared in films like The Fugitive, Batman – The Dark Knight, and The Blues Brothers.
Tip – If time allows and you’re interested in classic Chicago sights, consider a detour to Macy’s (N. State Street) and the Chicago Theatre (Lake Street), both a short walk from the Richard Daley Center, though in the opposite direction of The Bean. Macy’s is a beautiful department store, famous for its Tiffany ceiling crafted from gold and mosaics. Other noteworthy features include chandeliers and the Walnut Room Restaurant. And, can you truly say you’ve been to Chicago without a photo of the iconic Chicago Theatre sign?
CLOUD GATE – AKA THE BEAN
A must-see for almost every visitor to Chicago is the iconic silver kidney bean, officially named Cloud Gate. It’s truly a remarkable sight. Having a similar Anish Kapoor sculpture in my hometown of Nottingham adds a personal connection to this gleaming artwork.
Unless you’re willing to wake up at 5 am (more likely if you are traveling with kids!), be prepared to share Cloud Gate with countless other visitors. Despite the crowds, it’s an epic experience. The reflections of people in the polished steel curves enhance the captivating effect. 168 steel plates are seamlessly welded together, creating an object that seems almost otherworldly – like a UFO incubating a silver form, waiting for an E.T. to emerge after observing Chicagoans through the mirrored surface.
Cloud Gate is located in Millennium Park, part of Chicago’s expansive green space known as its “front lawn.” Combined with adjacent Grant Park, this area is one of the best places to take kids in Chicago to escape the urban bustle. The towering skyscrapers can feel overwhelming after a while.
Grant Park’s 319 acres offer fountains, playgrounds, climbing walls, a “skate and scooters ribbon,” mini-golf, shaded picnic spots, and the interactive Crown Fountain video sculpture. This is where you can easily spend a budget equivalent to the Willis Tower Skydeck tickets and get excellent value for family fun – an hour on the climbing wall and a round of mini-golf will keep younger family members thoroughly entertained.
Tip – Download the Millennium Park app for the latest information on events and activities happening in the park.
WHERE TO EAT WITH KIDS NEAR MILLENNIUM PARK…
Giordano’s, a Chicago-based chain since 1974, serves classic deep-dish pizza and offers a great kids’ menu for under $5, including a drink. Trying deep-dish pizza in Chicago is practically mandatory!
NAVY PIER
Navy Pier is consistently listed as a top family attraction in Chicago and appears in most guidebooks… but we were slightly underwhelmed. Perhaps our timing was off (there seemed to be ongoing construction during our visit)? To us, it felt like a pier with a Ferris wheel, a carousel, and a few overpriced restaurants. It might have seen more excitement in 1918 when it served as a jail for “draft dodgers.” However, it remains one of Chicago’s main attractions for families, so it’s still worth considering for your Chicago trip itinerary.
Okay, Navy Pier does have fireworks! And it looks quite impressive illuminated at night, with a lively atmosphere in the evening. BUT… fireworks are only during summer, on Wednesdays and Saturdays. Live music is also featured, again, primarily in the summer months.
Tip – If you visit Chicago during the winter (which can extend from October to May), Navy Pier offers indoor attractions to escape the cold Chicago wind: The funhouse maze at Amazing Chicago and the Chicago Children’s Museum are popular options.
Day 2 In Chicago With Kids
RIDE THE ‘L’
You’re in Chicago – riding the ‘L’ train is a must! “L,” short for “Elevated,” is Chicago’s rapid transit system, essential for getting around the city. It’s a significant part of Chicago’s history and heritage.
Chicago has always been ambitious. Even after the Great Chicago Fire of 1871, which devastated three square miles of mostly wooden structures, the city rapidly rebuilt. Skyscrapers rose quickly, leading to congested streets below, likely filled with horse-drawn traffic. Land values soared, making elevated train tracks the logical solution. Plus, they were ready for filming While You Were Sleeping! (Film location buffs, the Randolph/Wabash station is your spot.)
From above, the ‘L’ system resembles a Catherine Wheel firework in slow motion – a downtown loop with branches extending to every corner of Chicago.
For family fun in Chicago, we recommend taking the Purple or Brown Line at Merchandise Mart towards The Loop. Complete a full loop to experience downtown Chicago from above. Then, retrace your route until you can get off at Sedgwick, a short walk southwest to the Lincoln Park Zoo.
LINCOLN PARK ZOO
Literally the wildest place to visit in Chicago! Open 365 days a year and completely free, the Lincoln Park Zoo is a definite must-do and one of the best things to do in Chicago with kids of all ages.
Our zoo visit was a highlight of our trip. The fact that it’s free means no pressure to maximize your visit to “get your money’s worth.” If polar bears and penguins are your priority, you can focus just on them.
However, it’s hard not to linger, especially when you learn about the zoo’s vital conservation and science programs. Scientists use the zoo to study animals and develop strategies to combat threats to wildlife and improve animal management. So, feel good about that gift shop purchase – it supports a worthy cause. You might even see scientists at work.
For us, the highlight was observing the apes up close, separated only by glass from these incredible primates. We spent a good half hour in the monkey house, completely captivated.
Lincoln Park Zoo isn’t just a zoo. The south end of the park is a popular wedding photo location – as you can see in our photo below, the cityscape backdrop is truly spectacular.
After your wildlife encounter, you’ll find yourself in an upscale neighborhood with excellent lunch and snack options. The Lincoln Park area borders Sheffield, a neighborhood known for unique gift shops and charming coffee shops.
LUNCH NEAR THE LINCOLN PARK ZOO
Walk along North Clark Street for a Firecakes donut or an empanada at Lito’s. For a daring Chicago experience, try ordering a Chicago dog at Wiener Circle – be prepared for some playful (and notorious) insults! Alternatively, Five Guys milkshakes are a reliable takeaway option. This area offers diverse and unique eateries with classic Chicago flavors. Oz Park, with its Wizard of Oz sculptures, is also nearby if you’d like to grab food to go and enjoy a whimsical picnic.
Hop back on the ‘L’ at Fullerton and take the Brown or Purple Line back towards the city center for your final evening in the Windy City. Refuel with a sandwich from Al’s Beef. Their wall of fame testifies to their quality – their Italian beef sandwiches are piled high with slow-cooked beef dipped in gravy, served on a sourdough bun. Honestly, some of the best food we had in Chicago! (Locations on Ontario Street or Wabash Avenue).
DO THE CHICAGO RIVERWALK AT NIGHT
You’ve seen the Loop by day, experienced it from the elevated ‘L’, and now it’s time to see downtown Chicago at night, best viewed from the Riverwalk.
Six blocks of landscaped paths run along the Chicago River, providing a fantastic vantage point for admiring the dazzling skyline. FreeToursByFoot.com offers donation-based tours explaining the surrounding architecture, including nighttime tours. Or, simply take a leisurely stroll and soak in the views.
For cool facts to impress the kids about the skyscrapers along the Riverwalk, check out our other post – Chicago Architecture Unwrapped For First Timers.
More Things To Do In Chicago With Kids…
Being the Windy City with sometimes lengthy winters, here are more suggestions for fun things to do in Chicago with kids, especially if the weather turns or for extra entertainment:
- Catch a baseball game at historic Wrigley Field.
- Explore the Field Museum to see Sue the T-rex and learn about mummies.
- Watch dolphins and penguins at Chicago’s Shedd Aquarium.
- Discover space exploration at the Adler Planetarium.
- Teenagers will enjoy shopping on the Magnificent Mile.
- If you have a car and time before a flight, visit the Lizzadro Museum for its gem and stone collection – a worthwhile 30-minute stop near Chicago airport.
So, there you have our two-day Chicago itinerary for families. No one will leave disappointed (or hungry!). Have you visited Chicago with family? Can you recommend other family-friendly places or food spots in Chicago? Share your suggestions below – we’d love to hear them!
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