Tony Bennett famously left his heart in San Francisco. I left mine on a sunny riverbank in Naperville, Illinois.  

Bennett’s signature tune came from two California songwriters who’d moved to New York City to make it in the pop music business. They missed their City by the Bay so much they set their lament to music, and a hit was born. I know how they felt, having recently moved to Arizona to help care for my ailing father. But my heart remains in Naperville, a city not by a bay, but, rather, Chicago.

Fortunately, I can visit my heart whenever the urge strikes. So can you, and here are 23 fun things to do in Naperville, a great day trip from the Windy City.

Bring the kids; Naperville is as family-friendly as it gets.

1. Naperville Riverwalk

The DuPage River cuts a lazy curve through the heart of downtown Naperville, and the Riverwalk is the picture frame that shows it off to the world. I strolled hundreds of miles on those paths, and so can you.

If you do, you’ll join thousands who throng the city every year to stroll its several miles of cherry-red paver bricks. They pass trees, gardens, a fountain that spouts water into the shape of a dandelion head, covered bridges, work and picnic spaces with shade and power, a playground, ice skating rink, swimming hole with beach, skateboarding park, City Hall, Naperville Public Library and its original limestone Nichols Library, whose meticulous preservation let it become high-end office space. And statues including founder Joseph Naper, the Cat In the Hat,  and Dick Tracy. Alongside all that sit hundreds of restaurants, bars, shops, and other places of interest.

Or, like the two in the above photo, you can chill in the breeze if you prefer.

Built in 1981 to honor the city’s 150th anniversary, Naperville’s Riverwalk is one of the nation’s crown jewels of linear riverside parks, and one the best outdoor activities in Naperville.

2. Naperville’s Downtown

 The city was founded at river’s edge in the early 1800s. It has grown from that handful of dirt streets to a sprawling, world-class, high-tech city that routinely makes the nation’s “Best Places to Live” lists.

If the river is Naperville’s heart, the downtown area is its soul, with shops and restaurants housed in buildings from the 1800s and 1900s as well as modern architecture. Old and new are seamlessly integrated with the Riverwalk and the DuPage River that literally cuts the city in two.

SheBuysTravel Tip: Parking is free on the street and in downtown garages, so you can easily spend hours eating, shopping, and admiring old-meets-new. Want a map? Here you go, everybody likes a map, right?

3. Eats and Treats

Naperville offers food and drinks galore: I counted more than 200 places on Yelp and that’s not all of them. Many are downtown, just blocks from the DuPage River; others are as far-flung as the city is wide and long. Places I’ve loved over the years and happily survived Covid:

Yamado

A fan of fresh sushi? It doesn’t get better than this. Yamado is a small restaurant in a strip mall next to a pawn shop. But don’t let location fool you, the sushi and Japanese cuisine are out of this world. (My go-to: white ocean fire roll.) It’s not a fancy-dress place with a three-month wait, either. Just drop in and eat, at the sushi bar or one of a dozen tables.  

Lou Malnati’s

Chicago is the home of deep-dish pizza—pies three inches thick and heavy as sledgehammers, not the fold-and-run pizza of New York City. In the deep-dish world, nobody’s recipe is better than Lou’s. I’ve eaten it for decades and never experienced a bad pie. Lou’s offers other Italian food, but what’s the point? If you prefer thin-crust, my go-to’s are Home Run Inn and Aurelio’s. All three are, like me, Chicago natives.

Meson Sabika

The first clue you’re in food heaven is the setting: a graceful old mansion near downtown. The next is the heavenly smell of tapas, paella, and other Spanish specialties. But most come here for the tapas, those appetizer-sized “small plates” that let you try a dozen or more in a single meal. The charming atmosphere is a bonus.

Buttermilk

Omelets are huge and pancakes are to die for. My favorite breakfast hangout.

Granite City Food & Brewery

This brew pub has outstanding food, not just standard pub fare, and the beer is fresh and tasty. I am a fiend for dark-and-heavy—stouts and porters—and Granite City does a phenomenal job with both.

SheBuys Travel Tip: Hungry for more? Here’s the complete dining guide from TripAdvisor, and here’e the one from Yelp.   

4. Naper Settlement

Decades ago, several of Naperville’s historic buildings were in danger of being demolished for development. Farsighted residents hatched a plan to have it both ways—erect those modern buildings downtown, sure, but move the most significant pioneer-era buildings to a nearby 13-acre “living history” outdoor museum.

The plan turned into Naper Settlement, an outdoor living history museum that showcases 1800s Naperville through costumed re-enactments, live demonstrations of blacksmithing and other American crafts, music, weddings in the relocated pioneer chapel, and special events like Oktoberfest and my personal favorite, Ale Fest.

The latter is held in the bone-chill of February but features 150 craft beers to keep you warm and fuzzy.

5. Centennial Beach

Illinois summers are hot and humid, so why not include a dip on your trip?

Centennial Beach is a historic limestone quarry that, in 1931, was turned into a sprawling public  “swimming hole,” complete with lifeguards, diving boards, a sand beach with zero-depth entry into the water and changing rooms.  

The imported “beach” at Centennial Beach is small, but there is plenty of grassy area to lay out some towels or a blanket for a picnic or just to rest between splashes.

6. Paddleboat Quarry

Rent a paddleboat, kayak, or paddleboard and glide around Paddleboat Quarry, Naperville’s other quarry lake. It’s not a large body of water, but the memories will be when your kids push those paddle pedals with shrieking delight. It’s on the Riverwalk.

Paddleboat, paddleboard and one- and two-person kayak rentals are available onsite.

SheBuysTravel Tip: When you’re done, buy tasty treats at the snack shop. Yes, you totally deserve that second scoop of rocky road.  

7. DuPage Children’s Museum

As the name suggests, it’s fun time for the kiddos! The museum is a few blocks from the Metra train stop in downtown Naperville, so you can drive or take the train from Chicago and other stations along the route.

The large, colorful museum—most of Naperville is located within DuPage County, providing the name—features interactive activities including LEGO construction, play areas, and events for infants, toddlers, and kids till early teens. Family bathrooms and a nursing room, along with a café, complete the treat.

8. The Ball Factory

One of the most energetic places I’ve seen, The Ball Factory is the motherlode for active kids and the parents who love them . . .  or at least want the young’uns to burn off a bunch of energy before heading home for naps.

It’s a sprawling indoor playground with ball-blasting zones (hence the name) and other areas in which kids from infants to age 12 can have a ball, pun intended. There’s also a café and private party rooms, perfect for holding birthday parties without having to clean up the mess.

9. Millennium Carillon

A friend of mine plays the bells in this literal skyscraper of a musical instrument. The effect of her and fellow players’ music is magical, with tones from tinkle to GWONG reverberating across the adjacent Rotary Hill on which you can spread a blanket or unfold a chair to listen to the concerts . . . and sled down during winter.

The bells are inside Moser Tower, the 16-story, 72-bell structure built to commemorate Y2K—better known as the dawning of the Year 2000, the new millennium.

The tower is a few feet taller than the Statue of Liberty, and visitors can climb all 253 steps to the top on guided tours—or take the elevator to the gallery-level observation deck. On a clear day, you can see the Chicago skyline 30 miles to the east.

10. Sled, We Said

Winter in Northern Illinois brings snow and freezing temperatures. Rather than huddle indoors, why not head to one of the city’s sledding hills or ice-skating rinks? When ice and snow are thick enough, kids and kids-at-heart head for the Naperville Park District’s four skating rinks and eight sledding and snowboarding hills. Many are night-lighted, all are fun.

11. Cantigny Park

We move briefly to neighboring Wheaton, Illinois, for our next adventure: the 500-acre estate of Colonel Robert R. McCormick, legendary publisher of the Chicago Tribune.

In 1958, his home became a park named Cantigny. (The colonel fought in World War I, and “Cantigny” reflects that part of his life.) I’ve been going there since I was a kid, and it always delights.

Walking trails, a golf course, and 30 acres of truly fabulous gardens created by renowned landscape artist Franz Linn surround the First Division Museum. That museum is dedicated to the history of “The Big Red One,” the famed 1st Infantry Division of the U.S. Army. Many of the museum’s exhibits are interactive, including its full-walk-through WWI trench, with simulated artillery blasts and bullet zings demonstrating how tough life was in those mud-riven battle trenches.

Just outside the museum doors is my favorite memory of childhood: a park filled with army tanks, artillery, heavy weapons, and helicopters, all of which can be touched and climbed on by kids and adults alike.

12. Knoch Knolls Park

Back to Naperville to visit a park that sits on the same DuPage River we saw a few  miles to the north: Knoch Knolls. Miles of trails were cut through woods and fields, crisscrossing the river in several spots. Most are paved for hikers and bikers, but some, deeper into the woods, are good ole dirt just as Mother Nature intended.

Knoch Knolls Nature Center is impressive, as is its children’s playground. The nature center is home to a wealth of free information, self-guided activities, scavenger hunts and special events.

Canoes and kayaks can be launched into the river from several entry spots (bring your own or book a kayak tour) and those who enjoy Frisbee golf can sling to their heart’s content on the dedicated course.

13. North Central College

Buildings crafted of honey-colored limestone (recall that Centennial Beach was built in a limestone quarry?) intermingle with the “painted ladies,” those old, brightly painted mansions in Naperville’s Historic Home District northeast of downtown.

You’ve entered the campus of North Central College, the independent private college that opened in 1861, when the Civil War was raging and Abraham Lincoln was sworn in as the nation’s 16th president. The leafy campus is well worth the stroll, and it’s between downtown and the Metra train station.

The college is home to the Wentz Concert Hall and Fine Arts Center, a striking piece of urban architecture tailored for live performances. Wentz has showcased performances by singers, dancers, comedians, storytellers, and musicians from Yo-Yo Ma to The Beach Boys in its four auditoriums, and offers a variety of artworks in its galleries. It also has art galleries. If your schedule allows, I highly recommend buying tickets to a show.

14. In a Festive Mood?

Naperville is a beehive of festivals and events. There’s Ribfest, a multi-day thrum of live bands and smoked meats that draws more than 100,000 hungry visitors. The band-jammed Last Fling live music fest marks the end of summer. Naperville Art League’s Riverwalk Fine Arts Show displays the work of painters, sculptors, and other world-class artists along the winding paths of the Riverwalk.

In neighboring Wheaton, the DuPage County Fair is a lollapalooza of smoked turkey legs and smash-’em-up demolition derbies. Naperville also does up the holidays in style, from Halloween trick-or-treating downtown to Christmas light displays. Click here for dozens more.

15. Springbrook Prairie Forest Preserve

Like to hike and bike? Springbrook Prairie would love to have you. The 1,829-acre DuPage County Forest Preserve on Naperville’s South Side is one of the few remaining pieces of Illinois prairie. The county’s long and careful restoration has brought birds and butterflies—many, many butterflies—in droves.

That and a network of crushed-limestone trails makes this preserve one of my favorite places to hike, bike, and think about the day. You’ll also find an open-run dog park and a field dedicated to radio-controlled model planes.

The leafy suburbs get called that for a reason. In the western suburbs of Chicago, forest preserves are the reason. There are miles of woodlands, lakes, and rivers managed by the DuPage County Forest Preserve and Will County Forest Preserve districts. Why both counties? The northern two-thirds of Naperville sits in DuPage, while the southern portion sits in Will, also home to Plainfield and Joliet.

In addition to Springbrook, preserves at which I’ve personally hiked, biked, and listened to birdsong and heartily recommend are:

• Blackwell
• Danada
• Greene Valley
• Herrick Lake, which contains a lake carved by glaciers
• Lake Renwick Rookery and Huron Preserve. (An easy drive south to Plainfield.)
• McDowell Grove
• St. James Farm
• DuPage River Park, part of the much longer DuPage River Trail

16. Morton Arboretum

Thanks to the mile-high glaciers that scoured Illinois and most of the Midwest during the last Ice Age, Naperville is flat as a pancake. No mountains for you! But it contains rivers, lakes, several ravines, and thousands of shade trees, so hiking, biking, and picnicking sites are plentiful.

My favorite slice of Tree Heaven is the Morton Arboretum, a world-class landscape of trees just northeast of Naperville in the Village of Lisle. Morton arborists and staff members perform exhaustive tree, forest, and pest research in addition to keeping more than a thousand acres of forests, trails, maze, gardens, and visitor center trimmed and beautiful for its thousands of annual visitors.

17. Naperville Sportsman’s Club

Rare for any city but rarer still for being smack-dab downtown, Naperville has a trapshooting range that’s open to the public.

Shooting and hitting clay pigeons as they arc through the sky in the blink of an eye is harder than it looks. The first time I tried, I broke the first five clays—one shotgun blast, one pulverized pigeon. I missed the remaining 20. Surely you’ll do better.

18. Naperville Municipal Band

Yes, there’s a city band. Yes, it’s been playing since 1859. And yes, its concerts are free, open to the public, and held every Thursday through the summer.

When I first began attending concerts in the 1980s, the band shell was large, old, and worn, with seating on long wooden benches that might or might not hold you and your sandwiches without wobbling.

The site has been upgraded to comfortable seating at the foot of a first-class elevated band stage that would make a big-city orchestra proud. The uniformed band may look like something out of John Phillip Sousa and The Music Man, but it’s the real deal, 76 trombones and all.

19. Anderson’s Bookshop

This family-owned independent bookseller has been in Naperville since 1875, when books were sold at the family pharmacy. Anderson’s now books the hottest authors in publishing, from J.K. Rowling in her Harry Potter days to James Patterson to Tess Gerritsen to Lee and Andrew Child to, well, me, with Anderson’s being kind enough to host publication-day events for all four of my crime novels.

The store isn’t large in square footage, but it’s a 500-pound gorilla in matching readers with writers.

20. Naperville Trolley & Tours

A genuine trolley car converted to wheels for cruising city streets provides history tours of Naperville. It also hosts weddings, anniversary parties, class reunions, Christmas lights tours, and a hundred other ways of taking folks for rides down memory lane.

The trolley is heated and air-conditioned so the lovely bride will not wilt.

21. Brightside Theatre

 This peppy playhouse stages live performances year-round, from familiar classics to modern works.

22. Take a Public Art Stroll

Naperville Century Walk commissions, installs, and preserves public art throughout the city. It’s a glorious mishmash of styles, colors, and themes, from a larger-than-life statue of cartoon crimefighter Dick Tracy (Dick’s artist pal, Dick Locher of the Chicago Tribune, lives here) to bronzes, sculptures, murals, and mosaics.

23. Raging Waves Waterpark

Another neighboring attraction, Raging Waves is Illinois’ biggest waterpark. It’s located 40 minutes southwest of downtown Naperville in Yorkville. If you happen to be visiting Naperville with kids, you’ll definitely want to earmark a day at this massive water park, with its thrilling waterslides, giant wave pool, and fun sandy play area.

Frequently Asked Questions (FAQ)

Where In the World Is Naperville?

I would have told you right away, but you insisted on learning about eats and hiking trails and such. I get it, I would too. But since you asked, here’s the skinny:

Naperville, a city of 150,000 residents, lies 30 miles southwest of downtown Chicago and its glorious Lake Michigan. Bordering Naperville, clockwise from top, are the suburbs of Warrenville, Wheaton, Lisle, Woodridge, Bolingbrook, Plainfield, Oswego,  Aurora, and Eola. Joliet and Plainfield are a bit further south.  

What’s the Easiest Way to Get to Naperville from Chicago?

Driving is the best and simplest way to reach Naperville—U.S. 34 Ogden Avenue if you don’t like tollways, Interstate 88 if you do. Exit at Naperville Road and head south.

You can also take the Metra commuter train and disembark at Fifth Avenue Station, a mile northeast of downtown and its attractions.

Pace suburban bus service exists, but it’s spotty; Uber and taxis are better alternatives.

The best way to get around Naperville is to walk: downtown is compact and vibrant with new-meets-old, and the grand homes of the Historic District are stunning.

How Did Naperville Get its Name?

The city is named after Captain Joseph Naper. (Or, possibly, Napier. No one seems to know for sure. But since the Founders went with Naper, I will too.)

In any case, he was a first-generation American, having been born in Vermont in 1798 to Scottish immigrant parents. Naper captained steamships on the Great Lakes, and after retiring in 1831, he and wife Almeda grabbed up kids, kin, and kindred spirits from their homes in Ohio, sailed a schooner west to Lake Michigan, rolled wagons to a bend on the DuPage River, and put down roots in what would eventually become Naperville. The clan got along with the Pottawattomi Indians who lived there. From the Brookdale Homeowners Association:

“Prior to the arrival of white settlers in the 1830s, Naperville was home to Indigenous people for over 8,000 years. In 1673, the Illiniwek Indians greeted French explorers Father Jacques Marquette and Louis Joliet. By 1800, Pottawatomi Indian villages stood where Naperville is now.” The neighborliness was short-lived; just a few years later, the U.S. Army relocated the tribe to Oklahoma as part of the Indian Removals program.

Captain Naper built a flour mill and trading house, and in 1831 the little encampment became Naper’s Settlement. That turned into Naperville, which was incorporated in 1857, four years before the City of Chicago, a bragging point among Napervillians then and forever. A larger-than-life bronze of Naper pointing at the sky—er, pointing the way to the future!—sits on the site of his original homestead, located downtown. The statue was designed by Pulitzer Prize-winning cartoonist and Naperville resident Dick Locher, the longtime artist of the Dick Tracy comic strip.

Useless Yet Fascinating Sidebar About Town Names

The City of Joliet, the county seat of the Will County that’s home to the southern tip of Naperville, grabbed up French explorer Louis Joliet’s last name for its own. The neighboring Village of Romeoville said, “Hold my beer,” and named itself after a Shakespeare play, thus giving Will County the twin cities of Romeo and Juliet.

About Shane Gericke