The origins of this village in Chicago’s northwest suburbs can be traced back to the 1830s, as an overnight stop for people heading off into the Wisconsin Territory from Chicago.
Almost 200 years later people travel to Wheeling for Restaurant Row, a long line of mostly independent restaurants along Milwaukee Avenue (Illinois Route 21).
Wheeling sits on the west bank of the Des Plaines River, the banks of which are hugged by a series of Lake and Cook County forest preserves.
This remote hickory-oak woodland can be traversed along the Des Plaines River Trail, which runs unbroken for several miles north and south of Wheeling.
In and around the village there’s a fantastic central park, accompanied by a new mixed-use development, as well as amenities like an old school bowling alley, a legendary mini golf course, the Korean Cultural Center of Chicago and an indoor karting track.
1. Restaurant Row
Something to put Wheeling on the map is the long line of eateries on Milwaukee Avenue. In recent memory Wheeling’s reputation as a culinary hotspot goes back to the establishment of Le Francais in the early 1970s.
This hugely successful French restaurant had a six-month waiting list in its heyday and is even credited with a building boom in Wheeling.
But Milwaukee Avenue’s hospitality days go back even further, to the 1830s and a long row of taverns and eateries for travelers setting off for the Wisconsin Territory.
Restaurant Row is still going strong today with 20+ options, and something for all palates, pockets and appetites.
A few famous picks include Bob Chinn’s Crab House (393), Superdawg Drive-In (333), Rise n Dine Pancake Cafe (102), Saranello’s (601) and Cooper’s Hawk Winery & Restaurant (615).
2. Des Plaines River Trail
For 133 miles, the Des Plaines River weaves its way southwards from Kenosha, Wisconsin to the Illinois River at Joliet.
This watercourse passes by the east side of Wheeling, through a long chain of Lake and Cook county forest preserves. For most of Lake County and some of Cook County you can follow the route of the Des Plaines River along the multi-use Des Plaines River Trail.
Wheeling is right next to a long, unbroken section that runs for many miles through a long succession of preserves.
You can hike and cycle along grassy riverbank, through oak-hickory woodland, floodplain forest, sugar maple-basswood forest and backwater wetlands, encountering a glorious diversity of wildlife and few signs of human civilization on your adventure.
3. Heritage Park
Next to Wheeling Metra Station, this 100-acre park, combined with a new mixed-use development, provides a gathering space in the center of Wheeling.
In the summer the Performance Pavilion at Heritage Park stages a series of outdoor concerts, festivals and movie screenings, while the park is endowed with a wealth of other facilities.
We’ll talk about the outdoor Family Aquatic Center later, but there’s also a large pond, a top-notch playground area and the Community Recreation Center, with cardio and weight machines, an indoor pool and rooms for exercise classes.
Elsewhere you’ll find a Sports Complex, with baseball fields, football fields and a concession stand, as well as ample open green space for strolls.
4. Potawatomi Woods
Right beside Wheeling, in that green corridor along the Des Plaines River is a beautiful Cook County forest preserve under a mantle of hickory and oak woodland.
A spur on the Des Plaines River Trail here will take you to the secluded Lake Potawatomi. This is surrounded by grass space and dense hardwood forest, providing a habitat for waterfowl and wading birds like great blue herons.
You stand a good chance of spotting deer, especially early and late in the day, and the lake is a favored spot for fishing and model boating.
Further south there’s a picnic grove with a stone shelter and around a dozen picnic tables
5. Wheeling Family Aquatic Center
Open early June through Labor Day weekend, this pool complex in Heritage Park is a must for families.
Wrapped in the park’s greenery, the Family Aquatic Center has an impressive design, based around artificial rocky outcrops that serve as a platform for the park’s various slides.
There’s a large pool here, with beach entry and a wading area installed with spray equipment, a waterfall and various obstacles, as well as a training area with several lanes for lap swimming.
Also on site is a sprayground with climbing equipment and a tipping bucket for kids, and a smaller separate pool with a rickety bridge and a basketball net.
6. Windy City Aviation
One of the benefits of having Chicago Executive Airport so close is the presence of companies like Windy City Aviation.
This flight school provides a range of services, including training for existing pilots who need to keep their knowledge base and skills current and sharp.
But Windy City Aviation also caters to aspiring pilots working towards their private pilot license, as well as first-time flyers.
On a Discovery Flight you can acquaint yourself with an aircraft cockpit in the presence of an experienced instructor, while marveling at Chicago’s most famous landmarks, from the Willis Tower to Navy Pier and Wrigley Fields.
7. Pinheads Jeffery Lanes
Seeing Pinheads Jeffrey Lanes from the street on N Wolf Rd you’d be surprised there’s a bowling alley inside. Safe to say this place, established in the 1950s, is old school.
There are only eight lanes here, and no electronic scoring system, so you have to keep your own score with a pencil and paper.
On top of that the alley is rumored to be haunted by the original owner, Bud Miller, who passed away in the building.
There’s a fully stocked bar, two juke boxes, two karaoke nights a week and an annual bowling tournament between local firefighters and paramedics that has been going for more than 60 years.
8. Korean Cultural Center of Chicago
Next to the Chicago Executive Airport is a place where you can get in touch with Chicagoland’s large Korean community and its fascinating heritage.
The Korean Cultural Center of Chicago has several key purposes, including preserving and exhibiting the history of Korean immigrants, hosting Korean events and lectures and sharing Korean heritage, among others.
You can head to the Museum & Gallery for an art or history exhibition, while the center has a rich calendar of concerts, music competitions, talks and other events.
The center runs numerous courses and programs for dance, cooking, language, exercise, arts and crafts, traditional Korean music and much more.
9. Par-King Skill Golf
Another attraction with a real retro feel is this mini golf course a short drive north in Lincolnshire.
As a business, Par-King Skill Golf has been around since the late 1950s when it received nationwide acclaim for its unusual holes and obstacles.
The attraction relocated from Morton Grove to Lincolnshire in 1977, and there are now two 18-hole courses here.
These sit in elegant landscaping, with topiaries and neatly clipped hedges, featuring no fewer than 19 moving obstacles and 7 water holes. Par-King continues to offer a whimsical outing for kids, but also an engaging test for more serious players.
10. K1 Speed
K1 Speed is an indoor karting chain with more than 50 locations around the United States. One of these is right next to Chevy Chase Country Club in Buffalo Grove.
This facility has two tracks, expertly designed for high speeds and lots of overtaking action. You’ll be driving high-performance electric karts, manufactured in Europe and producing zero emissions.
These machines can hit top speeds of 45mph in a few seconds flat. K1 Speed caters to corporate events and parties for all ages, and organizes a range of leagues and cups.
But if you just want to get behind the wheel there are also Arrive & Drive sessions all week long. Both tracks at K1 Speed are overlooked by the Paddock Lounge restaurant.
11. Dam #1 Woods-East
The most convenient way to reach that green corridor along the banks of the Des Plaines River is to head for this preserve, a couple of minutes east of Heritage Park.
Traveling east on E Dundee Rd, one second you’re surrounded by chains like McDonalds and Walgreens, and the next you’re in blissful wilderness.
If you’re just looking for somewhere peaceful to have lunch, the preserve has two picnic groves with large shelters, and you could not choose a lovelier place to have a picnic on an autumn day when the colors are spellbinding.
12. Wheeling Town Center
If you haven’t been past for a while, the space around Wheeling Metra Station is almost unrecognizable.
A large mixed-use development, Wheeling Town Center, has sprouted over the last few years on the west side of Heritage Park.
Making the most of the convenient transit link to Chicago’s Union Station, Wheeling Town Center combines hundreds of apartment units with extensive retail, dining and entertainment space.
When it comes to food and drink you can choose from a modern pub (CityWorks), contemporary Mexican (Mia’s Cantina), healthy breakfast options (Eggsperience), bubble tea/rolled ice cream (Arctic Spoon) and Chicago-style comfort food (Meat & Potato Urban Kitchen). And for an upscale movie and dining experience there’s CMX CinéBistro.
13. Wheeling Historical Society Museum
If you’re looking for something to do on a Sunday afternoon you can drop by the newly renovated Wheeling Historical Museum in Chamber Park.
Run by volunteers, this small but well cared for attraction is a glimpse of life in the village across more than 130 years.
Typically you’ll see household appliances, farming tools, furniture, textiles, toys, fashion, sports equipment and a superb library of photographs giving an intimate impression of Wheeling’s residents since the 1890s.
Every December the museum hosts Lollipop Lane, with a gorgeous display of vintage festive decorations donated by local families, and a visit from Santa Claus himself.
14. River Trail Nature Center
Five minutes from Wheeling by road, this treasured facility can be found on the Des Plaines River Trail in Allison Woods.
This is perfect if you want to know more about the tapestry of habitats along the trail. You can peruse interesting interactive exhibits on the natural history of the Des Plaines River and its wildlife today, and see live animals including coyotes, owls, eagles and hawks.
The center also maintains numerous bird feeders, and you can spend a few minutes watching a dazzling array of singbirds coming and going.
There are also three shorter trails to discover on the center’s grounds, as well as all kinds of workshops and demonstrations to attend throughout the year.
15. Chevy Chase Country Club
Now approaching its centennial, Chevy Chase Country Club (1927) is a historic facility open to the public.
When you see the exquisite Tudor Revival clubhouse nestled in the lush, water-rich grounds, you’ll understand how this is one of the most popular wedding venues in the area.
The 18-hole course is a delight, in beautiful, mature nature, with pristine fairways and immaculate, fast greens.
Water is ever-present, but truly comes to the fore on nine holes. And despite the history of the club, the course makes use of state-of-the-art technology, GPS on the golf carts to calculate yardage and real time GPS leaderboard for your group.