Things to do in Illinois: Exploring the Prairie State beyond the Windy City

Most visitors to the Midwestern state of Illinois set their sights on Chicago. This culture-rich metropolis, wrapped around the south-western finger of sprawling Lake Michigan, has an iconic skyline and plenty to entice travellers. But while the Windy City’s musical heritage, impressive architecture and cherished local food scene capture the imagination, there’s lots to explore beyond its urban limits.

Illinois stands up to its Prairie State nickname. Its countryside is characterised by endless cornfields and historical small towns such as Galena and Rockford, home to some impressive architecture dating back to the 19th century. A road trip through the wider state also reveals state parks featuring extraordinary canyons and beautiful wildflowers. Here’s what you shouldn’t miss…

In Chicago, be sure to book a ticket for one of the famed architecture tours along the river. First Lady Cruises (firstlady.com) offer narrated 90-minute boat rides, providing insight into the city’s impressive structures and the impact of the Great Fire of 1871. The Art Institute of Chicago is also a must-visit, thanks to its transcendent collection of Impressionist and Post-Impressionist works.

Drive two hours south-west of Chicago to reach jewels such as Starved Rock State Park, home to rocky terrain and abundant waterfalls, and the smaller Matthiessen State Park, which bursts with colour between July and August as its sunflowers bloom.

Chicago’s art and architecture should be at the heart of any itinerary, but I found the city’s sand-trimmed coastline to be a pleasant surprise. A vast expanse of urban beaches hug Lake Michigan, where you can have a go at everything from paddleboarding to jet-skiing.

Elsewhere, try a cycling tour with Bobby’s Bike Hike (bobbysbikehike.com), which follows Chicago’s urban trails and provides views of both the city’s skyline and Lake Michigan. It also includes some classic food stops.

Locals take pride in their deep-dish pizza, and while these ‘pies’ and their signature buttery crust are everywhere, Illinois chain Lou Malnati’s is among the signature go-tos. Elsewhere, The Wieners Circle on North Clark Street is a must for Chicago-style hot dogs (typically made with an all-beef frankfurter). Expect comically surly staff, especially if you ask for non-traditional ketchup.

Beyond the metropolis, small towns such as Rockford (145km north-west of Chicago) are worth the drive. Make time to tour Laurent House, a restored masterpiece by architect Frank Lloyd Wright. Completed for the Second World War veteran Kenneth Laurent in 1952, it is the only house in Wright’s portfolio that was designed to be wheelchair accessible. This single-storey building in the Usonian style (a term coined by Wright to depict his vision of America’s architecture) is flooded with daylight, while the grounds feature a koi pond and gardens swarmed by crimson-coloured cardinal birds.

In the far north-western corner of the state lies the town of Galena. It is best known for its well-preserved 19th-century buildings, including the Italianate Belvedere Mansion, as well as its welcoming LGBTQ+ community. Visitors will find an abundance of inclusive accommodation, and June’s Pride Picnic in Grant Park is now an annual highlight.

In Galena, I met with many locals who had left behind Chicago in favour of a quiet life. One Galena native whose story stuck with me was Geoffrey Mikol, a photographer with Down syndrome, who is the owner of the River Bend Gallery in the heart of town. His photos touch on the beauty of the region and the wider Midwest, capturing forests turned golden in the fall and rolling farmland.

Top tip

Exploring Illinois’ unspoilt countryside is one of the ultimate joys of a road trip here, but the views are even better from above. If the winds are in your favour, balloon flights with Galena on the Fly (buyaballoonride.com) are a fabulous way to take in the state’s rippling prairies.

Cautionary tale

Illinois is large, so you may end up spending a lot of time on the road. For example, a straight drive across the length of the state, north to south, should typically take around six hours. That said, there are plenty of worthwhile stops along the way.

State capital Springfield, in the heart of Illinois, is a great place to break up a road trip. Follow in the footsteps of the 16th president at the Lincoln Home National Historic Site (where ‘Honest Abe’ lived from 1844 to 1861), then take a tour of the Capitol building.

Allocate plenty of time to visit The Art Institute of Chicago. I spent an entire afternoon admiring the permanent exhibits there, which featured Claude Monet, Jackson Pollock and Vincent van Gogh, but had very little time to explore the temporary shows. Also bear in mind that Illinois changes with the seasons. The waterfalls and hiking trails at Starved Rock State Park were impressive when I visited in the fall, but it’s a different world as the region fills with wildflowers in spring.

Anything else?

Don’t miss out on Illinois’ elegant gardens. In Rockford, visit Anderson Japanese Gardens, just five minutes from Frank Lloyd Wright’s Laurent House. This tranquil five-hectare space is dotted with bonsai trees, koi ponds and waterfalls, and it also has a tea house that hosts traditional Japanese tea ceremonies.

Another must-see is Cantigny in DuPage County, 40 minutes’ drive west of Chicago. This 200-hectare estate once belonged to Robert R McCormick, a former editor of the Chicago Tribune; it now features a peaceful botanical garden, a military museum and several hiking trails worth exploring.

Further reading

Visit enjoyillinois.com for help planning trips.

The author travelled with support from the Illinois Office of Tourism.