Rochelle, IL
The dining venue of Chicagoland Skydiving Center, which has been dropping jumpers since 1968; nothing else on a Midwest field is quite like it. Global-inspired pub menu from an open kitchen, craft beer, and the Merit Patio pointed straight at the landing area: you eat, they fall, everyone waves. Beer garden, sand volleyball, bonfire pits, weekend breakfast with Sunday brunch, and event space that swallows 500. Woman-owned. Summer hours run daily (Monday to 3, Sunday brunch to 3, otherwise 11 to 9); winter shrinks the week hard, so check before a cold-season run. Watch the canopies stack up over dessert and remember you get to fly home.
Two miles south of Rochelle, just off Interstate 88 and Illinois 251. Single runway 07/25, PAPI both ends. Home to the Chicagoland Skydiving Center — one of the busiest jump operations in the Midwest. The sectional "intensive parachute activity" warning is not idle: on good summer days there can be near-continuous Caravan loads of jumpers in the pattern with chutists in the sky. Contact KRFD 121.0 for parachute advisory before approach. Non-towered, but always expect skydiving traffic.
Starved Rock is the closest thing the Midwest has to a slot-canyon park. At the end of the last Ice Age — somewhere between 14,000 and 17,000 years ago — a catastrophic flood of glacial meltwater called the Kankakee Torrent ripped through this stretch of central Illinois. The flood found the softest layer of bedrock (St. Peter Sandstone, deposited as beach sand 470 million years ago) and gouged 18 narrow canyons into the south bank of what is now the Illinois River. The result is a 2,630-acre park of vertical sandstone walls, mossy seeps, and waterfalls fed by spring runoff — landforms that look like they belong in Utah, transplanted to the middle of corn country. It is the most visited state park in Illinois (over 2 million visitors a year) and was the state's second park, purchased in 1911 to keep it from being quarried for sandstone. The "Starved Rock" itself is a 125-foot sandstone butte at a bend in the Illinois River. Native American oral tradition says the name comes from an 18th-century siege — a band of Illiniwek warriors took refuge atop the butte to escape Ottawa and Potawatomi war parties avenging the 1769 killing of Chief Pontiac, and starved there. French explorers Jacques Marquette and Louis Jolliet passed through this stretch in 1673; the French built Fort St. Louis on top of the butte in 1682-83. The Civilian Conservation Corps built much of the trail infrastructure (stone stairways, shelters, the lodge) in the 1930s. The site was designated a National Historic Landmark in 1966. Immediately downstream of the butte is Starved Rock Lock and Dam — one of eight in the Illinois Waterway that take barges over the 163-foot drop from Lake Michigan to the Mississippi. Bald eagles winter on the open water below the dam; the park is one of the best eagle-watching sites in the Midwest December through February.
Cantigny is just off KDPA in Wheaton; from the air it's a 500-acre estate with formal gardens, and on the south lawn a row of US Army armor sitting in the grass: a Sherman, a Patton, a Bradley, and the guns that worked with them. That armor is the tell for what this place is. Robert McCormick, the Chicago Tribune publisher, led artillery supporting the 1st Infantry Division at the Battle of Cantigny in France in 1918, the first American victory of World War I, and it marked him for life. He named his estate after the battle, hosted Big Red One reunions here for decades, and willed the 500 acres to the people of Illinois. The First Division Museum on the grounds tells the division's story from WWI to now, with recreated environments you walk through: a Western Front trench, the cliffs above Omaha Beach, a Vietnam jungle. Alexander Hamilton commanded the same field artillery regiment during the Revolution; it's one of the oldest in the Army.
Frank Lloyd Wright built his own house in Oak Park in 1889 when he was 22, financed in part by a $5,000 loan from his employer Louis Sullivan. He lived there for the next 20 years and added a studio in 1898, where he developed what would become the Prairie School — the first uniquely American architectural style of the 20th century. The suspended drafting balcony in the studio was one of his earliest structural innovations. Oak Park has the highest concentration of Wright-designed buildings anywhere — more than 25 within walking distance of the Home & Studio. Among them is Unity Temple (1908), one of the most influential public buildings of the early 20th century: a poured-concrete cube with no traditional front door, designed to dissolve the boundary between interior and exterior space. Wright called it his "little jewel." The Robie House (1910) in Hyde Park is the consummate Prairie style — designed at the Oak Park studio for manufacturing executive Frederick Robie. Its dramatic horizontal cantilevered roof, banded art-glass windows, and three-car garage (exceedingly rare in 1910) made it a complete departure from traditional residential architecture. The seminary that owned it twice proposed demolition (1941 and 1957); Wright himself joined the protest, supposedly quipping that the episode showed the danger of entrusting anything spiritual to the clergy. In 2019 UNESCO designated eight Wright buildings as a World Heritage Site — "The 20th-Century Architecture of Frank Lloyd Wright." Two of those eight are in Illinois: Unity Temple and the Robie House. The Oak Park Home & Studio is separately a National Historic Landmark.
Wrigley Field opened in 1914 as Weeghman Park, home of the Federal League's Chicago Whales. The Cubs moved in two years later, and chewing-gum magnate William Wrigley Jr. bought the team and renamed the park in 1927. It is the second-oldest active ballpark in Major League Baseball, behind only Fenway in Boston (1912), and the oldest National League park. The ivy on the outfield walls was planted by Bill Veeck Jr. in 1937. The hand-operated scoreboard above the center-field bleachers was built the same year and is still operated by hand — the only major-league scoreboard that still is. Lights were installed in 1988, making Wrigley the last MLB park to host night baseball. For 108 years between 1908 and 2016, the Cubs did not win a World Series — the longest championship drought in major American professional sports. The story of the supposed Curse of the Billy Goat (1945, when a goat was ejected from a Series game) became part of Chicago folklore. The drought ended November 2, 2016. The "W" flag that flies after every Cubs win is visible from blocks away. The rooftops on Waveland Avenue (left field) and Sheffield Avenue (right field) have hosted bleacher-seating businesses since the 1980s — uniquely Chicago — and were the subject of a long copyright fight before the Cubs reached a 2004 royalty agreement. Today the rooftops are licensed and many were rebuilt with proper grandstands. Field capacity is approximately 41,650.