Chicago Midway International

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.

Out of Midway (KMDW), the Museum of Science and Industry is in the only building left from the 1893 World's Fair, a Beaux-Arts pile on the lakefront (renamed the Griffin Museum in 2024, though locals still say MSI). The thing to see is the U-505, the only German submarine the US Navy ever captured intact. On June 4, 1944, two days before Normandy, a task group cornered it off West Africa; a boarding party from the USS Pillsbury jumped aboard while it was still under power, the first US Navy boarding of an enemy warship since 1815, and saved it before the German crew's scuttling charges blew. They took codebooks and Enigma cipher rotors. The capture was kept secret: the German crew was held in Louisiana for the rest of the war and their families were told they had died. They came home in 1946 to families that had buried them. The boat, 252 feet, was barged up through the Great Lakes in 1954 and sat outdoors for fifty years before being moved into an underground hall in 2005.

The Chicago skyline is one of the great urban approaches in American aviation. From any general aviation field in the western Chicago suburbs, the city rises as a vertical wall of steel and glass out of an otherwise flat prairie — visible from 25+ nautical miles on a clear day. Willis Tower (formerly Sears Tower from 1973-2009) is the anchor at 1,450 feet to the roof and 1,729 feet to the antenna tips. It was the tallest building in the world from 1973 until 1998 (passed by the Petronas Towers in Kuala Lumpur) and remains the third-tallest in the US. The diagonal X-bracing tower north of it is 875 N Michigan (formerly the John Hancock Center) at 1,128 feet — the second-tallest in Chicago and an easier visual reference because of its tapered black profile. Trump Tower (1,388 feet) and the St. Regis Chicago (1,191 feet, the tallest building in the world designed by a woman, Jeanne Gang) round out the high points. Lake Michigan provides the eastern boundary — an inland sea so large it has its own horizon. Lake Shore Drive curves along the shore from Hyde Park in the south to Lincoln Park in the north, with Navy Pier projecting into the lake like a hook. The Loop street grid sits at roughly 45 degrees offset from the surrounding citywide grid — a tell that you are over downtown. Class B airspace is the principal constraint. Most GA pilots either request Class B transition with ATC, transit the VFR corridor along the lakefront when published, or stay clear by skirting the southern or western shelves. The City of Chicago Heliport on the lakefront and the (now-demolished) Meigs Field site are landmarks worth knowing.

Northerly Island was envisioned by Daniel Burnham in his 1909 Plan of Chicago as the first of five offshore islands in a chain of lakefront parks. Only one was ever built — and it was built as a peninsula in 1925, not an island, despite the name. The site hosted the 1933-34 Century of Progress World's Fair. In 1948 it became Merrill C. Meigs Field, a single-runway downtown airport projecting into Lake Michigan three minutes from the Loop. For 55 years Meigs was a working downtown airport — corporate jets, executive turboprops, presidential trips, GA traffic. It was the closest civilian field to downtown Chicago of any US city. In the middle of the night on March 30, 2003, Mayor Richard M. Daley ordered city crews to bulldoze giant X-shaped trenches into the runway. There was no notice to the FAA, no notice to the airport's tenants, and no warning to 16 aircraft that were tied down on the ramp — those aircraft were trapped on the field for weeks before they could be disassembled and trucked out. Daley justified it as a post-9/11 security measure (Meigs sat across the lake from the Sears Tower). The FAA later fined the City $33,000. The Department of Justice declined to prosecute. AOPA and pilot groups sued unsuccessfully. The destruction has been on the AOPA bumper-sticker for two decades: "Don't Bulldoze My Airport." The site has been Northerly Island Park since 2005 — prairie restoration, a concert pavilion, hiking trails. The runway scar was visible from the air for years and is still partly traceable today. The adjacent Museum Campus — three institutions all opened within months of each other around 1930 — is what most visitors come for now. The Adler Planetarium (1930) was the first planetarium in the Western Hemisphere; donor Max Adler funded it after seeing the Zeiss projector in Munich. Field Museum of Natural History (current building 1921) is one of the largest natural history museums in the world; its star is Sue the T. rex, the most complete specimen ever found. Shedd Aquarium (1930) was the largest indoor aquarium in the world when it opened. Soldier Field, the 1924 colonnaded stadium with the controversial 2003 spaceship-style modernization, sits immediately west.