Chicago → Miami

Chicago to Miami is the Midwest's essential winter escape route — an 1,100-nautical-mile corridor that carries executives, entrepreneurs, and families from the frozen shores of Lake Michigan to the subtropical warmth of South Florida in under three hours. When Chicago's brutal winters set in, this route transforms from a leisure option into a near-necessity for the city's business elite, many of whom maintain dual residences or have business interests spanning both metropolitan areas.

Airport & FBO Analysis

Chicago Executive Airport (KPWK) in Wheeling serves as the primary private aviation departure point for Chicago's North Shore and suburban business community. The airport offers multiple FBOs including Hawthorne Global Aviation Services and Signature Flight Support, with heated hangars that prove essential during Chicago's frigid winter departures. For clients in downtown Chicago, Midway (KMDW) offers closer proximity, though KPWK's less congested operations typically result in faster departures.

Miami-Opa Locka Executive Airport (KOPF) is the preferred private aviation facility in Miami, providing a dedicated business aviation environment without the commercial traffic congestion of Miami International. Fontainebleau Aviation offers premium FBO services with a modern lounge, covered parking, and efficient customs processing for any international connections. The airport sits 20 minutes from Miami Beach and 15 minutes from the Design District and Wynwood.

Aircraft Recommendations

At 1,100 nautical miles and 2.7 hours flight time, this route accommodates everything from light jets to heavy iron. A Phenom 300E or Citation CJ4 at $9,000 to $15,000 provides excellent value for couples or small families making a weekend getaway. For corporate groups or larger families, a midsize Citation Latitude or Learjet 75 at $16,000 to $26,000 offers the step up in cabin space and amenities. Heavy jets in the $28,000 to $44,000 range are available for parties of 10 or more or clients combining this leg with onward Caribbean travel.

Seasonal Pricing Intelligence

Winter dominates the pricing calendar on this route with unmistakable clarity. December through March sees rates climb 25 to 35 percent, with Art Basel week (early December) commanding the single highest premium of the year. The Super Bowl, when held in Miami, creates extraordinary one-week demand spikes. Spring break adds a March-April surge driven by families. Conversely, summer offers the best pricing, as both cities maintain adequate aircraft inventory but southbound demand from Chicago drops significantly. Empty leg opportunities multiply in October and November as operators begin repositioning aircraft to Florida for the winter season.

Ground Experience

In Miami, the Faena Hotel, Four Seasons Surf Club, and The Setai are the addresses of choice for private jet arrivals from Chicago, each within 25 minutes of KOPF. For Art Basel visitors, the Design District hotels and South Beach properties coordinate event transportation. In Chicago, The Peninsula Chicago, Waldorf Astoria Chicago, and the Langham are popular pre-departure bases, all within 30 to 45 minutes of KPWK depending on traffic.

Booking Tips

• Art Basel week (first week of December) should be booked 3 to 4 weeks in advance — both aircraft and Miami hotel inventory become extremely tight.
• Empty legs southbound from Chicago to Miami are abundant in late fall as aircraft migrate to Florida for winter — savings of 30 to 50 percent are common.
• Consider flexible departure airports: KMDW and KORD both handle private aviation and may offer better positioning depending on your Chicago location.
• Winter departures from Chicago can face de-icing delays; build 30 to 60 minutes of buffer into your schedule during severe cold snaps.