Private charter between Madison and Chicago starts at US$10,000 aboard a turboprop.
We fly Madison (MSN) ⇄ Chicago (ORD) in both directions, on the same aircraft and guide pricing.
The straight-line distance between Madison and Chicago is about 174 km (108 miles), or 94 nautical miles.
From US$10,000 · Reply within the hour · No obligation
Chartering a private jet from Madison to Chicago (and Chicago to Madison) ranges from US$10,000 for a turboprop like the Pilatus PC-12 NGX, up to US$15,500 for a very light jet such as the Embraer Phenom 100EV. Charters on this route are dog- and pet-friendly, with in-cabin access for your companion.
Short-runway specialist — ideal for remote airstrips and island hops. It seats 6-9 and is a frequent choice on sectors of this length.
Efficient for short hops with two to four passengers. It seats 4-6 and is a frequent choice on sectors of this length.
| Category | Outbound | Return (±10% wind) | From (USD) | Seats |
|---|---|---|---|---|
| Turboprop · rec. | 45 min | 41 min – 50 min | US$10,000 | 6-9 |
| Very Light Jet | 38 min | 34 min – 42 min | US$10,000 | 4-6 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Pilatus PC-12 NGX | 45 min | US$10,000 – US$11,000 | 6-9 |
| King Air 350 | 43 min | US$10,000 – US$12,000 | 8-11 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Embraer Phenom 100EV | 38 min | US$10,000 – US$13,500 | 4-6 |
| Cessna Citation M2 | 38 min | US$10,500 – US$15,000 | 4-6 |
| HondaJet Elite II | 37 min | US$11,500 – US$16,000 | 4-6 |
The return leg uses the same aircraft and guide pricing; timings may shift up to ±10% depending on winds.
Guide prices are one-way estimates incl. positioning; taxes/handling extra. Round-trip and one-way both available.
What determines the price between Madison and Chicago? Primarily: flight distance and typical jet-stream winds, fuel costs at both ends, and the handling and parking fees charged at each airport. We confirm everything against real-time aircraft availability.
Both cities are served by several airports, giving flexibility on slots and routing:
Madison, United States: Dane County Regional Truax Field, Southern Wisconsin Regional Airport, Baraboo Wisconsin Dells Regional Airport, Dodge County Airport, Monroe Municipal Airport and Tri-County Regional Airport.
Chicago, United States: Chicago O'Hare International Airport, Dupage Airport, Chicago Executive Airport, Chicago Midway International Airport, Gary/Chicago International Airport and Lewis University Airport.
Counts every airfield flown for each city — Madison: Madison (MSN), Janesville (JVL); Chicago: Chicago (MDW, ORD), Chicago/West Chicago (DPA), Chicago/Prospect Heights/Wheeling (PWK).
Observed traffic makes this an end-of-week route — Friday departures dominate: departures cluster on Fri, most often around 19:00 UTC.
Block times are close to symmetrical in both directions.
Sat is the quietest day we observe on this pairing, which is usually when an aircraft is easiest to source at short notice.
| Direction | Departures observed | Typical block | Fastest seen | Aircraft observed |
|---|---|---|---|---|
| Madison → Chicago | 21 | 30 min | 18 min | Bombardier Challenger 300 (4), Cessna Citation CJ3 (2), Dassault Falcon 2000 (2), Bombardier Challenger 350 (2) |
| Chicago → Madison | 31 | 29 min | — | Bombardier Challenger 350 (9), Cessna Citation Latitude (5), Hawker BEECHCRAFT Hawker 750/850 (5), Cessna Citation Longitude (3) |
52 movements observed, 2025-08-17 to 2026-08-16.
| Dane County Regional Truax Field | Chicago O'Hare International Airport | |
|---|---|---|
| Code | KMSN / MSN | KORD / ORD |
| Longest hard runway | 9,006 ft | 13,000 ft |
| Surface | Concrete | Concrete |
| Field elevation | 887 ft | 680 ft |
All 21 aircraft we quote for Madison to Chicago can use both airfields and fly the route non-stop. Dane County Regional Truax Field has 9,006 ft and Chicago O'Hare International Airport 13,000 ft, both comfortably beyond the 6,000 ft the largest types here need, so field length is not what decides the aircraft on this route — cabin size and range are. The leg is 174 km.
Alternates within range: Southern Wisconsin Regional Airport (7,302 ft, 63 km) · Baraboo Wisconsin Dells Regional Airport (5,010 ft, 55 km) · Dodge County Airport (5,070 ft, 60 km) · Monroe Municipal Airport (5,000 ft, 62 km) · Dupage Airport (7,571 ft, 30 km) · Chicago Executive Airport (5,001 ft, 15 km) · Chicago Midway International Airport (6,522 ft, 25 km) · Gary/Chicago International Airport (8,859 ft, 57 km)
From boarding to arrival, the aircraft is exclusively yours. Discretion is built into every private charter.
Travel Madison–Chicago with your dog, cat or other pet beside you in the cabin. Simply flag it when you request a quote.
Every aircraft and crew we place is from a certified, audited operator. You fly with professionals, not unknowns.
Our team responds to Madison–Chicago quote requests within the hour during business hours, with real aircraft options.
Demand on Madison–Chicago comes from corporate trips and getaways in equal measure — a domestic route where private charter pays off in time and privacy.
Budget US$10,000 – US$15,500 one-way depending on aircraft; a turboprop sits at the entry point. We confirm a firm figure against live availability.
About 45 min gate to gate over 174 km (108 miles), similar both ways; larger jets are marginally faster.
Turboprop, Very Light Jet are the usual choices here; our pick is a turboprop for value and comfort on this distance.
Yes — we handle last-minute Madison–Chicago charters, often with as little as 4 hours' notice, subject to aircraft and crew availability.
Yes. Our Madison–Chicago charters are dog- and pet-friendly with in-cabin access — note your pet in the enquiry.
Yes — the route is fully bidirectional, with the same guide price and timing on the return leg.
Other flights from Madison | Chicago | United States | North America
