Charter Milwaukee to Chicago privately from US$10,000, about 37 min in the air. Request your price in minutes.
We fly Milwaukee (MKE) ⇄ Chicago (ORD) in both directions, on the same aircraft and guide pricing.
As the crow flies, Milwaukee to Chicago is roughly 108 kilometres — 67 miles, or 58 nautical miles.
From US$10,000 · Reply within the hour · No obligation
Chartering a private jet from Milwaukee to Chicago (and Chicago to Milwaukee) 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. With seating for 6-9, it balances cabin comfort against running cost.
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. | 37 min | 33 min – 41 min | US$10,000 | 6-9 |
| Very Light Jet | 33 min | 30 min – 36 min | US$10,000 | 4-6 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Pilatus PC-12 NGX | 37 min | US$10,000 – US$11,000 | 6-9 |
| King Air 350 | 36 min | US$10,000 – US$12,000 | 8-11 |
| Aircraft | Flight time | Cost range (USD) | Passengers |
|---|---|---|---|
| Embraer Phenom 100EV | 33 min | US$10,000 – US$13,500 | 4-6 |
| Cessna Citation M2 | 33 min | US$10,500 – US$15,000 | 4-6 |
| HondaJet Elite II | 32 min | US$11,500 – US$16,000 | 4-6 |
Outbound and return are priced alike on identical aircraft; expect roughly ±10% variation in time by wind.
Guide prices are one-way estimates incl. positioning; taxes/handling extra. Round-trip and one-way both available.
The guide range for Milwaukee–Chicago is derived from the sector distance and typical winds, fuel costs at both ends, and the handling and landing charges levied at both airports. Final pricing is locked once we check live aircraft schedules.
Both cities are served by several airports, giving flexibility on slots and routing:
Milwaukee, United States: General Mitchell International Airport, Kenosha Regional Airport, John H Batten Airport, Waukesha County Airport and Waukegan National 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.
Observed traffic makes this a weekday route with afternoon departures: departures cluster on Tue, most often around 19:00 UTC.
Block times are close to symmetrical in both directions.
Fri 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 |
|---|---|---|---|---|
| Milwaukee → Chicago | 95 | 22 min | 13 min | Hawker BEECHCRAFT Hawker 750/850 (20), Cessna Citation CJ4 (13), Cessna Citation XLS (7), Cessna Citation Latitude (7) |
| Chicago → Milwaukee | 84 | 20 min | — | Hawker BEECHCRAFT Hawker 750/850 (21), Cessna Citation CJ4 (11), Embraer Phenom 300 (5), Bombardier Challenger 350 (5) |
179 movements observed, 2025-08-17 to 2026-08-16.
| General Mitchell International Airport | Chicago O'Hare International Airport | |
|---|---|---|
| Code | KMKE / MKE | KORD / ORD |
| Longest hard runway | 9,990 ft | 13,000 ft |
| Surface | Porous friction course | Concrete |
| Field elevation | 723 ft | 680 ft |
| Aircraft | Needs | Range | On this route |
|---|---|---|---|
| Pilatus PC-12 NGX Turboprop |
1,500 ft | 1,800 km | Non-stop |
| King Air 350 Turboprop |
2,000 ft | 2,700 km | Non-stop |
| Embraer Phenom 100EV Very Light Jet |
3,200 ft | 2,180 km | Non-stop |
| Cessna Citation M2 Very Light Jet |
2,900 ft | 2,410 km | Non-stop |
| King Air 250 Turboprop |
3,000 ft | 2,900 km | Non-stop |
| Cessna Caravan 208B Short-Field Turboprop |
1,500 ft | 1,980 km | Non-stop |
| De Havilland Twin Otter 400 Short-Field Turboprop |
1,200 ft | 1,480 km | Non-stop |
| Cessna Citation CJ3+ Light Jet |
3,500 ft | 3,700 km | Non-stop |
| Embraer Phenom 300E Light Jet |
3,278 ft | 3,650 km | Non-stop |
| Cessna Citation XLS+ Midsize Jet |
4,200 ft | 3,900 km | Non-stop |
| Hawker 900XP Midsize Jet |
5,576 ft | 4,600 km | Non-stop |
| Challenger 350 Super Midsize Jet |
4,930 ft | 5,926 km | Non-stop |
| Cessna Citation Longitude Super Midsize Jet |
4,900 ft | 6,400 km | Non-stop |
| Embraer Praetor 600 Super Midsize Jet |
4,692 ft | 7,220 km | Non-stop |
| Challenger 605 Heavy Jet |
5,440 ft | 7,400 km | Non-stop |
| Gulfstream G450 Heavy Jet |
5,300 ft | 7,800 km | Non-stop |
| Falcon 2000LXS Heavy Jet |
4,790 ft | 7,400 km | Non-stop |
| Bombardier Global 7500 Ultra Long Range Jet |
6,000 ft | 14,260 km | Non-stop |
| Bombardier Global 6000 Long Range Jet |
5,800 ft | 11,112 km | Non-stop |
| Gulfstream G650 Long Range Jet |
6,000 ft | 12,960 km | Non-stop |
| Falcon 8X Long Range Jet |
4,800 ft | 11,945 km | Non-stop |
Alternates within range: Kenosha Regional Airport (6,600 ft, 39 km) · John H Batten Airport (6,574 ft, 22 km) · Waukesha County Airport (5,849 ft, 30 km) · Waukegan National Airport (6,001 ft, 58 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)
Private terminals mean check-in takes minutes. The 108 km flight is the fastest part of the door-to-door journey.
More airport choice means fewer ground miles. We match the airfield to your final address, not the nearest hub.
We publish the price band (US$10,000 – US$15,500) so you can plan before committing. The confirmed quote has no surprises.
Your group travels alone. No strangers, no overheard calls — just your party from Milwaukee to Chicago.
The Milwaukee to Chicago route is a popular domestic private-jet path for both business travellers and leisure flyers seeking direct access without commercial schedules.
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.
Roughly 37 min airborne across the 108 km sector — timings shift a little with winds and aircraft.
This sector is mainly served by Turboprop, Very Light Jet. We lead with a turboprop for the best balance of cost, cabin and range.
Often yes: same-day and next-day Milwaukee–Chicago departures are possible when aircraft and crew are positioned nearby.
Yes. Our Milwaukee–Chicago charters are dog- and pet-friendly with in-cabin access — note your pet in the enquiry.
Of course: Chicago to Milwaukee runs on the same aircraft and pricing, so round trips are straightforward.
Other flights from Milwaukee | Chicago | United States | North America
