Chicago/Prospect Heights/Wheeling (KPWK) -> Pontiac (KPTK)
Jul 10, 2026 to Jul 10, 2026, 07:00
Aircraft
Cessna Citation Bravo
Category
Light jet
Seats
8
USD 10,400
Pricing and schedule subject to change
Chicagoland
Chicago Empty Leg Flights
Current empty leg inventory for Chicago airports, including downtown-friendly and suburban executive options.
Available right now
38
from or to these airports
Current empty legs in Chicago
These routes are pulled from the main leg pool and filtered by the airports listed for this area.
Showing 24 of 38
Chicago (KORD) -> Grand Rapids (KGRR)
Jul 10, 2026 to Jul 12, 2026, 07:00
Aircraft
Cessna Citation Excel
Category
Midsize jet
Seats
8
USD 3,000
Pricing and schedule subject to change
Toronto (CYYZ) -> Chicago (KMDW)
Jul 12, 2026 to Jul 13, 2026, 07:00
Aircraft
Cessna Citation Ultra
Category
Light jet
Seats
7
USD 9,500
Pricing and schedule subject to change
Panama City Beach (KECP) -> Chicago (KMDW)
Jul 15, 2026 to Jul 15, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 11,400
Pricing and schedule subject to change
Pellston (KPLN) -> Chicago/Prospect Heights/Wheeling (KPWK)
Jul 15, 2026 to Jul 15, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 6,700
Pricing and schedule subject to change
Panama City Beach (KECP) -> Chicago (KMDW)
Jul 15, 2026 to Jul 15, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
8
USD 12,400
Pricing and schedule subject to change
Hyannis (KHYA) -> Chicago (KMDW)
Jul 16, 2026 to Jul 16, 2026, 07:00
Aircraft
Bombardier Challenger 300
Category
Super midsize jet
Seats
8
USD 17,390
Pricing and schedule subject to change
Chicago (KORD) -> Teterboro (KTEB)
Jul 16, 2026 to Jul 16, 2026, 07:00
Aircraft
Gulfstream G650ER
Category
Ultra long range
Seats
18
USD 10,510
Pricing and schedule subject to change
Syracuse (KSYR) -> Kenosha (KENW)
Jul 17, 2026 to Jul 17, 2026, 07:00
Aircraft
Gulfstream G200
Category
Super midsize jet
Seats
8
USD 26,070
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Philadelphia (KPHL)
Jul 18, 2026 to Jul 19, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 100
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Houston (KTME)
Jul 19, 2026 to Jul 20, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 15,000
Pricing and schedule subject to change
Chicago (KMDW) -> Denver (KBJC)
Jul 19, 2026 to Jul 19, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 15,000
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Houston (KTME)
Jul 19, 2026 to Jul 20, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 16,300
Pricing and schedule subject to change
Chicago (KMDW) -> Denver (KBJC)
Jul 19, 2026 to Jul 19, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
8
USD 16,300
Pricing and schedule subject to change
Providence (KPVD) -> Chicago/Prospect Heights/Wheeling (KPWK)
Jul 23, 2026 to Jul 24, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 15,600
Pricing and schedule subject to change
Chicago/West Chicago (KDPA) -> Dallas (KDAL)
Jul 23, 2026 to Jul 23, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 13,300
Pricing and schedule subject to change
Providence (KPVD) -> Chicago/Prospect Heights/Wheeling (KPWK)
Jul 23, 2026 to Jul 24, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 16,900
Pricing and schedule subject to change
Chicago/West Chicago (KDPA) -> Dallas (KDAL)
Jul 23, 2026 to Jul 23, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
8
USD 14,400
Pricing and schedule subject to change
Indianapolis (KIND) -> Chicago/Prospect Heights/Wheeling (KPWK)
Jul 26, 2026 to Jul 26, 2026, 07:00
Aircraft
Bombardier Challenger 850
Category
Heavy jet
Seats
15
USD 28,690
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Punta Gorda (KPGD)
Aug 01, 2026 to Aug 03, 2026, 07:00
Aircraft
Cessna Citation V
Category
Light jet
Seats
7
USD 17,360
Pricing and schedule subject to change
Pinehurst/Southern Pines (KSOP) -> Chicago/Prospect Heights/Wheeling (KPWK)
Aug 06, 2026 to Aug 06, 2026, 07:00
Aircraft
Gulfstream G200
Category
Super midsize jet
Seats
10
USD 11,220
Pricing and schedule subject to change
Branson (KBBG) -> Chicago/Prospect Heights/Wheeling (KPWK)
Aug 10, 2026 to Aug 10, 2026, 07:00
Aircraft
Bombardier Challenger 300
Category
Super midsize jet
Seats
9
USD 23,490
Pricing and schedule subject to change
Nashville (KBNA) -> Kenosha (KENW)
Aug 12, 2026 to Aug 12, 2026, 07:00
Aircraft
Dassault Falcon 900C
Category
Heavy jet
Seats
12
USD 28,690
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Branson (KBBG)
Aug 13, 2026 to Aug 13, 2026, 07:00
Aircraft
Bombardier Challenger 300
Category
Super midsize jet
Seats
9
USD 23,490
Pricing and schedule subject to change
Airport operations and local support
Practical airport data for dispatch and passenger planning. Weather summary stays visible, raw data is available on demand.
Chicago Midway International Airport
Chicago, Illinois (KMDW / MDW)
IFR IFR
15 matching legs
Closer to downtown than many suburban alternatives.
International-ready operations with longer runway support.
FBO
Signature Aviation, Atlantic Aviation
Catering
Air Culinaire Worldwide, Chicago Executive Catering
Transport
Uber, Lyft, Chicago Taxi
Recent routes for this airport
- Toronto (CYYZ) -> Chicago (KMDW)
- Panama City Beach (KECP) -> Chicago (KMDW)
- Hyannis (KHYA) -> Chicago (KMDW)
Weather summary
30 at 7 kt wind. Visibility 8 SM. No significant weather. broken clouds at 800 ft, broken clouds at 7,500 ft.
Opening forecast: wind 20 at 7 kt, visibility 6+ SM, showers, scattered clouds at 700 ft, broken clouds at 3,500 ft.
View raw data
METAR code
METAR KMDW 100753Z 03007KT 8SM BKN008 BKN075 22/21 A2986 RMK AO2 SLP102 T02220211
TAF code
TAF KMDW 100529Z 1006/1112 02007KT P6SM VCSH SCT007 BKN035 FM100800 02005KT 6SM BR SCT008 OVC015 TEMPO 1008/1012 3SM BR BKN008 FM101300 03008KT P6SM SCT012 BKN020 FM101800 04011KT P6SM SCT040 BKN250 FM110500 36005KT P6SM SCT250
Chicago O'Hare International Airport
Chicago, Illinois (KORD / ORD)
VFR VFR
5 matching legs
Large network airport used for long-range and premium cabin requests.
International-ready operations with longer runway support.
FBO
Signature Aviation, Atlantic Aviation
Catering
Air Culinaire Worldwide, Chicago Executive Catering
Transport
Uber, Lyft, Chicago Taxi
Recent routes for this airport
- Chicago (KORD) -> Grand Rapids (KGRR)
- Chicago (KORD) -> Teterboro (KTEB)
- Chicago (KORD) -> Kansas City (KMKC)
Weather summary
30 at 7 kt wind. Visibility 10+ SM. No significant weather. scattered clouds at 700 ft, broken clouds at 3,400 ft.
Opening forecast: wind 20 at 7 kt, visibility 6+ SM, showers, scattered clouds at 700 ft, broken clouds at 3,500 ft.
View raw data
METAR code
SPECI KORD 100810Z 03007KT 10SM SCT007 BKN034 21/19 A2987 RMK AO2 T02110194 $
TAF code
TAF KORD 100529Z 1006/1112 02007KT P6SM VCSH SCT007 BKN035 TEMPO 1006/1008 BKN007 FM100800 02005KT 6SM BR SCT008 OVC015 TEMPO 1008/1012 3SM BR BKN008 FM101300 03008KT P6SM SCT012 BKN020 FM101800 04011KT P6SM SCT040 BKN250 FM110500 36005KT P6SM SCT250
Chicago Executive Airport
Wheeling, Illinois (KPWK / PWK)
VFR VFR
12 matching legs
Popular executive airport for northern suburbs.
Business-aviation focused field with faster turns and less congestion.
FBO
Signature Aviation, Atlantic Aviation
Catering
Air Culinaire Worldwide, North Shore Catering
Transport
Uber, Lyft, North Shore Taxi
Recent routes for this airport
- Chicago/Prospect Heights/Wheeling (KPWK) -> Pontiac (KPTK)
- Pellston (KPLN) -> Chicago/Prospect Heights/Wheeling (KPWK)
- Chicago/Prospect Heights/Wheeling (KPWK) -> Philadelphia (KPHL)
Weather summary
330 at 3 kt wind. Visibility 10+ SM. No significant weather. few clouds at 7,500 ft.
No terminal forecast is currently issued for KPWK.
View raw data
METAR code
METAR KPWK 100752Z AUTO 33003KT 10SM FEW075 20/19 A2989 RMK AO2 SLP116 T02000194
TAF code
No raw TAF available.
DuPage Airport
West Chicago, Illinois (KDPA / DPA)
IFR IFR
4 matching legs
Flexible operations and strong runway profile for larger aircraft.
Balanced airport for private charter traffic and repositioning operations.
FBO
DuPage Flight Center, AAR
Catering
Air Culinaire Worldwide, DuPage Catering
Transport
Uber, Lyft, DuPage Taxi
Recent routes for this airport
- Chicago/West Chicago (KDPA) -> Dallas (KDAL)
- Gallatin (KXNX) -> Chicago/West Chicago (KDPA)
- Chicago/West Chicago (KDPA) -> Gallatin (KXNX)
Weather summary
30 at 6 kt wind. Visibility 7 SM. No significant weather. overcast at 500 ft.
Opening forecast: wind VRB at 4 kt, visibility 6+ SM, showers, scattered clouds at 2,000 ft, broken clouds at 3,500 ft.
View raw data
METAR code
METAR KDPA 100752Z AUTO 03006KT 7SM OVC005 21/21 A2987 RMK AO2 SLP110 T02110206
TAF code
TAF KDPA 100529Z 1006/1106 VRB04KT P6SM VCSH SCT020 BKN035 TEMPO 1006/1008 -SHRA FM100800 02005KT 6SM BR SCT007 OVC015 TEMPO 1008/1012 3SM BR BKN009 FM101300 03008KT P6SM SCT012 BKN020 FM101800 04009KT P6SM SCT040 BKN250
Kenosha Regional Airport
Kenosha, Wisconsin (KENW / ENW)
VFR VFR
2 matching legs
North side catchment option when Chicago slots are tight.
Balanced airport for private charter traffic and repositioning operations.
FBO
Kenosha Aero, Wisconsin Aviation
Catering
Air Culinaire Worldwide, Kenosha Catering
Transport
Uber, Lyft, Kenosha Taxi
Recent routes for this airport
- Syracuse (KSYR) -> Kenosha (KENW)
- Nashville (KBNA) -> Kenosha (KENW)
Weather summary
0 at 0 kt wind. Visibility 10+ SM. No significant weather. broken clouds at 4,100 ft.
Opening forecast: wind 0 at 0 kt, visibility 6+ SM, no significant weather, broken clouds at 3,500 ft.
View raw data
METAR code
METAR KENW 100753Z AUTO 00000KT 10SM BKN041 19/19 A2990 RMK AO2 SLP119 T01940189
TAF code
TAF KENW 100520Z 1006/1106 00000KT P6SM BKN035 FM100800 00000KT 2SM BR BKN005 FM101100 VRB04KT 4SM BR BKN013 FM101300 03005KT P6SM BKN040 FM101700 05009KT P6SM SCT050 SCT150 FM110300 VRB04KT P6SM BKN250
FAQ
How often are Chicago empty leg flights updated?
New legs appear as repositioning inventory is added. This page refreshes current legs directly from our database feed.
Can I depart from any airport listed for Chicago?
Yes, if that leg is still open when you request it. Some trips can be adjusted with paid repositioning if needed.
Why are some offers gone quickly?
Empty legs are byproduct flights tied to schedule changes. When base trips shift, these offers can close quickly.