Chicago/Prospect Heights/Wheeling (KPWK) -> Rhinelander (KRHI)
May 26, 2026 to May 26, 2026, 07:00
Aircraft
Embraer Praetor 500
Category
Super midsize jet
Seats
9
USD 23,490
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
35
from or to these airports
KMDWKORDKPWKKDPAKENW
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 35
Chicago (KMDW) -> Mattoon/Charleston (KMTO)
May 26, 2026 to May 26, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 23,490
Pricing and schedule subject to change
Farmingdale (KFRG) -> Chicago (KMDW)
May 28, 2026 to May 28, 2026, 07:00
Aircraft
Gulfstream G550
Category
Ultra long range
Seats
16
USD 11,000
Pricing and schedule subject to change
Delaware (KDLZ) -> Chicago/West Chicago (KDPA)
May 31, 2026 to May 31, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 6,700
Pricing and schedule subject to change
Gallatin (KXNX) -> Chicago/West Chicago (KDPA)
May 31, 2026 to May 31, 2026, 07:00
Aircraft
Cirrus Vision SF50
Category
Super light jet
Seats
6
USD 10,400
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Destin (KDTS)
May 31, 2026 to May 31, 2026, 07:00
Aircraft
Bombardier Learjet 45
Category
Super light jet
Seats
8
USD 9,330
Pricing and schedule subject to change
Chicago (KMDW) -> Farmingdale (KFRG)
May 31, 2026 to May 31, 2026, 07:00
Aircraft
Gulfstream G550
Category
Ultra long range
Seats
16
USD 11,000
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Leesburg (KLEE)
May 31, 2026 to May 31, 2026, 07:00
Aircraft
Cessna Citation XLS+
Category
Midsize jet
Seats
8
USD 14,570
Pricing and schedule subject to change
Chicago/West Chicago (KDPA) -> Gallatin (KXNX)
Jun 01, 2026 to Jun 01, 2026, 07:00
Aircraft
Cirrus Vision SF50
Category
Super light jet
Seats
6
USD 10,400
Pricing and schedule subject to change
Concord (KCCR) -> Chicago/Prospect Heights/Wheeling (KPWK)
Jun 01, 2026 to Jun 02, 2026, 07:00
Aircraft
Cessna Citation XLS
Category
Midsize jet
Seats
8
USD 18,020
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Fort Worth (KFTW)
Jun 03, 2026 to Jun 03, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 13,800
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Fort Worth (KFTW)
Jun 03, 2026 to Jun 03, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 15,000
Pricing and schedule subject to change
Pawtucket (KSFZ) -> Kenosha (KENW)
Jun 04, 2026 to Jun 04, 2026, 07:00
Aircraft
Dassault Falcon 900C
Category
Heavy jet
Seats
12
USD 14,470
Pricing and schedule subject to change
Fort Myers (KRSW) -> Chicago/Prospect Heights/Wheeling (KPWK)
Jun 04, 2026 to Jun 06, 2026, 07:00
Aircraft
Cessna Citation XLS
Category
Midsize jet
Seats
8
USD 20,000
Pricing and schedule subject to change
Chicago/West Chicago (KDPA) -> Fayetteville (KFYV)
Jun 05, 2026 to Jun 05, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 10,400
Pricing and schedule subject to change
Gallatin (KXNX) -> Chicago/West Chicago (KDPA)
Jun 05, 2026 to Jun 05, 2026, 07:00
Aircraft
Cirrus Vision SF50
Category
Super light jet
Seats
6
USD 10,400
Pricing and schedule subject to change
Duluth (KDLH) -> Chicago (KMDW)
Jun 07, 2026 to Jun 07, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 6,000
Pricing and schedule subject to change
Teterboro (KTEB) -> Chicago (KMDW)
Jun 08, 2026 to Jun 08, 2026, 07:00
Aircraft
Gulfstream G IV SP
Category
Heavy jet
Seats
14
USD 10,580
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Naples (KAPF)
Jun 08, 2026 to Jun 10, 2026, 07:00
Aircraft
Cessna Citation XLS
Category
Midsize jet
Seats
8
USD 13,500
Pricing and schedule subject to change
Pellston (KPLN) -> Chicago (KMDW)
Jun 10, 2026 to Jun 10, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 23,490
Pricing and schedule subject to change
Iron Mountain / Kingsford (KIMT) -> Chicago/Prospect Heights/Wheeling (KPWK)
Jun 11, 2026 to Jun 11, 2026, 07:00
Aircraft
Cessna Citation XLS+
Category
Midsize jet
Seats
8
USD 23,490
Pricing and schedule subject to change
Chicago (KMDW) -> Memphis (KMEM)
Jun 14, 2026 to Jun 14, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 9,100
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Iron Mountain / Kingsford (KIMT)
Jun 14, 2026 to Jun 14, 2026, 07:00
Aircraft
Cessna Citation XLS+
Category
Midsize jet
Seats
8
USD 23,490
Pricing and schedule subject to change
Chicago/West Chicago (KDPA) -> Orlando (KORL)
Jun 15, 2026 to Jun 15, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 13,800
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)
🟢 VFR
8 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
- Chicago (KMDW) -> Mattoon/Charleston (KMTO)
- Farmingdale (KFRG) -> Chicago (KMDW)
- Chicago (KMDW) -> Farmingdale (KFRG)
Weather summary
Wind 080 at 10 kt, visibility not reported, weather not reported.
Forecast preview: TAF KMDW 230627Z 2306/2412 08008KT P6SM VCSH OVC025 TEMPO 2306/2308 6SM -SHRA BKN020 FM230900 03007KT P6SM SCT008 OVC015...
View raw data
METAR code
METAR KMDW 230553Z 08010KT 10SM OVC036 16/10 A2997 RMK AO2 SLP146 T01610100 10183 20161 401940117 58004
TAF code
TAF KMDW 230627Z 2306/2412 08008KT P6SM VCSH OVC025 TEMPO 2306/2308 6SM -SHRA BKN020 FM230900 03007KT P6SM SCT008 OVC015 TEMPO 2311/2315 BKN008 FM231600 01005KT P6SM BKN025 FM231800 05010KT P6SM SCT030 BKN050 FM240000 08006KT P6SM SCT035 BKN050
Chicago O'Hare International Airport
Chicago, Illinois (KORD / ORD)
🟡 MVFR
2 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) -> Kansas City (KMKC)
- Kansas City (KMKC) -> Chicago (KORD)
Weather summary
Wind 080 at 8 kt, visibility not reported, weather not reported.
Forecast preview: TAF KORD 230539Z 2306/2412 08008KT P6SM OVC025 FM231000 03007KT P6SM SCT008 OVC015 TEMPO 2312/2315 BKN008 FM231600 01005KT P6SM...
View raw data
METAR code
METAR KORD 230551Z 08008KT 10SM BKN026 BKN040 OVC110 16/09 A2997 RMK AO2 SLP146 T01610094 10172 20161 401890111 56005
TAF code
TAF KORD 230539Z 2306/2412 08008KT P6SM OVC025 FM231000 03007KT P6SM SCT008 OVC015 TEMPO 2312/2315 BKN008 FM231600 01005KT P6SM BKN025 FM231800 05010KT P6SM SCT030 BKN050 FM240000 08006KT P6SM SCT035 BKN050
Chicago Executive Airport
Wheeling, Illinois (KPWK / PWK)
🟡 MVFR
14 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) -> Rhinelander (KRHI)
- Chicago/Prospect Heights/Wheeling (KPWK) -> Destin (KDTS)
- Chicago/Prospect Heights/Wheeling (KPWK) -> Leesburg (KLEE)
Weather summary
Wind 100 at 4 kt, visibility not reported, weather not reported.
TAF unavailable right now.
View raw data
METAR code
METAR KPWK 230552Z AUTO 10004KT 10SM OVC028 15/10 A2999 RMK AO2 SLP156 T01500100 10156 20144 401780100 58006
TAF code
No raw TAF available.
DuPage Airport
West Chicago, Illinois (KDPA / DPA)
🟢 VFR
10 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
- Delaware (KDLZ) -> Chicago/West Chicago (KDPA)
- Gallatin (KXNX) -> Chicago/West Chicago (KDPA)
- Chicago/West Chicago (KDPA) -> Gallatin (KXNX)
Weather summary
Wind 090 at 10 kt, visibility not reported, weather not reported.
Forecast preview: TAF KDPA 230539Z 2306/2406 08010KT P6SM BKN050 OVC080 FM230900 03006KT P6SM SCT010 BKN020 FM231800 29007KT P6SM SCT030 BKN050...
View raw data
METAR code
METAR KDPA 230552Z 09010KT 10SM OVC035 17/10 A2996 RMK AO2 SLP143 T01670100 10178 20161 402060083 58007
TAF code
TAF KDPA 230539Z 2306/2406 08010KT P6SM BKN050 OVC080 FM230900 03006KT P6SM SCT010 BKN020 FM231800 29007KT P6SM SCT030 BKN050 FM240000 08008KT P6SM BKN050
Kenosha Regional Airport
Kenosha, Wisconsin (KENW / ENW)
🟢 VFR
1 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
- Pawtucket (KSFZ) -> Kenosha (KENW)
Weather summary
Wind 060 at 7 kt, visibility not reported, weather not reported.
Forecast preview: TAF KENW 230521Z 2306/2406 09007KT P6SM BKN040 TEMPO 2308/2310 BKN030 FM231000 07005KT P6SM OVC019 FM231300 05006KT P6SM OVC009...
View raw data
METAR code
METAR KENW 230553Z AUTO 06007KT 10SM OVC032 12/08 A3001 RMK AO2 SLP164 T01220078 10156 20122 401830089 58007
TAF code
TAF KENW 230521Z 2306/2406 09007KT P6SM BKN040 TEMPO 2308/2310 BKN030 FM231000 07005KT P6SM OVC019 FM231300 05006KT P6SM OVC009 FM231800 04007KT P6SM OVC011 FM232100 06007KT P6SM BKN035 FM240500 VRB03KT P6SM BKN050
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.