Indianapolis (KIND) -> Chicago (KMDW)
May 23, 2026 to May 23, 2026, 07:00
Aircraft
Beechcraft Hawker 800XP
Category
Midsize jet
Seats
8
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
31
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 31
St Louis (KSUS) -> Chicago/Prospect Heights/Wheeling (KPWK)
May 26, 2026 to May 26, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 4,800
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Rhinelander (KRHI)
May 27, 2026 to May 27, 2026, 07:00
Aircraft
Embraer Praetor 500
Category
Super midsize jet
Seats
9
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
Chicago (KMDW) -> Charlotte (KCLT)
May 29, 2026 to May 29, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 100
Pricing and schedule subject to change
Kansas City (KMKC) -> Chicago/West Chicago (KDPA)
May 31, 2026 to May 31, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 5,400
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/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
El Paso (KELP) -> Chicago (KMDW)
Jun 10, 2026 to Jun 10, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 24,570
Pricing and schedule subject to change
El Paso (KELP) -> Chicago (KMDW)
Jun 10, 2026 to Jun 10, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
8
USD 16,300
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) -> Visalia (KVIS)
Jun 16, 2026 to Jun 16, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 25,800
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
9 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
- Indianapolis (KIND) -> Chicago (KMDW)
- Farmingdale (KFRG) -> Chicago (KMDW)
- Chicago (KMDW) -> Charlotte (KCLT)
Weather summary
Wind 050 at 6 kt, visibility not reported, weather not reported.
Forecast preview: TAF KMDW 222329Z 2300/2406 04011KT P6SM BKN050 OVC080 FM230200 10010KT P6SM SCT025 BKN035 OVC080 TEMPO 2303/2306 BKN025 FM230600...
View raw data
METAR code
METAR KMDW 230053Z 05006KT 10SM BKN049 OVC250 17/07 A2998 RMK AO2 SLP149 T01720067
TAF code
TAF KMDW 222329Z 2300/2406 04011KT P6SM BKN050 OVC080 FM230200 10010KT P6SM SCT025 BKN035 OVC080 TEMPO 2303/2306 BKN025 FM230600 09008KT P6SM OVC020 FM230900 06007KT P6SM SCT007 OVC015 TEMPO 2311/2315 6SM BR BKN007 FM231700 01005KT P6SM BKN025 FM232000 05010KT P6SM SCT030 BKN050
Chicago O'Hare International Airport
Chicago, Illinois (KORD / ORD)
🟢 VFR
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 050 at 11 kt, visibility not reported, weather not reported.
Forecast preview: TAF KORD 222329Z 2300/2406 04011KT P6SM BKN050 OVC080 FM230300 10010KT P6SM SCT025 BKN035 OVC080 TEMPO 2304/2306 BKN025 FM230600...
View raw data
METAR code
METAR KORD 230051Z 05011KT 10SM BKN048 BKN075 OVC250 16/05 A2998 RMK AO2 SLP151 T01610050
TAF code
TAF KORD 222329Z 2300/2406 04011KT P6SM BKN050 OVC080 FM230300 10010KT P6SM SCT025 BKN035 OVC080 TEMPO 2304/2306 BKN025 FM230600 09008KT P6SM OVC020 FM231000 06007KT P6SM SCT007 OVC015 TEMPO 2312/2316 6SM BR BKN007 FM231600 01005KT P6SM BKN025 FM232000 05010KT P6SM SCT030 BKN050
Chicago Executive Airport
Wheeling, Illinois (KPWK / PWK)
🟢 VFR
13 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
- St Louis (KSUS) -> Chicago/Prospect Heights/Wheeling (KPWK)
- Chicago/Prospect Heights/Wheeling (KPWK) -> Rhinelander (KRHI)
- Chicago/Prospect Heights/Wheeling (KPWK) -> Destin (KDTS)
Weather summary
Wind 060 at 9 kt, visibility not reported, weather not reported.
TAF unavailable right now.
View raw data
METAR code
METAR KPWK 230052Z 06009KT 10SM FEW049 OVC080 15/05 A3000 RMK AO2 SLP161 T01500050
TAF code
No raw TAF available.
DuPage Airport
West Chicago, Illinois (KDPA / DPA)
🟢 VFR
6 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
- Kansas City (KMKC) -> Chicago/West Chicago (KDPA)
- Chicago/West Chicago (KDPA) -> Fayetteville (KFYV)
- Gallatin (KXNX) -> Chicago/West Chicago (KDPA)
Weather summary
Wind 050 at 10 kt, visibility not reported, weather not reported.
Forecast preview: TAF KDPA 222329Z 2300/2324 08010KT P6SM BKN050 OVC080 FM230900 03006KT P6SM SCT007 BKN020 TEMPO 2312/2316 5SM BR BKN007...
View raw data
METAR code
METAR KDPA 230052Z 05010KT 10SM BKN085 17/06 A2997 RMK AO2 SLP149 T01720056
TAF code
TAF KDPA 222329Z 2300/2324 08010KT P6SM BKN050 OVC080 FM230900 03006KT P6SM SCT007 BKN020 TEMPO 2312/2316 5SM BR BKN007 OVC015 FM231800 29007KT P6SM SCT030 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 040 at 7 kt, visibility not reported, weather not reported.
Forecast preview: TAF KENW 222356Z 2300/2324 05010KT P6SM BKN050 FM230500 09008KT P6SM OVC025 FM230900 07005KT P6SM OVC019 FM231300 05006KT P6SM...
View raw data
METAR code
METAR KENW 230053Z 04007KT 10SM BKN060 OVC085 14/03 A3003 RMK AO2 SLP171 T01440033
TAF code
TAF KENW 222356Z 2300/2324 05010KT P6SM BKN050 FM230500 09008KT P6SM OVC025 FM230900 07005KT P6SM OVC019 FM231300 05006KT P6SM OVC009 FM231800 04007KT P6SM OVC011 FM232100 06007KT P6SM BKN030
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.