Pittsburgh (KPIT) -> Chicago (KMDW)
Apr 11, 2026 to Apr 11, 2026, 07:00
Aircraft
Cessna Citation Longitude
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
28
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 28
Chicago (KMDW) -> Riverton (KRIW)
Apr 11, 2026 to Apr 11, 2026, 07:00
Aircraft
Cessna Citation Longitude
Category
Super midsize jet
Seats
9
USD 23,190
Pricing and schedule subject to change
Teterboro (KTEB) -> Chicago (KORD)
Apr 11, 2026 to Apr 12, 2026, 07:00
Aircraft
Cessna Citation XLS
Category
Midsize jet
Seats
8
USD 23,830
Pricing and schedule subject to change
New Haven (KHVN) -> Chicago (KORD)
Apr 11, 2026 to Apr 12, 2026, 07:00
Aircraft
Cessna Citation XLS
Category
Midsize jet
Seats
8
USD 16,210
Pricing and schedule subject to change
Chicago (KORD) -> Cleveland (KCGF)
Apr 11, 2026 to Apr 11, 2026, 07:00
Aircraft
Bombardier Learjet 40XR
Category
Super light jet
Seats
7
USD 6,500
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Coatesville (KMQS)
Apr 12, 2026 to Apr 12, 2026, 07:00
Aircraft
Embraer Praetor 500
Category
Super midsize jet
Seats
9
USD 21,560
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Fort Lauderdale (KFXE)
Apr 12, 2026 to Apr 13, 2026, 07:00
Aircraft
Embraer Legacy 500
Category
Super midsize jet
Seats
12
USD 18,500
Pricing and schedule subject to change
Tulsa (KTUL) -> Chicago/Prospect Heights/Wheeling (KPWK)
Apr 12, 2026 to Apr 12, 2026, 07:00
Aircraft
Cessna Citation XLS
Category
Midsize jet
Seats
8
USD 8,580
Pricing and schedule subject to change
Chicago (KMDW) -> Raleigh/Durham (KRDU)
Apr 15, 2026 to Apr 15, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
8
USD 19,880
Pricing and schedule subject to change
Kenosha (KENW) -> Boca Raton (KBCT)
Apr 15, 2026 to Apr 15, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
8
USD 17,400
Pricing and schedule subject to change
Chicago/West Chicago (KDPA) -> Fort Worth (KFTW)
Apr 15, 2026 to Apr 16, 2026, 07:00
Aircraft
Bombardier Challenger 604
Category
Heavy jet
Seats
10
USD 16,100
Pricing and schedule subject to change
Raleigh/Durham (KRDU) -> Chicago (KMDW)
Apr 16, 2026 to Apr 16, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
8
USD 19,880
Pricing and schedule subject to change
Chicago (KMDW) -> Provo (KPVU)
Apr 16, 2026 to Apr 16, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 19,800
Pricing and schedule subject to change
Chicago (KMDW) -> Provo (KPVU)
Apr 16, 2026 to Apr 16, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
8
USD 21,500
Pricing and schedule subject to change
Indianapolis (KMQJ) -> Chicago/West Chicago (KDPA)
Apr 16, 2026 to Apr 16, 2026, 07:00
Aircraft
Cessna Citation Excel
Category
Midsize jet
Seats
8
USD 23,490
Pricing and schedule subject to change
Chicago/West Chicago (KDPA) -> Indianapolis (KTYQ)
Apr 17, 2026 to Apr 17, 2026, 07:00
Aircraft
Cessna Citation Excel
Category
Midsize jet
Seats
8
USD 23,490
Pricing and schedule subject to change
Chicago/West Chicago (KDPA) -> Cincinnati (KLUK)
Apr 17, 2026 to Apr 17, 2026, 07:00
Aircraft
Bombardier Learjet 60
Category
Midsize jet
Seats
7
USD 4,800
Pricing and schedule subject to change
Teterboro (KTEB) -> Chicago/Prospect Heights/Wheeling (KPWK)
Apr 22, 2026 to Apr 22, 2026, 07:00
Aircraft
Gulfstream G450
Category
Heavy jet
Seats
14
USD 10,700
Pricing and schedule subject to change
Cleveland (KCLE) -> Chicago (KORD)
Apr 23, 2026 to Apr 23, 2026, 07:00
Aircraft
Bombardier Learjet 40XR
Category
Super light jet
Seats
7
USD 10,400
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Teterboro (KTEB)
Apr 27, 2026 to Apr 27, 2026, 07:00
Aircraft
Gulfstream G450
Category
Heavy jet
Seats
14
USD 10,700
Pricing and schedule subject to change
Chicago (KMDW) -> Charlotte (KCLT)
Apr 30, 2026 to Apr 30, 2026, 07:00
Aircraft
Cessna Citation Excel
Category
Midsize jet
Seats
8
USD 19,310
Pricing and schedule subject to change
Indianapolis (KMQJ) -> Chicago (KMDW)
May 01, 2026 to May 01, 2026, 07:00
Aircraft
Cessna Citation Excel
Category
Midsize jet
Seats
8
USD 23,490
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Oklahoma City (KOKC)
May 04, 2026 to May 04, 2026, 07:00
Aircraft
Cessna Citation XLS+
Category
Midsize jet
Seats
8
USD 23,090
Pricing and schedule subject to change
Chicago/Prospect Heights/Wheeling (KPWK) -> Ottawa (CYOW)
May 05, 2026 to May 05, 2026, 07:00
Aircraft
Cessna Citation XLS
Category
Midsize jet
Seats
8
USD 21,460
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
10 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
- Pittsburgh (KPIT) -> Chicago (KMDW)
- Chicago (KMDW) -> Riverton (KRIW)
- Chicago (KMDW) -> Raleigh/Durham (KRDU)
Weather summary
Wind 320 at 14 kt, visibility not reported, weather not reported.
Forecast preview: TAF KMDW 052103Z 0521/0624 29012G22KT P6SM FEW035 FM060000 25009KT P6SM FEW050 SCT100 TEMPO 0605/0608 6SM -SHRA SCT025 OVC040...
View raw data
METAR code
METAR KMDW 052053Z 32014G19KT 10SM FEW035 12/M05 A3016 RMK AO2 WSHFT 2020 SLP218 T01171050 58002
TAF code
TAF KMDW 052103Z 0521/0624 29012G22KT P6SM FEW035 FM060000 25009KT P6SM FEW050 SCT100 TEMPO 0605/0608 6SM -SHRA SCT025 OVC040 FM060800 30011G18KT P6SM BKN025 FM061500 31014G24KT P6SM BKN040
Chicago O'Hare International Airport
Chicago, Illinois (KORD / ORD)
🟢 VFR
6 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
- Teterboro (KTEB) -> Chicago (KORD)
- New Haven (KHVN) -> Chicago (KORD)
- Chicago (KORD) -> Cleveland (KCGF)
Weather summary
Wind 310 at 13 kt, visibility not reported, weather not reported.
Forecast preview: TAF KORD 052103Z 0521/0624 29012G22KT P6SM FEW035 FM060000 25009KT P6SM FEW050 SCT100 TEMPO 0605/0608 6SM -SHRA SCT025 OVC040...
View raw data
METAR code
METAR KORD 052051Z 31013G21KT 10SM FEW035 12/M06 A3015 RMK AO2 SLP212 T01171061 58003 $
TAF code
TAF KORD 052103Z 0521/0624 29012G22KT P6SM FEW035 FM060000 25009KT P6SM FEW050 SCT100 TEMPO 0605/0608 6SM -SHRA SCT025 OVC040 FM060800 30011G18KT P6SM BKN025 FM061500 31014G24KT P6SM BKN040
Chicago Executive Airport
Wheeling, Illinois (KPWK / PWK)
🟢 VFR
7 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) -> Coatesville (KMQS)
- Chicago/Prospect Heights/Wheeling (KPWK) -> Fort Lauderdale (KFXE)
- Tulsa (KTUL) -> Chicago/Prospect Heights/Wheeling (KPWK)
Weather summary
Wind 320 at 15 kt, visibility not reported, weather not reported.
TAF unavailable right now.
View raw data
METAR code
METAR KPWK 052052Z 32015G23KT 10SM FEW085 11/M06 A3015 RMK AO2 PK WND 33026/2012 SLP214 T01111056 58004 $
TAF code
No raw TAF available.
DuPage Airport
West Chicago, Illinois (KDPA / DPA)
🟢 VFR
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) -> Fort Worth (KFTW)
- Indianapolis (KMQJ) -> Chicago/West Chicago (KDPA)
- Chicago/West Chicago (KDPA) -> Indianapolis (KTYQ)
Weather summary
Wind 300 at 18 kt, visibility not reported, weather not reported.
Forecast preview: TAF KDPA 051720Z 0518/0618 29012G22KT P6SM FEW035 FM060000 25009KT P6SM FEW050 SCT100 TEMPO 0605/0608 6SM -SHRA SCT025 OVC040...
View raw data
METAR code
METAR KDPA 052052Z 30018G25KT 10SM CLR 11/M04 A3017 RMK AO2 PK WND 31026/2001 SLP219 T01061039 58001
TAF code
TAF KDPA 051720Z 0518/0618 29012G22KT P6SM FEW035 FM060000 25009KT P6SM FEW050 SCT100 TEMPO 0605/0608 6SM -SHRA SCT025 OVC040 FM060800 30011G18KT P6SM BKN025 FM061500 31014G24KT P6SM BKN040
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
- Kenosha (KENW) -> Boca Raton (KBCT)
Weather summary
Wind 300 at 16 kt, visibility not reported, weather not reported.
Forecast preview: TAF KENW 051738Z 0518/0618 30016G25KT P6SM FEW060 FM060000 27008KT P6SM SCT110 PROB30 0604/0605 4SM -SHRA OVC025 FM060500 27008KT...
View raw data
METAR code
METAR KENW 052053Z 30016G23KT 10SM CLR 11/M06 A3013
TAF code
TAF KENW 051738Z 0518/0618 30016G25KT P6SM FEW060 FM060000 27008KT P6SM SCT110 PROB30 0604/0605 4SM -SHRA OVC025 FM060500 27008KT P6SM BKN027 PROB30 0605/0606 4SM -SHRA OVC015 FM060700 28008KT P6SM BKN050 FM061100 30009KT P6SM BKN029 FM061200 30009KT P6SM BKN035
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.