Boca Raton (KBCT) -> Chicago (KMDW)
Jan 14, 2026 to Jan 15, 2026, 07:00
Aircraft
Learjet 60
Category
Midsize jet
Seats
7
USD 16,300
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
62
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 62
Fort Lauderdale (KFXE) -> Chicago (KMDW)
Jan 14, 2026 to Jan 15, 2026, 07:00
Aircraft
Learjet 60
Category
Midsize jet
Seats
7
USD 13,000
Pricing and schedule subject to change
St Petersburg-Clearwater (KPIE) -> Chicago (KMDW)
Jan 15, 2026 to Jan 15, 2026, 07:00
Aircraft
Falcon 2000EX EASy
Category
Heavy jet
Seats
8
USD 19,650
Pricing and schedule subject to change
Farmingdale (KFRG) -> Chicago (KMDW)
Jan 15, 2026 to Jan 15, 2026, 07:00
Aircraft
Learjet 60
Category
Midsize jet
Seats
7
USD 6,780
Pricing and schedule subject to change
Lynchburg (KLYH) -> Chicago (KMDW)
Jan 17, 2026 to Jan 17, 2026, 07:00
Aircraft
Learjet 40XR
Category
Super light jet
Seats
7
USD 7,990
Pricing and schedule subject to change
Chicago (KMDW) -> Cleveland (KCLE)
Jan 18, 2026 to Jan 18, 2026, 07:00
Aircraft
Learjet 40XR
Category
Super light jet
Seats
7
USD 5,990
Pricing and schedule subject to change
Venice (KVNC) -> Chicago (KMDW)
Jan 18, 2026 to Jan 18, 2026, 07:00
Aircraft
Hawker 400XP
Category
Light jet
Seats
8
USD 14,000
Pricing and schedule subject to change
Chicago (KMDW) -> Farmingdale (KFRG)
Jan 19, 2026 to Jan 19, 2026, 07:00
Aircraft
Learjet 60
Category
Midsize jet
Seats
7
USD 6,210
Pricing and schedule subject to change
KPWK -> KARV
Jan 19, 2026 to Jan 19, 2026, 07:00
Aircraft
Praetor 500
Category
Super midsize jet
Seats
9
USD 5,490
Pricing and schedule subject to change
KENW -> KMQJ
Jan 19, 2026 to Jan 19, 2026, 07:00
Aircraft
Cessna Citation X
Category
Super midsize jet
Seats
8
USD 4,100
Pricing and schedule subject to change
KMQJ -> KENW
Jan 20, 2026 to Jan 20, 2026, 07:00
Aircraft
Cessna Citation X
Category
Super midsize jet
Seats
8
USD 5,300
Pricing and schedule subject to change
Chicago (KMDW) -> Marco Island (KMKY)
Jan 20, 2026 to Jan 20, 2026, 07:00
Aircraft
Hawker 400XP
Category
Light jet
Seats
8
USD 14,000
Pricing and schedule subject to change
White Plains (KHPN) -> Chicago (KMDW)
Jan 20, 2026 to Jan 20, 2026, 07:00
Aircraft
Hawker 400XP
Category
Light jet
Seats
8
USD 12,000
Pricing and schedule subject to change
Fort Myers (KRSW) -> Chicago (KMDW)
Jan 23, 2026 to Jan 23, 2026, 07:00
Aircraft
Hawker 400XP
Category
Light jet
Seats
8
USD 12,000
Pricing and schedule subject to change
KMDW -> KX07
Jan 26, 2026 to Jan 26, 2026, 07:00
Aircraft
Hawker 400XP
Category
Light jet
Seats
8
USD 12,000
Pricing and schedule subject to change
KTEB -> KPWK
Jan 27, 2026 to Jan 27, 2026, 07:00
Aircraft
Legacy 600
Category
Heavy jet
Seats
13
USD 15,460
Pricing and schedule subject to change
Chicago (KMDW) -> Stuart (KSUA)
Jan 27, 2026 to Jan 27, 2026, 07:00
Aircraft
Beechjet 400A
Category
Light jet
Seats
8
USD 14,000
Pricing and schedule subject to change
Cleveland (KCLE) -> Chicago (KMDW)
Jan 29, 2026 to Jan 29, 2026, 07:00
Aircraft
Learjet 40XR
Category
Super light jet
Seats
7
USD 3,540
Pricing and schedule subject to change
KPWK -> KTEB
Feb 03, 2026 to Feb 03, 2026, 07:00
Aircraft
Legacy 600
Category
Heavy jet
Seats
13
USD 14,220
Pricing and schedule subject to change
Chicago (KMDW) -> Marco Island (KMKY)
Feb 03, 2026 to Feb 03, 2026, 07:00
Aircraft
Beechjet 400A
Category
Light jet
Seats
8
USD 14,000
Pricing and schedule subject to change
Chicago (KORD) -> Atlanta (KPDK)
Feb 04, 2026 to Feb 04, 2026, 07:00
Aircraft
Hawker 850XP
Category
Midsize jet
Seats
9
USD 8,270
Pricing and schedule subject to change
KSGR -> KPWK
Feb 04, 2026 to Feb 07, 2026, 07:00
Aircraft
Cessna Citation Excel
Category
Midsize jet
Seats
8
USD 11,250
Pricing and schedule subject to change
Chicago (KMDW) -> Apalachicola (KAAF)
Feb 05, 2026 to Feb 05, 2026, 07:00
Aircraft
Hawker 400XP
Category
Light jet
Seats
8
USD 14,000
Pricing and schedule subject to change
KTEB -> KPWK
Feb 14, 2026 to Feb 14, 2026, 07:00
Aircraft
Gulfstream G450
Category
Heavy jet
Seats
14
USD 7,120
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
27 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
- Boca Raton (KBCT) -> Chicago (KMDW)
- Fort Lauderdale (KFXE) -> Chicago (KMDW)
- St Petersburg-Clearwater (KPIE) -> Chicago (KMDW)
Weather summary
Wind 000 at 0 kt, visibility not reported, weather not reported.
Forecast preview: TAF KMDW 240258Z 2403/2506 15003KT P6SM BKN150 FM240900 19008KT P6SM BKN150 FM241200 19012G22KT P6SM OVC150 FM241600 20020G33KT P6SM...
View raw data
METAR code
METAR KMDW 240253Z 00000KT 10SM FEW250 M05/M10 A3033 RMK AO2 SLP286 T10501100 58015
TAF code
TAF KMDW 240258Z 2403/2506 15003KT P6SM BKN150 FM240900 19008KT P6SM BKN150 FM241200 19012G22KT P6SM OVC150 FM241600 20020G33KT P6SM FEW050 OVC100 FM242300 26012G22KT P6SM SCT025 BKN050
Chicago O'Hare International Airport
Chicago, Illinois (KORD / ORD)
🟢 VFR
4 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) -> Atlanta (KPDK)
- Chicago (KORD) -> Las Vegas (KLAS)
- Chicago (KORD) -> Cleveland (KCLE)
Weather summary
Wind 130 at 3 kt, visibility not reported, weather not reported.
Forecast preview: TAF KORD 240258Z 2403/2506 VRB03KT P6SM BKN150 FM240900 19008KT P6SM BKN150 FM241200 19012G22KT P6SM OVC150 FM241600 20020G33KT P6SM...
View raw data
METAR code
METAR KORD 240251Z 13003KT 10SM BKN250 M06/M11 A3032 RMK AO2 SLP277 T10561106 58015
TAF code
TAF KORD 240258Z 2403/2506 VRB03KT P6SM BKN150 FM240900 19008KT P6SM BKN150 FM241200 19012G22KT P6SM OVC150 FM241600 20020G33KT P6SM FEW050 OVC100 FM242300 26012G22KT P6SM SCT025 BKN050
Chicago Executive Airport
Wheeling, Illinois (KPWK / PWK)
🟢 VFR
21 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
- KPWK -> KARV
- KTEB -> KPWK
- KPWK -> KTEB
Weather summary
Wind 000 at 0 kt, visibility not reported, weather not reported.
TAF unavailable right now.
View raw data
METAR code
METAR KPWK 240252Z 00000KT 10SM FEW075 FEW090 SCT100 M07/M09 A3034 RMK AO2 SLP284 T10671094 58016 $
TAF code
No raw TAF available.
DuPage Airport
West Chicago, Illinois (KDPA / DPA)
🟢 VFR
2 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) -> West Palm Beach (KPBI)
- Teterboro (KTEB) -> Chicago/West Chicago (KDPA)
Weather summary
Wind 110 at 3 kt, visibility not reported, weather not reported.
Forecast preview: TAF KDPA 232320Z 2400/2424 VRB04KT P6SM BKN150 FM241200 19012G22KT P6SM OVC150 FM241600 20020G32KT P6SM FEW050 OVC100 FM242300 26012G22KT...
View raw data
METAR code
METAR KDPA 240252Z 11003KT 10SM CLR M06/M11 A3031 RMK AO2 SLP275 T10611111 58017
TAF code
TAF KDPA 232320Z 2400/2424 VRB04KT P6SM BKN150 FM241200 19012G22KT P6SM OVC150 FM241600 20020G32KT P6SM FEW050 OVC100 FM242300 26012G22KT P6SM SCT025 BKN050
Kenosha Regional Airport
Kenosha, Wisconsin (KENW / ENW)
🟢 VFR
8 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
- KENW -> KMQJ
- KMQJ -> KENW
- Indianapolis (KIND) -> Kenosha (KENW)
Weather summary
Wind 000 at 0 kt, visibility not reported, weather not reported.
Forecast preview: TAF KENW 240315Z 2403/2424 VRB03KT P6SM BKN150 FM241000 19007KT P6SM BKN250 FM241600 19016G27KT P6SM BKN130 FM242100 23014G27KT 6SM...
View raw data
METAR code
METAR KENW 240253Z 00000KT 10SM CLR M08/M12 A3031
TAF code
TAF KENW 240315Z 2403/2424 VRB03KT P6SM BKN150 FM241000 19007KT P6SM BKN250 FM241600 19016G27KT P6SM BKN130 FM242100 23014G27KT 6SM -SN BKN040
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.