Empty Leg Flights to Chicago
Chicago is one of the busiest tourist destinations and attracts travelers from all over the world to the U.S. state of Illinois. In addition, private jets are a common way to travel from state to state. What’s more, thanks to the world-famous attractions, great vacation destinations, and popularity among private travelers, you have multiple prospects to benefit from empty leg flights.
Empty Legs Instant Quote to/from Chicago
Empty Leg Private Jet Flights Chicago
Updated daily. Last update – Tue, 13 May 2025
| From | To | Aircraft | Seats | Date | Price |
|---|---|---|---|---|---|
| CHICAGO O’HARE INTL, CHICAGO (ORD) | TETERBORO, TETERBORO (TEB) | Gulfstream G-IVSP | 14 | from Tue, 13 May – to Wed, 14 May | $ 16,800 * |
| CHICAGO MIDWAY INTL, CHICAGO (MDW) | NAPLES, NAPLES (APF) | Citation Excel | 8 | from Wed, 14 May – to Wed, 14 May | $ 18,000 * |
| CHICAGO MIDWAY INTL, CHICAGO (MDW) | JACKSONVILLE INTL, JACKSONVILLE (JAX) | Hawker 400XP | 8 | from Thu, 15 May – to Thu, 15 May | $ 14,400 * |
| CHICAGO MIDWAY INTL, CHICAGO (MDW) | DEKALB-PEACHTREE, ATLANTA (PDK) | Citation XLS Gen 2 | 9 | from Wed, 14 May – to Wed, 14 May | $ 12,000 * |
| CHICAGO EXECUTIVE, CHICAGO/WHEELING (PWK) | BOCA RATON, BOCA RATON (BCT) | Citation Excel | 8 | from Tue, 13 May – to Tue, 13 May | $ 19,200 * |
| CHICAGO EXECUTIVE, CHICAGO/WHEELING (PWK) | VERO BEACH MUNI, VERO BEACH (VRB) | Nextant 400XTi | 8 | from Fri, 16 May – to Fri, 16 May | $ 13,200 * |
| BOWMAN FIELD, LOUISVILLE (LOU) | WESTCHESTER COUNTY, WHITE PLAINS (HPN) | Citation Sovereign | 8 | from Tue, 13 May – to Wed, 14 May | $ 9,840 * |
| NASHVILLE INTL, NASHVILLE (BNA) | REPUBLIC, FARMINGDALE (FRG) | Citation CJ | 0 | from Tue, 13 May – to Tue, 13 May | $ 9,600 * |
| SPIRIT OF ST LOUIS, ST LOUIS (SUS) | GREENE COUNTY REGIONAL, GREENSBORO () | Challenger 604 | 11 | from Sat, 17 May – to Sat, 17 May | $ 21,000 * |
| QUAD CITY INTL, MOLINE (MLI) | SEBRING REGIONAL, SEBRING (SEF) | Nextant 400XTi | 8 | from Fri, 16 May – to Sat, 17 May | $ 20,640 * |
| KALAMAZOO COUNTY, KALAMAZOO (AZO) | NAPLES, NAPLES (APF) | Citation X | 8 | from Wed, 14 May – to Wed, 14 May | $ 19,680 * |
| ST CLOUD REGIONAL, ST CLOUD (STC) | HOLLYWOOD INTL, FORT LAUDERDALE (FLL) | Citation CJ4 Gen2 | 9 | from Thu, 15 May – to Thu, 15 May | $ 15,000 * |
| GENERAL MITCHELL INTL, MILWAUKEE (MKE) | HILTON HEAD, HILTON HEAD ISLAND (HHH) | Citation CJ4 Gen2 | 9 | from Fri, 16 May – to Fri, 16 May | $ 14,400 * |
| WAUKESHA COUNTY, WAUKESHA (UES) | GREATER ROCHESTER INTL, ROCHESTER (ROC) | Citation Bravo | 8 | from Fri, 16 May – to Fri, 16 May | $ 12,840 * |
| DANE COUNTY REGIONAL, MADISON (MSN) | TRI-STATE INT’L, HUNTINGTON (HTS) | Citation Ultra | 8 | from Wed, 14 May – to Wed, 14 May | $ 12,720 * |
| MOUNT PLEASANT MUNI, MOUNT PLEASANT (MOP) | HOLLYWOOD INTL, FORT LAUDERDALE (FLL) | Citation CJ4 Gen2 | 9 | from Wed, 14 May – to Wed, 14 May | $ 12,000 * |
| FORT WAYNE INTERNATIONAL, FORT WAYNE (FWA) | COVINGTON MUNI, ATLANTA () | Pilatus PC12 NGX | 8 | from Wed, 14 May – to Thu, 15 May | $ 7,560 * |
| SOUTH BEND INTERNATIONAL, SOUTH BEND (SBN) | LEE GILMER MEMORIAL, GAINESVILLE () | Citation Ultra | 7 | from Sat, 17 May – to Sun, 18 May | $ 5,760 * |
| BOWMAN FIELD, LOUISVILLE (LOU) | CHARLESTON EXECUTIVE, CHARLESTON () | King Air 300 | 8 | from Sat, 17 May – to Sun, 18 May | $ 5,460 * |
| TETERBORO, TETERBORO (TEB) | DUPAGE, CHICAGO/WEST CHICAGO (DPA) | Hawker 750 | 8 | from Thu, 15 May – to Fri, 16 May | $ 15,840 * |
| TETERBORO, TETERBORO (TEB) | SAN FRANCISCO INTL, SAN FRANCISCO (SFO) | Challenger 300 | 0 | from Sat, 17 May – to Sat, 17 May | $ 42,000 * |
| TETERBORO, TETERBORO (TEB) | SAN FRANCISCO INTL, SAN FRANCISCO (SFO) | Citation X | 8 | from Sat, 17 May – to Sat, 17 May | $ 31,200 * |
| TETERBORO, TETERBORO (TEB) | VAN NUYS, VAN NUYS (VNY) | Citation X | 8 | from Fri, 16 May – to Fri, 16 May | $ 28,800 * |
| TETERBORO, TETERBORO (TEB) | BOEING FIELD INTL, SEATTLE (BFI) | Citation X | 8 | from Wed, 14 May – to Wed, 14 May | $ 27,600 * |
| TETERBORO, TETERBORO (TEB) | JOHN WAYNE/ORANGE COUNTY, SANTA ANA (SNA) | Citation X | 8 | from Thu, 15 May – to Thu, 15 May | $ 26,400 * |
| TETERBORO, TETERBORO (TEB) | SARASOTA/BRADENTON INTL, SARASOTA/BRADENTON (SRQ) | Challenger 300 | 8 | from Thu, 15 May – to Thu, 15 May | $ 21,600 * |
| TETERBORO, TETERBORO (TEB) | OPA-LOCKA EXECUTIVE, MIAMI (OPF) | Gulfstream G-IVSP | 0 | from Wed, 14 May – to Thu, 15 May | $ 21,600 * |
| TETERBORO, TETERBORO (TEB) | STATESVILLE MUNI, STATESVILLE (SVH) | Challenger 604 | 10 | from Sat, 17 May – to Sat, 17 May | $ 18,180 * |
| TETERBORO, TETERBORO (TEB) | OPA-LOCKA EXECUTIVE, MIAMI (OPF) | Citation X | 8 | from Fri, 16 May – to Fri, 16 May | $ 16,800 * |
| TETERBORO, TETERBORO (TEB) | OPA-LOCKA EXECUTIVE, MIAMI (OPF) | Citation Bravo | 8 | from Fri, 16 May – to Tue, 20 May | $ 16,200 * |
| TETERBORO, TETERBORO (TEB) | BOCA RATON, BOCA RATON (BCT) | Citation CJ4 | 8 | from Thu, 15 May – to Fri, 16 May | $ 15,600 * |
| TETERBORO, TETERBORO (TEB) | KEOKUK MUNI, KEOKUK (EOK) | Citation Excel | 9 | from Fri, 16 May – to Fri, 16 May | $ 15,240 * |
| TETERBORO, TETERBORO (TEB) | NAPLES, NAPLES (APF) | Citation X | 8 | from Fri, 16 May – to Fri, 16 May | $ 14,400 * |
| TETERBORO, TETERBORO (TEB) | OPA-LOCKA EXECUTIVE, MIAMI (OPF) | Learjet 60 | 7 | from Mon, 12 May – to Wed, 14 May | $ 14,164 * |
| TETERBORO, TETERBORO (TEB) | OPA-LOCKA EXECUTIVE, MIAMI (OPF) | Citation X | 8 | from Wed, 14 May – to Wed, 14 May | $ 12,000 * |
| TETERBORO, TETERBORO (TEB) | GENERAL MITCHELL INTL, MILWAUKEE (MKE) | Citation CJ4 Gen2 | 9 | from Wed, 14 May – to Wed, 14 May | $ 10,200 * |
| TETERBORO, TETERBORO (TEB) | OAKLAND COUNTY INTL, PONTIAC (PTK) | Falcon 20F-5 | 9 | from Fri, 16 May – to Fri, 16 May | $ 7,680 * |
| WESTCHESTER COUNTY, WHITE PLAINS (HPN) | SAN ANTONIO INTL, SAN ANTONIO (SAT) | Gulfstream G-V | 16 | from Mon, 12 May – to Tue, 13 May | $ 34,200 * |
| FRANCIS S GABRESKI, WESTHAMPTON BEACH (FOK) | LOS ANGELES INTL, LOS ANGELES (LAX) | Citation X | 8 | from Thu, 15 May – to Thu, 15 May | $ 27,600 * |
| WESTCHESTER COUNTY, WHITE PLAINS (HPN) | NEW CENTURY AIRCENTER, OLATHE () | Challenger 300 | 8 | from Thu, 15 May – to Fri, 16 May | $ 21,000 * |
| REPUBLIC, FARMINGDALE (FRG) | PALM BEACH INTL, WEST PALM BEACH (PBI) | Learjet 60 | 7 | from Wed, 14 May – to Thu, 15 May | $ 20,940 * |
| REPUBLIC, FARMINGDALE (FRG) | PALM BEACH INTL, WEST PALM BEACH (PBI) | Learjet 60 | 7 | from Wed, 14 May – to Wed, 14 May | $ 20,160 * |
| FRANCIS S GABRESKI, WESTHAMPTON BEACH (FOK) | NASHVILLE INTL, NASHVILLE (BNA) | Citation Excel | 8 | from Wed, 14 May – to Wed, 14 May | $ 16,440 * |
| WESTCHESTER COUNTY, WHITE PLAINS (HPN) | ST LUCIE COUNTY INTL, FORT PIERCE (FPR) | Hawker 800XP | 0 | from Wed, 14 May – to Thu, 15 May | $ 16,200 * |
| WESTCHESTER COUNTY, WHITE PLAINS (HPN) | HOLLYWOOD INTL, FORT LAUDERDALE (FLL) | Phenom 300 | 7 | from Tue, 13 May – to Wed, 14 May | $ 15,120 * |
| WESTCHESTER COUNTY, WHITE PLAINS (HPN) | ASHEVILLE REGIONAL, ASHEVILLE (AVL) | Learjet 60 | 7 | from Wed, 14 May – to Wed, 14 May | $ 11,760 * |
| CHARLESTON EXECUTIVE, CHARLESTON () | CHICAGO EXECUTIVE, CHICAGO/WHEELING (PWK) | Gulfstream G-150 | 8 | from Fri, 16 May – to Fri, 16 May | $ 10,980 * |
| FRANCIS S GABRESKI, WESTHAMPTON BEACH (FOK) | JACKSONVILLE INTL, JACKSONVILLE (JAX) | Hawker 400XP | 8 | from Thu, 15 May – to Fri, 16 May | $ 10,800 * |
| WESTCHESTER COUNTY, WHITE PLAINS (HPN) | HOLLYWOOD INTL, FORT LAUDERDALE (FLL) | Citation CJ4 Gen2 | 9 | from Tue, 13 May – to Tue, 13 May | $ 9,600 * |
| REPUBLIC, FARMINGDALE (FRG) | DEKALB-PEACHTREE, ATLANTA (PDK) | Citation CJ | 6 | from Tue, 13 May – to Wed, 14 May | $ 9,000 * |
| MORRISTOWN MUNI, MORRISTOWN (MMU) | CENTENNIAL, DENVER (APA) | Gulfstream G-IVSP | 13 | from Sat, 17 May – to Sat, 17 May | $ 36,000 * |
*Estimated price before taxes & fees.
When Do Empty Leg Flights Become Available to Chicago?
The empty leg system allows you to take advantage of all the benefits of private aviation with a clear price advantage. Simply put, these are flights made by a jet that returns to the airport after flying another. For example, with us, you can book private jet Chicago empty leg flights at a discount of about 75%.
For example, if the private jet was rented for a one-way flight, it is possible to book empty leg flights from Chicago. It does not matter how many passengers you may have on the plane.
What are the Benefits of Chartering Empty Leg Flights to Chicago?
With empty leg flights to Chicago, you can enjoy all the benefits of VIP service and fly comfortably to your destination. It allows you to focus on work or relax during your flight. Enjoy a cozy atmosphere, gourmet meals, and drinks. Empty Leg flight prices vary by destination. So enjoy a stress-free travel experience. To pick up an Empty Leg flight to/from Chicago, you need to contact our manager in any convenient way.
Airports Serving Chicago
The private jet may land closer to your desired destination than is possible with commercial flights. We offer immediate access to the most extensive inventory of empty leg flights to and from Chicago. Expanding your destination means opening up your itinerary to new destinations that were previously unavailable.
| Chicago Midway International Airport | MDW | On the southwest side of Chicago is one of the busiest airports in the country. |
| Chicago Executive Airport | PWK | PWK is 18 miles from downtown Chicago in Cook County. |
| O’Hare International Airport | ORD | It is 17 miles from the Loop business district. |
| Aurora Municipal Airport | AUZ | AUZ is a public airport 50 miles from downtown Chicago and 8 miles from the city of Aurora. |
| Gary/Chicago International Airport | GYY | It is located 25 miles from the Chicago Loop. |
Empty Leg Private Jet Charter Flights To Chicago
With access to 4,000 aircraft worldwide, Mercury Jets’ empty leg search portal allows users to search for travel routes by custom departure and arrival locations, several passengers, dates and times, and aircraft. In addition, our dedicated charter representatives are available 24/7 to help you search for empty legs. To book a flight or speak to a representative, call us at +1 212 840 8000.