Empty Leg Flights to and from Chicago
Looking for great deals on empty leg flights to or from Chicago? Take advantage of private jet savings with one-way and return empty leg flights. Whether you're heading to Chicago (CHI) or departing from it, book your next flight today and enjoy luxurious, cost-effective travel.
From:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
29.08.2026
29.08.2026
Aircraft:
Citation XLS+
Citation XLS+
Capacity:
8
8
$16,130
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 25 minutes
Cost per person:
$2016.2
Cost per hour:
$11342.07
From:
Naples, Municipal (APF), FL, US
Naples, Municipal (APF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
31.08.2026
31.08.2026
Aircraft:
Citation Excel
Citation Excel
Capacity:
9
9
$14,320
Distance between APF - MDW:
1133 mi (1823 km)
Cost per person:
$1591.15
Cost per hour:
$10069.83
From:
Miami, Opa-locka Executive (OPF), FL, US
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
07.09.2026
07.09.2026
Aircraft:
Challenger 300
Challenger 300
Capacity:
9
9
$16,076
Distance between OPF - MDW:
1177 mi (1895 km)
Estimated flight duration:
2 hours : 13 minutes
Cost per person:
$1786.22
Cost per hour:
$7211.72
From:
Miami-Opa Locka Executive Airport
Miami-Opa Locka Executive Airport
To:
Chicago Midway International Airport
Chicago Midway International Airport
Departure date:
08.09.2026
08.09.2026
Aircraft:
Bombardier Challenger 300
Bombardier Challenger 300
Capacity:
9
9
$16,500
Distance between OPF - MDW:
1177 mi (1895 km)
Cost per person:
$1833.33
Cost per hour:
$7401.95
From:
Miami, Opa-locka Executive (OPF), FL, US
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
10.09.2026
10.09.2026
Aircraft:
Citation CJ4 Gen2
Citation CJ4 Gen2
Capacity:
8
8
$16,612
Distance between OPF - PWK:
1201 mi (1933 km)
Cost per person:
$2076.44
Cost per hour:
$7451.98
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
Departure date:
01.09.2026
01.09.2026
Aircraft:
Citation X
Citation X
Capacity:
8
8
$12,853
Distance between MDW - TEB:
712 mi (1146 km)
Estimated flight duration:
1 hours : 10 minutes
Cost per person:
$1606.59
Cost per hour:
$10966.68
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Miami, Opa-locka Executive (OPF), FL, US
Miami, Opa-locka Executive (OPF), FL, US
Departure date:
04.09.2026
04.09.2026
Aircraft:
Challenger 300
Challenger 300
Capacity:
9
9
$15,423
Distance between MDW - OPF:
1177 mi (1895 km)
Estimated flight duration:
2 hours : 13 minutes
Cost per person:
$1713.69
Cost per hour:
$6918.92
From:
Chicago Midway International Airport
Chicago Midway International Airport
To:
Miami-Opa Locka Executive Airport
Miami-Opa Locka Executive Airport
Departure date:
04.09.2026
04.09.2026
Aircraft:
Bombardier Challenger 300
Bombardier Challenger 300
Capacity:
9
9
$15,840
Distance between MDW - OPF:
1177 mi (1895 km)
Cost per person:
$1760
Cost per hour:
$7105.88
From:
Nashville, Nashville International Airport (BNA), TN, US
Nashville, Nashville International Airport (BNA), TN, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$8,675
Distance between BNA - PWK:
419 mi (674 km)
Estimated flight duration:
0 hours : 50 minutes
Cost per person:
$963.94
Cost per hour:
$10351.35
From:
Provo, Municipal (PVU), UT, US
Provo, Municipal (PVU), UT, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
10
10
$23,708
Distance between PVU - PWK:
1242 mi (1999 km)
Estimated flight duration:
2 hours : 21 minutes
Cost per person:
$2370.83
Cost per hour:
$10080.5
From:
Miami, Kendall-Tamiami Executive (TMB), FL, US
Miami, Kendall-Tamiami Executive (TMB), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Citation XLS
Capacity:
9
9
$24,953
Distance between TMB - MDW:
1191 mi (1916 km)
Estimated flight duration:
2 hours : 20 minutes
Cost per person:
$2772.52
Cost per hour:
$10626.03
From:
Southern Pines, Moore County (SOP), NC, US
Southern Pines, Moore County (SOP), NC, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G200
Gulfstream G200
Capacity:
9
9
$15,312
Distance between SOP - PWK:
660 mi (1063 km)
Estimated flight duration:
1 hours : 15 minutes
Cost per person:
$1701.36
Cost per hour:
$12248.66
From:
Fort Worth, Meacham International (FTW), TX, US
Fort Worth, Meacham International (FTW), TX, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
8
8
$16,464
Distance between FTW - MDW:
817 mi (1314 km)
Estimated flight duration:
1 hours : 32 minutes
Cost per person:
$2057.99
Cost per hour:
$10649.59
From:
Omaha, Eppley Airfield (OMA), NE, US
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G200
Gulfstream G200
Capacity:
10
10
$11,663
Distance between OMA - MDW:
429 mi (690 km)
Estimated flight duration:
0 hours : 48 minutes
Cost per person:
$1166.32
Cost per hour:
$14368.95
From:
West Palm Beach, Palm Beach International (PBI), FL, US
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation CJ3
Citation CJ3
Capacity:
7
7
$10,843
Distance between PBI - MDW:
1129 mi (1817 km)
Estimated flight duration:
2 hours : 21 minutes
Cost per person:
$1549.05
Cost per hour:
$4594.11
From:
Birmingham, Shuttlesworth International (BHM), AL, US
Birmingham, Shuttlesworth International (BHM), AL, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Aircraft:
Gulfstream G-IVSP
Gulfstream G-IVSP
Capacity:
12
12
$21,698
Distance between BHM - DPA:
583 mi (938 km)
Cost per person:
$1808.14
Cost per hour:
$9192.88
From:
Omaha, Eppley Airfield (OMA), NE, US
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$8,788
Distance between OMA - PWK:
422 mi (679 km)
Estimated flight duration:
0 hours : 50 minutes
Cost per person:
$976.41
Cost per hour:
$10404.33
From:
Islip, Long Island Mac Arthur (ISP), NY, US
Islip, Long Island Mac Arthur (ISP), NY, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Gulfstream G450
Gulfstream G450
Capacity:
12
12
$16,464
Distance between ISP - UGN:
769 mi (1237 km)
Estimated flight duration:
1 hours : 22 minutes
Cost per person:
$1371.99
Cost per hour:
$12019.04
From:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$7,574
Distance between MSP - PWK:
334 mi (537 km)
Estimated flight duration:
0 hours : 40 minutes
Cost per person:
$841.53
Cost per hour:
$11341.53
From:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Learjet 60
Learjet 60
Capacity:
7
7
$11,196
Distance between MSP - UGN:
326 mi (525 km)
Estimated flight duration:
0 hours : 40 minutes
Cost per person:
$1599.42
Cost per hour:
$16605.42
From:
Provo, Municipal (PVU), UT, US
Provo, Municipal (PVU), UT, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
10
10
$23,764
Distance between PVU - PWK:
1242 mi (1999 km)
Estimated flight duration:
2 hours : 21 minutes
Cost per person:
$2376.44
Cost per hour:
$10104.36
From:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Citation XLS
Citation XLS
Capacity:
9
9
$8,727
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 25 minutes
Cost per person:
$969.63
Cost per hour:
$6136.44
From:
Panama City, Northwest Florida Beaches International (ECP), FL, US
Panama City, Northwest Florida Beaches International (ECP), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 60
Learjet 60
Capacity:
7
7
$16,091
Distance between ECP - MDW:
797 mi (1283 km)
Estimated flight duration:
1 hours : 38 minutes
Cost per person:
$2298.65
Cost per hour:
$9755.81
From:
Dallas, Addison (ADS), TX, US
Dallas, Addison (ADS), TX, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$13,283
Distance between ADS - MDW:
814 mi (1309 km)
Estimated flight duration:
1 hours : 37 minutes
Cost per person:
$1475.93
Cost per hour:
$8157.32
From:
Philadelphia, Northeast Philadelphia (PNE), PA, US
Philadelphia, Northeast Philadelphia (PNE), PA, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
8
8
$13,091
Distance between PNE - DPA:
701 mi (1128 km)
Estimated flight duration:
1 hours : 19 minutes
Cost per person:
$1636.33
Cost per hour:
$9861.58
From:
Westhampton Beach, Francis S Gabreski (FOK), NY, US
Westhampton Beach, Francis S Gabreski (FOK), NY, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
8
8
$16,503
Distance between FOK - DPA:
810 mi (1304 km)
Estimated flight duration:
1 hours : 32 minutes
Cost per person:
$2062.87
Cost per hour:
$10756.41
From:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
8
8
$13,283
Distance between TEB - DPA:
738 mi (1188 km)
Estimated flight duration:
1 hours : 23 minutes
Cost per person:
$1660.42
Cost per hour:
$9501.89
From:
Naples, Municipal (APF), FL, US
Naples, Municipal (APF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
8
8
$19,693
Distance between APF - MDW:
1133 mi (1823 km)
Estimated flight duration:
2 hours : 8 minutes
Cost per person:
$2461.66
Cost per hour:
$9183.25
From:
Missoula, Missoula International Airport (MSO), MT, US
Missoula, Missoula International Airport (MSO), MT, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation Excel
Citation Excel
Capacity:
8
8
$14,445
Distance between MSO - UGN:
1322 mi (2127 km)
Cost per person:
$1805.6
Cost per hour:
$6735.83
From:
Zelienople, Municipal (PJC), PA, US
Zelienople, Municipal (PJC), PA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Citation XLS
Capacity:
8
8
$8,855
Distance between PJC - MDW:
4894 mi (7876 km)
Estimated flight duration:
9 hours : 39 minutes
Cost per person:
$1106.85
Cost per hour:
$917.41
From:
Hayward, Sawyer County (HYR), WI, US
Hayward, Sawyer County (HYR), WI, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$7,637
Distance between HYR - PWK:
322 mi (519 km)
Estimated flight duration:
0 hours : 38 minutes
Cost per person:
$848.58
Cost per hour:
$11834.82
From:
Hayward, Sawyer County (HYR), WI, US
Hayward, Sawyer County (HYR), WI, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G200
Gulfstream G200
Capacity:
9
9
$9,520
Distance between HYR - PWK:
322 mi (519 km)
Estimated flight duration:
0 hours : 36 minutes
Cost per person:
$1057.74
Cost per hour:
$15595.95
From:
Amsterdam, Airport Schiphol (AMS), NL
Amsterdam, Airport Schiphol (AMS), NL
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Aircraft:
Falcon 8X
Falcon 8X
Capacity:
14
14
$98,120
Distance between AMS - DPA:
4128 mi (6643 km)
Estimated flight duration:
7 hours : 48 minutes
Cost per person:
$7008.55
Cost per hour:
$12555.53
From:
Toronto, Lester B. Pearson International (YYZ), ON, CA
Toronto, Lester B. Pearson International (YYZ), ON, CA
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Global 6000
Global 6000
Capacity:
14
14
$17,104
Distance between YYZ - MDW:
433 mi (696 km)
Estimated flight duration:
0 hours : 46 minutes
Cost per person:
$1221.74
Cost per hour:
$22154.7
From:
Georgetown, Sussex County (GED), DE, US
Georgetown, Sussex County (GED), DE, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$14,142
Distance between GED - MDW:
687 mi (1105 km)
Estimated flight duration:
1 hours : 22 minutes
Cost per person:
$1571.36
Cost per hour:
$10286.99
From:
Pellston, Regional Airport of Emmet County (PLN), MI, US
Pellston, Regional Airport of Emmet County (PLN), MI, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 60
Learjet 60
Capacity:
8
8
$11,084
Distance between PLN - MDW:
300 mi (483 km)
Estimated flight duration:
0 hours : 37 minutes
Cost per person:
$1385.46
Cost per hour:
$17857.66
From:
Sacramento, Sacramento International Airport (SMF), CA, US
Sacramento, Sacramento International Airport (SMF), CA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 60XR
Learjet 60XR
Capacity:
6
6
$25,348
Distance between SMF - MDW:
1787 mi (2876 km)
Cost per person:
$4224.66
Cost per hour:
$40839.69
From:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 60XR
Learjet 60XR
Capacity:
6
6
$16,655
Distance between TEB - MDW:
712 mi (1146 km)
Cost per person:
$2775.91
Cost per hour:
$26834.64
Benefits of Booking Empty Leg Flights in Chicago
Booking an empty leg flight in Chicago can offer numerous benefits to travelers. One major advantage is the potential for significant cost savings. Since these flights are often operated at a lower cost than standard charter flights, passengers can enjoy a more affordable option without compromising on luxury or convenience. Another benefit is flexibility – empty leg flights can provide a flexible schedule that allows travelers to book a flight that suits their needs, even if it's not during peak travel hours. Additionally, these flights often offer a unique and exclusive travel experience, complete with amenities like gourmet catering, comfortable seating, and personalized service.
How to Find the Best Deals on Empty Leg Flights in Chicago
To find the best deals on empty leg flights in Chicago, travelers can try the following:
- Maintain a flexible schedule and be open to different flight dates and times.
- Contact local brokers or charter companies, who often have access to a wider range of empty leg flights.
Popular Routes from Chicago
Some popular empty leg flight routes from Chicago include:
- Chicago to Miami: This route is in high demand due to the city's thriving business community and the popularity of South Florida as a vacation destination.
- Chicago to New York City: As one of the most populous cities in the United States, NYC is a major hub for private jet travel, with many empty leg flights available from Chicago.
- Chicago to Los Angeles: This route is popular among entertainment industry professionals and business travelers looking to access LA's bustling airports and surrounding communities.
Local Airports and Private Jet Terminals in Chicago
In Chicago, there are several local airports and private jet terminals that serve empty leg flights. One notable option is the Pal-Waukee Airport (KPWA), a popular alternative to O'Hare International Airport for private aviation travelers. The airport offers amenities like fuel services, hangar space, and ground transportation, making it an ideal location for those seeking empty leg flights.
Are empty leg flights in Chicago always cheaper?
No, empty leg flights in Chicago are not always cheaper. While these flights can offer significant cost savings compared to standard charter flights, prices may still vary depending on factors like the distance of the flight, the type of aircraft, and the level of service required. However, by being flexible with your travel dates and times, you may be able to find a more affordable option.
Can I choose the exact departure time?
While empty leg flights often have fixed schedules due to their unique nature, some brokers or charter companies may offer flexibility in terms of departure time. However, this is not always possible, as the flight's itinerary and schedule are often determined by the original booking. In certain cases, you may be able to negotiate a revised departure time or find alternative flights that better suit your needs.
