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:
Washington Dulles International Airport
To:
Chicago Midway International Airport
Departure date:
03.09.2026
Aircraft:
Bombardier Challenger 300
Capacity:
10
$10,750
Distance between IAD - MDW:
576 mi (927 km)
Cost per person:
$1075
Cost per hour:
—

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
06.09.2026
Aircraft:
Citation X
Capacity:
8
$12,954
Distance between TEB - MDW:
712 mi (1146 km)
Estimated flight duration:
1 hours : 10 minutes
Cost per person:
$1619.25
Cost per hour:
$11053.08
Citation X image 1
Citation X image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
06.09.2026
Aircraft:
Challenger 300
Capacity:
9
$15,544
Distance between TEB - MDW:
712 mi (1146 km)
Estimated flight duration:
1 hours : 20 minutes
Cost per person:
$1727.11
Cost per hour:
$11527.21
Challenger 300 image 1
Challenger 300 image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
07.09.2026
Aircraft:
Challenger 300
Capacity:
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
Challenger 300 image 1
Challenger 300 image 2

From:
Teterboro Airport
To:
Chicago Midway International Airport
Departure date:
07.09.2026
Aircraft:
Bombardier Challenger 300
Capacity:
9
$15,695
Distance between TEB - MDW:
712 mi (1146 km)
Cost per person:
$1743.89
Cost per hour:
$7040.83

From:
Miami-Opa Locka Executive Airport
To:
Chicago Midway International Airport
Departure date:
08.09.2026
Aircraft:
Bombardier Challenger 300
Capacity:
9
$16,500
Distance between OPF - MDW:
1177 mi (1895 km)
Cost per person:
$1833.33
Cost per hour:
$7401.95

From:
Hailey, Friedman Memorial (SUN), ID, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
08.09.2026
Aircraft:
Hawker 400XP
Capacity:
8
$19,431
Distance between SUN - MDW:
1351 mi (2175 km)
Estimated flight duration:
2 hours : 39 minutes
Cost per person:
$2428.87
Cost per hour:
$7326.82
Hawker 400XP image 1
Hawker 400XP image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
10.09.2026
Aircraft:
Citation CJ4 Gen2
Capacity:
8
$16,612
Distance between OPF - PWK:
1201 mi (1933 km)
Cost per person:
$2076.44
Cost per hour:
$6263.71

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
23.09.2026
Aircraft:
Citation Excel
Capacity:
9
$15,112
Distance between APF - MDW:
1133 mi (1823 km)
Cost per person:
$1679.13
Cost per hour:
$5698.33

From:
Coatesville, Chester County G O Carlson (MQS), PA, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
24.09.2026
Aircraft:
Citation CJ3+
Capacity:
7
$9,715
Distance between MQS - PWK:
2578 mi (4149 km)
Cost per person:
$1387.84
Cost per hour:
$3663.18

From:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
26.09.2026
Aircraft:
Learjet 60
Capacity:
7
$11,011
Distance between MSP - MDW:
354 mi (570 km)
Estimated flight duration:
0 hours : 43 minutes
Cost per person:
$1572.93
Cost per hour:
$15023.92
Learjet 60 image 1
Learjet 60 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Miami, Opa-locka Executive (OPF), FL, US
Departure date:
04.09.2026
Aircraft:
Challenger 300
Capacity:
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
Challenger 300 image 1
Challenger 300 image 2

From:
Chicago Midway International Airport
To:
Miami-Opa Locka Executive Airport
Departure date:
04.09.2026
Aircraft:
Bombardier Challenger 300
Capacity:
9
$15,840
Distance between MDW - OPF:
1177 mi (1895 km)
Cost per person:
$1760
Cost per hour:
$7105.88

From:
Chicago Midway International Airport
To:
Teterboro Airport
Departure date:
04.09.2026
Aircraft:
Bombardier Challenger 300
Capacity:
9
$10,213
Distance between MDW - TEB:
712 mi (1146 km)
Cost per person:
$1134.78
Cost per hour:
$4581.58

From:
Chicago, Dupage (DPA), IL, US
To:
West Palm Beach, Palm Beach International (PBI), FL, US
Departure date:
04.09.2026
Aircraft:
Citation Latitude
Capacity:
9
$23,749
Distance between DPA - PBI:
1148 mi (1848 km)
Estimated flight duration:
2 hours : 42 minutes
Cost per person:
$2638.72
Cost per hour:
$8763.01
Citation Latitude image 1
Citation Latitude image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Teterboro, Teterboro Airport (TEB), NJ, US
Departure date:
04.09.2026
Aircraft:
Challenger 300
Capacity:
9
$15,544
Distance between MDW - TEB:
712 mi (1146 km)
Estimated flight duration:
1 hours : 20 minutes
Cost per person:
$1727.11
Cost per hour:
$11527.21
Challenger 300 image 1
Challenger 300 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Atlanta, DeKalb Peachtree (PDK), GA, US
Departure date:
06.09.2026
Aircraft:
Legacy 650
Capacity:
14
$16,732
Distance between MDW - PDK:
578 mi (931 km)
Estimated flight duration:
1 hours : 7 minutes
Cost per person:
$1195.16
Cost per hour:
$14900.19
Legacy 650 image 1
Legacy 650 image 2

From:
Chicago, Dupage (DPA), IL, US
To:
Omaha, Eppley Airfield (OMA), NE, US
Departure date:
08.09.2026
Aircraft:
Challenger 604
Capacity:
12
$15,112
Distance between DPA - OMA:
403 mi (649 km)
Estimated flight duration:
0 hours : 45 minutes
Cost per person:
$1259.35
Cost per hour:
$19889.7
Challenger 604 image 1
Challenger 604 image 2

From:
Chicago, Dupage (DPA), IL, US
To:
Denver, Centennial (APA), CO, US
Departure date:
09.09.2026
Aircraft:
Citation XLS
Capacity:
9
$20,240
Distance between DPA - APA:
887 mi (1427 km)
Estimated flight duration:
1 hours : 44 minutes
Cost per person:
$2248.87
Cost per hour:
$11573.29
Citation XLS image 1
Citation XLS image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Capacity:
9
$22,669
Distance between OPF - MDW:
1177 mi (1895 km)
Estimated flight duration:
2 hours : 19 minutes
Cost per person:
$2518.76
Cost per hour:
$9762.53
Citation XLS image 1
Citation XLS image 2

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Excel
Capacity:
9
$14,320
Distance between APF - MDW:
1133 mi (1823 km)
Cost per person:
$1591.15
Cost per hour:
$6167.19

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation XLS+
Capacity:
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
Citation XLS+ image 1
Citation XLS+ image 2

From:
Oklahoma City, Wiley Post (PWA), OK, US
To:
Gary, Chicago International (GYY), IN, US
Aircraft:
Nextant 400XTi
Capacity:
8
$13,996
Distance between PWA - GYY:
692 mi (1113 km)
Cost per person:
$1749.48
Cost per hour:
$9841.63

From:
Nashville, Nashville International Airport (BNA), TN, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 45
Capacity:
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
Learjet 45 image 1
Learjet 45 image 2

From:
Provo, Municipal (PVU), UT, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Capacity:
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
Challenger 300 image 1
Challenger 300 image 2

From:
Miami, Kendall-Tamiami Executive (TMB), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Capacity:
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
Citation XLS image 1
Citation XLS image 2

From:
Southern Pines, Moore County (SOP), NC, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G200
Capacity:
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
Gulfstream G200 image 1
Gulfstream G200 image 2

From:
Fort Worth, Meacham International (FTW), TX, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Challenger 300
Capacity:
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
Challenger 300 image 1
Challenger 300 image 2

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G200
Capacity:
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
Gulfstream G200 image 1
Gulfstream G200 image 2

From:
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation CJ3
Capacity:
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
Citation CJ3 image 1
Citation CJ3 image 2

From:
Birmingham, Shuttlesworth International (BHM), AL, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Gulfstream G-IVSP
Capacity:
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
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 45
Capacity:
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
Learjet 45 image 1
Learjet 45 image 2

From:
Islip, Long Island Mac Arthur (ISP), NY, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Gulfstream G450
Capacity:
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
Gulfstream G450 image 1
Gulfstream G450 image 2

From:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 45
Capacity:
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
Learjet 45 image 1
Learjet 45 image 2

From:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Learjet 60
Capacity:
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
Learjet 60 image 1
Learjet 60 image 2

From:
Provo, Municipal (PVU), UT, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Capacity:
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
Challenger 300 image 1
Challenger 300 image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation XLS
Capacity:
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
Citation XLS image 1
Citation XLS image 2

From:
Panama City, Northwest Florida Beaches International (ECP), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 60
Capacity:
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
Learjet 60 image 1
Learjet 60 image 2

From:
Dallas, Addison (ADS), TX, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Capacity:
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
Learjet 45 image 1
Learjet 45 image 2

From:
Philadelphia, Northeast Philadelphia (PNE), PA, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Challenger 300
Capacity:
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
Challenger 300 image 1
Challenger 300 image 2

From:
Westhampton Beach, Francis S Gabreski (FOK), NY, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Challenger 300
Capacity:
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
Challenger 300 image 1
Challenger 300 image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Challenger 300
Capacity:
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
Challenger 300 image 1
Challenger 300 image 2

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Challenger 300
Capacity:
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
Challenger 300 image 1
Challenger 300 image 2

From:
Missoula, Missoula International Airport (MSO), MT, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation Excel
Capacity:
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
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Capacity:
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
Citation XLS image 1
Citation XLS image 2

From:
Hayward, Sawyer County (HYR), WI, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 45
Capacity:
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
Learjet 45 image 1
Learjet 45 image 2

From:
Hayward, Sawyer County (HYR), WI, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G200
Capacity:
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
Gulfstream G200 image 1
Gulfstream G200 image 2

From:
Amsterdam, Airport Schiphol (AMS), NL
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Falcon 8X
Capacity:
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
Falcon 8X image 1
Falcon 8X image 2

From:
Toronto, Lester B. Pearson International (YYZ), ON, CA
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Global 6000
Capacity:
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
Global 6000 image 1
Global 6000 image 2

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.

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