Empty Leg Flights to and from Fort Sheridan
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From:
Boca Raton, Boca Raton Airport (BCT), FL, US
Boca Raton, Boca Raton Airport (BCT), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
10.10.2025
10.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$15,124
Distance between BCT - MDW:
1152 mi (1854 km)
Estimated flight duration:
2 hours : 15 minutes
Cost per person:
$1890.54
Cost per hour:
$6687.76
From:
Joplin, Joplin Regional Airport (JLN), MO, US
Joplin, Joplin Regional Airport (JLN), MO, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
10.10.2025
10.10.2025
Aircraft:
Pilatus PC-12/47
Pilatus PC-12/47
Capacity:
8
8
$5,897
Distance between JLN - PWK:
491 mi (790 km)
Cost per person:
$737.19
Cost per hour:
$2607.78
From:
Myrtle Beach, Myrtle Beach International Airport (MYR), SC, US
Myrtle Beach, Myrtle Beach International Airport (MYR), SC, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
11.10.2025
11.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$9,828
Distance between MYR - MDW:
739 mi (1189 km)
Estimated flight duration:
1 hours : 27 minutes
Cost per person:
$1228.54
Cost per hour:
$6775.69
From:
Concord, Concord Regional Airport (JQF), NC, US
Concord, Concord Regional Airport (JQF), NC, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
11.10.2025
11.10.2025
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$11,361
Distance between JQF - MDW:
579 mi (931 km)
Estimated flight duration:
1 hours : 9 minutes
Cost per person:
$1262.29
Cost per hour:
$9806.07
From:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
Clearwater, St Petersburg Clearwater International (PIE), FL, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Departure date:
12.10.2025
12.10.2025
Aircraft:
Hawker 850XP
Hawker 850XP
Capacity:
8
8
$13,368
Distance between PIE - DPA:
1017 mi (1637 km)
Estimated flight duration:
2 hours : 11 minutes
Cost per person:
$1670.94
Cost per hour:
$6084.72
From:
New Orleans, Louis Armstrong New Orleans International (MSY), LA, US
New Orleans, Louis Armstrong New Orleans International (MSY), LA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
13.10.2025
13.10.2025
Aircraft:
Falcon 900EX
Falcon 900EX
Capacity:
13
13
$21,593
Distance between MSY - MDW:
827 mi (1332 km)
Estimated flight duration:
1 hours : 24 minutes
Cost per person:
$1660.98
Cost per hour:
$15405.14
From:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
Clearwater, St Petersburg Clearwater International (PIE), FL, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Departure date:
13.10.2025
13.10.2025
Aircraft:
Hawker 850XP
Hawker 850XP
Capacity:
8
8
$13,366
Distance between PIE - DPA:
1017 mi (1637 km)
Estimated flight duration:
2 hours : 11 minutes
Cost per person:
$1670.79
Cost per hour:
$6084.17
From:
Ft Myers, Southwest Florida International (RSW), FL, US
Ft Myers, Southwest Florida International (RSW), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
14.10.2025
14.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$13,104
Distance between RSW - MDW:
1107 mi (1782 km)
Estimated flight duration:
2 hours : 10 minutes
Cost per person:
$1638
Cost per hour:
$6030.88
From:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Departure date:
14.10.2025
14.10.2025
Aircraft:
Gulfstream G200
Gulfstream G200
Capacity:
9
9
$6,527
Distance between TEB - DPA:
738 mi (1188 km)
Estimated flight duration:
1 hours : 23 minutes
Cost per person:
$725.22
Cost per hour:
$4668.91
From:
Tucson, Tucson International Airport (TUS), AZ, US
Tucson, Tucson International Airport (TUS), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
14.10.2025
14.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$18,335
Distance between TUS - MDW:
1434 mi (2308 km)
Estimated flight duration:
2 hours : 48 minutes
Cost per person:
$2291.92
Cost per hour:
$6515.11
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:
14.10.2025
14.10.2025
Aircraft:
Citation Latitude
Citation Latitude
Capacity:
9
9
$21,733
Distance between OPF - PWK:
1201 mi (1933 km)
Estimated flight duration:
2 hours : 50 minutes
Cost per person:
$2414.79
Cost per hour:
$7666.55
From:
West Palm Beach, Palm Beach International (PBI), FL, US
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
15.10.2025
15.10.2025
Aircraft:
Citation CJ3+
Citation CJ3+
Capacity:
6
6
$14,129
Distance between PBI - PWK:
1153 mi (1856 km)
Cost per person:
$2354.8
Cost per hour:
$4984.07
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
Departure date:
16.10.2025
16.10.2025
Aircraft:
Falcon 900B
Falcon 900B
Capacity:
14
14
$15,718
Distance between BNA - PWK:
419 mi (674 km)
Cost per person:
$1122.75
Cost per hour:
$5544.84
From:
Naples, Municipal (APF), FL, US
Naples, Municipal (APF), FL, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
19.10.2025
19.10.2025
Aircraft:
Citation Sovereign
Citation Sovereign
Capacity:
8
8
$19,037
Distance between APF - PWK:
1157 mi (1861 km)
Estimated flight duration:
2 hours : 11 minutes
Cost per person:
$2379.61
Cost per hour:
$8713.45
From:
East St. Louis, St Louis Downtown (CPS), IL, US
East St. Louis, St Louis Downtown (CPS), IL, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Departure date:
20.10.2025
20.10.2025
Aircraft:
Citation III
Citation III
Capacity:
9
9
$5,977
Distance between CPS - PWK:
6113 mi (9837 km)
Estimated flight duration:
11 hours : 9 minutes
Cost per person:
$664.09
Cost per hour:
$535.27
From:
Jacksonville, Jacksonville International Airport (JAX), FL, US
Jacksonville, Jacksonville International Airport (JAX), FL, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Departure date:
21.10.2025
21.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$10,375
Distance between JAX - DPA:
880 mi (1417 km)
Estimated flight duration:
1 hours : 43 minutes
Cost per person:
$1482.13
Cost per hour:
$6005.19
From:
Tucson, Tucson International Airport (TUS), AZ, US
Tucson, Tucson International Airport (TUS), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
22.10.2025
22.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$18,454
Distance between TUS - MDW:
1434 mi (2308 km)
Estimated flight duration:
2 hours : 48 minutes
Cost per person:
$2306.72
Cost per hour:
$6557.16
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
Departure date:
22.10.2025
22.10.2025
Aircraft:
Citation Latitude
Citation Latitude
Capacity:
9
9
$19,531
Distance between TEB - MDW:
712 mi (1146 km)
Estimated flight duration:
1 hours : 40 minutes
Cost per person:
$2170.11
Cost per hour:
$11621.18
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:
22.10.2025
22.10.2025
Aircraft:
Citation Latitude
Citation Latitude
Capacity:
9
9
$22,787
Distance between OPF - MDW:
1177 mi (1895 km)
Estimated flight duration:
2 hours : 46 minutes
Cost per person:
$2531.91
Cost per hour:
$8201.97
From:
South Lake Tahoe, Lake Tahoe (TVL), CA, US
South Lake Tahoe, Lake Tahoe (TVL), CA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
29.10.2025
29.10.2025
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$21,733
Distance between TVL - MDW:
1701 mi (2737 km)
Estimated flight duration:
3 hours : 24 minutes
Cost per person:
$2414.79
Cost per hour:
$6384.03
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
Departure date:
30.10.2025
30.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$11,467
Distance between ECP - MDW:
797 mi (1283 km)
Estimated flight duration:
1 hours : 33 minutes
Cost per person:
$1638.11
Cost per hour:
$7327.69
From:
Venice, Municipal (VNC), FL, US
Venice, Municipal (VNC), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
30.10.2025
30.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$13,041
Distance between VNC - MDW:
1061 mi (1707 km)
Estimated flight duration:
2 hours : 4 minutes
Cost per person:
$1862.94
Cost per hour:
$6263.11
From:
Palm Springs, Palm Springs International Airport (PSP), CA, US
Palm Springs, Palm Springs International Airport (PSP), CA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Departure date:
08.11.2025
08.11.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$18,565
Distance between PSP - MDW:
1657 mi (2666 km)
Estimated flight duration:
3 hours : 15 minutes
Cost per person:
$2320.59
Cost per hour:
$5709.09
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Windsor Locks, Bradley International (BDL), CT, US
Windsor Locks, Bradley International (BDL), CT, US
Departure date:
10.10.2025
10.10.2025
Aircraft:
Citation X
Citation X
Capacity:
9
9
$13,104
Distance between MDW - BDL:
774 mi (1246 km)
Estimated flight duration:
1 hours : 16 minutes
Cost per person:
$1456
Cost per hour:
$10287.54
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:
12.10.2025
12.10.2025
Aircraft:
Challenger 601
Challenger 601
Capacity:
9
9
$10,865
Distance between MDW - TEB:
712 mi (1146 km)
Estimated flight duration:
1 hours : 20 minutes
Cost per person:
$1207.26
Cost per hour:
$8095.48
From:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
To:
Teterboro, Teterboro Airport (TEB), NJ, US
Teterboro, Teterboro Airport (TEB), NJ, US
Departure date:
13.10.2025
13.10.2025
Aircraft:
Gulfstream G-IVSP
Gulfstream G-IVSP
Capacity:
14
14
$17,351
Distance between DPA - TEB:
738 mi (1188 km)
Cost per person:
$1239.35
Cost per hour:
$12927.67
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Portland, International Jetport (PWM), ME, US
Portland, International Jetport (PWM), ME, US
Departure date:
13.10.2025
13.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$13,482
Distance between MDW - PWM:
893 mi (1437 km)
Estimated flight duration:
1 hours : 45 minutes
Cost per person:
$1685.28
Cost per hour:
$7695.55
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Charlotte, Douglas International (CLT), NC, US
Charlotte, Douglas International (CLT), NC, US
Departure date:
15.10.2025
15.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$9,127
Distance between MDW - CLT:
587 mi (944 km)
Estimated flight duration:
1 hours : 9 minutes
Cost per person:
$1140.85
Cost per hour:
$7925.57
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Houston, William P Hobby (HOU), TX, US
Houston, William P Hobby (HOU), TX, US
Departure date:
15.10.2025
15.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$12,884
Distance between MDW - HOU:
938 mi (1510 km)
Estimated flight duration:
1 hours : 50 minutes
Cost per person:
$1840.63
Cost per hour:
$6997.28
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Nashville, Nashville International Airport (BNA), TN, US
Nashville, Nashville International Airport (BNA), TN, US
Departure date:
15.10.2025
15.10.2025
Aircraft:
Citation CJ
Citation CJ
Capacity:
6
6
$4,613
Distance between MDW - BNA:
395 mi (636 km)
Cost per person:
$768.8
Cost per hour:
$2505.13
From:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
To:
Buffalo, Niagara International (BUF), NY, US
Buffalo, Niagara International (BUF), NY, US
Departure date:
16.10.2025
16.10.2025
Aircraft:
Falcon 900B
Falcon 900B
Capacity:
14
14
$15,827
Distance between PWK - BUF:
463 mi (745 km)
Cost per person:
$1130.5
Cost per hour:
$8595.37
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Cleveland, Hopkins International (CLE), OH, US
Cleveland, Hopkins International (CLE), OH, US
Departure date:
18.10.2025
18.10.2025
Aircraft:
Citation XLS
Citation XLS
Capacity:
8
8
$8,702
Distance between MDW - CLE:
313 mi (503 km)
Estimated flight duration:
0 hours : 37 minutes
Cost per person:
$1087.78
Cost per hour:
$14105.93
From:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
To:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
Clearwater, St Petersburg Clearwater International (PIE), FL, US
Departure date:
18.10.2025
18.10.2025
Aircraft:
Hawker 850XP
Hawker 850XP
Capacity:
8
8
$12,770
Distance between DPA - PIE:
1017 mi (1637 km)
Estimated flight duration:
2 hours : 11 minutes
Cost per person:
$1596.22
Cost per hour:
$5812.61
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
Departure date:
19.10.2025
19.10.2025
Aircraft:
Citation XLS
Citation XLS
Capacity:
8
8
$15,734
Distance between MDW - FLL:
1166 mi (1876 km)
Estimated flight duration:
2 hours : 17 minutes
Cost per person:
$1966.79
Cost per hour:
$6843.35
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Morristown, Municipal (MMU), NJ, US
Morristown, Municipal (MMU), NJ, US
Departure date:
20.10.2025
20.10.2025
Aircraft:
Beechjet 400A
Beechjet 400A
Capacity:
8
8
$12,012
Distance between MDW - MMU:
695 mi (1118 km)
Cost per person:
$1501.52
Cost per hour:
$5224.44
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Windsor Locks, Bradley International (BDL), CT, US
Windsor Locks, Bradley International (BDL), CT, US
Departure date:
20.10.2025
20.10.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$13,026
Distance between MDW - BDL:
774 mi (1246 km)
Estimated flight duration:
1 hours : 31 minutes
Cost per person:
$1628.24
Cost per hour:
$8574.15
From:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
To:
Naples, Municipal (APF), FL, US
Naples, Municipal (APF), FL, US
Departure date:
24.10.2025
24.10.2025
Aircraft:
Citation Sovereign
Citation Sovereign
Capacity:
7
7
$20,749
Distance between PWK - APF:
1157 mi (1861 km)
Estimated flight duration:
2 hours : 11 minutes
Cost per person:
$2964.08
Cost per hour:
$9496.9
From:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
To:
Naples, Municipal (APF), FL, US
Naples, Municipal (APF), FL, US
Departure date:
24.10.2025
24.10.2025
Aircraft:
Citation Ultra
Citation Ultra
Capacity:
7
7
$20,668
Distance between PWK - APF:
1157 mi (1861 km)
Estimated flight duration:
2 hours : 20 minutes
Cost per person:
$2952.57
Cost per hour:
$8838.26
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Pellston, Regional Airport of Emmet County (PLN), MI, US
Pellston, Regional Airport of Emmet County (PLN), MI, US
Departure date:
27.10.2025
27.10.2025
Aircraft:
Citation Ultra
Citation Ultra
Capacity:
8
8
$11,630
Distance between MDW - PLN:
300 mi (483 km)
Estimated flight duration:
0 hours : 36 minutes
Cost per person:
$1453.78
Cost per hour:
$19171.79
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Missoula, Missoula International Airport (MSO), MT, US
Missoula, Missoula International Airport (MSO), MT, US
Departure date:
03.11.2025
03.11.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$17,473
Distance between MDW - MSO:
1342 mi (2160 km)
Estimated flight duration:
2 hours : 38 minutes
Cost per person:
$2184.11
Cost per hour:
$6633.3
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:
03.11.2025
03.11.2025
Aircraft:
Beechjet 400A
Beechjet 400A
Capacity:
8
8
$12,012
Distance between MDW - TEB:
712 mi (1146 km)
Cost per person:
$1501.52
Cost per hour:
$4560.22
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Dallas, Addison (ADS), TX, US
Dallas, Addison (ADS), TX, US
Departure date:
06.11.2025
06.11.2025
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$11,467
Distance between MDW - ADS:
814 mi (1309 km)
Estimated flight duration:
1 hours : 35 minutes
Cost per person:
$1433.35
Cost per hour:
$7181.89
From:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
To:
Naples, Municipal (APF), FL, US
Naples, Municipal (APF), FL, US
Departure date:
06.11.2025
06.11.2025
Aircraft:
Beechjet 400A
Beechjet 400A
Capacity:
8
8
$14,196
Distance between MDW - APF:
1133 mi (1823 km)
Cost per person:
$1774.49
Cost per hour:
$8891.21
From:
Colorado Springs, City of Colorado Springs Municipal (COS), CO, US
Colorado Springs, City of Colorado Springs Municipal (COS), CO, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$12,943
Distance between COS - MDW:
921 mi (1483 km)
Estimated flight duration:
1 hours : 48 minutes
Cost per person:
$1849
Cost per hour:
$7157.65
From:
Asheville, Asheville Regional Airport (AVL), NC, US
Asheville, Asheville Regional Airport (AVL), NC, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 800XP
Hawker 800XP
Capacity:
8
8
$15,726
Distance between AVL - MDW:
521 mi (839 km)
Estimated flight duration:
1 hours : 7 minutes
Cost per person:
$1965.73
Cost per hour:
$13971.22
From:
Phoenix, Mesa-Gateway (IWA), AZ, US
Phoenix, Mesa-Gateway (IWA), AZ, US
To:
Chicago, Dupage (DPA), IL, US
Chicago, Dupage (DPA), IL, US
Aircraft:
Gulfstream G-IVSP
Gulfstream G-IVSP
Capacity:
14
14
$23,823
Distance between IWA - DPA:
5000 mi (8046 km)
Cost per person:
$1701.64
Cost per hour:
$21164.93
From:
Dallas, Love Field (DAL), TX, US
Dallas, Love Field (DAL), TX, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Challenger 300
Capacity:
9
9
$10,878
Distance between DAL - PWK:
806 mi (1297 km)
Estimated flight duration:
1 hours : 31 minutes
Cost per person:
$1208.61
Cost per hour:
$7127.49
From:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
Clearwater, St Petersburg Clearwater International (PIE), FL, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 40
Learjet 40
Capacity:
6
6
$10,821
Distance between PIE - PWK:
1024 mi (1648 km)
Estimated flight duration:
1 hours : 56 minutes
Cost per person:
$1803.57
Cost per hour:
$5593.06
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:
Hawker 900XP
Hawker 900XP
Capacity:
8
8
$9,010
Distance between OMA - PWK:
422 mi (679 km)
Cost per person:
$1126.21
Cost per hour:
$4656.68
From:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
Clearwater, St Petersburg Clearwater International (PIE), FL, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 40
Learjet 40
Capacity:
6
6
$11,636
Distance between PIE - PWK:
1024 mi (1648 km)
Estimated flight duration:
1 hours : 56 minutes
Cost per person:
$1939.39
Cost per hour:
$6014.28
From:
Santa Barbara, Municipal (SBA), CA, US
Santa Barbara, Municipal (SBA), CA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$17,387
Distance between SBA - MDW:
1799 mi (2896 km)
Estimated flight duration:
3 hours : 31 minutes
Cost per person:
$2483.92
Cost per hour:
$4923.65
From:
Stuart, Witham Field (SUA), FL, US
Stuart, Witham Field (SUA), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$13,579
Distance between SUA - MDW:
1094 mi (1760 km)
Estimated flight duration:
2 hours : 8 minutes
Cost per person:
$1939.8
Cost per hour:
$6326.05
From:
Sarasota, Bradenton International (SRQ), FL, US
Sarasota, Bradenton International (SRQ), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$13,579
Distance between SRQ - MDW:
1038 mi (1670 km)
Estimated flight duration:
2 hours : 2 minutes
Cost per person:
$1697.33
Cost per hour:
$6668.12
From:
Clarinda, Schenck Field (ICL), IA, US
Clarinda, Schenck Field (ICL), IA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Excel
Citation Excel
Capacity:
8
8
$10,856
Distance between ICL - MDW:
386 mi (621 km)
Cost per person:
$1356.95
Cost per hour:
$5330.9
From:
Huntsville, International Carl T Jones Field (HSV), AL, US
Huntsville, International Carl T Jones Field (HSV), AL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$8,650
Distance between HSV - MDW:
492 mi (791 km)
Estimated flight duration:
0 hours : 57 minutes
Cost per person:
$1081.23
Cost per hour:
$8961.96
From:
Nashville, Nashville International Airport (BNA), TN, US
Nashville, Nashville International Airport (BNA), TN, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-V
Gulfstream G-V
Capacity:
16
16
$19,685
Distance between BNA - MDW:
395 mi (636 km)
Cost per person:
$1230.29
Cost per hour:
$20395.1
From:
Marco, Island (MKY), FL, US
Marco, Island (MKY), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Excel
Citation Excel
Capacity:
8
8
$10,819
Distance between MKY - MDW:
8869 mi (14274 km)
Cost per person:
$1352.37
Cost per hour:
$11209.4
From:
Concord, Concord Regional Airport (JQF), NC, US
Concord, Concord Regional Airport (JQF), NC, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$11,352
Distance between JQF - MDW:
579 mi (931 km)
Estimated flight duration:
1 hours : 9 minutes
Cost per person:
$1261.34
Cost per hour:
$9798.69
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
$8,695
Distance between PJC - MDW:
4894 mi (7876 km)
Estimated flight duration:
9 hours : 39 minutes
Cost per person:
$1086.87
Cost per hour:
$900.85
From:
Dallas, Love Field (DAL), TX, US
Dallas, Love Field (DAL), TX, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$11,949
Distance between DAL - MDW:
794 mi (1279 km)
Estimated flight duration:
1 hours : 33 minutes
Cost per person:
$1706.95
Cost per hour:
$7662.93
From:
Chesterfield, Spirit of St Louis (SUS), MO, US
Chesterfield, Spirit of St Louis (SUS), MO, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Hawker 750
Hawker 750
Capacity:
8
8
$12,836
Distance between SUS - PWK:
266 mi (428 km)
Cost per person:
$1604.45
Cost per hour:
$8231.74
From:
Dallas, Love Field (DAL), TX, US
Dallas, Love Field (DAL), TX, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
7
7
$11,916
Distance between DAL - MDW:
794 mi (1279 km)
Estimated flight duration:
1 hours : 33 minutes
Cost per person:
$1702.25
Cost per hour:
$7641.8
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:
Challenger 605
Challenger 605
Capacity:
11
11
$12,988
Distance between TEB - MDW:
712 mi (1146 km)
Estimated flight duration:
1 hours : 20 minutes
Cost per person:
$1180.74
Cost per hour:
$9677.12
From:
Oxford, University Oxford (UOX), MS, US
Oxford, University Oxford (UOX), MS, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Ultra
Citation Ultra
Capacity:
8
8
$12,010
Distance between UOX - PWK:
541 mi (871 km)
Estimated flight duration:
1 hours : 5 minutes
Cost per person:
$1501.21
Cost per hour:
$10969.83
From:
San Antonio, San Antonio International Airport (SAT), TX, US
San Antonio, San Antonio International Airport (SAT), TX, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$13,288
Distance between SAT - PWK:
1057 mi (1702 km)
Estimated flight duration:
2 hours : 4 minutes
Cost per person:
$1661.03
Cost per hour:
$6403.54
From:
San Antonio, San Antonio International Airport (SAT), TX, US
San Antonio, San Antonio International Airport (SAT), TX, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Beechjet 400A
Beechjet 400A
Capacity:
7
7
$11,595
Distance between SAT - PWK:
1057 mi (1702 km)
Cost per person:
$1656.41
Cost per hour:
$5587.52
From:
Hot Springs, Memorial Field (HOT), AR, US
Hot Springs, Memorial Field (HOT), AR, US
To:
Chicago, Executive (PWK), IL, US
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 604
Challenger 604
Capacity:
10
10
$19,432
Distance between HOT - PWK:
598 mi (962 km)
Estimated flight duration:
1 hours : 7 minutes
Cost per person:
$1943.22
Cost per hour:
$17246.45
From:
Harrisburg, Harrisburg International Airport (MDT), PA, US
Harrisburg, Harrisburg International Airport (MDT), PA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$13,482
Distance between MDT - MDW:
583 mi (938 km)
Estimated flight duration:
1 hours : 10 minutes
Cost per person:
$1498.02
Cost per hour:
$11551.63
From:
Vero Beach, Municipal (VRB), FL, US
Vero Beach, Municipal (VRB), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Beechjet 400A
Capacity:
8
8
$14,122
Distance between VRB - MDW:
1061 mi (1707 km)
Cost per person:
$1765.19
Cost per hour:
$12099.37
From:
Toluca, Licenciado Adolfo Lopez Mateos International (TLC), MX
Toluca, Licenciado Adolfo Lopez Mateos International (TLC), MX
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-IV
Gulfstream G-IV
Capacity:
14
14
$17,940
Distance between TLC - MDW:
1706 mi (2745 km)
Estimated flight duration:
3 hours : 2 minutes
Cost per person:
$1281.44
Cost per hour:
$5901.57
From:
Austin, Bergstrom International (AUS), TX, US
Austin, Bergstrom International (AUS), TX, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Hawker 400XP
Capacity:
8
8
$12,492
Distance between AUS - MDW:
971 mi (1563 km)
Estimated flight duration:
1 hours : 54 minutes
Cost per person:
$1561.45
Cost per hour:
$6552.38
From:
San Jose, Norman Y. Mineta San Jose International (SJC), CA, US
San Jose, Norman Y. Mineta San Jose International (SJC), CA, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 800XP
Hawker 800XP
Capacity:
9
9
$28,454
Distance between SJC - MDW:
1833 mi (2950 km)
Estimated flight duration:
3 hours : 57 minutes
Cost per person:
$3161.56
Cost per hour:
$7185.42
From:
Sanford, Orlando Sanford International (SFB), FL, US
Sanford, Orlando Sanford International (SFB), FL, US
To:
Chicago, Midway International (MDW), IL, US
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Learjet 45
Capacity:
9
9
$13,958
Distance between SFB - MDW:
970 mi (1562 km)
Estimated flight duration:
1 hours : 56 minutes
Cost per person:
$1550.89
Cost per hour:
$7185.61
Benefits of Booking Empty Leg Flights in Fort Sheridan
The benefits of booking empty leg flights, including cost savings and flexibility. These one-way trips offer a unique opportunity to travel privately while saving up to 75% compared to traditional charter options.
Statistics and Market Trends in Fort Sheridan
According to recent industry reports, private jet travel in Fort Sheridan has increased by 20% over the past five years. Empty leg flights now account for approximately 15% of all private jet movements in the region.
How to Find the Best Deals on Empty Leg Flights in Fort Sheridan
To get the best price on empty leg flights, book early, use charter brokers, and monitor real-time availability on online platforms. By being proactive and adaptable, travelers can snag these incredible deals and make the most of their private jet experience.
Popular Routes from Fort Sheridan
- New York City (JFK/LGA/EWR)
- Chicago (ORD)
- Miami (MIA)
- Washington D.C. (DCA/JAT)
- Cincinnati (CVG)
Local Airports and Private Jet Terminals in Fort Sheridan
The following airports and terminals facilitate empty leg flights in the Fort Sheridan region:
- Sherman Army Airfield (HHR)
- Meigs Field (6I5)
- Northbrook Field (NWB)
Frequently Asked Questions
Are empty leg flights in Fort Sheridan always cheaper?
Yes, empty leg flights typically cost 50-75% less than regular private jet charters.
Can I choose the exact departure time?
No, since these flights follow a fixed schedule based on aircraft availability.
