Empty Leg Flights to and from Fort Sheridan

Looking for great deals on empty leg flights to or from Fort Sheridan? Take advantage of private jet savings with one-way and return empty leg flights. Whether you're heading to Fort Sheridan (FSN) or departing from it, book your next flight today and enjoy luxurious, cost-effective travel.

From:
Chesterfield, Spirit of St Louis (SUS), MO, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
27.10.2025
Aircraft:
Hawker 900XP
Capacity:
8
$7,724
Distance between SUS - PWK:
266 mi (428 km)
Cost per person:
$965.48
Cost per hour:
$INF

From:
South Lake Tahoe, Lake Tahoe (TVL), CA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
29.10.2025
Aircraft:
Learjet 45
Capacity:
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
Learjet 45 image 1
Learjet 45 image 2

From:
Panama City, Northwest Florida Beaches International (ECP), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
30.10.2025
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Scottsdale, Scottsdale Airport (SDL), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
30.10.2025
Aircraft:
Gulfstream G-IV
Capacity:
14
$19,719
Distance between SDL - MDW:
4143 mi (6668 km)
Estimated flight duration:
7 hours : 23 minutes
Cost per person:
$1408.49
Cost per hour:
$2670.47
Gulfstream G-IV image 1
Gulfstream G-IV image 2

From:
Venice, Municipal (VNC), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
30.10.2025
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Marco, Island (MKY), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
07.11.2025
Aircraft:
Learjet 45
Capacity:
9
$16,348
Distance between MKY - MDW:
8869 mi (14274 km)
Estimated flight duration:
17 hours : 45 minutes
Cost per person:
$1816.44
Cost per hour:
$920.85
Learjet 45 image 1
Learjet 45 image 2

From:
Palm Springs, Palm Springs International Airport (PSP), CA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
08.11.2025
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Aspen, Pitkin Co/Sardy Field (ASE), CO, US
Departure date:
27.10.2025
Aircraft:
Challenger 604
Capacity:
10
$19,719
Distance between MDW - ASE:
1018 mi (1639 km)
Estimated flight duration:
1 hours : 55 minutes
Cost per person:
$1971.89
Cost per hour:
$10275.65
Challenger 604 image 1
Challenger 604 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Pellston, Regional Airport of Emmet County (PLN), MI, US
Departure date:
27.10.2025
Aircraft:
Citation Ultra
Capacity:
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
Citation Ultra image 1
Citation Ultra image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Eagle, County Regional (EGE), CO, US
Departure date:
28.10.2025
Aircraft:
Gulfstream G-IV
Capacity:
14
$21,910
Distance between MDW - EGE:
985 mi (1586 km)
Estimated flight duration:
1 hours : 45 minutes
Cost per person:
$1565
Cost per hour:
$12476.56
Gulfstream G-IV image 1
Gulfstream G-IV image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Bridgetown, Sir Grantley Adams International (BGI), BB
Departure date:
28.10.2025
Aircraft:
Gulfstream G-IV
Capacity:
14
$40,524
Distance between MDW - BGI:
2610 mi (4200 km)
Estimated flight duration:
4 hours : 39 minutes
Cost per person:
$2894.54
Cost per hour:
$8712.28
Gulfstream G-IV image 1
Gulfstream G-IV image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Missoula, Missoula International Airport (MSO), MT, US
Departure date:
03.11.2025
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Teterboro, Teterboro Airport (TEB), NJ, US
Departure date:
03.11.2025
Aircraft:
Beechjet 400A
Capacity:
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
To:
Dallas, Addison (ADS), TX, US
Departure date:
06.11.2025
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Naples, Municipal (APF), FL, US
Departure date:
06.11.2025
Aircraft:
Beechjet 400A
Capacity:
8
$14,196
Distance between MDW - APF:
1133 mi (1823 km)
Cost per person:
$1774.49
Cost per hour:
$8891.21

From:
Chicago, Midway International (MDW), IL, US
To:
Scottsdale, Scottsdale Airport (SDL), AZ, US
Departure date:
11.11.2025
Aircraft:
Learjet 45
Capacity:
9
$18,617
Distance between MDW - SDL:
4143 mi (6668 km)
Estimated flight duration:
8 hours : 17 minutes
Cost per person:
$2068.58
Cost per hour:
$2244.85
Learjet 45 image 1
Learjet 45 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Marco, Island (MKY), FL, US
Departure date:
14.11.2025
Aircraft:
Learjet 45
Capacity:
9
$17,437
Distance between MDW - MKY:
8869 mi (14274 km)
Estimated flight duration:
17 hours : 45 minutes
Cost per person:
$1937.5
Cost per hour:
$982.22
Learjet 45 image 1
Learjet 45 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
West Palm Beach, Palm Beach International (PBI), FL, US
Departure date:
20.11.2025
Aircraft:
Citation CJ1+
Capacity:
5
$9,860
Distance between MDW - PBI:
1129 mi (1817 km)
Cost per person:
$1972.01
Cost per hour:
$555.4

From:
Ft Lauderdale, Fort Lauderdale Hollywood International (FLL), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation CJ4 Gen2
Capacity:
8
$15,803
Distance between FLL - PWK:
1190 mi (1915 km)
Cost per person:
$1975.33
Cost per hour:
$890.13

From:
Denver, Centennial (APA), CO, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$13,146
Distance between APA - MDW:
912 mi (1468 km)
Estimated flight duration:
1 hours : 47 minutes
Cost per person:
$1643.19
Cost per hour:
$7343.17
Hawker 400XP image 1
Hawker 400XP image 2

From:
Tucson, Tucson International Airport (TUS), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Latitude
Capacity:
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
Citation Latitude image 1
Citation Latitude image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Latitude
Capacity:
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
Citation Latitude image 1
Citation Latitude image 2

From:
Jacksonville, Jacksonville International Airport (JAX), FL, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Scottsdale, Scottsdale Airport (SDL), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$17,437
Distance between SDL - MDW:
4143 mi (6668 km)
Estimated flight duration:
8 hours : 7 minutes
Cost per person:
$2179.68
Cost per hour:
$2144.44
Hawker 400XP image 1
Hawker 400XP image 2

From:
East St. Louis, St Louis Downtown (CPS), IL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation III
Capacity:
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
Citation III image 1
Citation III image 2

From:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Citation X
Capacity:
8
$8,686
Distance between MSP - DPA:
329 mi (529 km)
Estimated flight duration:
0 hours : 32 minutes
Cost per person:
$1085.8
Cost per hour:
$16048.23
Citation X image 1
Citation X image 2

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Sovereign
Capacity:
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
Citation Sovereign image 1
Citation Sovereign image 2

From:
Oklahoma City, Will Rogers World (OKC), OK, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Gulfstream G-IV
Capacity:
14
$21,782
Distance between OKC - PWK:
691 mi (1113 km)
Estimated flight duration:
1 hours : 13 minutes
Cost per person:
$1555.85
Cost per hour:
$17674.79
Gulfstream G-IV image 1
Gulfstream G-IV image 2

From:
Sarasota, Bradenton International (SRQ), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$13,078
Distance between SRQ - MDW:
1038 mi (1670 km)
Estimated flight duration:
2 hours : 2 minutes
Cost per person:
$1868.34
Cost per hour:
$6422.49
Hawker 400XP image 1
Hawker 400XP image 2

From:
Rochester, Greater Rochester International (ROC), NY, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Falcon 900EX
Capacity:
13
$16,720
Distance between ROC - PWK:
528 mi (849 km)
Estimated flight duration:
0 hours : 53 minutes
Cost per person:
$1286.16
Cost per hour:
$18698.64
Falcon 900EX image 1
Falcon 900EX image 2

From:
Nashville, Nashville International Airport (BNA), TN, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Falcon 900B
Capacity:
14
$15,718
Distance between BNA - PWK:
419 mi (674 km)
Cost per person:
$1122.75
Cost per hour:
$17578.49

From:
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation CJ3+
Capacity:
6
$14,129
Distance between PBI - PWK:
1153 mi (1856 km)
Cost per person:
$2354.8
Cost per hour:
$15800.72

From:
Ft Myers, Southwest Florida International (RSW), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Gulfstream G200
Capacity:
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
Gulfstream G200 image 1
Gulfstream G200 image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Latitude
Capacity:
9
$19,713
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 42 minutes
Cost per person:
$2190.31
Cost per hour:
$11585.37
Citation Latitude image 1
Citation Latitude image 2

From:
Tucson, Tucson International Airport (TUS), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Latitude
Capacity:
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
Citation Latitude image 1
Citation Latitude image 2

From:
New Orleans, Louis Armstrong New Orleans International (MSY), LA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Falcon 900EX
Capacity:
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
Falcon 900EX image 1
Falcon 900EX image 2

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 60
Capacity:
8
$9,528
Distance between OMA - MDW:
429 mi (690 km)
Estimated flight duration:
0 hours : 53 minutes
Cost per person:
$1191.03
Cost per hour:
$10744.32
Learjet 60 image 1
Learjet 60 image 2

From:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Hawker 850XP
Capacity:
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
Hawker 850XP image 1
Hawker 850XP image 2

From:
New Orleans, Louis Armstrong New Orleans International (MSY), LA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Falcon 900EX
Capacity:
13
$21,793
Distance between MSY - MDW:
827 mi (1332 km)
Estimated flight duration:
1 hours : 24 minutes
Cost per person:
$1676.37
Cost per hour:
$15547.88
Falcon 900EX image 1
Falcon 900EX image 2

From:
Washington, Dulles International (IAD), DC, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Hawker 850XP
Capacity:
8
$10,677
Distance between IAD - DPA:
603 mi (971 km)
Estimated flight duration:
1 hours : 18 minutes
Cost per person:
$1334.68
Cost per hour:
$8193.1
Hawker 850XP image 1
Hawker 850XP image 2

From:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Hawker 850XP
Capacity:
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
Hawker 850XP image 1
Hawker 850XP image 2

From:
Myrtle Beach, Myrtle Beach International Airport (MYR), SC, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Concord, Concord Regional Airport (JQF), NC, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Capacity:
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
Learjet 45 image 1
Learjet 45 image 2

From:
Boca Raton, Boca Raton Airport (BCT), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Joplin, Joplin Regional Airport (JLN), MO, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Pilatus PC-12/47
Capacity:
8
$5,897
Distance between JLN - PWK:
491 mi (790 km)
Cost per person:
$737.19
Cost per hour:
$2607.78

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.

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