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:
Clemson, Oconee County Regional (CEU), SC, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
31.08.2025
Aircraft:
Citation XLS+
Capacity:
8
$10,788
Distance between CEU - PWK:
582 mi (937 km)
Estimated flight duration:
1 hours : 8 minutes
Cost per person:
$1348.56
Cost per hour:
$9398.03
Citation XLS+ image 1
Citation XLS+ image 2

From:
Dallas, Addison (ADS), TX, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
01.09.2025
Aircraft:
Learjet 45
Capacity:
9
$13,214
Distance between ADS - MDW:
814 mi (1309 km)
Estimated flight duration:
1 hours : 37 minutes
Cost per person:
$1468.2
Cost per hour:
$8114.61
Learjet 45 image 1
Learjet 45 image 2

From:
Sarasota, Bradenton International (SRQ), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
01.09.2025
Aircraft:
Hawker 400XP
Capacity:
8
$13,616
Distance between SRQ - MDW:
1038 mi (1670 km)
Estimated flight duration:
2 hours : 2 minutes
Cost per person:
$1702.05
Cost per hour:
$6686.7
Hawker 400XP image 1
Hawker 400XP image 2

From:
Burlington, Alamance Regional (BUY), NC, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Departure date:
03.09.2025
Aircraft:
Citation X
Capacity:
8
$10,832
Distance between BUY - UGN:
11021 mi (17737 km)
Estimated flight duration:
18 hours : 8 minutes
Cost per person:
$1354.05
Cost per hour:
$597.28
Citation X image 1
Citation X image 2

From:
Colorado Springs, City of Colorado Springs Municipal (COS), CO, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
05.09.2025
Aircraft:
Hawker 400XP
Capacity:
8
$12,032
Distance between COS - MDW:
921 mi (1483 km)
Estimated flight duration:
1 hours : 48 minutes
Cost per person:
$1503.96
Cost per hour:
$6653.66
Hawker 400XP image 1
Hawker 400XP image 2

From:
Charlottesville, Albemarle (CHO), VA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
05.09.2025
Aircraft:
Hawker 400XP
Capacity:
8
$10,348
Distance between CHO - MDW:
553 mi (889 km)
Estimated flight duration:
1 hours : 5 minutes
Cost per person:
$1293.51
Cost per hour:
$9541.37
Hawker 400XP image 1
Hawker 400XP image 2

From:
Pittsburgh, Allegheny County (AGC), PA, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
05.09.2025
Aircraft:
Hawker 400XP
Capacity:
7
$9,804
Distance between AGC - MDW:
6104 mi (9823 km)
Estimated flight duration:
11 hours : 58 minutes
Cost per person:
$1400.56
Cost per hour:
$818.4
Hawker 400XP image 1
Hawker 400XP image 2

From:
Fernandina Beach, Municipal (FHB), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
11.09.2025
Aircraft:
Hawker 400XP
Capacity:
8
$11,851
Distance between FHB - MDW:
6104 mi (9823 km)
Estimated flight duration:
11 hours : 58 minutes
Cost per person:
$1481.39
Cost per hour:
$989.3
Hawker 400XP image 1
Hawker 400XP image 2

From:
Dallas, Love Field (DAL), TX, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
27.09.2025
Aircraft:
Hawker 400XP
Capacity:
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
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Kansas City, Charles B. Wheeler Downtown (MKC), MO, US
Departure date:
31.08.2025
Aircraft:
Hawker 900XP
Capacity:
8
$5,524
Distance between MDW - MKC:
407 mi (654 km)
Cost per person:
$690.52
Cost per hour:
$3542.75

From:
Chicago, Midway International (MDW), IL, US
To:
Huntsville, International Carl T Jones Field (HSV), AL, US
Departure date:
03.09.2025
Aircraft:
Beechjet 400A
Capacity:
8
$9,914
Distance between MDW - HSV:
492 mi (791 km)
Cost per person:
$1239.22
Cost per hour:
$6357.87

From:
Chicago, Midway International (MDW), IL, US
To:
Huntsville, International Carl T Jones Field (HSV), AL, US
Departure date:
03.09.2025
Aircraft:
Hawker 400XP
Capacity:
8
$8,812
Distance between MDW - HSV:
492 mi (791 km)
Estimated flight duration:
0 hours : 57 minutes
Cost per person:
$1101.51
Cost per hour:
$9130.08
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Executive (PWK), IL, US
To:
Jerome, County (JER), ID, US
Departure date:
03.09.2025
Aircraft:
Citation Ultra
Capacity:
8
$14,705
Distance between PWK - JER:
3943 mi (6345 km)
Estimated flight duration:
7 hours : 58 minutes
Cost per person:
$1838.08
Cost per hour:
$1844.74
Citation Ultra image 1
Citation Ultra image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Denver, Rocky Mountain Metropolitan (BJC), CO, US
Departure date:
03.09.2025
Aircraft:
Hawker 400XP
Capacity:
8
$13,071
Distance between MDW - BJC:
913 mi (1469 km)
Estimated flight duration:
1 hours : 47 minutes
Cost per person:
$1633.89
Cost per hour:
$7294.24
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Asheville, Asheville Regional Airport (AVL), NC, US
Departure date:
04.09.2025
Aircraft:
Beechjet 400A
Capacity:
8
$9,914
Distance between MDW - AVL:
521 mi (839 km)
Cost per person:
$1239.22
Cost per hour:
$5532.3

From:
Chicago, Midway International (MDW), IL, US
To:
Clearwater, St Petersburg Clearwater International (PIE), FL, US
Departure date:
06.09.2025
Aircraft:
Hawker 400XP
Capacity:
8
$13,616
Distance between MDW - PIE:
1000 mi (1610 km)
Estimated flight duration:
1 hours : 57 minutes
Cost per person:
$1702.05
Cost per hour:
$6935.77
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Naples, Municipal (APF), FL, US
Departure date:
09.09.2025
Aircraft:
Citation Excel
Capacity:
9
$14,052
Distance between MDW - APF:
1133 mi (1823 km)
Cost per person:
$1561.33
Cost per hour:
$7157.62

From:
Chicago, Midway International (MDW), IL, US
To:
Pittsburgh, Allegheny County (AGC), PA, US
Departure date:
13.09.2025
Aircraft:
Hawker 400XP
Capacity:
7
$10,832
Distance between MDW - AGC:
6104 mi (9823 km)
Estimated flight duration:
11 hours : 58 minutes
Cost per person:
$1547.48
Cost per hour:
$904.26
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Quebec, Jean Lesage International (YQB), QC, CA
Departure date:
23.09.2025
Aircraft:
Learjet 45
Capacity:
9
$12,093
Distance between MDW - YQB:
884 mi (1423 km)
Estimated flight duration:
1 hours : 46 minutes
Cost per person:
$1343.63
Cost per hour:
$6830.38
Learjet 45 image 1
Learjet 45 image 2

From:
Chicago, Midway International (MDW), IL, US
To:
Bangor, Bangor International Airport (BGR), ME, US
Departure date:
26.09.2025
Aircraft:
Hawker 400XP
Capacity:
7
$12,999
Distance between MDW - BGR:
972 mi (1564 km)
Estimated flight duration:
1 hours : 54 minutes
Cost per person:
$1857.01
Cost per hour:
$6814.68
Hawker 400XP image 1
Hawker 400XP image 2

From:
Denver, Rocky Mountain Metropolitan (BJC), CO, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$13,071
Distance between BJC - MDW:
913 mi (1469 km)
Estimated flight duration:
1 hours : 47 minutes
Cost per person:
$1633.89
Cost per hour:
$7294.24
Hawker 400XP image 1
Hawker 400XP image 2

From:
Cleveland, Burke Lakefront (BKL), OH, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Cessna Conquest II
Capacity:
5
$5,458
Distance between BKL - MDW:
313 mi (504 km)
Cost per person:
$1091.66
Cost per hour:
$3045.96

From:
Erie, International Tom Ridge Field (ERI), PA, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Excel
Capacity:
7
$10,825
Distance between ERI - PWK:
396 mi (637 km)
Cost per person:
$1546.44
Cost per hour:
$6040.87

From:
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Cessna Conquest II
Capacity:
5
$11,015
Distance between PBI - MDW:
1129 mi (1817 km)
Cost per person:
$2203.08
Cost per hour:
$6147.07

From:
Missoula, Missoula International Airport (MSO), MT, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Capacity:
9
$20,929
Distance between MSO - MDW:
1342 mi (2160 km)
Estimated flight duration:
2 hours : 41 minutes
Cost per person:
$2325.46
Cost per hour:
$7790.39
Learjet 45 image 1
Learjet 45 image 2

From:
Aiken, Municipal (AIK), SC, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Capacity:
8
$10,464
Distance between AIK - MDW:
656 mi (1056 km)
Cost per person:
$1307.99
Cost per hour:
$3894.97

From:
Lakeland, Linder Regional (LAL), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Falcon 2000
Capacity:
10
$22,028
Distance between LAL - PWK:
1031 mi (1659 km)
Cost per person:
$2202.83
Cost per hour:
$8199.55

From:
Rutland, Southern Vermont Regional (RUT), VT, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Excel
Capacity:
8
$6,387
Distance between RUT - PWK:
763 mi (1228 km)
Cost per person:
$798.34
Cost per hour:
$2377.31

From:
Hyannis, Barnstable Municipal Boardman Polando Field (HYA), MA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Challenger 601
Capacity:
9
$15,230
Distance between HYA - MDW:
899 mi (1447 km)
Estimated flight duration:
1 hours : 41 minutes
Cost per person:
$1692.28
Cost per hour:
$8989.05
Challenger 601 image 1
Challenger 601 image 2

From:
Tampa, Tampa International Airport (TPA), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45
Capacity:
9
$17,624
Distance between TPA - MDW:
1002 mi (1612 km)
Estimated flight duration:
2 hours : 0 minutes
Cost per person:
$1958.24
Cost per hour:
$8790.81
Learjet 45 image 1
Learjet 45 image 2

From:
Oakland, Metropolitan Oakland International (OAK), CA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
7
$19,465
Distance between OAK - MDW:
1842 mi (2964 km)
Estimated flight duration:
3 hours : 36 minutes
Cost per person:
$2780.73
Cost per hour:
$5385.64
Hawker 400XP image 1
Hawker 400XP image 2

From:
Boca Raton, Boca Raton Airport (BCT), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$13,769
Distance between BCT - MDW:
1152 mi (1854 km)
Estimated flight duration:
2 hours : 15 minutes
Cost per person:
$1721.12
Cost per hour:
$6088.42
Hawker 400XP image 1
Hawker 400XP image 2

From:
Daytona Beach, Daytona Beach International Airport (DAB), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$13,071
Distance between DAB - MDW:
948 mi (1525 km)
Estimated flight duration:
1 hours : 51 minutes
Cost per person:
$1633.89
Cost per hour:
$7026.14
Hawker 400XP image 1
Hawker 400XP image 2

From:
Scottsdale, Scottsdale Airport (SDL), AZ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Capacity:
8
$17,429
Distance between SDL - MDW:
4143 mi (6668 km)
Cost per person:
$2178.62
Cost per hour:
$9368.62

From:
Boca Raton, Boca Raton Airport (BCT), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$13,024
Distance between BCT - MDW:
1152 mi (1854 km)
Estimated flight duration:
2 hours : 15 minutes
Cost per person:
$1627.94
Cost per hour:
$5758.8
Hawker 400XP image 1
Hawker 400XP image 2

From:
Farmingdale, Republic (FRG), NY, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Praetor 600
Capacity:
9
$16,183
Distance between FRG - PWK:
756 mi (1216 km)
Cost per person:
$1798.14
Cost per hour:
$7156.02

From:
Sarasota, Bradenton International (SRQ), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$13,219
Distance between SRQ - MDW:
1038 mi (1670 km)
Estimated flight duration:
2 hours : 2 minutes
Cost per person:
$1652.34
Cost per hour:
$6491.38
Hawker 400XP image 1
Hawker 400XP image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Sovereign
Capacity:
8
$17,239
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 21 minutes
Cost per person:
$2154.83
Cost per hour:
$12656.68
Citation Sovereign image 1
Citation Sovereign image 2

From:
Islip, Long Island Mac Arthur (ISP), NY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$10,853
Distance between ISP - MDW:
763 mi (1227 km)
Estimated flight duration:
1 hours : 29 minutes
Cost per person:
$1356.64
Cost per hour:
$7251.07
Hawker 400XP image 1
Hawker 400XP image 2

From:
Islip, Long Island Mac Arthur (ISP), NY, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Beechjet 400A
Capacity:
8
$10,892
Distance between ISP - MDW:
763 mi (1227 km)
Cost per person:
$1361.52
Cost per hour:
$7277.15

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Capacity:
9
$10,575
Distance between OMA - MDW:
429 mi (690 km)
Estimated flight duration:
0 hours : 50 minutes
Cost per person:
$1175
Cost per hour:
$12507.12
Citation XLS image 1
Citation XLS image 2

From:
Wildwood, Cape May County (WWD), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation Sovereign
Capacity:
8
$17,239
Distance between WWD - PWK:
714 mi (1150 km)
Estimated flight duration:
1 hours : 20 minutes
Cost per person:
$2154.83
Cost per hour:
$12775.21
Citation Sovereign image 1
Citation Sovereign image 2

From:
Pellston, Regional Airport of Emmet County (PLN), MI, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G550
Capacity:
14
$21,117
Distance between PLN - MDW:
300 mi (483 km)
Estimated flight duration:
0 hours : 34 minutes
Cost per person:
$1508.36
Cost per hour:
$37171.57
Gulfstream G550 image 1
Gulfstream G550 image 2

From:
Yakima, Air Terminal McAllister Field (YKM), WA, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation X
Capacity:
8
$19,393
Distance between YKM - PWK:
1629 mi (2621 km)
Estimated flight duration:
2 hours : 40 minutes
Cost per person:
$2424.14
Cost per hour:
$7236.63
Citation X image 1
Citation X image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation X
Capacity:
8
$13,053
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 11 minutes
Cost per person:
$1631.6
Cost per hour:
$11000.69
Citation X image 1
Citation X image 2

From:
Nashville, John C Tune (JWN), TN, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation XLS+
Capacity:
8
$4,242
Distance between JWN - UGN:
6314 mi (10162 km)
Estimated flight duration:
12 hours : 27 minutes
Cost per person:
$530.24
Cost per hour:
$340.63
Citation XLS+ image 1
Citation XLS+ image 2

From:
Nashville, Nashville International Airport (BNA), TN, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation XLS+
Capacity:
8
$4,382
Distance between BNA - UGN:
435 mi (701 km)
Estimated flight duration:
0 hours : 51 minutes
Cost per person:
$547.78
Cost per hour:
$5103.47
Citation XLS+ image 1
Citation XLS+ image 2

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation V
Capacity:
7
$11,342
Distance between APF - PWK:
1157 mi (1861 km)
Cost per person:
$1620.33
Cost per hour:
$13209.07

From:
Houston, William P Hobby (HOU), TX, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation V
Capacity:
7
$8,531
Distance between HOU - PWK:
954 mi (1535 km)
Cost per person:
$1218.78
Cost per hour:
$9935.57

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Challenger 300
Capacity:
8
$11,015
Distance between TEB - MDW:
712 mi (1146 km)
Estimated flight duration:
1 hours : 20 minutes
Cost per person:
$1376.92
Cost per hour:
$8168.84
Challenger 300 image 1
Challenger 300 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.

Statistics and Market Trends in Chicago

A growing demand for private jet travel has led to an increase in empty leg flights in Chicago. According to recent statistics, the number of private flights in the United States has seen a significant surge over the past few years, with Chicago being one of the busiest hubs. In fact, a study by the General Aviation Manufacturers Association found that private jet travel is experiencing steady growth, with many industry experts predicting continued expansion in the coming years. Furthermore, the rise of on-demand charter services and online booking platforms has made it easier for passengers to find and book empty leg flights, further fueling market demand.

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.
  • Use online platforms or apps that specialize in private jet travel, such as JetSmarter or Victor.
  • 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.

Frequently Asked Questions

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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