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:
West Palm Beach, Palm Beach International (PBI), FL, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
23.03.2026
Aircraft:
Citation CJ3
Capacity:
5
$10,898
Distance between PBI - MDW:
1129 mi (1817 km)
Estimated flight duration:
2 hours : 21 minutes
Cost per person:
$2179.65
Cost per hour:
$4617.37
Citation CJ3 image 1
Citation CJ3 image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
25.03.2026
Aircraft:
Legacy 600
Capacity:
12
$16,247
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 23 minutes
Cost per person:
$1353.9
Cost per hour:
$11606.43
Legacy 600 image 1
Legacy 600 image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Departure date:
26.03.2026
Aircraft:
Legacy 600
Capacity:
12
$16,304
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 23 minutes
Cost per person:
$1358.67
Cost per hour:
$11647.4
Legacy 600 image 1
Legacy 600 image 2

From:
White Plains, Westchester County (HPN), NY, US
To:
Chicago, Midway International (MDW), IL, US
Departure date:
29.03.2026
Aircraft:
Hawker 400XP
Capacity:
7
$12,065
Distance between HPN - MDW:
728 mi (1172 km)
Estimated flight duration:
1 hours : 25 minutes
Cost per person:
$1723.51
Cost per hour:
$8440.76
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Executive (PWK), IL, US
To:
Lincoln, Lincoln Airport (LNK), NE, US
Departure date:
22.03.2026
Aircraft:
Falcon 2000EX EASy
Capacity:
8
$21,278
Distance between PWK - LNK:
466 mi (751 km)
Cost per person:
$2659.75
Cost per hour:
$14886.77

From:
Chicago, Midway International (MDW), IL, US
To:
Tucson, Tucson International Airport (TUS), AZ, US
Departure date:
24.03.2026
Aircraft:
Hawker 400XP
Capacity:
7
$17,548
Distance between MDW - TUS:
1434 mi (2308 km)
Estimated flight duration:
2 hours : 48 minutes
Cost per person:
$2506.93
Cost per hour:
$6235.5
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chicago, Executive (PWK), IL, US
To:
W.B. Scranton, Wilkes Barre Scranton International (AVP), PA, US
Departure date:
26.03.2026
Aircraft:
Gulfstream G-V
Capacity:
16
$13,131
Distance between PWK - AVP:
623 mi (1002 km)
Cost per person:
$820.68
Cost per hour:
$4665.79

From:
Chicago, Midway International (MDW), IL, US
To:
Sarasota, Bradenton International (SRQ), FL, US
Departure date:
26.03.2026
Aircraft:
Hawker 400XP
Capacity:
7
$15,355
Distance between MDW - SRQ:
1038 mi (1670 km)
Estimated flight duration:
2 hours : 2 minutes
Cost per person:
$2193.56
Cost per hour:
$7540.43
Hawker 400XP image 1
Hawker 400XP image 2

From:
Asheville, Asheville Regional Airport (AVL), NC, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 60
Capacity:
7
$9,323
Distance between AVL - MDW:
521 mi (839 km)
Estimated flight duration:
1 hours : 4 minutes
Cost per person:
$1331.89
Cost per hour:
$8649.91
Learjet 60 image 1
Learjet 60 image 2

From:
Pittsburgh, Pittsburgh International Airport (PIT), PA, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Capacity:
10
$11,023
Distance between PIT - PWK:
485 mi (781 km)
Estimated flight duration:
0 hours : 55 minutes
Cost per person:
$1102.27
Cost per hour:
$12001.12
Challenger 300 image 1
Challenger 300 image 2

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Learjet 45XR
Capacity:
8
$8,645
Distance between OMA - PWK:
422 mi (679 km)
Estimated flight duration:
0 hours : 50 minutes
Cost per person:
$1080.62
Cost per hour:
$10235.33
Learjet 45XR image 1
Learjet 45XR image 2

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Capacity:
9
$10,200
Distance between OMA - MDW:
429 mi (690 km)
Estimated flight duration:
0 hours : 50 minutes
Cost per person:
$1133.38
Cost per hour:
$12064.15
Citation XLS image 1
Citation XLS image 2

From:
Nashville, Nashville International Airport (BNA), TN, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation XLS
Capacity:
8
$10,200
Distance between BNA - PWK:
419 mi (674 km)
Estimated flight duration:
0 hours : 49 minutes
Cost per person:
$1275.05
Cost per hour:
$12352.61
Citation XLS image 1
Citation XLS image 2

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Capacity:
8
$15,246
Distance between TEB - PWK:
721 mi (1160 km)
Estimated flight duration:
1 hours : 21 minutes
Cost per person:
$1905.79
Cost per hour:
$11167.67
Challenger 300 image 1
Challenger 300 image 2

From:
Nashville, Nashville International Airport (BNA), TN, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Gulfstream G-V
Capacity:
16
$20,990
Distance between BNA - DPA:
409 mi (657 km)
Cost per person:
$1311.88
Cost per hour:
$15374.87

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Excel
Capacity:
8
$16,357
Distance between TEB - MDW:
712 mi (1146 km)
Cost per person:
$2044.57
Cost per hour:
$11980.87

From:
George Town, Owen Roberts International (GCM), KY
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Hawker 900XP
Capacity:
8
$26,262
Distance between GCM - PWK:
1623 mi (2612 km)
Cost per person:
$3282.72
Cost per hour:
$19236.24

From:
Madrid, Barajas International (MAD), ES
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-IVSP
Capacity:
13
$81,431
Distance between MAD - MDW:
4188 mi (6740 km)
Cost per person:
$6263.95
Cost per hour:
$59647

From:
Toronto, Lester B. Pearson International (YYZ), ON, CA
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation Excel
Capacity:
8
$16,414
Distance between YYZ - MDW:
433 mi (696 km)
Cost per person:
$2051.74
Cost per hour:
$12022.87

From:
Philadelphia, Philadelphia International Airport (PHL), PA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$10,942
Distance between PHL - MDW:
669 mi (1076 km)
Estimated flight duration:
1 hours : 18 minutes
Cost per person:
$1367.77
Cost per hour:
$8336.3
Hawker 400XP image 1
Hawker 400XP image 2

From:
Hilton Head, Hilton Head Airport (HXD), SC, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Capacity:
10
$17,125
Distance between HXD - PWK:
6113 mi (9837 km)
Estimated flight duration:
11 hours : 34 minutes
Cost per person:
$1712.51
Cost per hour:
$1479.72
Challenger 300 image 1
Challenger 300 image 2

From:
Tampa, Tampa International Airport (TPA), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-IVSP
Capacity:
12
$32,828
Distance between TPA - MDW:
1002 mi (1612 km)
Cost per person:
$2735.65
Cost per hour:
$2836.52

From:
Zelienople, Municipal (PJC), PA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation XLS
Capacity:
8
$8,754
Distance between PJC - MDW:
4894 mi (7876 km)
Estimated flight duration:
9 hours : 39 minutes
Cost per person:
$1094.19
Cost per hour:
$906.92
Citation XLS image 1
Citation XLS image 2

From:
Clarinda, Schenck Field (ICL), IA, US
To:
Gary, Chicago International (GYY), IN, US
Aircraft:
Nextant 400XTi
Capacity:
8
$9,191
Distance between ICL - GYY:
401 mi (645 km)
Cost per person:
$1148.94
Cost per hour:
$952.3

From:
Teterboro, Teterboro Airport (TEB), NJ, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Gulfstream G-IVSP
Capacity:
13
$10,693
Distance between TEB - MDW:
712 mi (1146 km)
Cost per person:
$822.56
Cost per hour:
$1107.9

From:
Chesterfield, Spirit of St Louis (SUS), MO, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Challenger 300
Capacity:
10
$7,737
Distance between SUS - PWK:
266 mi (428 km)
Estimated flight duration:
0 hours : 30 minutes
Cost per person:
$773.72
Cost per hour:
$15351.77
Challenger 300 image 1
Challenger 300 image 2

From:
Nashville, John C Tune (JWN), TN, US
To:
Chicago, Lewis University (LOT), IL, US
Aircraft:
Citation Excel
Capacity:
9
$5,928
Distance between JWN - LOT:
6365 mi (10244 km)
Cost per person:
$658.66
Cost per hour:
$11761.95

From:
Omaha, Eppley Airfield (OMA), NE, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Learjet 45XR
Capacity:
8
$8,492
Distance between OMA - MDW:
429 mi (690 km)
Estimated flight duration:
0 hours : 51 minutes
Cost per person:
$1061.55
Cost per hour:
$9896.37
Learjet 45XR image 1
Learjet 45XR image 2

From:
Miami, Opa-locka Executive (OPF), FL, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Citation Excel
Capacity:
13
$18,185
Distance between OPF - DPA:
1196 mi (1925 km)
Cost per person:
$1398.87
Cost per hour:
$21191.68

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 800XPi
Capacity:
6
$20,325
Distance between APF - MDW:
1133 mi (1823 km)
Cost per person:
$3387.53
Cost per hour:
$23685.32

From:
Stuart, Witham Field (SUA), FL, US
To:
Chicago, Executive (PWK), IL, US
Aircraft:
Citation XLS
Capacity:
9
$15,435
Distance between SUA - PWK:
1118 mi (1799 km)
Estimated flight duration:
2 hours : 12 minutes
Cost per person:
$1715.05
Cost per hour:
$7002.95
Citation XLS image 1
Citation XLS image 2

From:
Atlanta, Hartsfield Jackson Atlanta International (ATL), GA, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Hawker 400XP
Capacity:
8
$8,590
Distance between ATL - MDW:
585 mi (941 km)
Estimated flight duration:
1 hours : 8 minutes
Cost per person:
$1073.75
Cost per hour:
$7483.16
Hawker 400XP image 1
Hawker 400XP image 2

From:
Chesterfield, Spirit of St Louis (SUS), MO, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation XLS
Capacity:
8
$8,590
Distance between SUS - UGN:
283 mi (456 km)
Estimated flight duration:
0 hours : 33 minutes
Cost per person:
$1073.75
Cost per hour:
$15384.17
Citation XLS image 1
Citation XLS image 2

From:
Hazleton, Municipal (HZL), PA, US
To:
Gary, Chicago International (GYY), IN, US
Aircraft:
Gulfstream G-V
Capacity:
16
$16,614
Distance between HZL - GYY:
594 mi (957 km)
Cost per person:
$1038.37
Cost per hour:
$29754.53

From:
Naples, Municipal (APF), FL, US
To:
Chicago, Dupage (DPA), IL, US
Aircraft:
Hawker 850XP
Capacity:
8
$18,865
Distance between APF - DPA:
1150 mi (1850 km)
Estimated flight duration:
2 hours : 29 minutes
Cost per person:
$2358.11
Cost per hour:
$7595.57
Hawker 850XP image 1
Hawker 850XP image 2

From:
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation CJ3
Capacity:
6
$13,374
Distance between BZN - MDW:
1196 mi (1925 km)
Estimated flight duration:
2 hours : 29 minutes
Cost per person:
$2228.94
Cost per hour:
$5350.22
Citation CJ3 image 1
Citation CJ3 image 2

From:
Bozeman, Bozeman Yellowstone Intl (BZN), MT, US
To:
Chicago, Midway International (MDW), IL, US
Aircraft:
Citation CJ3
Capacity:
6
$13,398
Distance between BZN - MDW:
1196 mi (1925 km)
Estimated flight duration:
2 hours : 29 minutes
Cost per person:
$2233.01
Cost per hour:
$5359.98
Citation CJ3 image 1
Citation CJ3 image 2

From:
Naples, Municipal (APF), FL, US
To:
Waukegan, Waukegan Regional Airport (UGN), IL, US
Aircraft:
Citation XLS
Capacity:
9
$15,512
Distance between APF - UGN:
1172 mi (1886 km)
Estimated flight duration:
2 hours : 18 minutes
Cost per person:
$1723.59
Cost per hour:
$6711.23
Citation XLS image 1
Citation XLS 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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