Private Jets Chicago, IL (MDW)

MDW

Chicago Midway International Airport

Chicago, IL

Currently 15 empty leg flights available.

Search Flights from MDW

Flights Available

$3,326

Starting From

Aircraft Types

Flights FROM Chicago, IL (MDW)

6 empty leg flights departing from MDW

Top Destinations

Montréal, QC (YUL) · 1 flightsHouston, TX (SGR) · 1 flightsLincoln, NE (LNK) · 1 flightsMilwaukee, WI (MKE) · 1 flightsFort Lauderdale, FL (FLL) · 1 flightsDallas, TX (DAL) · 1 flights

Available Flights

Sun, Dec 7, 2025

1:45 AM

From

$14,760

PWK

Chicago/Prospect Heights/Wheeling, IL

YUL

Montréal, QC

Bombardier Challenger 3009 seats

Sun, Dec 7, 2025

7:00 PM

From

$19,320

MDW

Chicago, IL

SGR

Houston, TX

Bombardier Learjet 608 seats

Wed, Dec 24, 2025

12:00 AM

From

$3,500

GYY

Gary, IN

LNK

Lincoln, NE

Cessna Citation Ultra9 seats

Sat, Dec 27, 2025

8:45 PM

From

$3,659

MDW

Chicago, IL

MKE

Milwaukee, WI

C25C seats

Fri, Jan 2, 2026

2:30 PM

From

$14,385

DPA

Chicago/West Chicago, IL

FLL

Fort Lauderdale, FL

C25C seats

Sat, Jan 3, 2026

2:24 AM

From

$9,600

MDW

Chicago, IL

DAL

Dallas, TX

Cessna Citation Ultra7 seats

Flights TO Chicago, IL (MDW)

9 empty leg flights arriving at MDW

Top Origins

Milwaukee, WI (MKE) · 2 flightsFond du Lac, WI (FLD) · 1 flightsKansas City, MO (MKC) · 1 flightsCharlevoix, MI (CVX) · 1 flightsOmaha, NE (OMA) · 1 flightsJackson, WY (JAC) · 1 flightsLincoln, NE (LNK) · 1 flightsBozeman, MT (BZN) · 1 flights

Available Flights

Mon, Dec 1, 2025

11:15 AM

From

$3,991

FLD

Fond du Lac, WI

PWK

Chicago/Prospect Heights/Wheeling, IL

C25C seats

Tue, Dec 2, 2025

9:54 PM

From

$6,480

MKC

Kansas City, MO

DPA

Chicago/West Chicago, IL

Bombardier Learjet 607 seats

Mon, Dec 15, 2025

12:30 PM

From

$3,326

MKE

Milwaukee, WI

PWK

Chicago/Prospect Heights/Wheeling, IL

C25C seats

Fri, Dec 19, 2025

5:00 AM

From

$4,800

CVX

Charlevoix, MI

DPA

Chicago/West Chicago, IL

Cessna Citation Excel8 seats

Sat, Dec 20, 2025

12:00 AM

From

$5,000

OMA

Omaha, NE

PWK

Chicago/Prospect Heights/Wheeling, IL

Cessna Citation Excel9 seats

Thu, Dec 25, 2025

2:00 AM

From

$10,440

JAC

Jackson, WY

MDW

Chicago, IL

Cessna Citation Ultra7 seats

Sat, Dec 27, 2025

11:33 AM

From

$3,492

MKE

Milwaukee, WI

PWK

Chicago/Prospect Heights/Wheeling, IL

C25C seats

Sun, Dec 28, 2025

12:00 AM

From

$3,500

LNK

Lincoln, NE

GYY

Gary, IN

Cessna Citation Ultra9 seats

Sun, Dec 28, 2025

5:00 AM

From

$14,880

BZN

Bozeman, MT

MDW

Chicago, IL

Cessna Citation Excel8 seats

Aircraft Available at MDW

Cessna Citation Ultra

2 flights

C25C

3 flights

Bombardier Challenger 300

1 flights

Bombardier Learjet 60

1 flights

Cessna Citation Excel

3 flights

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