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48
flights match your search
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Mon, Sep 7
Chicago
1h 15m
Washington D.C.
Challenger 300/350
Super Mid
8
seats
Good value
$6,670
Tomorrow, Sep 5
Chicago
1h 50m
Boston
Challenger 300/350
Super Mid
8
seats
Good value
$8,000
Thu, Sep 10
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Chicago
KUGN
2h 53m
Scottsdale
KSDL
Gulfstream GIV-SP
Heavy
12
seats
$31,069
Sun, Sep 13
Chicago
KGYY
2h 2m
Palm Beach
KSUA
Bombardier Global 5000
Ultra Long Range
13
seats
Estimated
$15k–$24k
Tue, Sep 8
Chicago
KPWK
1h 31m
New York
KFRG
Gulfstream G550
Heavy
16
seats
Estimated
$12k–$19k
Sep 4 → Sep 9
Flexible
· time set with operator
Chicago
KDPA
3h 38m
Los Angeles
KSNA
Gulfstream G280
Super Mid
10
seats
Estimated
$14k–$23k
Thu, Sep 17
Chicago
KORD
1h
Omaha
KOMA
Cessna Citation XLS
Mid
9
seats
Good value
$5,000
Thu, Sep 10
Chicago
KDPA
1h 8m
Tulsa
KTUL
Bombardier Challenger 605
Heavy
10
seats
Market rate
$12,272
Thu, Sep 10
Chicago
KMDW
1h 47m
Hartford
KHVN
Cessna Citation XLS
Mid
9
seats
Market rate
$9,650
Sat, Oct 3
Chicago
KMDW
1h 26m
New York
KTEB
Embraer Legacy 600
Heavy
13
seats
Estimated
$10k–$17k
Sun, Sep 6
Chicago
KMDW
1h
Rochester
KRST
Bombardier Learjet 60
Mid
7
seats
Market rate
$6,000
Sep 9 → Sep 12
Flexible
· time set with operator
Chicago
KPWK
2h 41m
Palm Beach
KPBI
Cessna Citation Excel
Mid
8
seats
Estimated
$10k–$17k
Sep 12 → Sep 17
Flexible
· time set with operator
Chicago
KGYY
1h
Cleveland
KCLE
Nextant 400XTi
Light
7
seats
Estimated
$3.2k–$5k
Mon, Sep 28
Chicago
KARR
2h 47m
Scottsdale
KSDL
Dassault Falcon 900B
Heavy
14
seats
Estimated
$18k–$27k
Mon, Sep 21
Chicago
KPWK
1h 42m
Denver
KAPA
Bombardier Global 6000
Ultra Long Range
16
seats
Estimated
$19k–$29k
Fri, Sep 25
Chicago
KORD
1h
Omaha
KOMA
Cessna Citation XLS
Mid
9
seats
Good value
$5,000
Dec 27 → Jan 1
Flexible
· time set with operator
Chicago
KDPA
2h 38m
Nassau
MYNN
Gulfstream G500
Heavy
16
seats
Estimated
$15k–$23k
Sep 21 → Sep 23
Flexible
· time set with operator
Chicago
KDPA
1h 27m
New York
KMMU
Gulfstream G500
Heavy
15
seats
Estimated
$10k–$16k
Sep 6 → Sep 10
Flexible
· time set with operator
Chicago
KGYY
1h
Louisville
KSDF
Cirrus Vision Jet SF50
Light
5
seats
Estimated
$3k–$4.8k
Sep 3 → Sep 6
Flexible
· time set with operator
Chicago
KDPA
1h
Fort Wayne
KFWA
Cessna Citation XLS
Mid
8
seats
Estimated
$3.7k–$6k
Sep 9 → Sep 11
Flexible
· time set with operator
Chicago
KGYY
1h 21m
Winston Salem
KINT
Nextant 400XTi
Light
7
seats
Estimated
$4.2k–$6.8k
Mon, Mar 29
Chicago
KMDW
1h
Minneapolis
KMSP
Bombardier Challenger 850
Heavy
15
seats
Estimated
$8k–$13k
Tue, Sep 8
Chicago
KDPA
1h 59m
Hayden
KHDN
Bombardier Challenger 604
Heavy
9
seats
Estimated
$12k–$20k
Sep 14 → Sep 19
Flexible
· time set with operator
Chicago
KGYY
1h
Pella
KPEA
Cirrus Vision Jet SF50
Light
5
seats
Estimated
$3.2k–$5k
Sep 22 → Sep 23
Flexible
· time set with operator
Chicago
KMDW
1h 46m
New York
KISP
Cessna Citation Sovereign
Mid
9
seats
Estimated
$8k–$12k
Sun, Sep 27
Chicago
KARR
1h
Kansas City
KMKC
Dassault Falcon 50
Super Mid
9
seats
Estimated
$7k–$11k
Dec 10 → Dec 15
Flexible
· time set with operator
Chicago
KPWK
2h 1m
Orlando
KORL
Gulfstream GIV
Heavy
12
seats
Estimated
$12k–$19k
Mon, Sep 28
Chicago
KMDW
1h
Detroit
KPTK
Gulfstream GIV-SP
Heavy
11
seats
Estimated
$7k–$11k
Tue, Sep 22
Chicago
KPWK
1h
Indianapolis
KTYQ
Cessna Citation Excel
Mid
8
seats
Estimated
$4.2k–$6.8k
Tue, Oct 20
Chicago
KARR
3h 32m
Santa Barbara
KSBA
Dassault Falcon 900B
Heavy
14
seats
Estimated
$21k–$33k
Fri, Oct 2
Chicago
KORD
3h 27m
Calgary
CYYC
Bombardier Learjet 45
Light
8
seats
Estimated
$8.5k–$13k
Tue, Sep 29
Chicago
KGYY
1h
Pellston
KPLN
CE-560-XLS (CITATION XLS)
Mid
9
seats
Estimated
$5k–$7.8k
Fri, Oct 9
Chicago
KMDW
1h 26m
Washington D.C.
KIAD
Cessna Citation CJ4
Light
6
seats
Estimated
$4.5k–$7k
Fri, Sep 11
Chicago
KPWK
2h 53m
Naples
KAPF
Embraer Phenom 300
Light
8
seats
Estimated
$7.7k–$12k
Sep 28 → Oct 3
Flexible
· time set with operator
Chicago
KDPA
2h 41m
Marathon
KMTH
Gulfstream G280
Super Mid
10
seats
Estimated
$12k–$19k
Oct 10 → Oct 12
Flexible
· time set with operator
Chicago
KLOT
1h 44m
New York
KHPN
Cessna Citation III
Mid
9
seats
Estimated
$7.7k–$12k
Mon, Sep 7
Chicago
KPWK
1h
Woodruff
KARV
Cessna Citation XLS+
Mid
8
seats
Estimated
$4.7k–$7.5k
Fri, Feb 19
Chicago
KMDW
1h
St. Louis
KCPS
Bombardier Challenger 850
Heavy
15
seats
Estimated
$7.2k–$11k
Sun, Sep 27
Chicago
KPWK
1h 40m
Savannah
KSAV
Embraer Praetor 500
Super Mid
9
seats
Estimated
$10k–$16k
Tue, Sep 8
Chicago
KPWK
1h
Minneapolis
KSTP
Bombardier Learjet 60
Mid
7
seats
$6,700
Tue, Nov 10
Chicago
KARR
1h
Kansas City
KMKC
Dassault Falcon 900B
Heavy
14
seats
Estimated
$8k–$13k
Sep 16 → Sep 21
Flexible
· time set with operator
Chicago
KDPA
2h 40m
Naples
KAPF
Hawker 850XP
Mid
8
seats
Estimated
$10k–$16k
Oct 14 → Oct 16
Flexible
· time set with operator
Chicago
KGYY
1h
Minneapolis
KMSP
Nextant 400XTi
Light
7
seats
Estimated
$3.5k–$5.8k
Fri, Sep 25
Chicago
KPWK
1h 32m
New York
KTEB
Embraer Praetor 500
Super Mid
9
seats
Estimated
$9.5k–$15k
Oct 14 → Oct 18
Flexible
· time set with operator
Chicago
KDPA
2h 27m
Naples
KAPF
Gulfstream G280
Super Mid
10
seats
Estimated
$11k–$18k
Thu, Oct 15
Chicago
KPWK
1h
Minneapolis
KMSP
Embraer Praetor 500
Super Mid
9
seats
Estimated
$6.7k–$11k
Dec 16 → Dec 21
Flexible
· time set with operator
Chicago
KPWK
2h 53m
Naples
KAPF
Embraer Phenom 300
Light
8
seats
Estimated
$7.7k–$12k
Thu, May 6
Chicago
KPWK
2h 53m
Naples
KAPF
Embraer Phenom 300
Light
8
seats
Estimated
$7.7k–$12k