Origin Hub·3 departure airports

Private Jet Charter from Chicago

Three airports serve Chicago-area charter departures. Every route includes pilot-analyzed pricing and aircraft recommendations.

Logistics

Chicago Departure Airports

Chicago Midway InternationalKMDW
10 mi from the Loop · Atlantic Aviation
Direct flights, shortest drive from downtown
Chicago ExecutiveKPWK
18 mi from the Loop · Signature Flight Support
Fewer crowds, better scheduling
DuPage AirportKDPA
30 mi from the Loop · DuPage Aerospace
Western suburbs, lowest ramp fees in the Chicago area
Pilot's Recommendation

For most Chicago departures, I default to Midway. It's the fastest to reach from downtown, Atlantic's FBO handles charter traffic all day, and most operators position to KMDW first when sourcing aircraft for Chicago trips. Executive is the right call if you live north of Evanston. DuPage only makes sense if you're coming from Naperville or further west.

At a Glance

Chicago Charter Intelligence

Live Routes
23
Price Range
$12K–$52K
Airports Covered
23
Shortest Flight
1h 0m
to Nashville
Longest Flight
3h 44m
to San Francisco
Departure Airports
3
KMDW · KPWK · KDPA
Live Routes

Routes from Chicago

Chicago → Aspen

KASE · 884 nm

Price
$20K–$35K
Time
2h 5m

Chicago → Atlanta

KPDK · 502 nm

Price
$14K–$22K
Time
1h 21m

Chicago → Austin

KAUS · 845 nm

Price
$20K–$26K
Time
2h 5m

Chicago → Boston

KBED · 733 nm

Price
$18K–$24K
Time
1h 51m

Chicago → Dallas

KDAL · 690 nm

Price
$17K–$30K
Time
1h 45m

Chicago → Denver

KAPA · 788 nm

Price
$19K–$25K
Time
1h 58m

Chicago → Houston

KHOU · 815 nm

Price
$19K–$26K
Time
2h 2m

Chicago → Jackson Hole

KJAC · 1,017 nm

Price
$26K–$30K
Time
2h 28m

Chicago → Las Vegas

KLAS · 1,319 nm

Price
$31K–$36K
Time
3h 7m

Chicago → Los Angeles

KVNY · 1,514 nm

Price
$29K–$40K
Time
3h 33m

Chicago → Martha's Vineyard

KMVY · 769 nm

Price
$18K–$25K
Time
1h 56m

Chicago → Miami

KOPF · 1,023 nm

Price
$26K–$34K
Time
2h 29m

Chicago → Nantucket

KACK · 795 nm

Price
$22K–$27K
Time
1h 59m

Chicago → Naples

KAPF · 984 nm

Price
$22K–$29K
Time
2h 24m

Chicago → Nashville

KBNA · 344 nm

Price
$12K–$16K
Time
1h 0m

Chicago → San Francisco

KOAK · 1,599 nm

Price
$31K–$52K
Time
3h 44m

Chicago → Scottsdale

KSDL · 1,242 nm

Price
$29K–$42K
Time
2h 57m

Chicago → Sun Valley

KSUN · 1,172 nm

Price
$24K–$33K
Time
2h 48m

Chicago → Telluride

KTEX · 954 nm

Price
$25K–$28K
Time
2h 20m

Chicago → New York City

KTEB · 619 nm

Price
$18K–$28K
Time
1h 36m

Chicago → Vail

KEGE · 880 nm

Price
$23K–$27K
Time
2h 10m

Chicago → Washington DC

KIAD · 500 nm

Price
$14K–$22K
Time
1h 20m

Chicago → West Palm Beach

KPBI · 982 nm

Price
$25K–$35K
Time
2h 23m
Coming Soon

Planned Routes

P

Phelipe

ATP-Rated Airline Pilot · E175 Type Rating · CFI/CFII/MEI · 7+ Years Aviation

Verify Airman Certificate

Data sources: Pricing: Aviapages Q2 2026 · Airport data: FAA NASR · Aircraft performance: Published POH · Analysis: ATP-rated airline pilot