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Tailwheel Training in Illinois

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Holiday Airways
Address: Schaumburg Regional Airport (06C), 905 W Irving Park Rd, Schaumburg, IL 60193
Phone: (847) 812-7000
Email: [email protected] / [email protected]
Website: https://www.flyholidayairways.com
Description: Grassroots Chicagoland flight school specializing in tailwheel and aerobatic training. Fleet includes Piper J-3 Cubs, Citabria 7KCAB, Stearman PT-17, and Pitts S-2B. Offers tailwheel endorsements, sport pilot, aerobatics, and upset recovery.
Blue Sky Aero
Address: Morris Municipal Airport (KC09), 9980 N Route 47, Morris, IL 60450 (Mail: 3220 W Waupecan Rd, Verona, IL)
Phone: (815) 671-2512 (Nick Scholtes)
Email: [email protected]
Website: https://www.blueskyaero.com
Description: Tailwheel-focused operation using a Boeing PT-17 Stearman. Offers tailwheel endorsements, BFRs, and introductory aerobatic instruction. Known for a grassroots, community atmosphere.
Gambit Aviation
Address: Aurora Municipal Airport (KARR), 43W752 US-30, Sugar Grove, IL 60554
Phone: (815) 322-7126
Email: [email protected]
Website: https://flygambit.com
Description: Boutique flight school focusing on advanced flight training, including tailwheel transitions, aerobatics, warbird training. Fleet includes Citabria, Decathlon, Pitts, Extra 330LX, and T-6 Texans. Run by airshow and competition pilots.
Jet Air, Inc.
Address: Galesburg Municipal Airport (KGBG), 275 Lloyd Stearman Dr, Galesburg, IL 61401
Phone: (888) 253-8247
Website: https://jetairinc.com
Description: Full-service flight school offering tailwheel endorsements in an American Legend AL3. Also offers Private, Instrument, Commercial, and Warbird training.
Poplar Grove Airmotive Flight School
Address: Poplar Grove Airport (IL81), 11619 Route 76, Poplar Grove, IL 61065
Phone: (815) 544-2300
Email: [email protected]
Website: https://www.poplargroveairmotive.com
Description: Community-focused flight school offering tailwheel endorsements in a Piper J-3 Cub and Cessna 140. Emphasizes old-fashioned, grassroots flying.
J. Charnes Flight Instruction
Address: Elmwood Park, IL (Chicago Executive Airport, KDPA)
Phone: (708) 452-8608
Email: [email protected]
Description: Independent CFI offering personalized tailwheel endorsement and aerobatic training, primarily in Citabria/Decathlon-type aircraft.

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