| Chicago Executive → Teterboro PWK–TEB | 17 | 30 | 17% | 723 | Jet Aviation Flight Services, Inc., Air Alsie A/S, Air Hamburg..., Concierge U Ltd. d/b/a Jet... | Jan 2025 – Jul 2026 |
| Chicago Executive → Waukegan Ntl PWK–UGN | 9 | 0 | 0% | 21 | Jet Aviation Flight Services, Inc. | Apr 2025 – Jul 2026 |
| Chicago Executive → Dupage PWK–DPA | 6 | 3 | 6% | 22 | Jet Aviation Flight Services, Inc. | Apr 2026 – Jun 2026 |
| Chicago Executive → Chicago Midway International PWK–MDW | 6 | 0 | 0% | 24 | Jet Aviation Flight Services, Inc., CFM Inc d/b/a Contour... | Jan 2025 – Jul 2026 |
| Chicago Executive → Westchester County PWK–HPN | 4 | 10 | 29% | 738 | Jet Aviation Flight Services, Inc., CFM Inc d/b/a Contour... | Jan 2025 – Jun 2026 |
| Chicago Executive → Toronto PWK–YYZ international | 4 | 6 | 17% | 433 | Jet Aviation Flight Services, Inc., Chartright Air Inc. | Jul 2025 – Jun 2026 |
| Chicago Executive → University Of Illinois/Willard PWK–CMI | 3 | 6 | 22% | 145 | Jet Aviation Flight Services, Inc. | Nov 2025 – Mar 2026 |
| Chicago Executive → Columbia Regional PWK–COU | 3 | 13 | 31% | 321 | Air Hamburg... | Feb 2025 – Feb 2026 |
| Chicago Executive → Francis S Gabreski PWK–FOK | 3 | 14 | 38% | 796 | Jet Aviation Flight Services, Inc., CFM Inc d/b/a Contour... | Aug 2025 – May 2026 |
| Chicago Executive → Fort Wayne International PWK–FWA | 3 | 4 | 15% | 161 | Jet Aviation Flight Services, Inc. | Dec 2025 – May 2026 |
| Chicago Executive → Cuyahoga County PWK–CGF | 2 | 5 | 28% | 333 | Jet Aviation Flight Services, Inc. | May 2026 – May 2026 |
| Chicago Executive → John Glenn Columbus International PWK–CMH | 2 | 3 | 21% | 300 | Scott Aviation, LLC d/b/a..., CFM Inc d/b/a Contour... | Mar 2026 – Apr 2026 |
| Chicago Executive → Derby PWK–EMA international | 2 | 4 | 14% | 3,871 | Air Alsie A/S, Concierge U Ltd. d/b/a Jet... | Mar 2026 – Jun 2026 |
| Chicago Executive → Morristown Municipal PWK–MMU | 2 | 2 | 25% | 705 | Air Hamburg..., CFM Inc d/b/a Contour... | Jan 2026 – Jul 2026 |
| Chicago Executive → West Palm Beach/Palm Beach PWK–PBI | 2 | 3 | 17% | 1,152 | Jet Aviation Flight Services, Inc. | Mar 2026 – Mar 2026 |
| Chicago Executive → Oakland County International PWK–PTK | 2 | 2 | 11% | 233 | Jet Aviation Flight Services, Inc. | Nov 2025 – Apr 2026 |
| Chicago Executive → Rifle Garfield County PWK–RIL | 2 | 14 | 48% | 1,052 | Jet Aviation Flight Services, Inc. | Jun 2025 – Jul 2026 |
| Chicago Executive → Sarasota/Bradenton International PWK–SRQ | 2 | 8 | 44% | 1,059 | Jet Aviation Flight Services, Inc. | Dec 2025 – Jan 2026 |
| Chicago Executive → St. Louis Lambert International PWK–STL | 2 | 2 | 11% | 266 | Jet Aviation Flight Services, Inc. | Jan 2025 – Feb 2026 |
| Chicago Executive → Addison PWK–ADS | 1 | 3 | 33% | 798 | Jet Aviation Flight Services, Inc. | Aug 2025 – Aug 2025 |
| Chicago Executive → Naples Municipal PWK–APF | 1 | 3 | 33% | 1,154 | Jet Aviation Flight Services, Inc. | Apr 2026 – Apr 2026 |
| Chicago Executive → Aspen-Pitkin County/Sardy Field PWK–ASE | 1 | 3 | 19% | 1,014 | Jet Aviation Flight Services, Inc. | Mar 2025 – Jul 2026 |
| Chicago Executive → Boeing Fld/King County International PWK–BFI | 1 | 4 | 31% | 1,717 | Jet Aviation Flight Services, Inc. | Jan 2025 – Jun 2026 |
| Chicago Executive → General Edward Lawrence Logan International PWK–BOS | 1 | 2 | 17% | 865 | Air Alsie A/S | Aug 2025 – Aug 2025 |
| Chicago Executive → Hollywood Burbank PWK–BUR | 1 | 3 | 33% | 1,735 | Scott Aviation, LLC d/b/a... | Nov 2025 – Nov 2025 |
| Chicago Executive → Cleveland-Hopkins International PWK–CLE | 1 | 7 | 117% | 316 | Scott Aviation, LLC d/b/a... | Mar 2026 – Mar 2026 |
| Chicago Executive → City Of Colorado Springs Municipal PWK–COS | 1 | 4 | 44% | 913 | Jet Aviation Flight Services, Inc. | Feb 2026 – Feb 2026 |
| Chicago Executive → Cincinnati/Northern Kentucky International PWK–CVG | 1 | 0 | 0% | 271 | CFM Inc d/b/a Contour... | May 2026 – May 2026 |
| Chicago Executive → Edinburgh PWK–EDI international | 1 | 7 | 50% | 3,705 | VistaJet Limited | Jun 2026 – Jun 2026 |
| Chicago Executive → Eagle River Union PWK–EGV | 1 | 5 | 36% | 272 | Jet Aviation Flight Services, Inc. | Jun 2025 – Aug 2025 |
| Chicago Executive → Claremore Regional PWK–GCM international | 1 | 3 | 25% | 1,618 | Air Alsie A/S | Nov 2025 – Nov 2025 |
| Chicago Executive → Cedar Lake PWK–IN7 | 1 | 12 | 86% | 196 | Jet Aviation Flight Services, Inc. | Apr 2026 – Apr 2026 |
| Chicago Executive → John F Kennedy International PWK–JFK | 1 | 0 | | 740 | Air Hamburg... | Oct 2025 – Oct 2025 |
| Chicago Executive → Los Angeles International PWK–LAX | 1 | 6 | 43% | 1,746 | Jet Aviation Flight Services, Inc. | Jan 2026 – Jan 2026 |
| Chicago Executive → London PWK–LTN international | 1 | 6 | 43% | 3,937 | VistaJet Limited | Jun 2026 – Jun 2026 |
| Chicago Executive → Harrisburg International PWK–MDT | 1 | 2 | 25% | 595 | CFM Inc d/b/a Contour... | Jul 2026 – Jul 2026 |
| Chicago Executive → Smyrna PWK–MQY | 1 | 0 | 0% | 428 | CFM Inc d/b/a Contour... | May 2026 – May 2026 |
| Chicago Executive → Knox Ridge PWK–MT3 | 1 | 1 | 8% | 1,205 | Jet Aviation Flight Services, Inc. | Aug 2025 – Aug 2025 |
| Chicago Executive → Nice PWK–NCE international | 1 | 2 | 14% | 4,536 | Air Alsie A/S | Apr 2025 – Nov 2025 |
| Chicago Executive → Lakefront PWK–NEW | 1 | 8 | 62% | 841 | Jet Aviation Flight Services, Inc. | May 2025 – Apr 2026 |
| Chicago Executive → Ogdensburg International PWK–OGS | 1 | 2 | 12% | 650 | Jet Aviation Flight Services, Inc. | May 2025 – Jul 2026 |
| Chicago Executive → Eppley Airfield PWK–OMA | 1 | 4 | 44% | 417 | Jet Aviation Flight Services, Inc. | May 2026 – May 2026 |
| Chicago Executive → Chicago O'Hare International PWK–ORD | 1 | 0 | 0% | 9 | CFM Inc d/b/a Contour... | Jul 2026 – Jul 2026 |
| Chicago Executive → Philadelphia International PWK–PHL | 1 | 23 | 77% | 679 | CFM Inc d/b/a Contour... | Jan 2026 – Jan 2026 |
| Chicago Executive → Pittsfield Municipal PWK–PSF | 1 | 1 | 8% | 748 | Jet Aviation Flight Services, Inc. | Jun 2025 – Oct 2025 |
| Chicago Executive → Rhode Island TF Green International PWK–PVD | 1 | 0 | 0% | 848 | CFM Inc d/b/a Contour... | Jul 2025 – Feb 2026 |
| Chicago Executive → Southwest Florida International PWK–RSW | 1 | 4 | 31% | 1,129 | Jet Aviation Flight Services, Inc. | Jun 2026 – Jun 2026 |
| Chicago Executive → Santa Barbara Municipal PWK–SBA | 1 | 10 | 77% | 1,804 | CFM Inc d/b/a Contour... | May 2026 – May 2026 |
| Chicago Executive → Sidney Municipal PWK–SCA | 1 | 1 | 11% | 234 | Jet Aviation Flight Services, Inc. | May 2026 – May 2026 |
| Chicago Executive → Moore County PWK–SOP | 1 | 7 | 50% | 660 | Jet Aviation Flight Services, Inc. | May 2026 – May 2026 |
| Chicago Executive → New York Stewart International PWK–SWF | 1 | 4 | 29% | 713 | Jet Aviation Flight Services, Inc. | Jun 2025 – Jun 2026 |
| Chicago Executive → Philipsburg PWK–SXM international | 1 | 9 | 64% | 2,209 | Air Hamburg... | Apr 2026 – Apr 2026 |
| Chicago Executive → Toulon/Hyeres PWK–TLN international | 1 | 6 | 43% | 4,515 | VistaJet Limited | Jul 2026 – Jul 2026 |
| Chicago Executive → Miami Executive PWK–TMB | 1 | 3 | 19% | 1,212 | Jet Aviation Flight Services, Inc. | Aug 2025 – Aug 2025 |
| Chicago Executive → Jacqueline Cochran Regional PWK–TRM | 1 | 2 | 29% | 1,643 | ADVANCED AIR, LLC | Nov 2025 – Nov 2025 |
| Chicago Executive → Tucson International PWK–TUS | 1 | 1 | 7% | 1,441 | Jet Aviation Flight Services, Inc. | Apr 2026 – Apr 2026 |
| Chicago Executive → Waukesha County PWK–UES | 1 | 0 | 0% | 66 | Jet Aviation Flight Services, Inc. | Mar 2026 – Mar 2026 |
| Chicago Executive → Van Nuys PWK–VNY | 1 | 1 | 8% | 1,742 | Jet Aviation Flight Services, Inc. | May 2026 – May 2026 |