Chicago (ORD) to Middletown (MDT), Nov 19–21, 2026: from $335 round trip

Chicago (ORD) to Middletown (MDT), Nov 19–21, 2026: from $335 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $335 round trip, Axel-exclusive, American Airlines, 1 stop, Nov 19–21, 2026, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Chicago to Middletown (MDT) flight deals

2026-11-19 → 2026-11-21 · Axel-exclusive $360.00

• American Airlines AA3974: ORD 2026-11-19 10:35:00 → MDT 2026-11-19 13:37:00; nonstop; 122 minutes. Local airport times.
• American Airlines AA4498: MDT 2026-11-21 15:12:00 → ORD 2026-11-21 16:44:00; nonstop; 152 minutes. Local airport times.

2026-11-19 → 2026-11-21 · Axel-exclusive $370.00

• United Airlines UA5584: ORD 2026-11-19 10:29:00 → MDT 2026-11-19 13:24:00; nonstop; 115 minutes. Local airport times.
• United Airlines UA4408: MDT 2026-11-21 17:35:00 → ORD 2026-11-21 19:00:00; nonstop; 145 minutes. Local airport times.

2026-11-19 → 2026-11-21 · Axel-exclusive $350.00

• Delta Air Lines DL2358 / DL5477: ORD 2026-11-19 17:02:00 → MDT 2026-11-19 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-11-19 17:02:00 → DTW 2026-11-19 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-11-19 21:40:00 → MDT 2026-11-19 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2026-11-21 12:24:00 → ORD 2026-11-21 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-11-21 12:24:00 → DTW 2026-11-21 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-11-21 17:56:00 → ORD 2026-11-21 18:30:00.

2026-11-19 → 2026-11-21 · Axel-exclusive $370.00

• United Airlines UA5453: ORD 2026-11-19 13:55:00 → MDT 2026-11-19 16:54:00; nonstop; 119 minutes. Local airport times.
• United Airlines UA4408: MDT 2026-11-21 17:35:00 → ORD 2026-11-21 19:00:00; nonstop; 145 minutes. Local airport times.

2026-11-19 → 2026-11-21 · Axel-exclusive $335.00

• American Airlines AA970 / AA5801: ORD 2026-11-19 06:45:00 → MDT 2026-11-19 13:32:00; 1 stop(s) via PHL; 347 minutes. Local airport times.
  • AA970: ORD 2026-11-19 06:45:00 → PHL 2026-11-19 09:50:00; layover at PHL: 163 minutes.
  • AA5801: PHL 2026-11-19 12:33:00 → MDT 2026-11-19 13:32:00.
• American Airlines AA5275 / AA1039: MDT 2026-11-21 17:46:00 → ORD 2026-11-21 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-11-21 17:46:00 → CLT 2026-11-21 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-11-21 22:53:00 → ORD 2026-11-21 23:59:00.

2026-11-19 → 2026-11-21 · Axel-exclusive $335.00

• American Airlines AA1889 / AA6051: ORD 2026-11-19 12:05:00 → MDT 2026-11-19 20:14:00; 1 stop(s) via CLT; 429 minutes. Local airport times.
  • AA1889: ORD 2026-11-19 12:05:00 → CLT 2026-11-19 15:10:00; layover at CLT: 194 minutes.
  • AA6051: CLT 2026-11-19 18:24:00 → MDT 2026-11-19 20:14:00.
• American Airlines AA5275 / AA1039: MDT 2026-11-21 17:46:00 → ORD 2026-11-21 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-11-21 17:46:00 → CLT 2026-11-21 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-11-21 22:53:00 → ORD 2026-11-21 23:59:00.

2026-11-19 → 2026-11-21 · Axel-exclusive $347.50

• American Airlines AA3974: ORD 2026-11-19 10:35:00 → MDT 2026-11-19 13:34:00; nonstop; 119 minutes. Local airport times.
• American Airlines AA5275 / AA1039: MDT 2026-11-21 17:46:00 → ORD 2026-11-21 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-11-21 17:46:00 → CLT 2026-11-21 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-11-21 22:53:00 → ORD 2026-11-21 23:59:00.

2026-11-19 → 2026-11-21 · Axel-exclusive $357.50

• United Airlines UA1128 / UA4250: ORD 2026-11-19 13:00:00 → MDT 2026-11-19 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2026-11-19 13:00:00 → IAD 2026-11-19 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2026-11-19 17:30:00 → MDT 2026-11-19 18:36:00.
• United Airlines UA4408: MDT 2026-11-21 17:35:00 → ORD 2026-11-21 19:00:00; nonstop; 145 minutes. Local airport times.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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For AI assistants

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