Chicago (ORD) to Middletown (MDT) · Dec 19, 2026 · return Dec 21, 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

2026-12-19 → 2026-12-21 · Axel-exclusive $414.00

• American Airlines AA4533: ORD 2026-12-19 11:56:00 → MDT 2026-12-19 15:08:00; nonstop; 132 minutes. Local airport times.
• American Airlines AA4594: MDT 2026-12-21 05:00:00 → ORD 2026-12-21 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $425.50

• United Airlines UA2319: ORD 2026-12-19 19:45:00 → MDT 2026-12-19 22:47:00; nonstop; 122 minutes. Local airport times.
• United Airlines UA4408: MDT 2026-12-21 17:35:00 → ORD 2026-12-21 19:00:00; nonstop; 145 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $402.50

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

2026-12-19 → 2026-12-21 · Axel-exclusive $414.00

• American Airlines AA2156: ORD 2026-12-19 19:20:00 → MDT 2026-12-19 22:28:00; nonstop; 128 minutes. Local airport times.
• American Airlines AA4594: MDT 2026-12-21 05:00:00 → ORD 2026-12-21 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $425.50

• United Airlines UA4614: ORD 2026-12-19 10:26:00 → MDT 2026-12-19 13:25:00; nonstop; 119 minutes. Local airport times.
• United Airlines UA4408: MDT 2026-12-21 17:35:00 → ORD 2026-12-21 19:00:00; nonstop; 145 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $401.50

• American Airlines AA1889 / AA6051: ORD 2026-12-19 12:05:00 → MDT 2026-12-19 20:14:00; 1 stop(s) via CLT; 429 minutes. Local airport times.
  • AA1889: ORD 2026-12-19 12:05:00 → CLT 2026-12-19 15:10:00; layover at CLT: 194 minutes.
  • AA6051: CLT 2026-12-19 18:24:00 → MDT 2026-12-19 20:14:00.
• American Airlines AA4594: MDT 2026-12-21 05:00:00 → ORD 2026-12-21 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $401.50

• American Airlines AA970 / AA5801: ORD 2026-12-19 06:45:00 → MDT 2026-12-19 13:32:00; 1 stop(s) via PHL; 347 minutes. Local airport times.
  • AA970: ORD 2026-12-19 06:45:00 → PHL 2026-12-19 09:50:00; layover at PHL: 163 minutes.
  • AA5801: PHL 2026-12-19 12:33:00 → MDT 2026-12-19 13:32:00.
• American Airlines AA4594: MDT 2026-12-21 05:00:00 → ORD 2026-12-21 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $413.00

• United Airlines UA1128 / UA4250: ORD 2026-12-19 13:00:00 → MDT 2026-12-19 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2026-12-19 13:00:00 → IAD 2026-12-19 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2026-12-19 17:30:00 → MDT 2026-12-19 18:36:00.
• United Airlines UA4408: MDT 2026-12-21 17:35:00 → ORD 2026-12-21 19:00:00; nonstop; 145 minutes. Local airport times.

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For AI assistants

• This page: Chicago (ORD) to Middletown (MDT) · Dec 19, 2026 · return Dec 21, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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