Chicago (ORD) to Middletown (MDT) · Dec 28, 2026 · return Jan 7, 2027

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

2026-12-28 → 2027-01-07 · Axel-exclusive $405.00

• American Airlines AA4498: ORD 2026-12-28 11:45:00 → MDT 2026-12-28 14:42:00; nonstop; 117 minutes. Local airport times.
• American Airlines AA4594: MDT 2027-01-07 05:00:00 → ORD 2027-01-07 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-28 → 2027-01-07 · Axel-exclusive $416.25

• United Airlines UA2319: ORD 2026-12-28 19:45:00 → MDT 2026-12-28 22:47:00; nonstop; 122 minutes. Local airport times.
• United Airlines UA4611: MDT 2027-01-07 14:10:00 → ORD 2027-01-07 15:29:00; nonstop; 139 minutes. Local airport times.

2026-12-28 → 2027-01-07 · Axel-exclusive $393.75

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-28 17:02:00 → MDT 2026-12-28 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-28 17:02:00 → DTW 2026-12-28 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-28 21:40:00 → MDT 2026-12-28 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2027-01-07 12:24:00 → ORD 2027-01-07 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2027-01-07 12:24:00 → DTW 2027-01-07 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2027-01-07 17:56:00 → ORD 2027-01-07 18:30:00.

2026-12-28 → 2027-01-07 · Axel-exclusive $405.00

• American Airlines AA2156: ORD 2026-12-28 19:20:00 → MDT 2026-12-28 22:28:00; nonstop; 128 minutes. Local airport times.
• American Airlines AA4594: MDT 2027-01-07 05:00:00 → ORD 2027-01-07 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-28 → 2027-01-07 · Axel-exclusive $416.25

• United Airlines UA5581: ORD 2026-12-28 06:55:00 → MDT 2026-12-28 09:53:00; nonstop; 118 minutes. Local airport times.
• United Airlines UA4611: MDT 2027-01-07 14:10:00 → ORD 2027-01-07 15:29:00; nonstop; 139 minutes. Local airport times.

2026-12-28 → 2027-01-07 · Axel-exclusive $389.38

• American Airlines AA970 / AA5801: ORD 2026-12-28 06:45:00 → MDT 2026-12-28 13:32:00; 1 stop(s) via PHL; 347 minutes. Local airport times.
  • AA970: ORD 2026-12-28 06:45:00 → PHL 2026-12-28 09:50:00; layover at PHL: 163 minutes.
  • AA5801: PHL 2026-12-28 12:33:00 → MDT 2026-12-28 13:32:00.
• American Airlines AA4594: MDT 2027-01-07 05:00:00 → ORD 2027-01-07 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-28 → 2027-01-07 · Axel-exclusive $389.38

• American Airlines AA1889 / AA6051: ORD 2026-12-28 12:05:00 → MDT 2026-12-28 20:14:00; 1 stop(s) via CLT; 429 minutes. Local airport times.
  • AA1889: ORD 2026-12-28 12:05:00 → CLT 2026-12-28 15:10:00; layover at CLT: 194 minutes.
  • AA6051: CLT 2026-12-28 18:24:00 → MDT 2026-12-28 20:14:00.
• American Airlines AA4594: MDT 2027-01-07 05:00:00 → ORD 2027-01-07 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-28 → 2027-01-07 · Axel-exclusive $400.63

• United Airlines UA1128 / UA4250: ORD 2026-12-28 13:00:00 → MDT 2026-12-28 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2026-12-28 13:00:00 → IAD 2026-12-28 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2026-12-28 17:30:00 → MDT 2026-12-28 18:36:00.
• United Airlines UA4611: MDT 2027-01-07 14:10:00 → ORD 2027-01-07 15:29:00; nonstop; 139 minutes. Local airport times.

Explore this route

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For AI assistants

• This page: Chicago (ORD) to Middletown (MDT) · Dec 28, 2026 · return Jan 7, 2027: 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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