Middletown (MDT) to Chicago (ORD) · Dec 11, 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: Middletown to Chicago (ORD) flight deals

2026-12-11 → 2026-12-21 · Axel-exclusive $365.63

• American Airlines AA2777: MDT 2026-12-11 07:02:00 → ORD 2026-12-11 08:30:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA2156: ORD 2026-12-21 19:20:00 → MDT 2026-12-21 22:28:00; nonstop; 128 minutes. Local airport times.

2026-12-11 → 2026-12-21 · Axel-exclusive $376.88

• United Airlines UA3454: MDT 2026-12-11 08:19:00 → ORD 2026-12-11 09:45:00; nonstop; 146 minutes. Local airport times.
• United Airlines UA5581: ORD 2026-12-21 06:55:00 → MDT 2026-12-21 09:53:00; nonstop; 118 minutes. Local airport times.

2026-12-11 → 2026-12-21 · Axel-exclusive $376.88

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

2026-12-11 → 2026-12-21 · Axel-exclusive $365.63

• American Airlines AA3974: MDT 2026-12-11 14:13:00 → ORD 2026-12-11 15:34:00; nonstop; 141 minutes. Local airport times.
• American Airlines AA2156: ORD 2026-12-21 19:20:00 → MDT 2026-12-21 22:28:00; nonstop; 128 minutes. Local airport times.

2026-12-11 → 2026-12-21 · Axel-exclusive $376.88

• United Airlines UA4408: MDT 2026-12-11 17:35:00 → ORD 2026-12-11 19:00:00; nonstop; 145 minutes. Local airport times.
• United Airlines UA5581: ORD 2026-12-21 06:55:00 → MDT 2026-12-21 09:53:00; nonstop; 118 minutes. Local airport times.

2026-12-11 → 2026-12-21 · Axel-exclusive $358.13

• American Airlines AA5275 / AA1039: MDT 2026-12-11 17:46:00 → ORD 2026-12-11 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-12-11 17:46:00 → CLT 2026-12-11 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-12-11 22:53:00 → ORD 2026-12-11 23:59:00.
• American Airlines AA2156: ORD 2026-12-21 19:20:00 → MDT 2026-12-21 22:28:00; nonstop; 128 minutes. Local airport times.

2026-12-11 → 2026-12-21 · Axel-exclusive $358.13

• American Airlines AA5801 / AA3177: MDT 2026-12-11 13:59:00 → ORD 2026-12-11 20:30:00; 1 stop(s) via PHL; 451 minutes. Local airport times.
  • AA5801: MDT 2026-12-11 13:59:00 → PHL 2026-12-11 14:55:00; layover at PHL: 220 minutes.
  • AA3177: PHL 2026-12-11 18:35:00 → ORD 2026-12-11 20:30:00.
• American Airlines AA2156: ORD 2026-12-21 19:20:00 → MDT 2026-12-21 22:28:00; nonstop; 128 minutes. Local airport times.

2026-12-11 → 2026-12-21 · Axel-exclusive $369.38

• United Airlines UA4974 / UA1786: MDT 2026-12-11 10:30:00 → ORD 2026-12-11 16:54:00; 1 stop(s) via IAD; 444 minutes. Local airport times.
  • UA4974: MDT 2026-12-11 10:30:00 → IAD 2026-12-11 11:30:00; layover at IAD: 240 minutes.
  • UA1786: IAD 2026-12-11 15:30:00 → ORD 2026-12-11 16:54:00.
• United Airlines UA5581: ORD 2026-12-21 06:55:00 → MDT 2026-12-21 09:53:00; nonstop; 118 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 10, 2026 · Return options
• Dec 12, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Middletown (MDT) to Chicago (ORD) · Dec 11, 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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