Middletown (MDT) to Chicago (ORD) · Dec 25, 2026 · return Jan 3, 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: Middletown to Chicago (ORD) flight deals

2026-12-25 → 2027-01-03 · Axel-exclusive $388.38

• American Airlines AA4533: MDT 2026-12-25 15:37:00 → ORD 2026-12-25 17:09:00; nonstop; 152 minutes. Local airport times.
• American Airlines AA2156: ORD 2027-01-03 19:20:00 → MDT 2027-01-03 22:28:00; nonstop; 128 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $400.33

• United Airlines UA2684: MDT 2026-12-25 06:03:00 → ORD 2026-12-25 07:30:00; nonstop; 147 minutes. Local airport times.
• United Airlines UA4430: ORD 2027-01-03 06:50:00 → MDT 2027-01-03 09:50:00; nonstop; 120 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $400.33

• Delta Air Lines DL5287 / DL1084: MDT 2026-12-25 12:24:00 → ORD 2026-12-25 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-12-25 12:24:00 → DTW 2026-12-25 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-12-25 17:56:00 → ORD 2026-12-25 18:30:00.
• Delta Air Lines DL2358 / DL5477: ORD 2027-01-03 17:02:00 → MDT 2027-01-03 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2027-01-03 17:02:00 → DTW 2027-01-03 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2027-01-03 21:40:00 → MDT 2027-01-03 23:10:00.

2026-12-25 → 2027-01-03 · Axel-exclusive $388.38

• American Airlines AA4594: MDT 2026-12-25 05:00:00 → ORD 2026-12-25 06:28:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA2156: ORD 2027-01-03 19:20:00 → MDT 2027-01-03 22:28:00; nonstop; 128 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $400.33

• United Airlines UA4611: MDT 2026-12-25 14:10:00 → ORD 2026-12-25 15:29:00; nonstop; 139 minutes. Local airport times.
• United Airlines UA4430: ORD 2027-01-03 06:50:00 → MDT 2027-01-03 09:50:00; nonstop; 120 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $379.00

• American Airlines AA5275 / AA1039: MDT 2026-12-25 17:46:00 → ORD 2026-12-25 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-12-25 17:46:00 → CLT 2026-12-25 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-12-25 22:53:00 → ORD 2026-12-25 23:59:00.
• American Airlines AA2156: ORD 2027-01-03 19:20:00 → MDT 2027-01-03 22:28:00; nonstop; 128 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $379.00

• American Airlines AA5801 / AA3177: MDT 2026-12-25 13:59:00 → ORD 2026-12-25 20:30:00; 1 stop(s) via PHL; 451 minutes. Local airport times.
  • AA5801: MDT 2026-12-25 13:59:00 → PHL 2026-12-25 14:55:00; layover at PHL: 220 minutes.
  • AA3177: PHL 2026-12-25 18:35:00 → ORD 2026-12-25 20:30:00.
• American Airlines AA2156: ORD 2027-01-03 19:20:00 → MDT 2027-01-03 22:28:00; nonstop; 128 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $390.95

• United Airlines UA4974 / UA1786: MDT 2026-12-25 10:30:00 → ORD 2026-12-25 16:54:00; 1 stop(s) via IAD; 444 minutes. Local airport times.
  • UA4974: MDT 2026-12-25 10:30:00 → IAD 2026-12-25 11:30:00; layover at IAD: 240 minutes.
  • UA1786: IAD 2026-12-25 15:30:00 → ORD 2026-12-25 16:54:00.
• United Airlines UA4430: ORD 2027-01-03 06:50:00 → MDT 2027-01-03 09:50:00; nonstop; 120 minutes. Local airport times.

2026-12-25 → 2027-01-03 · Axel-exclusive $391.78

• United Airlines UA2684: MDT 2026-12-25 06:17:00 → ORD 2026-12-25 07:35:00; nonstop; 138 minutes. Local airport times.
• United Airlines UA1128 / UA4250: ORD 2027-01-03 13:00:00 → MDT 2027-01-03 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2027-01-03 13:00:00 → IAD 2027-01-03 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2027-01-03 17:30:00 → MDT 2027-01-03 18:36:00.

Explore this route

• All dates for this route
• Dec 24, 2026 · Return options
• Dec 26, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Middletown (MDT) to Chicago (ORD) · Dec 25, 2026 · return Jan 3, 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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