Chicago (ORD) to Middletown (MDT) · Dec 30, 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: Chicago to Middletown (MDT) flight deals

2026-12-30 → 2027-01-03 · Axel-exclusive $450.00

• American Airlines AA3974: ORD 2026-12-30 10:35:00 → MDT 2026-12-30 13:34:00; nonstop; 119 minutes. Local airport times.
• American Airlines AA4594: MDT 2027-01-03 05:00:00 → ORD 2027-01-03 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-30 → 2027-01-03 · Axel-exclusive $462.50

• United Airlines UA4614: ORD 2026-12-30 10:26:00 → MDT 2026-12-30 13:25:00; nonstop; 119 minutes. Local airport times.
• United Airlines UA4611: MDT 2027-01-03 14:10:00 → ORD 2027-01-03 15:29:00; nonstop; 139 minutes. Local airport times.

2026-12-30 → 2027-01-03 · Axel-exclusive $437.50

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

2026-12-30 → 2027-01-03 · Axel-exclusive $450.00

• American Airlines AA4703: ORD 2026-12-30 20:45:00 → MDT 2026-12-30 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA4594: MDT 2027-01-03 05:00:00 → ORD 2027-01-03 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-30 → 2027-01-03 · Axel-exclusive $462.50

• United Airlines UA2319: ORD 2026-12-30 17:59:00 → MDT 2026-12-30 20:54:00; nonstop; 115 minutes. Local airport times.
• United Airlines UA4611: MDT 2027-01-03 14:10:00 → ORD 2027-01-03 15:29:00; nonstop; 139 minutes. Local airport times.

2026-12-30 → 2027-01-03 · Axel-exclusive $434.38

• American Airlines AA970 / AA5801: ORD 2026-12-30 06:45:00 → MDT 2026-12-30 13:32:00; 1 stop(s) via PHL; 347 minutes. Local airport times.
  • AA970: ORD 2026-12-30 06:45:00 → PHL 2026-12-30 09:50:00; layover at PHL: 163 minutes.
  • AA5801: PHL 2026-12-30 12:33:00 → MDT 2026-12-30 13:32:00.
• American Airlines AA4594: MDT 2027-01-03 05:00:00 → ORD 2027-01-03 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-30 → 2027-01-03 · Axel-exclusive $434.38

• American Airlines AA1889 / AA6051: ORD 2026-12-30 12:05:00 → MDT 2026-12-30 20:14:00; 1 stop(s) via CLT; 429 minutes. Local airport times.
  • AA1889: ORD 2026-12-30 12:05:00 → CLT 2026-12-30 15:10:00; layover at CLT: 194 minutes.
  • AA6051: CLT 2026-12-30 18:24:00 → MDT 2026-12-30 20:14:00.
• American Airlines AA4594: MDT 2027-01-03 05:00:00 → ORD 2027-01-03 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-30 → 2027-01-03 · Axel-exclusive $446.88

• United Airlines UA1128 / UA4250: ORD 2026-12-30 13:00:00 → MDT 2026-12-30 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2026-12-30 13:00:00 → IAD 2026-12-30 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2026-12-30 17:30:00 → MDT 2026-12-30 18:36:00.
• United Airlines UA4611: MDT 2027-01-03 14:10:00 → ORD 2027-01-03 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 30, 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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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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