Chicago (ORD) to Middletown (MDT), Dec 26, 2026: round trips from $402, one way from $247

Chicago (ORD) to Middletown (MDT), Dec 26, 2026: round trips from $402, one way from $247 on Axel, checked Oct 29, 2026. Lowest published fares: $402 round trip, Axel-exclusive, American Airlines, 1 stop, Dec 26, 2026 – Jan 9, 2027; $247 one way, Axel-exclusive, Delta Air Lines, 1 stop, Dec 26, 2026; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Route overview: Chicago to Middletown (MDT) flight deals

2026-12-26 · one way · Axel-exclusive $247.00

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 23:10:00.

2026-12-26 · one way · Axel-exclusive $253.50

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.

2026-12-26 → 2026-12-27 · Axel-exclusive $455.00

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2026-12-27 12:24:00 → ORD 2026-12-27 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-12-27 12:24:00 → DTW 2026-12-27 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-12-27 17:56:00 → ORD 2026-12-27 18:30:00.

2026-12-26 → 2026-12-27 · Axel-exclusive $468.00

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA4533: MDT 2026-12-27 15:37:00 → ORD 2026-12-27 17:09:00; nonstop; 152 minutes. Local airport times.

2026-12-26 → 2026-12-28 · Axel-exclusive $446.25

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2026-12-28 12:24:00 → ORD 2026-12-28 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-12-28 12:24:00 → DTW 2026-12-28 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-12-28 17:56:00 → ORD 2026-12-28 18:30:00.

2026-12-26 → 2026-12-28 · Axel-exclusive $459.00

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA4594: MDT 2026-12-28 05:00:00 → ORD 2026-12-28 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-26 → 2026-12-29 · Axel-exclusive $446.25

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2026-12-29 12:24:00 → ORD 2026-12-29 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-12-29 12:24:00 → DTW 2026-12-29 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-12-29 17:56:00 → ORD 2026-12-29 18:30:00.

2026-12-26 → 2026-12-29 · Axel-exclusive $459.00

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA4533: MDT 2026-12-29 15:37:00 → ORD 2026-12-29 17:09:00; nonstop; 152 minutes. Local airport times.

2026-12-26 → 2026-12-30 · Axel-exclusive $446.25

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2026-12-30 12:24:00 → ORD 2026-12-30 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-12-30 12:24:00 → DTW 2026-12-30 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-12-30 17:56:00 → ORD 2026-12-30 18:30:00.

2026-12-26 → 2026-12-30 · Axel-exclusive $459.00

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA3042: MDT 2026-12-30 06:34:00 → ORD 2026-12-30 08:00:00; nonstop; 146 minutes. Local airport times.

2026-12-26 → 2027-01-01 · Axel-exclusive $446.25

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2027-01-01 12:24:00 → ORD 2027-01-01 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2027-01-01 12:24:00 → DTW 2027-01-01 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2027-01-01 17:56:00 → ORD 2027-01-01 18:30:00.

2026-12-26 → 2027-01-01 · Axel-exclusive $459.00

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA4533: MDT 2027-01-01 15:37:00 → ORD 2027-01-01 17:09:00; nonstop; 152 minutes. Local airport times.

2026-12-26 → 2027-01-02 · Axel-exclusive $443.38

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA5275 / AA1039: MDT 2027-01-02 17:46:00 → ORD 2027-01-02 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2027-01-02 17:46:00 → CLT 2027-01-02 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2027-01-02 22:53:00 → ORD 2027-01-02 23:59:00.

2026-12-26 → 2027-01-02 · Axel-exclusive $471.75

• United Airlines UA2319: ORD 2026-12-26 19:45:00 → MDT 2026-12-26 22:47:00; nonstop; 122 minutes. Local airport times.
• United Airlines UA4408: MDT 2027-01-02 17:35:00 → ORD 2027-01-02 19:00:00; nonstop; 145 minutes. Local airport times.

2026-12-26 → 2027-01-03 · Axel-exclusive $446.25

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 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.

2026-12-26 → 2027-01-03 · Axel-exclusive $459.00

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 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.

2026-12-26 → 2027-01-05 · Axel-exclusive $402.50

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2027-01-05 12:24:00 → ORD 2027-01-05 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2027-01-05 12:24:00 → DTW 2027-01-05 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2027-01-05 17:56:00 → ORD 2027-01-05 18:30:00.

2026-12-26 → 2027-01-05 · Axel-exclusive $414.00

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA4533: MDT 2027-01-05 15:37:00 → ORD 2027-01-05 17:09:00; nonstop; 152 minutes. Local airport times.

2026-12-26 → 2027-01-06 · Axel-exclusive $402.50

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2027-01-06 12:24:00 → ORD 2027-01-06 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2027-01-06 12:24:00 → DTW 2027-01-06 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2027-01-06 17:56:00 → ORD 2027-01-06 18:30:00.

2026-12-26 → 2027-01-06 · Axel-exclusive $414.00

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA3042: MDT 2027-01-06 06:34:00 → ORD 2027-01-06 08:00:00; nonstop; 146 minutes. Local airport times.

2026-12-26 → 2027-01-07 · Axel-exclusive $402.50

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-26 17:02:00 → MDT 2026-12-26 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-26 17:02:00 → DTW 2026-12-26 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-26 21:40:00 → MDT 2026-12-26 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.

2026-12-26 → 2027-01-07 · Axel-exclusive $414.00

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 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.

2026-12-26 → 2027-01-09 · Axel-exclusive $401.50

• American Airlines AA4703: ORD 2026-12-26 20:45:00 → MDT 2026-12-26 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA5275 / AA1039: MDT 2027-01-09 17:46:00 → ORD 2027-01-09 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2027-01-09 17:46:00 → CLT 2027-01-09 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2027-01-09 22:53:00 → ORD 2027-01-09 23:59:00.

2026-12-26 → 2027-01-09 · Axel-exclusive $425.50

• United Airlines UA2319: ORD 2026-12-26 19:45:00 → MDT 2026-12-26 22:47:00; nonstop; 122 minutes. Local airport times.
• United Airlines UA4408: MDT 2027-01-09 17:35:00 → ORD 2027-01-09 19:00:00; nonstop; 145 minutes. Local airport times.

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