Chicago (ORD) to Middletown (MDT), Dec 25, 2026: round trips from $403, one way from $241

Chicago (ORD) to Middletown (MDT), Dec 25, 2026: round trips from $403, one way from $241 on Axel, checked Oct 29, 2026. Lowest published fares: $403 round trip, Axel-exclusive, Delta Air Lines, 1 stop, Dec 25, 2026 – Jan 4, 2027; $241 one way, Axel-exclusive, United Airlines, 1 stop, Dec 25, 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

2026-12-25 · one way · Axel-exclusive $240.50

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

2026-12-25 · one way · Axel-exclusive $253.50

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 23:56:00; nonstop; 131 minutes. Local airport times.

2026-12-25 → 2026-12-26 · Axel-exclusive $451.75

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA5275 / AA1039: MDT 2026-12-26 17:46:00 → ORD 2026-12-26 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-12-26 17:46:00 → CLT 2026-12-26 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-12-26 22:53:00 → ORD 2026-12-26 23:59:00.

2026-12-25 → 2026-12-26 · Axel-exclusive $455.00

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2026-12-26 12:24:00 → ORD 2026-12-26 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-12-26 12:24:00 → DTW 2026-12-26 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-12-26 17:56:00 → ORD 2026-12-26 18:30:00.

2026-12-25 → 2026-12-27 · Axel-exclusive $455.00

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 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.

2026-12-25 → 2026-12-27 · Axel-exclusive $468.00

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 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.

2026-12-25 → 2026-12-28 · Axel-exclusive $446.25

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 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.

2026-12-25 → 2026-12-28 · Axel-exclusive $459.00

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 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.

2026-12-25 → 2026-12-29 · Axel-exclusive $446.25

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 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.

2026-12-25 → 2026-12-29 · Axel-exclusive $459.00

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 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.

2026-12-25 → 2026-12-31 · Axel-exclusive $446.25

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2026-12-31 12:24:00 → ORD 2026-12-31 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-12-31 12:24:00 → DTW 2026-12-31 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-12-31 17:56:00 → ORD 2026-12-31 18:30:00.

2026-12-25 → 2026-12-31 · Axel-exclusive $459.00

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA4533: MDT 2026-12-31 15:37:00 → ORD 2026-12-31 17:09:00; nonstop; 152 minutes. Local airport times.

2026-12-25 → 2027-01-01 · Axel-exclusive $446.25

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 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.

2026-12-25 → 2027-01-01 · Axel-exclusive $459.00

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 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.

2026-12-25 → 2027-01-02 · Axel-exclusive $443.38

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 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.

2026-12-25 → 2027-01-02 · Axel-exclusive $446.25

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

2026-12-25 → 2027-01-04 · Axel-exclusive $402.50

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2027-01-04 12:24:00 → ORD 2027-01-04 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2027-01-04 12:24:00 → DTW 2027-01-04 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2027-01-04 17:56:00 → ORD 2027-01-04 18:30:00.

2026-12-25 → 2027-01-04 · Axel-exclusive $414.00

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA4594: MDT 2027-01-04 05:00:00 → ORD 2027-01-04 06:28:00; nonstop; 148 minutes. Local airport times.

2026-12-25 → 2027-01-05 · Axel-exclusive $402.50

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 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.

2026-12-25 → 2027-01-05 · Axel-exclusive $414.00

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 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.

2026-12-25 → 2027-01-06 · Axel-exclusive $402.50

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 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.

2026-12-25 → 2027-01-06 · Axel-exclusive $414.00

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 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.

2026-12-25 → 2027-01-08 · Axel-exclusive $402.50

• Delta Air Lines DL2358 / DL5477: ORD 2026-12-25 17:02:00 → MDT 2026-12-25 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-25 17:02:00 → DTW 2026-12-25 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-25 21:40:00 → MDT 2026-12-25 23:10:00.
• Delta Air Lines DL5287 / DL1084: MDT 2027-01-08 12:24:00 → ORD 2027-01-08 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2027-01-08 12:24:00 → DTW 2027-01-08 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2027-01-08 17:56:00 → ORD 2027-01-08 18:30:00.

2026-12-25 → 2027-01-08 · Axel-exclusive $414.00

• American Airlines AA4703: ORD 2026-12-25 20:45:00 → MDT 2026-12-25 23:56:00; nonstop; 131 minutes. Local airport times.
• American Airlines AA4594: MDT 2027-01-08 05:00:00 → ORD 2027-01-08 06:28:00; nonstop; 148 minutes. Local airport times.

Explore this route

• All dates for this route
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• This page: Chicago (ORD) to Middletown (MDT) · Dec 25, 2026 · choose your return date: 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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