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Chicago → Middletown

Dec 21, 2026 · return Dec 26, 2026

ORD → MDT1 adulteconomyRound trip

7 flight options · 3 airlines

Nonstop flights

Mon, Dec 21 – Sat, Dec 26

United Airlines
6:55 amORD
1h 58m
Nonstop
9:53 amMDT
United Airlines
5:35 pmMDT
2h 25m
Nonstop
7:00 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

United Airlines
5:59 pmORD
1h 55m
Nonstop
8:54 pmMDT
United Airlines
5:35 pmMDT
2h 25m
Nonstop
7:00 pmORD

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Sat, Dec 26

American Airlines
12:05 pmORD
7h 9m
CLT · 3h 14m
8:14 pmMDT
American Airlines
5:46 pmMDT
7h 13m
CLT · 3h 19m
11:59 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

Delta Air Lines
5:02 pmORD
5h 8m
DTW · 2h 16m
11:10 pmMDT
Delta Air Lines
12:24 pmMDT
7h 6m
DTW · 3h 59m
6:30 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

American Airlines
6:45 amORD
5h 47m
PHL · 2h 43m
1:32 pmMDT
American Airlines
5:46 pmMDT
7h 13m
CLT · 3h 19m
11:59 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

American Airlines
7:20 pmORD
1h 55m
Nonstop
10:15 pmMDT
American Airlines
5:46 pmMDT
7h 13m
CLT · 3h 19m
11:59 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Sat, Dec 26

United Airlines
1:00 pmORD
4h 36m
IAD · 1h 27m
6:36 pmMDT
United Airlines
5:35 pmMDT
2h 25m
Nonstop
7:00 pmORD

Round-trip total · 1 adult · Taxes included

Make this trip yours

ORD ⇄ MDT

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeOct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 13, 2026 → Nov 16, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 11, 2026 → Dec 14, 2026Dec 12, 2026 → Dec 19, 2026Dec 22, 2026 → Dec 27, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Dec 30, 2026 → Jan 2, 2027Jan 8, 2027 → Jan 11, 2027Jan 9, 2027 → Jan 16, 2027Jan 15, 2027 → Jan 18, 2027Jan 22, 2027 → Jan 25, 2027Jan 23, 2027 → Jan 30, 2027Feb 5, 2027 → Feb 8, 2027Feb 6, 2027 → Feb 13, 2027Feb 12, 2027 → Feb 15, 2027Mar 5, 2027 → Mar 8, 2027Mar 6, 2027 → Mar 13, 2027Mar 25, 2027 → Mar 29, 2027Apr 2, 2027 → Apr 5, 2027Apr 3, 2027 → Apr 10, 2027Apr 30, 2027 → May 3, 2027May 1, 2027 → May 8, 2027May 28, 2027 → May 31, 2027May 29, 2027 → Jun 5, 2027Jun 25, 2027 → Jun 28, 2027Jun 26, 2027 → Jul 3, 2027Jul 2, 2027 → Jul 6, 2027Jul 23, 2027 → Jul 26, 2027Jul 24, 2027 → Jul 31, 2027Aug 20, 2027 → Aug 23, 2027Aug 21, 2027 → Aug 28, 2027Sep 3, 2027 → Sep 6, 2027Sep 17, 2027 → Sep 20, 2027Oct 30, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2026-12-26United AirlinesUA5581 / UA4408$481.002026-10-29T01:53:11Z
2026-12-21 → 2026-12-26American AirlinesAA1889 + AA6051 / AA5275 + AA1039$435.502026-10-29T01:53:11Z
2026-12-21 → 2026-12-26Delta Air LinesDL2358 + DL5477 / DL5287 + DL1084$455.002026-10-29T01:53:11Z
2026-12-21 → 2026-12-26United AirlinesUA2319 / UA4408$481.002026-10-29T01:53:11Z
2026-12-21 → 2026-12-26American AirlinesAA970 + AA5801 / AA5275 + AA1039$435.502026-10-29T01:53:11Z
2026-12-21 → 2026-12-26American AirlinesAA2663 / AA5275 + AA1039$451.752026-10-29T01:53:11Z
2026-12-21 → 2026-12-26United AirlinesUA1128 + UA4250 / UA4408$464.752026-10-29T01:53:11Z

2026-12-21 → 2026-12-26 · $481.00

  • United Airlines UA5581: ORD 2026-12-21 06:55:00 → MDT 2026-12-21 09:53:00; nonstop; 118 minutes. Local airport times.
  • United Airlines UA4408: MDT 2026-12-26 17:35:00 → ORD 2026-12-26 19:00:00; nonstop; 145 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $435.50

  • American Airlines AA1889 / AA6051: ORD 2026-12-21 12:05:00 → MDT 2026-12-21 20:14:00; 1 stop(s) via CLT; 429 minutes. Local airport times.
    • AA1889: ORD 2026-12-21 12:05:00 → CLT 2026-12-21 15:10:00; layover at CLT: 194 minutes.
    • AA6051: CLT 2026-12-21 18:24:00 → MDT 2026-12-21 20:14:00.
  • 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.

2026-12-21 → 2026-12-26 · $455.00

  • 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.
  • 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.

2026-12-21 → 2026-12-26 · $481.00

  • United Airlines UA2319: ORD 2026-12-21 17:59:00 → MDT 2026-12-21 20:54:00; nonstop; 115 minutes. Local airport times.
  • United Airlines UA4408: MDT 2026-12-26 17:35:00 → ORD 2026-12-26 19:00:00; nonstop; 145 minutes. Local airport times.

2026-12-21 → 2026-12-26 · $435.50

  • American Airlines AA970 / AA5801: ORD 2026-12-21 06:45:00 → MDT 2026-12-21 13:32:00; 1 stop(s) via PHL; 347 minutes. Local airport times.
    • AA970: ORD 2026-12-21 06:45:00 → PHL 2026-12-21 09:50:00; layover at PHL: 163 minutes.
    • AA5801: PHL 2026-12-21 12:33:00 → MDT 2026-12-21 13:32:00.
  • 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.

2026-12-21 → 2026-12-26 · $451.75

  • American Airlines AA2663: ORD 2026-12-21 19:20:00 → MDT 2026-12-21 22:15:00; nonstop; 115 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.

2026-12-21 → 2026-12-26 · $464.75

  • United Airlines UA1128 / UA4250: ORD 2026-12-21 13:00:00 → MDT 2026-12-21 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
    • UA1128: ORD 2026-12-21 13:00:00 → IAD 2026-12-21 16:03:00; layover at IAD: 87 minutes.
    • UA4250: IAD 2026-12-21 17:30:00 → MDT 2026-12-21 18:36:00.
  • United Airlines UA4408: MDT 2026-12-26 17:35:00 → ORD 2026-12-26 19:00:00; nonstop; 145 minutes. Local airport times.

More dates for this route