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Middletown → Chicago

Dec 21, 2026 · return Dec 24, 2026

MDT → ORD1 adulteconomyRound trip

8 flight options · 3 airlines

Nonstop flights

Mon, Dec 21 – Thu, Dec 24

American Airlines
5:00 amMDT
2h 28m
Nonstop
6:28 amORD
American Airlines
7:20 pmORD
1h 55m
Nonstop
10:15 pmMDT

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

United Airlines
10:42 amMDT
2h 17m
Nonstop
11:59 amORD
United Airlines
10:29 amORD
1h 55m
Nonstop
1:24 pmMDT

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

American Airlines
2:13 pmMDT
2h 21m
Nonstop
3:34 pmORD
American Airlines
7:20 pmORD
1h 55m
Nonstop
10:15 pmMDT

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

United Airlines
2:10 pmMDT
2h 18m
Nonstop
3:28 pmORD
United Airlines
10:29 amORD
1h 55m
Nonstop
1:24 pmMDT

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Thu, Dec 24

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

American Airlines
1:59 pmMDT
7h 31m
PHL · 3h 40m
8:30 pmORD
American Airlines
7:20 pmORD
1h 55m
Nonstop
10:15 pmMDT

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

United Airlines
10:30 amMDT
7h 24m
IAD · 4h
4:54 pmORD
United Airlines
10:29 amORD
1h 55m
Nonstop
1:24 pmMDT

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDT ⇄ ORD

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 routeNov 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 2027
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 → 2026-12-24American AirlinesAA4594 / AA2663$406.262026-10-29T01:29:03Z
2026-12-21 → 2026-12-24United AirlinesUA6054 / UA5584$418.762026-10-29T01:29:03Z
2026-12-21 → 2026-12-24Delta Air LinesDL5287 + DL1084 / DL2358 + DL5477$418.762026-10-29T01:29:03Z
2026-12-21 → 2026-12-24American AirlinesAA3974 / AA2663$406.262026-10-29T01:29:03Z
2026-12-21 → 2026-12-24United AirlinesUA5613 / UA5584$418.762026-10-29T01:29:03Z
2026-12-21 → 2026-12-24American AirlinesAA5275 + AA1039 / AA2663$396.882026-10-29T01:29:03Z
2026-12-21 → 2026-12-24American AirlinesAA5801 + AA3177 / AA2663$396.882026-10-29T01:29:03Z
2026-12-21 → 2026-12-24United AirlinesUA4974 + UA1786 / UA5584$409.382026-10-29T01:29:03Z

2026-12-21 → 2026-12-24 · $406.26

  • American Airlines AA4594: MDT 2026-12-21 05:00:00 → ORD 2026-12-21 06:28:00; nonstop; 148 minutes. Local airport times.
  • American Airlines AA2663: ORD 2026-12-24 19:20:00 → MDT 2026-12-24 22:15:00; nonstop; 115 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $418.76

  • United Airlines UA6054: MDT 2026-12-21 10:42:00 → ORD 2026-12-21 11:59:00; nonstop; 137 minutes. Local airport times.
  • United Airlines UA5584: ORD 2026-12-24 10:29:00 → MDT 2026-12-24 13:24:00; nonstop; 115 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $418.76

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

2026-12-21 → 2026-12-24 · $406.26

  • American Airlines AA3974: MDT 2026-12-21 14:13:00 → ORD 2026-12-21 15:34:00; nonstop; 141 minutes. Local airport times.
  • American Airlines AA2663: ORD 2026-12-24 19:20:00 → MDT 2026-12-24 22:15:00; nonstop; 115 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $418.76

  • United Airlines UA5613: MDT 2026-12-21 14:10:00 → ORD 2026-12-21 15:28:00; nonstop; 138 minutes. Local airport times.
  • United Airlines UA5584: ORD 2026-12-24 10:29:00 → MDT 2026-12-24 13:24:00; nonstop; 115 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $396.88

  • American Airlines AA5275 / AA1039: MDT 2026-12-21 17:46:00 → ORD 2026-12-21 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
    • AA5275: MDT 2026-12-21 17:46:00 → CLT 2026-12-21 19:34:00; layover at CLT: 199 minutes.
    • AA1039: CLT 2026-12-21 22:53:00 → ORD 2026-12-21 23:59:00.
  • American Airlines AA2663: ORD 2026-12-24 19:20:00 → MDT 2026-12-24 22:15:00; nonstop; 115 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $396.88

  • American Airlines AA5801 / AA3177: MDT 2026-12-21 13:59:00 → ORD 2026-12-21 20:30:00; 1 stop(s) via PHL; 451 minutes. Local airport times.
    • AA5801: MDT 2026-12-21 13:59:00 → PHL 2026-12-21 14:55:00; layover at PHL: 220 minutes.
    • AA3177: PHL 2026-12-21 18:35:00 → ORD 2026-12-21 20:30:00.
  • American Airlines AA2663: ORD 2026-12-24 19:20:00 → MDT 2026-12-24 22:15:00; nonstop; 115 minutes. Local airport times.

2026-12-21 → 2026-12-24 · $409.38

  • United Airlines UA4974 / UA1786: MDT 2026-12-21 10:30:00 → ORD 2026-12-21 16:54:00; 1 stop(s) via IAD; 444 minutes. Local airport times.
    • UA4974: MDT 2026-12-21 10:30:00 → IAD 2026-12-21 11:30:00; layover at IAD: 240 minutes.
    • UA1786: IAD 2026-12-21 15:30:00 → ORD 2026-12-21 16:54:00.
  • United Airlines UA5584: ORD 2026-12-24 10:29:00 → MDT 2026-12-24 13:24:00; nonstop; 115 minutes. Local airport times.

More dates for this route