Middletown (MDT) to Chicago (ORD) · Jan 13, 2027 · return Jan 14, 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.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Jan 13–14, 2027 · 1 night · 2 adults, 1 room): 3★ The Willows Hotel, $95 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $114 total · 5★ Nobu Hotel Chicago, $349 total

All hotels in Chicago

Route overview: Middletown to Chicago (ORD) flight deals

2027-01-13 → 2027-01-14 · Axel-exclusive $308.76

• American Airlines AA4594: MDT 2027-01-13 05:00:00 → ORD 2027-01-13 06:28:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA4703: ORD 2027-01-14 20:45:00 → MDT 2027-01-14 23:56:00; nonstop; 131 minutes. Local airport times.

2027-01-13 → 2027-01-14 · Axel-exclusive $318.26

• United Airlines UA2684: MDT 2027-01-13 06:03:00 → ORD 2027-01-13 07:30:00; nonstop; 147 minutes. Local airport times.
• United Airlines UA4430: ORD 2027-01-14 06:50:00 → MDT 2027-01-14 09:50:00; nonstop; 120 minutes. Local airport times.

2027-01-13 → 2027-01-14 · Axel-exclusive $318.26

• Delta Air Lines DL5287 / DL1084: MDT 2027-01-13 12:24:00 → ORD 2027-01-13 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2027-01-13 12:24:00 → DTW 2027-01-13 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2027-01-13 17:56:00 → ORD 2027-01-13 18:30:00.
• Delta Air Lines DL2358 / DL5477: ORD 2027-01-14 17:02:00 → MDT 2027-01-14 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2027-01-14 17:02:00 → DTW 2027-01-14 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2027-01-14 21:40:00 → MDT 2027-01-14 23:10:00.

2027-01-13 → 2027-01-14 · Axel-exclusive $308.76

• American Airlines AA3042: MDT 2027-01-13 06:34:00 → ORD 2027-01-13 08:00:00; nonstop; 146 minutes. Local airport times.
• American Airlines AA4703: ORD 2027-01-14 20:45:00 → MDT 2027-01-14 23:56:00; nonstop; 131 minutes. Local airport times.

2027-01-13 → 2027-01-14 · Axel-exclusive $318.26

• United Airlines UA5613: MDT 2027-01-13 14:10:00 → ORD 2027-01-13 15:28:00; nonstop; 138 minutes. Local airport times.
• United Airlines UA4430: ORD 2027-01-14 06:50:00 → MDT 2027-01-14 09:50:00; nonstop; 120 minutes. Local airport times.

2027-01-13 → 2027-01-14 · Axel-exclusive $301.63

• American Airlines AA5275 / AA1039: MDT 2027-01-13 17:46:00 → ORD 2027-01-13 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2027-01-13 17:46:00 → CLT 2027-01-13 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2027-01-13 22:53:00 → ORD 2027-01-13 23:59:00.
• American Airlines AA4703: ORD 2027-01-14 20:45:00 → MDT 2027-01-14 23:56:00; nonstop; 131 minutes. Local airport times.

2027-01-13 → 2027-01-14 · Axel-exclusive $301.63

• American Airlines AA5801 / AA3177: MDT 2027-01-13 13:59:00 → ORD 2027-01-13 20:30:00; 1 stop(s) via PHL; 451 minutes. Local airport times.
  • AA5801: MDT 2027-01-13 13:59:00 → PHL 2027-01-13 14:55:00; layover at PHL: 220 minutes.
  • AA3177: PHL 2027-01-13 18:35:00 → ORD 2027-01-13 20:30:00.
• American Airlines AA4703: ORD 2027-01-14 20:45:00 → MDT 2027-01-14 23:56:00; nonstop; 131 minutes. Local airport times.

2027-01-13 → 2027-01-14 · Axel-exclusive $311.13

• United Airlines UA4974 / UA1786: MDT 2027-01-13 10:30:00 → ORD 2027-01-13 16:54:00; 1 stop(s) via IAD; 444 minutes. Local airport times.
  • UA4974: MDT 2027-01-13 10:30:00 → IAD 2027-01-13 11:30:00; layover at IAD: 240 minutes.
  • UA1786: IAD 2027-01-13 15:30:00 → ORD 2027-01-13 16:54:00.
• United Airlines UA4430: ORD 2027-01-14 06:50:00 → MDT 2027-01-14 09:50:00; nonstop; 120 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 12, 2027 · Return options
• Jan 14, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Middletown (MDT) to Chicago (ORD) · Jan 13, 2027 · return Jan 14, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
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