Middletown (MDT) to Chicago (ORD) · Dec 29, 2026 · return Jan 8, 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 (Dec 29 – Jan 8, 2027 · 10 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,116 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,332 total · 5★ Nobu Hotel Chicago, $3,819 total

All hotels in Chicago

Route overview: Middletown to Chicago (ORD) flight deals

2026-12-29 → 2027-01-08 · Axel-exclusive $349.38

• American Airlines AA2777: MDT 2026-12-29 07:02:00 → ORD 2026-12-29 08:30:00; nonstop; 148 minutes. Local airport times.
• American Airlines AA4703: ORD 2027-01-08 20:45:00 → MDT 2027-01-08 23:56:00; nonstop; 131 minutes. Local airport times.

2026-12-29 → 2027-01-08 · Axel-exclusive $360.13

• United Airlines UA2684: MDT 2026-12-29 06:17:00 → ORD 2026-12-29 07:35:00; nonstop; 138 minutes. Local airport times.
• United Airlines UA4430: ORD 2027-01-08 06:50:00 → MDT 2027-01-08 09:50:00; nonstop; 120 minutes. Local airport times.

2026-12-29 → 2027-01-08 · Axel-exclusive $360.13

• 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.
• Delta Air Lines DL2358 / DL5477: ORD 2027-01-08 17:02:00 → MDT 2027-01-08 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2027-01-08 17:02:00 → DTW 2027-01-08 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2027-01-08 21:40:00 → MDT 2027-01-08 23:10:00.

2026-12-29 → 2027-01-08 · Axel-exclusive $349.38

• American Airlines AA4533: MDT 2026-12-29 15:37:00 → ORD 2026-12-29 17:09:00; nonstop; 152 minutes. Local airport times.
• American Airlines AA4703: ORD 2027-01-08 20:45:00 → MDT 2027-01-08 23:56:00; nonstop; 131 minutes. Local airport times.

2026-12-29 → 2027-01-08 · Axel-exclusive $340.38

• American Airlines AA5801 / AA3177: MDT 2026-12-29 13:59:00 → ORD 2026-12-29 20:30:00; 1 stop(s) via PHL; 451 minutes. Local airport times.
  • AA5801: MDT 2026-12-29 13:59:00 → PHL 2026-12-29 14:55:00; layover at PHL: 220 minutes.
  • AA3177: PHL 2026-12-29 18:35:00 → ORD 2026-12-29 20:30:00.
• American Airlines AA4703: ORD 2027-01-08 20:45:00 → MDT 2027-01-08 23:56:00; nonstop; 131 minutes. Local airport times.

2026-12-29 → 2027-01-08 · Axel-exclusive $340.38

• American Airlines AA5275 / AA1039: MDT 2026-12-29 17:46:00 → ORD 2026-12-29 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-12-29 17:46:00 → CLT 2026-12-29 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-12-29 22:53:00 → ORD 2026-12-29 23:59:00.
• American Airlines AA4703: ORD 2027-01-08 20:45:00 → MDT 2027-01-08 23:56:00; nonstop; 131 minutes. Local airport times.

2026-12-29 → 2027-01-08 · Axel-exclusive $344.00

• United Airlines UA4974 / UA1786: MDT 2026-12-29 10:30:00 → ORD 2026-12-29 16:54:00; 1 stop(s) via IAD; 444 minutes. Local airport times.
  • UA4974: MDT 2026-12-29 10:30:00 → IAD 2026-12-29 11:30:00; layover at IAD: 240 minutes.
  • UA1786: IAD 2026-12-29 15:30:00 → ORD 2026-12-29 16:54:00.
• United Airlines UA1128 / UA4250: ORD 2027-01-08 13:00:00 → MDT 2027-01-08 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2027-01-08 13:00:00 → IAD 2027-01-08 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2027-01-08 17:30:00 → MDT 2027-01-08 18:36:00.

2026-12-29 → 2027-01-08 · Axel-exclusive $353.00

• United Airlines UA2684: MDT 2026-12-29 06:03:00 → ORD 2026-12-29 07:30:00; nonstop; 147 minutes. Local airport times.
• United Airlines UA1128 / UA4250: ORD 2027-01-08 13:00:00 → MDT 2027-01-08 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2027-01-08 13:00:00 → IAD 2027-01-08 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2027-01-08 17:30:00 → MDT 2027-01-08 18:36:00.

Explore this route

• All dates for this route
• Dec 28, 2026 · Return options
• Dec 30, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Middletown (MDT) to Chicago (ORD) · Dec 29, 2026 · return Jan 8, 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.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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