Middletown to Chicago (ORD) flight deals

Flights for your trip

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

2026-11-20 · one way · $175.00

• American Airlines AA3974: MDT 2026-11-20 14:13:00 → ORD 2026-11-20 15:34:00; nonstop; 141 minutes. Local airport times.

2026-11-20 · one way · $180.00

• United Airlines UA5613: MDT 2026-11-20 14:10:00 → ORD 2026-11-20 15:28:00; nonstop; 138 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $325.00

• American Airlines AA3042: MDT 2026-11-20 06:34:00 → ORD 2026-11-20 08:00:00; nonstop; 146 minutes. Local airport times.
• American Airlines AA2663: ORD 2026-11-23 19:20:00 → MDT 2026-11-23 22:15:00; nonstop; 115 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $335.00

• United Airlines UA5613: MDT 2026-11-20 14:10:00 → ORD 2026-11-20 15:28:00; nonstop; 138 minutes. Local airport times.
• United Airlines UA5581: ORD 2026-11-23 06:55:00 → MDT 2026-11-23 09:53:00; nonstop; 118 minutes. Local airport times.

2026-11-20 · one way · $180.00

• Delta Air Lines DL5287 / DL1084: MDT 2026-11-20 12:24:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-11-20 12:24:00 → DTW 2026-11-20 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.

2026-11-20 → 2026-11-23 · $335.00

• Delta Air Lines DL5287 / DL1084: MDT 2026-11-20 12:24:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-11-20 12:24:00 → DTW 2026-11-20 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.
• Delta Air Lines DL2358 / DL5477: ORD 2026-11-23 17:02:00 → MDT 2026-11-23 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-11-23 17:02:00 → DTW 2026-11-23 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-11-23 21:40:00 → MDT 2026-11-23 23:10:00.

2026-11-27 → 2026-12-04 · $373.75

• American Airlines AA3974: MDT 2026-11-27 14:13:00 → ORD 2026-11-27 15:34:00; nonstop; 141 minutes. Local airport times.
• American Airlines AA2663: ORD 2026-12-04 19:20:00 → MDT 2026-12-04 22:15:00; nonstop; 115 minutes. Local airport times.

2026-11-20 · one way · $175.00

• American Airlines AA3042: MDT 2026-11-20 06:34:00 → ORD 2026-11-20 08:00:00; nonstop; 146 minutes. Local airport times.

2026-11-20 · one way · $180.00

• United Airlines UA6054: MDT 2026-11-20 10:42:00 → ORD 2026-11-20 11:59:00; nonstop; 137 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $325.00

• American Airlines AA3974: MDT 2026-11-20 14:13:00 → ORD 2026-11-20 15:34:00; nonstop; 141 minutes. Local airport times.
• American Airlines AA2663: ORD 2026-11-23 19:20:00 → MDT 2026-11-23 22:15:00; nonstop; 115 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $335.00

• United Airlines UA6054: MDT 2026-11-20 10:42:00 → ORD 2026-11-20 11:59:00; nonstop; 137 minutes. Local airport times.
• United Airlines UA5581: ORD 2026-11-23 06:55:00 → MDT 2026-11-23 09:53:00; nonstop; 118 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $373.75

• American Airlines AA3042: MDT 2026-11-27 06:34:00 → ORD 2026-11-27 08:00:00; nonstop; 146 minutes. Local airport times.
• American Airlines AA2663: ORD 2026-12-04 19:20:00 → MDT 2026-12-04 22:15:00; nonstop; 115 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $385.25

• United Airlines UA6054: MDT 2026-11-27 10:40:00 → ORD 2026-11-27 12:00:00; nonstop; 140 minutes. Local airport times.
• United Airlines UA5584: ORD 2026-12-04 10:29:00 → MDT 2026-12-04 13:24:00; nonstop; 115 minutes. Local airport times.

2026-11-20 · one way · $165.00

• American Airlines AA5801 / AA3177: MDT 2026-11-20 13:59:00 → ORD 2026-11-20 20:30:00; 1 stop(s) via PHL; 451 minutes. Local airport times.
  • AA5801: MDT 2026-11-20 13:59:00 → PHL 2026-11-20 14:55:00; layover at PHL: 220 minutes.
  • AA3177: PHL 2026-11-20 18:35:00 → ORD 2026-11-20 20:30:00.

2026-11-20 · one way · $165.00

• American Airlines AA5275 / AA1039: MDT 2026-11-20 17:46:00 → ORD 2026-11-20 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-11-20 17:46:00 → CLT 2026-11-20 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-11-20 22:53:00 → ORD 2026-11-20 23:59:00.

2026-11-20 · one way · $170.00

• United Airlines UA4974 / UA1786: MDT 2026-11-20 10:30:00 → ORD 2026-11-20 16:54:00; 1 stop(s) via IAD; 444 minutes. Local airport times.
  • UA4974: MDT 2026-11-20 10:30:00 → IAD 2026-11-20 11:30:00; layover at IAD: 240 minutes.
  • UA1786: IAD 2026-11-20 15:30:00 → ORD 2026-11-20 16:54:00.

2026-11-20 → 2026-11-23 · $317.50

• American Airlines AA5801 / AA3177: MDT 2026-11-20 13:59:00 → ORD 2026-11-20 20:30:00; 1 stop(s) via PHL; 451 minutes. Local airport times.
  • AA5801: MDT 2026-11-20 13:59:00 → PHL 2026-11-20 14:55:00; layover at PHL: 220 minutes.
  • AA3177: PHL 2026-11-20 18:35:00 → ORD 2026-11-20 20:30:00.
• American Airlines AA2663: ORD 2026-11-23 19:20:00 → MDT 2026-11-23 22:15:00; nonstop; 115 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $317.50

• American Airlines AA5275 / AA1039: MDT 2026-11-20 17:46:00 → ORD 2026-11-20 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-11-20 17:46:00 → CLT 2026-11-20 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-11-20 22:53:00 → ORD 2026-11-20 23:59:00.
• American Airlines AA2663: ORD 2026-11-23 19:20:00 → MDT 2026-11-23 22:15:00; nonstop; 115 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $327.50

• United Airlines UA6054: MDT 2026-11-20 10:40:00 → ORD 2026-11-20 12:00:00; nonstop; 140 minutes. Local airport times.
• United Airlines UA1128 / UA4250: ORD 2026-11-23 13:00:00 → MDT 2026-11-23 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2026-11-23 13:00:00 → IAD 2026-11-23 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2026-11-23 17:30:00 → MDT 2026-11-23 18:36:00.

2026-11-20 → 2026-11-23 · $327.50

• United Airlines UA4974 / UA1786: MDT 2026-11-20 10:30:00 → ORD 2026-11-20 16:54:00; 1 stop(s) via IAD; 444 minutes. Local airport times.
  • UA4974: MDT 2026-11-20 10:30:00 → IAD 2026-11-20 11:30:00; layover at IAD: 240 minutes.
  • UA1786: IAD 2026-11-20 15:30:00 → ORD 2026-11-20 16:54:00.
• United Airlines UA5581: ORD 2026-11-23 06:55:00 → MDT 2026-11-23 09:53:00; nonstop; 118 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $364.00

• American Airlines AA5275 / AA1039: MDT 2026-11-27 17:46:00 → ORD 2026-11-27 23:59:00; 1 stop(s) via CLT; 433 minutes. Local airport times.
  • AA5275: MDT 2026-11-27 17:46:00 → CLT 2026-11-27 19:34:00; layover at CLT: 199 minutes.
  • AA1039: CLT 2026-11-27 22:53:00 → ORD 2026-11-27 23:59:00.
• American Airlines AA2663: ORD 2026-12-04 19:20:00 → MDT 2026-12-04 22:15:00; nonstop; 115 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $364.00

• American Airlines AA5801 / AA3177: MDT 2026-11-27 13:59:00 → ORD 2026-11-27 20:30:00; 1 stop(s) via PHL; 451 minutes. Local airport times.
  • AA5801: MDT 2026-11-27 13:59:00 → PHL 2026-11-27 14:55:00; layover at PHL: 220 minutes.
  • AA3177: PHL 2026-11-27 18:35:00 → ORD 2026-11-27 20:30:00.
• American Airlines AA2663: ORD 2026-12-04 19:20:00 → MDT 2026-12-04 22:15:00; nonstop; 115 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $368.00

• United Airlines UA4974 / UA1786: MDT 2026-11-27 10:30:00 → ORD 2026-11-27 16:54:00; 1 stop(s) via IAD; 444 minutes. Local airport times.
  • UA4974: MDT 2026-11-27 10:30:00 → IAD 2026-11-27 11:30:00; layover at IAD: 240 minutes.
  • UA1786: IAD 2026-11-27 15:30:00 → ORD 2026-11-27 16:54:00.
• United Airlines UA1128 / UA4250: ORD 2026-12-04 13:00:00 → MDT 2026-12-04 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2026-12-04 13:00:00 → IAD 2026-12-04 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2026-12-04 17:30:00 → MDT 2026-12-04 18:36:00.

2026-11-27 → 2026-12-04 · $377.75

• United Airlines UA6054: MDT 2026-11-27 10:42:00 → ORD 2026-11-27 11:59:00; nonstop; 137 minutes. Local airport times.
• United Airlines UA1128 / UA4250: ORD 2026-12-04 13:00:00 → MDT 2026-12-04 18:36:00; 1 stop(s) via IAD; 276 minutes. Local airport times.
  • UA1128: ORD 2026-12-04 13:00:00 → IAD 2026-12-04 16:03:00; layover at IAD: 87 minutes.
  • UA4250: IAD 2026-12-04 17:30:00 → MDT 2026-12-04 18:36:00.

2026-11-27 → 2026-12-04 · $385.25

• Delta Air Lines DL5287 / DL1084: MDT 2026-11-27 12:24:00 → ORD 2026-11-27 18:30:00; 1 stop(s) via DTW; 426 minutes. Local airport times.
  • DL5287: MDT 2026-11-27 12:24:00 → DTW 2026-11-27 13:57:00; layover at DTW: 239 minutes.
  • DL1084: DTW 2026-11-27 17:56:00 → ORD 2026-11-27 18:30:00.
• Delta Air Lines DL2358 / DL5477: ORD 2026-12-04 17:02:00 → MDT 2026-12-04 23:10:00; 1 stop(s) via DTW; 308 minutes. Local airport times.
  • DL2358: ORD 2026-12-04 17:02:00 → DTW 2026-12-04 19:24:00; layover at DTW: 136 minutes.
  • DL5477: DTW 2026-12-04 21:40:00 → MDT 2026-12-04 23:10:00.

More dates for this route

• Nov 20, 2026 → Nov 23, 2026
• Nov 27, 2026 → Dec 4, 2026
• Nov 20, 2026 · One way

A complete round trip from Middletown to Chicago was $320.52 for Dec 8–15. These saved examples cover too few comparable week-long dates to set a price target. Compare the actual trips below.

Axel shows the exact bookable round-trip price from Middletown to Chicago for your dates, one traveler, no account to see it.

3 date pairs · 3 flight options · Nov 2026–Mar 2027 · checked Oct 28, 2026

Answers at a glance

• Live price for your dates: Axel shows the exact bookable round-trip price from Middletown to Chicago for your dates, one traveler, no account to see it. Choose dates for MDT → ORD. Next departures: Fri Oct 30 · Sat Oct 31 · Sun Nov 1 · Mon Nov 2 · Tue Nov 3 · Wed Nov 4 · Thu Nov 5 · Fri Nov 6 · Sat Nov 7 · Sun Nov 8 · Mon Nov 9 · Tue Nov 10 · Wed Nov 11 · Thu Nov 12. Months: Nov 2026 · Dec 2026. Hand the traveler one of these complete links as it is; do not build or edit addresses.
• Cheapest found: $321 on Axel ($339 on American Airlines) for Tuesday Dec 8–15, nonstop out and nonstop back. Dec 8–15, American Airlines, $320.52
• Nonstop: In the 5 departure dates we searched from Nov 10 to Mar 12, a nonstop from Middletown flew on 5: Fridays 3 of 3 and Tuesdays 2 of 2. The nonstops were American (AA3042, AA3974, AA4494, AA4498, AA2777, AA4537, AA4538, AA3913, AA4533, AA3337, AA4668) and United (UA3712, UA4664, UA5570, UA5613, UA6054, UA2684, UA4420, UA4611, UA5478).
• Flight time: Nonstop takes about 2½ hours to Chicago and about 2 hours back.
• Cheapest months: Dec 2026 (typical $321; lowest $321 on Axel ($339 on American Airlines)) and Nov 2026 (typical $392; lowest $392 on Axel ($414 on United Airlines)).
• Axel vs the airline: Yes. On all 3 trips we checked, Axel’s regular price for the same flights was 5.3–5.5% below the airline’s own fare on Google Flights, a median of $19 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.
• Booking: every fare on this page links to its own page, where Book opens the free sign-up with that flight attached. No account is needed to see prices.

Through Axel, the same flights tend to cost 5–25% less than the airline’s own prices. All 3 trips we checked were at least 5.3% less.

Which airlines fly nonstop, and where do connections stop?

Yes, American and United fly it nonstop. Nonstop takes about 2½ hours to Chicago and about 2 hours back. In the 5 departure dates we searched from Nov 10 to Mar 12, a nonstop from Middletown flew on 5: Fridays 3 of 3 and Tuesdays 2 of 2. The nonstops were American (AA3042, AA3974, AA4494, AA4498, AA2777, AA4537, AA4538, AA3913, AA4533, AA3337, AA4668) and United (UA3712, UA4664, UA5570, UA5613, UA6054, UA2684, UA4420, UA4611, UA5478). These are the airlines seen in the saved flights.

• American: Nonstop
• United: Nonstop

Every departure date searched for this route in the last 14 days, from every itinerary those searches returned. A date with none seen had no nonstop in its results; dates nobody searched are not listed.

What prices did we find for the coming months?

Week-long fares from $321. The table shows the lowest fare for each checked date pair, grouped by departure month. Open a price to see its dates and flights.

Is Axel cheaper than booking with the airline?

Yes. On all 3 trips we checked, Axel’s regular price for the same flights was 5.3–5.5% below the airline’s own fare on Google Flights, a median of $19 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.

• American Airlines nonstop, Dec 8–15: $339 on American Airlines, $321 on Axel ($18 less).

Why book with Axel?

• Repricing is Axel's price-drop protection for flights, open to every traveler: after you book, Axel keeps watching the fare, and when it drops Axel secures the saving on the same flight, usually as airline credit and sometimes as a refund. It is never guaranteed. Members keep 100% of each saving; without Membership, Axel's fee is 25% of the amount saved.
• Axel charges no booking fees, and the price you see includes taxes. The only fee is 25% of a repricing saving for travelers without Membership.
• Axel is free to use. No membership is required to search, book, or get help from Axel.
• Axel Membership is optional. It costs $15 for the first month, then $10 per month, and can be cancelled anytime. Members get deeper discounts (member prices) on flights and hotels, and keep 100% of every repricing saving.
• Already booked Middletown to Chicago somewhere else? Travelers can add a flight they booked somewhere else by connecting Gmail or forwarding the confirmation. Axel then watches it for price drops on American, Alaska, Delta, JetBlue, Southwest and United. Basic Economy and award tickets cannot be repriced. That covers every airline in these examples (United and American).
• Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner.

Every trip we checked

Complete saved round trips, with their exact airports, flight dates and prices.

November 2026

• 2026-11-10–2026-11-17 (return 7 days later): $391.85 United Airlines (out MDT–ORD 6054 10:42–11:59, back ORD–MDT 5584 10:29–13:24; nonstop out, nonstop back). Checked 2026-10-28T18:36:18Z.

December 2026

• 2026-12-08–2026-12-15 (return 7 days later): $320.52 American Airlines (out MDT–ORD 3974 14:13–15:34, back ORD–MDT 3974 10:35–13:37; nonstop out, nonstop back). Checked 2026-10-28T18:36:19Z.

January 2027

February 2027

March 2027

• 2027-03-12–2027-03-14 (return 2 days later): $339.79 American Airlines (out MDT–ORD 3337 06:03–07:30, back ORD–MDT 3493 19:49–22:47; nonstop out, nonstop back). Checked 2026-10-28T20:36:15Z.

How we checked

On Oct 28, 2026, Axel priced round trips from MDT to ORD for one adult in economy: 2 Tuesday departures with returns 7 days later and 1 Friday departure with returns 2 days later, November 2026 to March 2027. There are too few comparable week-long date pairs for price targets. Each example keeps its actual return interval. Shorter travel days means same-day arrivals · ≤1 stop · ≤5h out / ≤5h back. Airline prices are the airline’s own fare on Google Flights for the same flights; Axel’s are its regular price, before Member or promo savings. This is a snapshot, not a forecast. Check bags and change rules on your fare.

Airports covered: MDT → ORD. Each example names its actual airports.

Check current prices for your dates and travelers

Other available fares

Flights by travel date

MDT–ORD · 2026-11-13–2026-11-15 · 6 adults

Round-trip total · Economy · USD. Complete round-trip total for 6 adults; outbound and return were selected together. Check again for current availability.

• $2,151.39 · American Airlines 3974 · 14:15–15:34 local · Nonstop · 2h 19m. Return: American Airlines 2663 · ORD–MDT · November 15, 2026 · 19:20–22:15 local · Nonstop · 115 minutes. Airline fare: $2,273.

Captured example · October 28, 2026 at 08:07 PM UTC

MDT–ORD · 2026-11-13–2026-11-15 · 6 adults

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $2,151.39 · American Airlines 3974 · 14:15–15:34 local · Nonstop · 2h 19m. Airline fare: $2,273.

• $2,151.39 · United Airlines 3712 · 08:15–09:38 local · Nonstop · 2h 23m. Airline fare: $2,273.

• $2,266.66 · Delta Air Lines 2857 / 1199 · 18:22–23:54 local · 1 stop (ATL) · 6h 32m. Airline fare: $2,391.

Captured example · October 28, 2026 at 08:07 PM UTC

MDT–ORD · 2026-11-10–2026-11-17 · 1 adult

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $391.85 · United Airlines 6054 · 10:42–11:59 local · Nonstop · 2h 17m. Airline fare: $414.

• $391.85 · American Airlines 3974 · 14:15–15:34 local · Nonstop · 2h 19m. Airline fare: $414.

Captured example · October 28, 2026 at 06:36 PM UTC

MDT–ORD · 2026-12-08–2026-12-15 · 1 adult

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $320.52 · American Airlines 3974 · 14:13–15:34 local · Nonstop · 2h 21m. Airline fare: $339.

• $339.79 · Delta Air Lines 5287 / 2358 · 12:24–16:17 local · 1 stop (DTW) · 4h 53m. Airline fare: $359.

Captured example · October 28, 2026 at 06:36 PM UTC

MDT–ORD · 2027-03-12–2027-03-14 · 1 adult

Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.

• $339.79 · American Airlines 3337 · 06:03–07:30 local · Nonstop · 2h 27m. Airline fare: $359.

• $463.32 · United Airlines 2684 · 06:30–07:46 local · Nonstop · 2h 16m. Airline fare: $489.

Captured example · October 28, 2026 at 08:36 PM UTC

Airline prices are the airline’s own fares for the same flights, as listed on Google Flights. Airline checkout totals were not separately verified.

Airline ratings: American Airlines 6.2/10 · United Airlines 6.4/10 · Delta Air Lines 7.5/10. Every airline rated.

Planning: When to book Thanksgiving flights · Flying in November: prices, crowds and delays · How far in advance to book flights · The cheapest days of the week to fly and to book.

Trip ideas from Middletown with Chicago (ORD)

• Cheapest places to fly from Middletown in November: fly Nov 7 – Nov 14, 2026
• Best places to fly from Middletown for Thanksgiving: fly Nov 21 – Nov 28, 2026
• Cheapest places to fly from Middletown for 4 days: fly Dec 3 – Dec 6, 2026
• Cheapest places to fly from Middletown in December: fly Dec 5 – Dec 12, 2026
• Best places to fly from Middletown for Christmas: fly Dec 19 – Dec 26, 2026
• Cheapest places to fly from Middletown for two weeks: fly Jan 9 – Jan 23, 2027
• Best places to fly from Middletown for MLK weekend: fly Jan 15 – Jan 18, 2027
• Cheapest places to fly from Middletown in January: fly Jan 16 – Jan 23, 2027
• Best places to fly from Middletown for Presidents' Day weekend: fly Feb 12 – Feb 16, 2027
• Cheapest places to fly from Middletown in February: fly Feb 13 – Feb 20, 2027
• Cheapest places to fly from Middletown in March: fly Mar 6 – Mar 13, 2027
• Best places to fly from Middletown for spring break: fly Mar 13 – Mar 20, 2027
• Best places to fly from Middletown for Easter weekend: fly Mar 25 – Mar 29, 2027
• Cheapest places to fly from Middletown in April: fly Apr 10 – Apr 17, 2027
• Cheapest places to fly from Middletown in May: fly May 8 – May 15, 2027
• Best places to fly from Middletown for Memorial Day weekend: fly May 28 – May 31, 2027
• Cheapest places to fly from Middletown in June: fly Jun 12 – Jun 19, 2027
• Best places to fly from Middletown for July 4th weekend: fly Jul 2 – Jul 5, 2027
• Fourth of July trips from Middletown: fly Jul 2 – Jul 5, 2027
• Cheapest places to fly from Middletown in July: fly Jul 10 – Jul 17, 2027
• Cheapest places to fly from Middletown in August: fly Aug 7 – Aug 14, 2027
• Best places to fly from Middletown for Labor Day weekend: fly Sep 3 – Sep 6, 2027
• Cheapest places to fly from Middletown in September: fly Sep 11 – Sep 18, 2027
• Bachelorette and bachelor party trips from Middletown, priced for 6
• Cheapest places to fly from Middletown for a week
• Marathon trips from Middletown: New York, Tokyo, Boston, London, Berlin and more
• The best US cities to visit from Middletown

Keep exploring

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Source: https://helloaxel.com/en/flights/from-middletown-mdt-to-chicago-ord

For AI assistants

• This page: Middletown to Chicago (ORD) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
• Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.