Lexington 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 AA3436: LEX 2026-11-20 05:05:00 → ORD 2026-11-20 05:48:00; nonstop; 103 minutes. Local airport times.

2026-11-20 · one way · $180.00

• United Airlines UA4791: LEX 2026-11-20 13:45:00 → ORD 2026-11-20 14:37:00; nonstop; 112 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $320.00

• American Airlines AA3974: LEX 2026-11-20 11:17:00 → ORD 2026-11-20 12:00:00; nonstop; 103 minutes. Local airport times.
• American Airlines AA6284: ORD 2026-11-23 08:15:00 → LEX 2026-11-23 10:50:00; nonstop; 95 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $330.00

• United Airlines UA5370: LEX 2026-11-20 09:00:00 → ORD 2026-11-20 09:40:00; nonstop; 100 minutes. Local airport times.
• United Airlines UA5813: ORD 2026-11-23 07:40:00 → LEX 2026-11-23 10:13:00; nonstop; 93 minutes. Local airport times.

2026-11-20 · one way · $190.00

• Delta Air Lines DL4964 / DL1716: LEX 2026-11-20 10:33:00 → ORD 2026-11-20 13:59:00; 1 stop(s) via DTW; 266 minutes. Local airport times.
  • DL4964: LEX 2026-11-20 10:33:00 → DTW 2026-11-20 12:02:00; layover at DTW: 85 minutes.
  • DL1716: DTW 2026-11-20 13:27:00 → ORD 2026-11-20 13:59:00.

2026-11-20 → 2026-11-23 · $340.00

• Delta Air Lines DL4964 / DL1716: LEX 2026-11-20 10:33:00 → ORD 2026-11-20 13:59:00; 1 stop(s) via DTW; 266 minutes. Local airport times.
  • DL4964: LEX 2026-11-20 10:33:00 → DTW 2026-11-20 12:02:00; layover at DTW: 85 minutes.
  • DL1716: DTW 2026-11-20 13:27:00 → ORD 2026-11-20 13:59:00.
• United Airlines UA5813: ORD 2026-11-23 07:40:00 → LEX 2026-11-23 10:13:00; nonstop; 93 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $368.00

• American Airlines AA3974: LEX 2026-11-27 11:17:00 → ORD 2026-11-27 12:00:00; nonstop; 103 minutes. Local airport times.
• American Airlines AA4989: ORD 2026-12-04 21:15:00 → LEX 2026-12-04 23:42:00; nonstop; 87 minutes. Local airport times.

2026-11-20 · one way · $175.00

• American Airlines AA3974: LEX 2026-11-20 11:17:00 → ORD 2026-11-20 12:00:00; nonstop; 103 minutes. Local airport times.

2026-11-20 · one way · $180.00

• United Airlines UA5370: LEX 2026-11-20 09:00:00 → ORD 2026-11-20 09:40:00; nonstop; 100 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $320.00

• American Airlines AA3436: LEX 2026-11-20 05:05:00 → ORD 2026-11-20 05:48:00; nonstop; 103 minutes. Local airport times.
• American Airlines AA6284: ORD 2026-11-23 08:15:00 → LEX 2026-11-23 10:50:00; nonstop; 95 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $330.00

• United Airlines UA4791: LEX 2026-11-20 13:45:00 → ORD 2026-11-20 14:37:00; nonstop; 112 minutes. Local airport times.
• United Airlines UA5813: ORD 2026-11-23 07:40:00 → LEX 2026-11-23 10:13:00; nonstop; 93 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $368.00

• American Airlines AA3436: LEX 2026-11-27 05:05:00 → ORD 2026-11-27 05:48:00; nonstop; 103 minutes. Local airport times.
• American Airlines AA4989: ORD 2026-12-04 21:15:00 → LEX 2026-12-04 23:42:00; nonstop; 87 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $379.50

• United Airlines UA5370: LEX 2026-11-27 09:00:00 → ORD 2026-11-27 09:40:00; nonstop; 100 minutes. Local airport times.
• United Airlines UA5423: ORD 2026-12-04 21:30:00 → LEX 2026-12-04 23:54:00; nonstop; 84 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $379.50

• United Airlines UA4791: LEX 2026-11-27 13:45:00 → ORD 2026-11-27 14:37:00; nonstop; 112 minutes. Local airport times.
• United Airlines UA5423: ORD 2026-12-04 21:30:00 → LEX 2026-12-04 23:54:00; nonstop; 84 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $392.50

• Delta Air Lines DL4964 / DL1716: LEX 2026-11-27 10:33:00 → ORD 2026-11-27 13:59:00; 1 stop(s) via DTW; 266 minutes. Local airport times.
  • DL4964: LEX 2026-11-27 10:33:00 → DTW 2026-11-27 12:02:00; layover at DTW: 85 minutes.
  • DL1716: DTW 2026-11-27 13:27:00 → ORD 2026-11-27 13:59:00.
• United Airlines UA5423: ORD 2026-12-04 21:30:00 → LEX 2026-12-04 23:54:00; nonstop; 84 minutes. Local airport times.

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 Lexington to Chicago was $303.05 for Jul 2–5. 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 Lexington to Chicago for your dates, one traveler, no account to see it.

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

Answers at a glance

• Live price for your dates: Axel shows the exact bookable round-trip price from Lexington to Chicago for your dates, one traveler, no account to see it. Choose dates for LEX → 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: $303 on Axel ($319 on American Airlines) for Friday Jul 2–5, nonstop out and nonstop back. Arrive home Jul 6. Jul 2–5, American Airlines, $303.05
• Nonstop: In the 4 departure dates we searched from Nov 10 to Jul 2, a nonstop from Lexington flew on 4: Tuesdays 2 of 2 and Fridays 2 of 2. The nonstops were American (AA4915, AA4955, AA6326, AA6308, AA4970, AA6188, AA6244) and United (UA4672, UA5370, UA5634, UA5803, UA5807, UA4542, UA4592, UA4739, UA4791, UA5679, UA6017, UA4428, UA4531, UA4606).
• Flight time: Nonstop takes about 1½ hours to Chicago and about 1½ hours back.
• Cheapest months: Dec 2026 (typical $303; lowest $303 on Axel ($319 on United Airlines)) and Nov 2026 (typical $359; lowest $359 on Axel ($379 on United Airlines)).
• Axel vs the airline: Yes. On all 3 trips we checked, Axel’s regular price for the same flights was 5–5.3% below the airline’s own fare on Google Flights, a median of $16 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% less.

Which airlines fly nonstop, and where do connections stop?

Yes, American and United fly it nonstop. Nonstop takes about 1½ hours to Chicago and about 1½ hours back. In the 4 departure dates we searched from Nov 10 to Jul 2, a nonstop from Lexington flew on 4: Tuesdays 2 of 2 and Fridays 2 of 2. The nonstops were American (AA4915, AA4955, AA6326, AA6308, AA4970, AA6188, AA6244) and United (UA4672, UA5370, UA5634, UA5803, UA5807, UA4542, UA4592, UA4739, UA4791, UA5679, UA6017, UA4428, UA4531, UA4606). 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 $303. 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 5–5.3% below the airline’s own fare on Google Flights, a median of $16 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, Jul 2–5: $319 on American Airlines, $303 on Axel ($16 less).
• United Airlines nonstop, Dec 8–15: $319 on United Airlines, $303 on Axel ($16 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 Lexington 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): $359.10 United Airlines (out LEX–ORD 5370 09:00–09:40, back ORD–LEX 5423 21:30–23:54; nonstop out, nonstop back). Checked 2026-10-28T18:44:37Z.

December 2026

• 2026-12-08–2026-12-15 (return 7 days later): $303.05 United Airlines (out LEX–ORD 4542 18:05–18:50, back ORD–LEX 5299 21:30–23:56; nonstop out, nonstop back). Checked 2026-10-28T18:44:38Z.

January 2027

February 2027

March 2027

April 2027

May 2027

June 2027

July 2027

• 2027-07-02–2027-07-05 (return 3 days later): $303.05 American Airlines (out LEX–ORD 6188 05:35–06:10, back ORD–LEX 4958 22:00–00:25+1; nonstop out, nonstop back). Arrive home Jul 6. Checked 2026-10-28T21:01:48Z.

How we checked

On Oct 28, 2026, Axel priced round trips from LEX to ORD for one adult in economy: 2 Tuesday departures with returns 7 days later and 1 Friday departure with returns 3 days later, November 2026 to July 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 · ≤4h out / ≤4h 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: LEX → ORD. Each example names its actual airports.

Check current prices for your dates and travelers

Other available fares

Flights by travel date

LEX–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.

• $1,985.21 · American Airlines 4955 · 05:14–05:59 local · Nonstop · 1h 45m. Return: American Airlines 4989 · ORD–LEX · November 15, 2026 · 21:15–23:48 local · Nonstop · 93 minutes. Airline fare: $2,093.

Captured example · October 28, 2026 at 09:37 PM UTC

LEX–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.

• $1,985.21 · United Airlines 5634 · 05:25–06:10 local · Nonstop · 1h 45m. Airline fare: $2,093.

• $1,985.21 · American Airlines 4955 · 05:14–05:59 local · Nonstop · 1h 45m. Airline fare: $2,093.

Captured example · October 28, 2026 at 09:37 PM UTC

LEX–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.

• $359.10 · United Airlines 5370 · 09:00–09:40 local · Nonstop · 1h 40m. Airline fare: $379.

• $359.10 · American Airlines 4955 · 05:14–05:59 local · Nonstop · 1h 45m. Airline fare: $379.

Captured example · October 28, 2026 at 06:44 PM UTC

LEX–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.

• $303.05 · United Airlines 4542 · 18:05–18:50 local · Nonstop · 1h 45m. Airline fare: $319.

• $303.05 · American Airlines 4955 · 05:08–05:59 local · Nonstop · 1h 51m. Airline fare: $319.

Captured example · October 28, 2026 at 06:44 PM UTC

LEX–ORD · 2027-07-02–2027-07-05 · 1 adult

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

• $303.05 · American Airlines 6188 · 05:35–06:10 local · Nonstop · 1h 35m. Airline fare: $319.

• $345.61 · United Airlines 4531 · 09:00–09:45 local · Nonstop · 1h 45m. Airline fare: $364.

• $362.88 · Delta Air Lines 3511 / 1665 · 17:48–20:37 local · 1 stop (DTW) · 3h 49m. Airline fare: $384.

Captured example · October 28, 2026 at 09:01 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 Lexington with Chicago (ORD)

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

Keep exploring

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Source: https://helloaxel.com/en/flights/from-lexington-lex-to-chicago-ord

For AI assistants

• This page: Lexington 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.