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Westchester County → Chicago

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HPN → ORD1 adulteconomy

15 flight options · 2 airlines

Round-trip flights

Fri, Nov 27 – Fri, Dec 4

American Airlines
12:13 pmHPN
2h 46m
Nonstop
1:59 pmORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
12:30 pmHPN
7h
DTW · 3h 28m
6:30 pmORD
Delta Air Lines
8:29 amORD
6h 18m
DTW · 3h 9m
3:47 pmHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

American Airlines
7:29 amHPN
2h 55m
Nonstop
9:24 amORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

American Airlines
7:29 amHPN
2h 55m
Nonstop
9:24 amORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

American Airlines
12:13 pmHPN
2h 46m
Nonstop
1:59 pmORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

American Airlines
10:00 amHPN
7h
CLT · 2h 36m
4:00 pmORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

American Airlines
6:30 amHPN
7h 38m
DCA · 3h 36m
1:08 pmORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

American Airlines
6:30 amHPN
7h 38m
DCA · 3h 36m
1:08 pmORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

Show 2 more flights

Fri, Nov 20 – Mon, Nov 23

American Airlines
10:00 amHPN
7h
CLT · 2h 36m
4:00 pmORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
12:30 pmHPN
7h
DTW · 3h 28m
6:30 pmORD
Delta Air Lines
8:29 amORD
6h 18m
DTW · 3h 9m
3:47 pmHPN

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

American Airlines
7:29 amHPN
2h 55m
Nonstop
9:24 amORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
12:30 pmHPN
7h
DTW · 3h 28m
6:30 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

American Airlines
12:13 pmHPN
2h 46m
Nonstop
1:59 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

American Airlines
10:00 amHPN
7h
CLT · 2h 36m
4:00 pmORD

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

American Airlines
6:30 amHPN
7h 38m
DCA · 3h 36m
1:08 pmORD

One-way total · 1 adult · Taxes included

Make this trip yours

HPN ⇄ ORD

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, American Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

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. How Axel works · About

More dates

Nov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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)
2026-11-20 · one wayAmerican AirlinesAA3496$249.752026-10-29T01:05:11Z
2026-11-27 → 2026-12-04American AirlinesAA3812 / AA5501$411.252026-10-29T01:05:11Z
2026-11-20 · one wayDelta Air LinesDL4645 + DL1084$243.002026-10-29T01:05:11Z
2026-11-27 → 2026-12-04Delta Air LinesDL4645 + DL1084 / DL3841 + DL4658$399.502026-10-29T01:05:11Z
2026-11-20 → 2026-11-23American AirlinesAA3496 / AA3812$472.502026-10-29T01:05:11Z
2026-11-20 · one wayAmerican AirlinesAA3812$249.752026-10-29T01:05:11Z
2026-11-27 → 2026-12-04American AirlinesAA3496 / AA5501$411.252026-10-29T01:05:11Z
2026-11-20 → 2026-11-23American AirlinesAA3812 / AA3812$472.502026-10-29T01:05:11Z
2026-11-20 · one wayAmerican AirlinesAA5431 + AA2509$229.502026-10-29T01:05:11Z
2026-11-20 · one wayAmerican AirlinesAA5678 + AA2612$229.502026-10-29T01:05:11Z
2026-11-27 → 2026-12-04American AirlinesAA5431 + AA2509 / AA5501$394.382026-10-29T01:05:11Z
2026-11-27 → 2026-12-04American AirlinesAA5678 + AA2612 / AA5501$394.382026-10-29T01:05:11Z
2026-11-20 → 2026-11-23American AirlinesAA5678 + AA2612 / AA3812$455.632026-10-29T01:05:11Z
2026-11-20 → 2026-11-23American AirlinesAA5431 + AA2509 / AA3812$455.632026-10-29T01:05:11Z
2026-11-20 → 2026-11-23Delta Air LinesDL4645 + DL1084 / DL3841 + DL4658$459.002026-10-29T01:05:11Z

2026-11-20 · one way · $249.75

  • American Airlines AA3496: HPN 2026-11-20 07:29:00 → ORD 2026-11-20 09:24:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $411.25

  • American Airlines AA3812: HPN 2026-11-27 12:13:00 → ORD 2026-11-27 13:59:00; nonstop; 166 minutes. Local airport times.
  • American Airlines AA5501: ORD 2026-12-04 12:45:00 → HPN 2026-12-04 15:59:00; nonstop; 134 minutes. Local airport times.

2026-11-20 · one way · $243.00

  • Delta Air Lines DL4645 / DL1084: HPN 2026-11-20 12:30:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 420 minutes. Local airport times.
    • DL4645: HPN 2026-11-20 12:30:00 → DTW 2026-11-20 14:28:00; layover at DTW: 208 minutes.
    • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.

2026-11-27 → 2026-12-04 · $399.50

  • Delta Air Lines DL4645 / DL1084: HPN 2026-11-27 12:30:00 → ORD 2026-11-27 18:30:00; 1 stop(s) via DTW; 420 minutes. Local airport times.
    • DL4645: HPN 2026-11-27 12:30:00 → DTW 2026-11-27 14:28:00; layover at DTW: 208 minutes.
    • DL1084: DTW 2026-11-27 17:56:00 → ORD 2026-11-27 18:30:00.
  • Delta Air Lines DL3841 / DL4658: ORD 2026-12-04 08:29:00 → HPN 2026-12-04 15:47:00; 1 stop(s) via DTW; 378 minutes. Local airport times.
    • DL3841: ORD 2026-12-04 08:29:00 → DTW 2026-12-04 10:52:00; layover at DTW: 189 minutes.
    • DL4658: DTW 2026-12-04 14:01:00 → HPN 2026-12-04 15:47:00.

2026-11-20 → 2026-11-23 · $472.50

  • American Airlines AA3496: HPN 2026-11-20 07:29:00 → ORD 2026-11-20 09:24:00; nonstop; 175 minutes. Local airport times.
  • American Airlines AA3812: ORD 2026-11-23 08:13:00 → HPN 2026-11-23 11:29:00; nonstop; 136 minutes. Local airport times.

2026-11-20 · one way · $249.75

  • American Airlines AA3812: HPN 2026-11-20 12:13:00 → ORD 2026-11-20 13:59:00; nonstop; 166 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $411.25

  • American Airlines AA3496: HPN 2026-11-27 07:29:00 → ORD 2026-11-27 09:24:00; nonstop; 175 minutes. Local airport times.
  • American Airlines AA5501: ORD 2026-12-04 12:45:00 → HPN 2026-12-04 15:59:00; nonstop; 134 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $472.50

  • American Airlines AA3812: HPN 2026-11-20 12:13:00 → ORD 2026-11-20 13:59:00; nonstop; 166 minutes. Local airport times.
  • American Airlines AA3812: ORD 2026-11-23 08:13:00 → HPN 2026-11-23 11:29:00; nonstop; 136 minutes. Local airport times.

2026-11-20 · one way · $229.50

  • American Airlines AA5431 / AA2509: HPN 2026-11-20 10:00:00 → ORD 2026-11-20 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
    • AA5431: HPN 2026-11-20 10:00:00 → CLT 2026-11-20 12:09:00; layover at CLT: 156 minutes.
    • AA2509: CLT 2026-11-20 14:45:00 → ORD 2026-11-20 16:00:00.

2026-11-20 · one way · $229.50

  • American Airlines AA5678 / AA2612: HPN 2026-11-20 06:30:00 → ORD 2026-11-20 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
    • AA5678: HPN 2026-11-20 06:30:00 → DCA 2026-11-20 08:10:00; layover at DCA: 216 minutes.
    • AA2612: DCA 2026-11-20 11:46:00 → ORD 2026-11-20 13:08:00.

2026-11-27 → 2026-12-04 · $394.38

  • American Airlines AA5431 / AA2509: HPN 2026-11-27 10:00:00 → ORD 2026-11-27 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
    • AA5431: HPN 2026-11-27 10:00:00 → CLT 2026-11-27 12:09:00; layover at CLT: 156 minutes.
    • AA2509: CLT 2026-11-27 14:45:00 → ORD 2026-11-27 16:00:00.
  • American Airlines AA5501: ORD 2026-12-04 12:45:00 → HPN 2026-12-04 15:59:00; nonstop; 134 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $394.38

  • American Airlines AA5678 / AA2612: HPN 2026-11-27 06:30:00 → ORD 2026-11-27 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
    • AA5678: HPN 2026-11-27 06:30:00 → DCA 2026-11-27 08:10:00; layover at DCA: 216 minutes.
    • AA2612: DCA 2026-11-27 11:46:00 → ORD 2026-11-27 13:08:00.
  • American Airlines AA5501: ORD 2026-12-04 12:45:00 → HPN 2026-12-04 15:59:00; nonstop; 134 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $455.63

  • American Airlines AA5678 / AA2612: HPN 2026-11-20 06:30:00 → ORD 2026-11-20 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
    • AA5678: HPN 2026-11-20 06:30:00 → DCA 2026-11-20 08:10:00; layover at DCA: 216 minutes.
    • AA2612: DCA 2026-11-20 11:46:00 → ORD 2026-11-20 13:08:00.
  • American Airlines AA3812: ORD 2026-11-23 08:13:00 → HPN 2026-11-23 11:29:00; nonstop; 136 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $455.63

  • American Airlines AA5431 / AA2509: HPN 2026-11-20 10:00:00 → ORD 2026-11-20 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
    • AA5431: HPN 2026-11-20 10:00:00 → CLT 2026-11-20 12:09:00; layover at CLT: 156 minutes.
    • AA2509: CLT 2026-11-20 14:45:00 → ORD 2026-11-20 16:00:00.
  • American Airlines AA3812: ORD 2026-11-23 08:13:00 → HPN 2026-11-23 11:29:00; nonstop; 136 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $459.00

  • Delta Air Lines DL4645 / DL1084: HPN 2026-11-20 12:30:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 420 minutes. Local airport times.
    • DL4645: HPN 2026-11-20 12:30:00 → DTW 2026-11-20 14:28:00; layover at DTW: 208 minutes.
    • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.
  • Delta Air Lines DL3841 / DL4658: ORD 2026-11-23 08:29:00 → HPN 2026-11-23 15:47:00; 1 stop(s) via DTW; 378 minutes. Local airport times.
    • DL3841: ORD 2026-11-23 08:29:00 → DTW 2026-11-23 10:52:00; layover at DTW: 189 minutes.
    • DL4658: DTW 2026-11-23 14:01:00 → HPN 2026-11-23 15:47:00.

More dates for this route