Flight price alerts: Chicago → New York
Sample round trips on this route start around EUR 270; December 2026 is often the cheapest month in our next-3-month window. FlexTrip Alerts is a free email service — set flexible travel dates and a max price, and we notify you when a round trip fits. We check fares about four times per day; we do not sell tickets.
Set a free tracker with flexible dates and your max price. We email you only when a round trip fits.
Sample fares from EUR 270. Cheapest month in our next-3-month sample: December 2026.
Set an alert and we email you when a round trip drops under your limit.
Set a price alertRound trips on this route
Cheapest-seen sample fares (next 3 months) — confirm the final price on the booking site when you click through.
Last updated .
- See deal
- Round trip · 7 nights
- Tue 01 Dec · 16:17
- Return Tue 08 Dec · 14:50
EUR 270
- See deal
- Round trip · 30 nights
- Thu 17 Dec · 06:35
- Return Sat 16 Jan · 20:29
EUR 288
- See deal
- Round trip · 4 nights
- Fri 25 Dec · 06:35
- Return Tue 29 Dec · 19:30
EUR 288
- See deal
- Round trip · 2 nights
- Mon 09 Nov · 06:44
- Return Wed 11 Nov · 10:40
EUR 300
- See deal
- Round trip · 6 nights
- Mon 23 Nov · 07:10
- Return Sun 29 Nov · 07:45
EUR 308
- See deal
- Round trip · 5 nights
- Tue 24 Nov · 16:17
- Return Sun 29 Nov · 07:45
EUR 308
- See deal
- Round trip · 3 nights
- Mon 21 Dec · 06:35
- Return Thu 24 Dec · 19:30
EUR 308
- See deal
- Round trip · 7 nights
- Fri 04 Dec · 14:34
- Return Fri 11 Dec · 14:50
EUR 310
- See deal
- Round trip · 1 night
- Mon 11 Jan · 10:35
- Return Tue 12 Jan · 20:29
EUR 311
- See deal
- Round trip · 1 night
- Sat 07 Nov · 05:00
- Return Sun 08 Nov · 10:40
EUR 315
- See deal
- Round trip · 3 nights
- Thu 10 Dec · 06:44
- Return Sun 13 Dec · 07:27
EUR 315
- See deal
- Round trip · 2 nights
- Wed 09 Dec · 06:44
- Return Fri 11 Dec · 14:50
EUR 321
- See deal
- Round trip · 1 night
- Sun 10 Jan · 10:35
- Return Mon 11 Jan · 20:29
EUR 325
- See deal
- Round trip · 4 nights
- Sat 21 Nov · 17:30
- Return Wed 25 Nov · 12:30
EUR 328
- See deal
- Round trip · 2 nights
- Fri 08 Jan · 10:35
- Return Sun 10 Jan · 20:29
EUR 333
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Tue 01 Dec · 16:17 | Tue 08 Dec · 14:50 | 7 nights | EUR 270 | See deal |
| Thu 17 Dec · 06:35 | Sat 16 Jan · 20:29 | 30 nights | EUR 288 | See deal |
| Fri 25 Dec · 06:35 | Tue 29 Dec · 19:30 | 4 nights | EUR 288 | See deal |
| Mon 09 Nov · 06:44 | Wed 11 Nov · 10:40 | 2 nights | EUR 300 | See deal |
| Mon 23 Nov · 07:10 | Sun 29 Nov · 07:45 | 6 nights | EUR 308 | See deal |
| Tue 24 Nov · 16:17 | Sun 29 Nov · 07:45 | 5 nights | EUR 308 | See deal |
| Mon 21 Dec · 06:35 | Thu 24 Dec · 19:30 | 3 nights | EUR 308 | See deal |
| Fri 04 Dec · 14:34 | Fri 11 Dec · 14:50 | 7 nights | EUR 310 | See deal |
| Mon 11 Jan · 10:35 | Tue 12 Jan · 20:29 | 1 night | EUR 311 | See deal |
| Sat 07 Nov · 05:00 | Sun 08 Nov · 10:40 | 1 night | EUR 315 | See deal |
| Thu 10 Dec · 06:44 | Sun 13 Dec · 07:27 | 3 nights | EUR 315 | See deal |
| Wed 09 Dec · 06:44 | Fri 11 Dec · 14:50 | 2 nights | EUR 321 | See deal |
| Sun 10 Jan · 10:35 | Mon 11 Jan · 20:29 | 1 night | EUR 325 | See deal |
| Sat 21 Nov · 17:30 | Wed 25 Nov · 12:30 | 4 nights | EUR 328 | See deal |
| Fri 08 Jan · 10:35 | Sun 10 Jan · 20:29 | 2 nights | EUR 333 | See deal |
Frequently asked questions
- How do I get email alerts when Chicago to New York flights drop in price?
- Create a free FlexTrip Alerts tracker for Chicago O'Hare International Airport (ORD) to New York John F. Kennedy Airport (JFK). Choose your flexible departure window, stay length, and maximum price — we email you when a round trip fits.
- Does FlexTrip Alerts book flights from Chicago to New York?
- No — we do not sell tickets. FlexTrip Alerts watches prices and emails you when a fare matches your plan. You book on the airline or travel site you prefer when you receive an alert.
- Can I set flexible travel dates for Chicago to New York alerts?
- Yes. Pick a departure window (not one fixed day) and how many nights you can stay. We match round trips that fit your window, stay length, and max price — then email you when one qualifies.
- How often does FlexTrip Alerts check Chicago to New York fares?
- We scan aggregated fares on a schedule — about four times per day (every ~6 hours, UTC). You can also trigger an on-demand check from your dashboard, with a short cooldown between manual refreshes.
- What is the cheapest month to fly from Chicago to New York?
- Based on recent fare samples on this page, December 2026 is currently the cheapest month to fly from Chicago to New York, with round trips from about EUR 270. Prices change — set an alert to catch the next drop.
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