Flight price alerts: Chicago → New York
Sample round trips on this route start around EUR 194; November 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 194. Cheapest month in our next-3-month sample: November 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 · 3 nights
- Sat 14 Nov · 13:00
- Return Tue 17 Nov · 13:26
EUR 194
- See deal
- Round trip · 8 nights
- Tue 06 Oct · 10:59
- Return Wed 14 Oct · 13:00
EUR 205
- See deal
- Round trip · 3 nights
- Tue 13 Oct · 06:10
- Return Fri 16 Oct · 20:15
EUR 207
- See deal
- Round trip · 2 nights
- Wed 11 Nov · 13:00
- Return Fri 13 Nov · 13:26
EUR 207
- See deal
- Round trip · 4 nights
- Sat 14 Nov · 13:00
- Return Wed 18 Nov · 13:26
EUR 207
- See deal
- Round trip · 4 nights
- Sat 03 Oct · 07:00
- Return Wed 07 Oct · 08:10
EUR 238
- See deal
- Round trip · 5 nights
- Mon 05 Oct · 07:00
- Return Sat 10 Oct · 20:15
EUR 257
- See deal
- Round trip · 7 nights
- Tue 20 Oct · 10:34
- Return Tue 27 Oct · 10:29
EUR 263
- See deal
- Round trip · 3 nights
- Fri 02 Oct · 10:59
- Return Mon 05 Oct · 20:05
EUR 268
- See deal
- Round trip · 1 night
- Sun 04 Oct · 10:59
- Return Mon 05 Oct · 20:05
EUR 268
- See deal
- Round trip · 2 nights
- Fri 13 Nov · 06:44
- Return Sun 15 Nov · 07:29
EUR 268
- See deal
- Round trip · 1 night
- Sat 24 Oct · 10:34
- Return Sun 25 Oct · 06:30
EUR 277
- See deal
- Round trip · Same day · 1h 39m at destination
- Wed 07 Oct · 10:59
- Return Wed 07 Oct · 19:02
EUR 278
- See deal
- Round trip · 3 nights
- Sat 07 Nov · 13:00
- Return Tue 10 Nov · 06:40
EUR 278
- See deal
- Round trip · 3 nights
- Fri 16 Oct · 06:10
- Return Mon 19 Oct · 20:15
EUR 289
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Sat 14 Nov · 13:00 | Tue 17 Nov · 13:26 | 3 nights | EUR 194 | See deal |
| Tue 06 Oct · 10:59 | Wed 14 Oct · 13:00 | 8 nights | EUR 205 | See deal |
| Tue 13 Oct · 06:10 | Fri 16 Oct · 20:15 | 3 nights | EUR 207 | See deal |
| Wed 11 Nov · 13:00 | Fri 13 Nov · 13:26 | 2 nights | EUR 207 | See deal |
| Sat 14 Nov · 13:00 | Wed 18 Nov · 13:26 | 4 nights | EUR 207 | See deal |
| Sat 03 Oct · 07:00 | Wed 07 Oct · 08:10 | 4 nights | EUR 238 | See deal |
| Mon 05 Oct · 07:00 | Sat 10 Oct · 20:15 | 5 nights | EUR 257 | See deal |
| Tue 20 Oct · 10:34 | Tue 27 Oct · 10:29 | 7 nights | EUR 263 | See deal |
| Fri 02 Oct · 10:59 | Mon 05 Oct · 20:05 | 3 nights | EUR 268 | See deal |
| Sun 04 Oct · 10:59 | Mon 05 Oct · 20:05 | 1 night | EUR 268 | See deal |
| Fri 13 Nov · 06:44 | Sun 15 Nov · 07:29 | 2 nights | EUR 268 | See deal |
| Sat 24 Oct · 10:34 | Sun 25 Oct · 06:30 | 1 night | EUR 277 | See deal |
| Wed 07 Oct · 10:59 | Wed 07 Oct · 19:02 | Same day · 1h 39m at destination | EUR 278 | See deal |
| Sat 07 Nov · 13:00 | Tue 10 Nov · 06:40 | 3 nights | EUR 278 | See deal |
| Fri 16 Oct · 06:10 | Mon 19 Oct · 20:15 | 3 nights | EUR 289 | 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, November 2026 is currently the cheapest month to fly from Chicago to New York, with round trips from about EUR 194. Prices change — set an alert to catch the next drop.
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