Flight price alerts: Chicago → New York
Sample round trips on this route start around EUR 161; September 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 161. Cheapest month in our next-3-month sample: September 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 · 4 nights
- Sat 19 Sept · 07:00
- Return Wed 23 Sept · 08:10
EUR 161
- See deal
- Round trip · 2 nights
- Mon 31 Aug · 06:00
- Return Wed 02 Sept · 06:55
EUR 164
- See deal
- Round trip · 6 nights
- Wed 12 Aug · 06:00
- Return Tue 18 Aug · 06:55
EUR 182
- See deal
- Round trip · 4 nights
- Thu 13 Aug · 06:00
- Return Mon 17 Aug · 14:29
EUR 182
- See deal
- Round trip · 5 nights
- Thu 13 Aug · 06:00
- Return Tue 18 Aug · 06:55
EUR 182
- See deal
- Round trip · 5 nights
- Fri 04 Sept · 06:00
- Return Wed 09 Sept · 13:00
EUR 191
- See deal
- Round trip · 40 nights
- Fri 11 Sept · 10:59
- Return Wed 21 Oct · 10:00
EUR 219
- See deal
- Round trip · 6 nights
- Fri 18 Sept · 10:59
- Return Thu 24 Sept · 08:10
EUR 223
- See deal
- Round trip · 3 nights
- Thu 10 Sept · 07:46
- Return Sun 13 Sept · 06:55
EUR 226
- See deal
- Round trip · 2 nights
- Wed 09 Sept · 10:59
- Return Fri 11 Sept · 20:05
EUR 228
- See deal
- Round trip · 2 nights
- Sat 12 Sept · 07:00
- Return Mon 14 Sept · 20:05
EUR 228
- See deal
- Round trip · 2 nights
- Tue 15 Sept · 07:05
- Return Thu 17 Sept · 20:05
EUR 229
- See deal
- Round trip · 3 nights
- Thu 17 Sept · 10:59
- Return Sun 20 Sept · 08:10
EUR 229
- See deal
- Round trip · 4 nights
- Thu 17 Sept · 10:59
- Return Mon 21 Sept · 08:10
EUR 229
- See deal
- Round trip · 3 nights
- Thu 01 Oct · 10:59
- Return Sun 04 Oct · 08:10
EUR 230
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Sat 19 Sept · 07:00 | Wed 23 Sept · 08:10 | 4 nights | EUR 161 | See deal |
| Mon 31 Aug · 06:00 | Wed 02 Sept · 06:55 | 2 nights | EUR 164 | See deal |
| Wed 12 Aug · 06:00 | Tue 18 Aug · 06:55 | 6 nights | EUR 182 | See deal |
| Thu 13 Aug · 06:00 | Mon 17 Aug · 14:29 | 4 nights | EUR 182 | See deal |
| Thu 13 Aug · 06:00 | Tue 18 Aug · 06:55 | 5 nights | EUR 182 | See deal |
| Fri 04 Sept · 06:00 | Wed 09 Sept · 13:00 | 5 nights | EUR 191 | See deal |
| Fri 11 Sept · 10:59 | Wed 21 Oct · 10:00 | 40 nights | EUR 219 | See deal |
| Fri 18 Sept · 10:59 | Thu 24 Sept · 08:10 | 6 nights | EUR 223 | See deal |
| Thu 10 Sept · 07:46 | Sun 13 Sept · 06:55 | 3 nights | EUR 226 | See deal |
| Wed 09 Sept · 10:59 | Fri 11 Sept · 20:05 | 2 nights | EUR 228 | See deal |
| Sat 12 Sept · 07:00 | Mon 14 Sept · 20:05 | 2 nights | EUR 228 | See deal |
| Tue 15 Sept · 07:05 | Thu 17 Sept · 20:05 | 2 nights | EUR 229 | See deal |
| Thu 17 Sept · 10:59 | Sun 20 Sept · 08:10 | 3 nights | EUR 229 | See deal |
| Thu 17 Sept · 10:59 | Mon 21 Sept · 08:10 | 4 nights | EUR 229 | See deal |
| Thu 01 Oct · 10:59 | Sun 04 Oct · 08:10 | 3 nights | EUR 230 | 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, September 2026 is currently the cheapest month to fly from Chicago to New York, with round trips from about EUR 161. Prices change — set an alert to catch the next drop.
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