Flight price alerts: New York → Chicago
Sample round trips on this route start around EUR 231; October 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 231. Cheapest month in our next-3-month sample: October 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 · 2 nights
- Sat 17 Oct · 13:00
- Return Mon 19 Oct · 06:10
EUR 231
- See deal
- Round trip · 4 nights
- Sat 03 Oct · 20:15
- Return Wed 07 Oct · 10:59
EUR 238
- See deal
- Round trip · 6 nights
- Sat 17 Oct · 13:00
- Return Fri 23 Oct · 12:38
EUR 247
- See deal
- Round trip · 3 nights
- Thu 29 Oct · 14:59
- Return Sun 01 Nov · 06:44
EUR 263
- See deal
- Round trip · 5 nights
- Mon 12 Oct · 20:15
- Return Sat 17 Oct · 12:38
EUR 279
- See deal
- Round trip · 1 night
- Tue 06 Oct · 08:10
- Return Wed 07 Oct · 10:59
EUR 280
- See deal
- Round trip · 3 nights
- Sat 10 Oct · 19:02
- Return Tue 13 Oct · 16:26
EUR 280
- See deal
- Round trip · 7 nights
- Wed 14 Oct · 09:30
- Return Wed 21 Oct · 12:38
EUR 280
- See deal
- Round trip · 4 nights
- Mon 12 Oct · 20:15
- Return Fri 16 Oct · 12:38
EUR 282
- See deal
- Round trip · 1 night
- Fri 16 Oct · 20:15
- Return Sat 17 Oct · 12:38
EUR 288
- See deal
- Round trip · 7 nights
- Tue 13 Oct · 09:30
- Return Tue 20 Oct · 06:10
EUR 290
- See deal
- Round trip · 10 nights
- Wed 07 Oct · 08:10
- Return Sat 17 Oct · 06:10
EUR 293
- See deal
- Round trip · 4 nights
- Sat 10 Oct · 20:15
- Return Wed 14 Oct · 12:38
EUR 293
- See deal
- Round trip · 5 nights
- Fri 16 Oct · 15:00
- Return Wed 21 Oct · 10:34
EUR 293
- See deal
- Round trip · 7 nights
- Wed 21 Oct · 15:00
- Return Wed 28 Oct · 10:34
EUR 293
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Sat 17 Oct · 13:00 | Mon 19 Oct · 06:10 | 2 nights | EUR 231 | See deal |
| Sat 03 Oct · 20:15 | Wed 07 Oct · 10:59 | 4 nights | EUR 238 | See deal |
| Sat 17 Oct · 13:00 | Fri 23 Oct · 12:38 | 6 nights | EUR 247 | See deal |
| Thu 29 Oct · 14:59 | Sun 01 Nov · 06:44 | 3 nights | EUR 263 | See deal |
| Mon 12 Oct · 20:15 | Sat 17 Oct · 12:38 | 5 nights | EUR 279 | See deal |
| Tue 06 Oct · 08:10 | Wed 07 Oct · 10:59 | 1 night | EUR 280 | See deal |
| Sat 10 Oct · 19:02 | Tue 13 Oct · 16:26 | 3 nights | EUR 280 | See deal |
| Wed 14 Oct · 09:30 | Wed 21 Oct · 12:38 | 7 nights | EUR 280 | See deal |
| Mon 12 Oct · 20:15 | Fri 16 Oct · 12:38 | 4 nights | EUR 282 | See deal |
| Fri 16 Oct · 20:15 | Sat 17 Oct · 12:38 | 1 night | EUR 288 | See deal |
| Tue 13 Oct · 09:30 | Tue 20 Oct · 06:10 | 7 nights | EUR 290 | See deal |
| Wed 07 Oct · 08:10 | Sat 17 Oct · 06:10 | 10 nights | EUR 293 | See deal |
| Sat 10 Oct · 20:15 | Wed 14 Oct · 12:38 | 4 nights | EUR 293 | See deal |
| Fri 16 Oct · 15:00 | Wed 21 Oct · 10:34 | 5 nights | EUR 293 | See deal |
| Wed 21 Oct · 15:00 | Wed 28 Oct · 10:34 | 7 nights | EUR 293 | See deal |
Frequently asked questions
- How do I get email alerts when New York to Chicago flights drop in price?
- Create a free FlexTrip Alerts tracker for New York John F. Kennedy Airport (JFK) to Chicago O'Hare International Airport (ORD). Choose your flexible departure window, stay length, and maximum price — we email you when a round trip fits.
- Does FlexTrip Alerts book flights from New York to Chicago?
- 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 New York to Chicago 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 New York to Chicago 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 New York to Chicago?
- Based on recent fare samples on this page, October 2026 is currently the cheapest month to fly from New York to Chicago, with round trips from about EUR 231. Prices change — set an alert to catch the next drop.
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