Flight price alerts: New York → Chicago
Sample round trips on this route start around EUR 255; 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 255. 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 · 7 nights
- Thu 19 Nov · 14:56
- Return Thu 26 Nov · 06:03
EUR 255
- See deal
- Round trip · 7 nights
- Wed 02 Dec · 14:50
- Return Wed 09 Dec · 06:44
EUR 295
- See deal
- Round trip · 3 nights
- Thu 10 Dec · 14:50
- Return Sun 13 Dec · 06:44
EUR 296
- See deal
- Round trip · 2 nights
- Wed 11 Nov · 10:40
- Return Fri 13 Nov · 16:31
EUR 301
- See deal
- Round trip · 6 nights
- Mon 07 Dec · 14:50
- Return Sun 13 Dec · 06:44
EUR 322
- See deal
- Round trip · 34 nights
- Sat 21 Nov · 10:18
- Return Fri 25 Dec · 06:35
EUR 346
- See deal
- Round trip · 3 nights
- Thu 19 Nov · 11:00
- Return Sun 22 Nov · 07:10
EUR 349
- See deal
- Round trip · 6 nights
- Tue 24 Nov · 12:30
- Return Mon 30 Nov · 11:00
EUR 359
- See deal
- Round trip · 2 nights
- Thu 26 Nov · 20:30
- Return Sat 28 Nov · 07:10
EUR 359
- See deal
- Round trip · 9 nights
- Mon 23 Nov · 10:12
- Return Wed 02 Dec · 06:40
EUR 360
- See deal
- Round trip · 14 nights
- Mon 28 Dec · 07:30
- Return Mon 11 Jan · 10:35
EUR 361
- See deal
- Round trip · 4 nights
- Mon 09 Nov · 13:26
- Return Fri 13 Nov · 16:31
EUR 378
- See deal
- Round trip · 3 nights
- Fri 13 Nov · 14:59
- Return Mon 16 Nov · 06:44
EUR 380
- See deal
- Round trip · 3 nights
- Sun 27 Dec · 14:54
- Return Wed 30 Dec · 10:20
EUR 387
- See deal
- Round trip · 4 nights
- Fri 06 Nov · 20:24
- Return Tue 10 Nov · 06:44
EUR 388
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Thu 19 Nov · 14:56 | Thu 26 Nov · 06:03 | 7 nights | EUR 255 | See deal |
| Wed 02 Dec · 14:50 | Wed 09 Dec · 06:44 | 7 nights | EUR 295 | See deal |
| Thu 10 Dec · 14:50 | Sun 13 Dec · 06:44 | 3 nights | EUR 296 | See deal |
| Wed 11 Nov · 10:40 | Fri 13 Nov · 16:31 | 2 nights | EUR 301 | See deal |
| Mon 07 Dec · 14:50 | Sun 13 Dec · 06:44 | 6 nights | EUR 322 | See deal |
| Sat 21 Nov · 10:18 | Fri 25 Dec · 06:35 | 34 nights | EUR 346 | See deal |
| Thu 19 Nov · 11:00 | Sun 22 Nov · 07:10 | 3 nights | EUR 349 | See deal |
| Tue 24 Nov · 12:30 | Mon 30 Nov · 11:00 | 6 nights | EUR 359 | See deal |
| Thu 26 Nov · 20:30 | Sat 28 Nov · 07:10 | 2 nights | EUR 359 | See deal |
| Mon 23 Nov · 10:12 | Wed 02 Dec · 06:40 | 9 nights | EUR 360 | See deal |
| Mon 28 Dec · 07:30 | Mon 11 Jan · 10:35 | 14 nights | EUR 361 | See deal |
| Mon 09 Nov · 13:26 | Fri 13 Nov · 16:31 | 4 nights | EUR 378 | See deal |
| Fri 13 Nov · 14:59 | Mon 16 Nov · 06:44 | 3 nights | EUR 380 | See deal |
| Sun 27 Dec · 14:54 | Wed 30 Dec · 10:20 | 3 nights | EUR 387 | See deal |
| Fri 06 Nov · 20:24 | Tue 10 Nov · 06:44 | 4 nights | EUR 388 | 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, November 2026 is currently the cheapest month to fly from New York to Chicago, with round trips from about EUR 255. Prices change — set an alert to catch the next drop.
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