Flight price alerts: New York → Chicago
Sample round trips on this route start around EUR 168; 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 168. 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
- Fri 02 Oct · 20:05
- Return Sun 04 Oct · 07:00
EUR 168
- See deal
- Round trip · 4 nights
- Thu 17 Sept · 16:30
- Return Mon 21 Sept · 07:00
EUR 176
- See deal
- Round trip · 3 nights
- Thu 20 Aug · 06:55
- Return Sun 23 Aug · 06:00
EUR 198
- See deal
- Round trip · 3 nights
- Thu 13 Aug · 06:55
- Return Sun 16 Aug · 06:00
EUR 204
- See deal
- Round trip · 2 nights
- Fri 21 Aug · 20:00
- Return Sun 23 Aug · 06:00
EUR 206
- See deal
- Round trip · 10 nights
- Sun 13 Sept · 08:10
- Return Wed 23 Sept · 10:59
EUR 214
- See deal
- Round trip · 5 nights
- Wed 30 Sept · 08:10
- Return Mon 05 Oct · 07:00
EUR 214
- See deal
- Round trip · 19 nights
- Wed 30 Sept · 08:10
- Return Mon 19 Oct · 13:00
EUR 216
- See deal
- Round trip · 6 nights
- Tue 29 Sept · 08:10
- Return Mon 05 Oct · 07:00
EUR 219
- See deal
- Round trip · 3 nights
- Sat 12 Sept · 08:10
- Return Tue 15 Sept · 10:59
EUR 220
- See deal
- Round trip · 4 nights
- Thu 10 Sept · 20:05
- Return Mon 14 Sept · 07:00
EUR 229
- See deal
- Round trip · 6 nights
- Thu 27 Aug · 07:00
- Return Wed 02 Sept · 06:00
EUR 231
- See deal
- Round trip · 1 night
- Sat 29 Aug · 14:29
- Return Sun 30 Aug · 06:00
EUR 233
- See deal
- Round trip · 3 nights
- Thu 27 Aug · 14:29
- Return Sun 30 Aug · 06:00
EUR 234
- See deal
- Round trip · 1 night
- Sat 17 Oct · 20:05
- Return Sun 18 Oct · 06:20
EUR 235
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Fri 02 Oct · 20:05 | Sun 04 Oct · 07:00 | 2 nights | EUR 168 | See deal |
| Thu 17 Sept · 16:30 | Mon 21 Sept · 07:00 | 4 nights | EUR 176 | See deal |
| Thu 20 Aug · 06:55 | Sun 23 Aug · 06:00 | 3 nights | EUR 198 | See deal |
| Thu 13 Aug · 06:55 | Sun 16 Aug · 06:00 | 3 nights | EUR 204 | See deal |
| Fri 21 Aug · 20:00 | Sun 23 Aug · 06:00 | 2 nights | EUR 206 | See deal |
| Sun 13 Sept · 08:10 | Wed 23 Sept · 10:59 | 10 nights | EUR 214 | See deal |
| Wed 30 Sept · 08:10 | Mon 05 Oct · 07:00 | 5 nights | EUR 214 | See deal |
| Wed 30 Sept · 08:10 | Mon 19 Oct · 13:00 | 19 nights | EUR 216 | See deal |
| Tue 29 Sept · 08:10 | Mon 05 Oct · 07:00 | 6 nights | EUR 219 | See deal |
| Sat 12 Sept · 08:10 | Tue 15 Sept · 10:59 | 3 nights | EUR 220 | See deal |
| Thu 10 Sept · 20:05 | Mon 14 Sept · 07:00 | 4 nights | EUR 229 | See deal |
| Thu 27 Aug · 07:00 | Wed 02 Sept · 06:00 | 6 nights | EUR 231 | See deal |
| Sat 29 Aug · 14:29 | Sun 30 Aug · 06:00 | 1 night | EUR 233 | See deal |
| Thu 27 Aug · 14:29 | Sun 30 Aug · 06:00 | 3 nights | EUR 234 | See deal |
| Sat 17 Oct · 20:05 | Sun 18 Oct · 06:20 | 1 night | EUR 235 | 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 168. Prices change — set an alert to catch the next drop.
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