Flight price alerts: London → Chicago
Sample round trips on this route start around EUR 622; 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 622. 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 · 28 nights
- Wed 02 Sept · 11:15
- Return Wed 30 Sept · 19:25
EUR 622
- See deal
- Round trip · 7 nights
- Sat 10 Oct · 21:25
- Return Sat 17 Oct · 19:25
EUR 691
- See deal
- Round trip · 7 nights
- Wed 28 Oct · 12:15
- Return Wed 04 Nov · 18:30
EUR 719
- See deal
- Round trip · 29 nights
- Tue 01 Sept · 13:00
- Return Wed 30 Sept · 22:25
EUR 723
- See deal
- Round trip · 7 nights
- Sun 09 Aug · 18:30
- Return Sun 16 Aug · 17:13
EUR 1265
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Wed 02 Sept · 11:15 | Wed 30 Sept · 19:25 | 28 nights | EUR 622 | See deal |
| Sat 10 Oct · 21:25 | Sat 17 Oct · 19:25 | 7 nights | EUR 691 | See deal |
| Wed 28 Oct · 12:15 | Wed 04 Nov · 18:30 | 7 nights | EUR 719 | See deal |
| Tue 01 Sept · 13:00 | Wed 30 Sept · 22:25 | 29 nights | EUR 723 | See deal |
| Sun 09 Aug · 18:30 | Sun 16 Aug · 17:13 | 7 nights | EUR 1265 | See deal |
Frequently asked questions
- How do I get email alerts when London to Chicago flights drop in price?
- Create a free FlexTrip Alerts tracker for London (All Airports) (LON) 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 London 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 London 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 London 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 London to Chicago?
- Based on recent fare samples on this page, September 2026 is currently the cheapest month to fly from London to Chicago, with round trips from about EUR 622. Prices change — set an alert to catch the next drop.
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