Flight price alerts: London → Chicago
Sample round trips on this route start around EUR 599; December 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 599. Cheapest month in our next-3-month sample: December 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 · 9 nights
- Tue 22 Dec · 06:40
- Return Thu 31 Dec · 19:10
EUR 599
- See deal
- Round trip · 12 nights
- Wed 23 Dec · 19:30
- Return Mon 04 Jan · 19:10
EUR 633
- See deal
- Round trip · 6 nights
- Tue 24 Nov · 07:05
- Return Mon 30 Nov · 19:10
EUR 692
- See deal
- Round trip · 17 nights
- Wed 16 Dec · 19:40
- Return Sat 02 Jan · 19:55
EUR 996
- See deal
- Round trip · 7 nights
- Sat 12 Dec · 12:15
- Return Sat 19 Dec · 16:45
EUR 1184
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Tue 22 Dec · 06:40 | Thu 31 Dec · 19:10 | 9 nights | EUR 599 | See deal |
| Wed 23 Dec · 19:30 | Mon 04 Jan · 19:10 | 12 nights | EUR 633 | See deal |
| Tue 24 Nov · 07:05 | Mon 30 Nov · 19:10 | 6 nights | EUR 692 | See deal |
| Wed 16 Dec · 19:40 | Sat 02 Jan · 19:55 | 17 nights | EUR 996 | See deal |
| Sat 12 Dec · 12:15 | Sat 19 Dec · 16:45 | 7 nights | EUR 1184 | 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, December 2026 is currently the cheapest month to fly from London to Chicago, with round trips from about EUR 599. Prices change — set an alert to catch the next drop.
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