Flight price alerts: London → Chicago
Sample round trips on this route start around EUR 482; 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 482. 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 · 5 nights
- Wed 11 Nov · 18:40
- Return Mon 16 Nov · 19:15
EUR 482
- See deal
- Round trip · 28 nights
- Thu 29 Oct · 07:55
- Return Thu 26 Nov · 18:30
EUR 502
- See deal
- Round trip · 7 nights
- Fri 23 Oct · 06:35
- Return Fri 30 Oct · 21:05
EUR 776
- See deal
- Round trip · 6 nights
- Mon 26 Oct · 19:30
- Return Sun 01 Nov · 19:15
EUR 801
- See deal
- Round trip · 7 nights
- Sat 10 Oct · 09:30
- Return Sat 17 Oct · 15:40
EUR 842
- See deal
- Round trip · 1 night
- Sun 25 Oct · 12:35
- Return Mon 26 Oct · 19:30
EUR 852
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Wed 11 Nov · 18:40 | Mon 16 Nov · 19:15 | 5 nights | EUR 482 | See deal |
| Thu 29 Oct · 07:55 | Thu 26 Nov · 18:30 | 28 nights | EUR 502 | See deal |
| Fri 23 Oct · 06:35 | Fri 30 Oct · 21:05 | 7 nights | EUR 776 | See deal |
| Mon 26 Oct · 19:30 | Sun 01 Nov · 19:15 | 6 nights | EUR 801 | See deal |
| Sat 10 Oct · 09:30 | Sat 17 Oct · 15:40 | 7 nights | EUR 842 | See deal |
| Sun 25 Oct · 12:35 | Mon 26 Oct · 19:30 | 1 night | EUR 852 | 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, November 2026 is currently the cheapest month to fly from London to Chicago, with round trips from about EUR 482. Prices change — set an alert to catch the next drop.
More routes from London
View all 35 routes from LondonSet alerts for other destinations from London (All Airports) (LON).
Flying to Chicago?
See all 8 departure cities with price alerts into Chicago O'Hare International Airport (ORD).
View routes to Chicago