Flight price alerts: Los Angeles → Chicago
Sample round trips on this route start around EUR 165; 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 165. 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 · 5 nights
- Thu 24 Sept · 06:15
- Return Tue 29 Sept · 06:30
EUR 165
- See deal
- Round trip · 6 nights
- Thu 24 Sept · 06:15
- Return Wed 30 Sept · 06:30
EUR 165
- See deal
- Round trip · 5 nights
- Mon 19 Oct · 00:21
- Return Sat 24 Oct · 20:01
EUR 165
- See deal
- Round trip · 3 nights
- Thu 12 Nov · 17:56
- Return Sun 15 Nov · 05:30
EUR 191
- See deal
- Round trip · 4 nights
- Tue 13 Oct · 06:15
- Return Sat 17 Oct · 20:01
EUR 197
- See deal
- Round trip · 3 nights
- Sun 11 Oct · 00:21
- Return Wed 14 Oct · 06:30
EUR 202
- See deal
- Round trip · 2 nights
- Fri 23 Oct · 22:35
- Return Sun 25 Oct · 05:55
EUR 207
- See deal
- Round trip · 14 nights
- Wed 30 Sept · 11:45
- Return Wed 14 Oct · 06:30
EUR 214
- See deal
- Round trip · 2 nights
- Mon 05 Oct · 21:40
- Return Wed 07 Oct · 06:30
EUR 230
- See deal
- Round trip · 4 nights
- Wed 18 Nov · 11:52
- Return Sun 22 Nov · 05:19
EUR 236
- See deal
- Round trip · 5 nights
- Fri 02 Oct · 20:24
- Return Wed 07 Oct · 06:30
EUR 239
- See deal
- Round trip · 5 nights
- Fri 25 Sept · 20:24
- Return Wed 30 Sept · 06:30
EUR 241
- See deal
- Round trip · 16 nights
- Mon 16 Nov · 20:35
- Return Wed 02 Dec · 06:21
EUR 241
- See deal
- Round trip · 3 nights
- Mon 05 Oct · 06:15
- Return Thu 08 Oct · 20:01
EUR 245
- See deal
- Round trip · 1 night
- Wed 23 Sept · 14:30
- Return Thu 24 Sept · 13:01
EUR 246
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Thu 24 Sept · 06:15 | Tue 29 Sept · 06:30 | 5 nights | EUR 165 | See deal |
| Thu 24 Sept · 06:15 | Wed 30 Sept · 06:30 | 6 nights | EUR 165 | See deal |
| Mon 19 Oct · 00:21 | Sat 24 Oct · 20:01 | 5 nights | EUR 165 | See deal |
| Thu 12 Nov · 17:56 | Sun 15 Nov · 05:30 | 3 nights | EUR 191 | See deal |
| Tue 13 Oct · 06:15 | Sat 17 Oct · 20:01 | 4 nights | EUR 197 | See deal |
| Sun 11 Oct · 00:21 | Wed 14 Oct · 06:30 | 3 nights | EUR 202 | See deal |
| Fri 23 Oct · 22:35 | Sun 25 Oct · 05:55 | 2 nights | EUR 207 | See deal |
| Wed 30 Sept · 11:45 | Wed 14 Oct · 06:30 | 14 nights | EUR 214 | See deal |
| Mon 05 Oct · 21:40 | Wed 07 Oct · 06:30 | 2 nights | EUR 230 | See deal |
| Wed 18 Nov · 11:52 | Sun 22 Nov · 05:19 | 4 nights | EUR 236 | See deal |
| Fri 02 Oct · 20:24 | Wed 07 Oct · 06:30 | 5 nights | EUR 239 | See deal |
| Fri 25 Sept · 20:24 | Wed 30 Sept · 06:30 | 5 nights | EUR 241 | See deal |
| Mon 16 Nov · 20:35 | Wed 02 Dec · 06:21 | 16 nights | EUR 241 | See deal |
| Mon 05 Oct · 06:15 | Thu 08 Oct · 20:01 | 3 nights | EUR 245 | See deal |
| Wed 23 Sept · 14:30 | Thu 24 Sept · 13:01 | 1 night | EUR 246 | See deal |
Frequently asked questions
- How do I get email alerts when Los Angeles to Chicago flights drop in price?
- Create a free FlexTrip Alerts tracker for Los Angeles International Airport (LAX) 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 Los Angeles 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 Los Angeles 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 Los Angeles 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 Los Angeles to Chicago?
- Based on recent fare samples on this page, September 2026 is currently the cheapest month to fly from Los Angeles to Chicago, with round trips from about EUR 165. Prices change — set an alert to catch the next drop.
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