Flight price alerts: Chicago → Miami
Sample round trips on this route start around EUR 143; 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 143. 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
- Mon 26 Oct · 08:04
- Return Wed 28 Oct · 11:15
EUR 143
- See deal
- Round trip · 7 nights
- Wed 14 Oct · 06:00
- Return Wed 21 Oct · 14:47
EUR 159
- See deal
- Round trip · 7 nights
- Tue 06 Oct · 07:11
- Return Tue 13 Oct · 21:58
EUR 161
- See deal
- Round trip · 3 nights
- Thu 29 Oct · 08:00
- Return Sun 01 Nov · 06:39
EUR 198
- See deal
- Round trip · 6 nights
- Sat 10 Oct · 08:04
- Return Fri 16 Oct · 13:07
EUR 202
- See deal
- Round trip · 3 nights
- Fri 30 Oct · 08:00
- Return Mon 02 Nov · 13:05
EUR 212
- See deal
- Round trip · 4 nights
- Thu 08 Oct · 19:29
- Return Mon 12 Oct · 19:02
EUR 239
- See deal
- Round trip · 6 nights
- Sun 11 Oct · 08:04
- Return Sat 17 Oct · 21:15
EUR 257
- See deal
- Round trip · 5 nights
- Thu 26 Nov · 07:55
- Return Tue 01 Dec · 21:29
EUR 259
- See deal
- Round trip · 6 nights
- Sun 04 Oct · 07:11
- Return Sat 10 Oct · 13:07
EUR 269
- See deal
- Round trip · 6 nights
- Sat 21 Nov · 15:55
- Return Fri 27 Nov · 06:42
EUR 274
- See deal
- Round trip · 5 nights
- Sun 11 Oct · 08:04
- Return Fri 16 Oct · 13:07
EUR 296
- See deal
- Round trip · 8 nights
- Sat 21 Nov · 15:55
- Return Sun 29 Nov · 21:37
EUR 346
- See deal
- Round trip · 3 nights
- Wed 23 Sept · 06:30
- Return Sat 26 Sept · 14:37
EUR 363
- See deal
- Round trip · 2 nights
- Fri 09 Oct · 08:04
- Return Sun 11 Oct · 13:07
EUR 370
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Mon 26 Oct · 08:04 | Wed 28 Oct · 11:15 | 2 nights | EUR 143 | See deal |
| Wed 14 Oct · 06:00 | Wed 21 Oct · 14:47 | 7 nights | EUR 159 | See deal |
| Tue 06 Oct · 07:11 | Tue 13 Oct · 21:58 | 7 nights | EUR 161 | See deal |
| Thu 29 Oct · 08:00 | Sun 01 Nov · 06:39 | 3 nights | EUR 198 | See deal |
| Sat 10 Oct · 08:04 | Fri 16 Oct · 13:07 | 6 nights | EUR 202 | See deal |
| Fri 30 Oct · 08:00 | Mon 02 Nov · 13:05 | 3 nights | EUR 212 | See deal |
| Thu 08 Oct · 19:29 | Mon 12 Oct · 19:02 | 4 nights | EUR 239 | See deal |
| Sun 11 Oct · 08:04 | Sat 17 Oct · 21:15 | 6 nights | EUR 257 | See deal |
| Thu 26 Nov · 07:55 | Tue 01 Dec · 21:29 | 5 nights | EUR 259 | See deal |
| Sun 04 Oct · 07:11 | Sat 10 Oct · 13:07 | 6 nights | EUR 269 | See deal |
| Sat 21 Nov · 15:55 | Fri 27 Nov · 06:42 | 6 nights | EUR 274 | See deal |
| Sun 11 Oct · 08:04 | Fri 16 Oct · 13:07 | 5 nights | EUR 296 | See deal |
| Sat 21 Nov · 15:55 | Sun 29 Nov · 21:37 | 8 nights | EUR 346 | See deal |
| Wed 23 Sept · 06:30 | Sat 26 Sept · 14:37 | 3 nights | EUR 363 | See deal |
| Fri 09 Oct · 08:04 | Sun 11 Oct · 13:07 | 2 nights | EUR 370 | See deal |
Frequently asked questions
- How do I get email alerts when Chicago to Miami flights drop in price?
- Create a free FlexTrip Alerts tracker for Chicago O'Hare International Airport (ORD) to Miami International Airport (MIA). Choose your flexible departure window, stay length, and maximum price — we email you when a round trip fits.
- Does FlexTrip Alerts book flights from Chicago to Miami?
- 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 Chicago to Miami 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 Chicago to Miami 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 Chicago to Miami?
- Based on recent fare samples on this page, October 2026 is currently the cheapest month to fly from Chicago to Miami, with round trips from about EUR 143. Prices change — set an alert to catch the next drop.
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