Flight price alerts: Chicago → Miami
Sample round trips on this route start around EUR 137; 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 137. 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 · 7 nights
- Sat 12 Dec · 07:25
- Return Sat 19 Dec · 14:17
EUR 137
- See deal
- Round trip · 6 nights
- Sat 14 Nov · 07:55
- Return Fri 20 Nov · 21:02
EUR 178
- See deal
- Round trip · 6 nights
- Fri 13 Nov · 07:55
- Return Thu 19 Nov · 13:05
EUR 181
- See deal
- Round trip · 2 nights
- Sat 12 Dec · 07:25
- Return Mon 14 Dec · 21:08
EUR 196
- See deal
- Round trip · 16 nights
- Tue 22 Dec · 05:58
- Return Thu 07 Jan · 11:34
EUR 205
- See deal
- Round trip · 1 night
- Sun 13 Dec · 22:29
- Return Mon 14 Dec · 21:08
EUR 206
- See deal
- Round trip · 7 nights
- Sun 06 Dec · 14:59
- Return Sun 13 Dec · 11:00
EUR 208
- See deal
- Round trip · 3 nights
- Mon 04 Jan · 13:10
- Return Thu 07 Jan · 11:34
EUR 217
- See deal
- Round trip · 5 nights
- Tue 01 Dec · 07:00
- Return Sun 06 Dec · 14:00
EUR 222
- See deal
- Round trip · 7 nights
- Fri 13 Nov · 07:55
- Return Fri 20 Nov · 06:10
EUR 223
- See deal
- Round trip · 15 nights
- Wed 23 Dec · 05:58
- Return Thu 07 Jan · 11:34
EUR 225
- See deal
- Round trip · 4 nights
- Mon 23 Nov · 19:50
- Return Fri 27 Nov · 05:17
EUR 234
- See deal
- Round trip · 3 nights
- Tue 24 Nov · 14:30
- Return Fri 27 Nov · 07:00
EUR 234
- See deal
- Round trip · 2 nights
- Sat 14 Nov · 07:55
- Return Mon 16 Nov · 13:05
EUR 237
- See deal
- Round trip · 6 nights
- Sun 20 Dec · 16:18
- Return Sat 26 Dec · 07:09
EUR 237
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Sat 12 Dec · 07:25 | Sat 19 Dec · 14:17 | 7 nights | EUR 137 | See deal |
| Sat 14 Nov · 07:55 | Fri 20 Nov · 21:02 | 6 nights | EUR 178 | See deal |
| Fri 13 Nov · 07:55 | Thu 19 Nov · 13:05 | 6 nights | EUR 181 | See deal |
| Sat 12 Dec · 07:25 | Mon 14 Dec · 21:08 | 2 nights | EUR 196 | See deal |
| Tue 22 Dec · 05:58 | Thu 07 Jan · 11:34 | 16 nights | EUR 205 | See deal |
| Sun 13 Dec · 22:29 | Mon 14 Dec · 21:08 | 1 night | EUR 206 | See deal |
| Sun 06 Dec · 14:59 | Sun 13 Dec · 11:00 | 7 nights | EUR 208 | See deal |
| Mon 04 Jan · 13:10 | Thu 07 Jan · 11:34 | 3 nights | EUR 217 | See deal |
| Tue 01 Dec · 07:00 | Sun 06 Dec · 14:00 | 5 nights | EUR 222 | See deal |
| Fri 13 Nov · 07:55 | Fri 20 Nov · 06:10 | 7 nights | EUR 223 | See deal |
| Wed 23 Dec · 05:58 | Thu 07 Jan · 11:34 | 15 nights | EUR 225 | See deal |
| Mon 23 Nov · 19:50 | Fri 27 Nov · 05:17 | 4 nights | EUR 234 | See deal |
| Tue 24 Nov · 14:30 | Fri 27 Nov · 07:00 | 3 nights | EUR 234 | See deal |
| Sat 14 Nov · 07:55 | Mon 16 Nov · 13:05 | 2 nights | EUR 237 | See deal |
| Sun 20 Dec · 16:18 | Sat 26 Dec · 07:09 | 6 nights | EUR 237 | 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, December 2026 is currently the cheapest month to fly from Chicago to Miami, with round trips from about EUR 137. Prices change — set an alert to catch the next drop.
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