FlexTrip Alerts

Flight price alerts: Chicago → Miami

Sample round trips on this route start around EUR 116; 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 116. 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 alert

Round 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 .

  • Round trip · 7 nights
    Tue 08 Sept · 08:05
    Return Tue 15 Sept · 12:53

    EUR 116

    See deal
  • Round trip · 4 nights
    Thu 24 Sept · 07:11
    Return Mon 28 Sept · 12:18

    EUR 153

    See deal
  • Round trip · Same day · 54m at destination
    Sat 05 Sept · 07:11
    Return Sat 05 Sept · 21:48

    EUR 160

    See deal
  • Round trip · 4 nights
    Thu 17 Sept · 13:01
    Return Mon 21 Sept · 05:50

    EUR 160

    See deal
  • Round trip · 3 nights
    Fri 25 Sept · 07:11
    Return Mon 28 Sept · 12:18

    EUR 178

    See deal
  • Round trip · 4 nights
    Sat 15 Aug · 07:00
    Return Wed 19 Aug · 11:00

    EUR 182

    See deal
  • Round trip · 1 night
    Tue 25 Aug · 14:35
    Return Wed 26 Aug · 21:05

    EUR 183

    See deal
  • Round trip · 4 nights
    Thu 15 Oct · 07:00
    Return Mon 19 Oct · 14:23

    EUR 186

    See deal
  • Round trip · 4 nights
    Fri 23 Oct · 14:35
    Return Tue 27 Oct · 11:00

    EUR 186

    See deal
  • Round trip · 5 nights
    Wed 07 Oct · 06:14
    Return Mon 12 Oct · 05:15

    EUR 187

    See deal
  • Round trip · 4 nights
    Fri 21 Aug · 07:00
    Return Tue 25 Aug · 11:00

    EUR 193

    See deal
  • Round trip · 5 nights
    Fri 21 Aug · 07:00
    Return Wed 26 Aug · 11:00

    EUR 193

    See deal
  • Round trip · 3 nights
    Fri 21 Aug · 14:35
    Return Mon 24 Aug · 21:05

    EUR 197

    See deal
  • Round trip · 6 nights
    Sun 23 Aug · 08:05
    Return Sat 29 Aug · 10:18

    EUR 198

    See deal
  • Round trip · 8 nights
    Wed 19 Aug · 07:00
    Return Thu 27 Aug · 10:18

    EUR 209

    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, September 2026 is currently the cheapest month to fly from Chicago to Miami, with round trips from about EUR 116. Prices change — set an alert to catch the next drop.

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