FlexTrip Alerts

Flight price alerts: Miami → Chicago

Sample round trips on this route start around EUR 134; 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 134. 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 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 · 4 nights
    Thu 15 Oct · 13:07
    Return Mon 19 Oct · 08:04

    EUR 134

    See deal
  • Round trip · 3 nights
    Fri 16 Oct · 13:07
    Return Mon 19 Oct · 08:04

    EUR 134

    See deal
  • Round trip · 4 nights
    Wed 14 Oct · 13:07
    Return Sun 18 Oct · 08:04

    EUR 174

    See deal
  • Round trip · 14 nights
    Wed 25 Nov · 21:15
    Return Wed 09 Dec · 07:00

    EUR 201

    See deal
  • Round trip · 4 nights
    Wed 07 Oct · 12:53
    Return Sun 11 Oct · 08:04

    EUR 211

    See deal
  • Round trip · 3 nights
    Mon 26 Oct · 21:35
    Return Thu 29 Oct · 08:00

    EUR 211

    See deal
  • Round trip · 4 nights
    Wed 25 Nov · 06:42
    Return Sun 29 Nov · 23:53

    EUR 315

    See deal
  • Round trip · 15 nights
    Wed 23 Sept · 12:53
    Return Thu 08 Oct · 08:04

    EUR 316

    See deal
  • Round trip · 3 nights
    Mon 05 Oct · 12:18
    Return Thu 08 Oct · 08:04

    EUR 317

    See deal
  • Round trip · 1 night
    Sat 21 Nov · 06:42
    Return Sun 22 Nov · 15:55

    EUR 322

    See deal
  • Round trip · 5 nights
    Tue 24 Nov · 06:54
    Return Sun 29 Nov · 23:53

    EUR 323

    See deal
  • Round trip · 3 nights
    Sat 26 Sept · 14:37
    Return Tue 29 Sept · 07:25

    EUR 383

    See deal

Frequently asked questions

How do I get email alerts when Miami to Chicago flights drop in price?
Create a free FlexTrip Alerts tracker for Miami International Airport (MIA) 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 Miami 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 Miami 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 Miami 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 Miami to Chicago?
Based on recent fare samples on this page, October 2026 is currently the cheapest month to fly from Miami to Chicago, with round trips from about EUR 134. Prices change — set an alert to catch the next drop.

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Flying to Chicago?

See all 8 departure cities with price alerts into Chicago O'Hare International Airport (ORD).

View routes to Chicago