Flight price alerts: Miami → Chicago
Sample round trips on this route start around EUR 120; 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 120. 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 · 3 nights
- Tue 15 Sept · 12:53
- Return Fri 18 Sept · 07:11
EUR 120
- See deal
- Round trip · 4 nights
- Thu 10 Sept · 12:18
- Return Mon 14 Sept · 07:11
EUR 121
- See deal
- Round trip · 1 night
- Tue 25 Aug · 10:18
- Return Wed 26 Aug · 08:05
EUR 129
- See deal
- Round trip · 4 nights
- Tue 01 Sept · 10:18
- Return Sat 05 Sept · 15:20
EUR 148
- See deal
- Round trip · 10 nights
- Wed 07 Oct · 12:53
- Return Sat 17 Oct · 14:35
EUR 150
- See deal
- Round trip · 2 nights
- Mon 24 Aug · 10:18
- Return Wed 26 Aug · 08:05
EUR 153
- See deal
- Round trip · 5 nights
- Wed 26 Aug · 10:18
- Return Mon 31 Aug · 07:05
EUR 156
- See deal
- Round trip · 3 nights
- Fri 28 Aug · 10:18
- Return Mon 31 Aug · 08:05
EUR 160
- See deal
- Round trip · 3 nights
- Sun 09 Aug · 08:30
- Return Wed 12 Aug · 07:05
EUR 164
- See deal
- Round trip · 2 nights
- Sun 09 Aug · 08:30
- Return Tue 11 Aug · 06:19
EUR 165
- See deal
- Round trip · 1 night
- Mon 24 Aug · 21:05
- Return Tue 25 Aug · 08:05
EUR 165
- See deal
- Round trip · 3 nights
- Mon 26 Oct · 22:06
- Return Thu 29 Oct · 05:05
EUR 174
- See deal
- Round trip · 2 nights
- Wed 02 Sept · 08:00
- Return Fri 04 Sept · 08:37
EUR 179
- See deal
- Round trip · 3 nights
- Wed 19 Aug · 11:10
- Return Sat 22 Aug · 13:59
EUR 223
- See deal
- Round trip · 2 nights
- Sat 15 Aug · 09:43
- Return Mon 17 Aug · 08:05
EUR 224
| Depart | Return | Stay | Price | Book |
|---|---|---|---|---|
| Tue 15 Sept · 12:53 | Fri 18 Sept · 07:11 | 3 nights | EUR 120 | See deal |
| Thu 10 Sept · 12:18 | Mon 14 Sept · 07:11 | 4 nights | EUR 121 | See deal |
| Tue 25 Aug · 10:18 | Wed 26 Aug · 08:05 | 1 night | EUR 129 | See deal |
| Tue 01 Sept · 10:18 | Sat 05 Sept · 15:20 | 4 nights | EUR 148 | See deal |
| Wed 07 Oct · 12:53 | Sat 17 Oct · 14:35 | 10 nights | EUR 150 | See deal |
| Mon 24 Aug · 10:18 | Wed 26 Aug · 08:05 | 2 nights | EUR 153 | See deal |
| Wed 26 Aug · 10:18 | Mon 31 Aug · 07:05 | 5 nights | EUR 156 | See deal |
| Fri 28 Aug · 10:18 | Mon 31 Aug · 08:05 | 3 nights | EUR 160 | See deal |
| Sun 09 Aug · 08:30 | Wed 12 Aug · 07:05 | 3 nights | EUR 164 | See deal |
| Sun 09 Aug · 08:30 | Tue 11 Aug · 06:19 | 2 nights | EUR 165 | See deal |
| Mon 24 Aug · 21:05 | Tue 25 Aug · 08:05 | 1 night | EUR 165 | See deal |
| Mon 26 Oct · 22:06 | Thu 29 Oct · 05:05 | 3 nights | EUR 174 | See deal |
| Wed 02 Sept · 08:00 | Fri 04 Sept · 08:37 | 2 nights | EUR 179 | See deal |
| Wed 19 Aug · 11:10 | Sat 22 Aug · 13:59 | 3 nights | EUR 223 | See deal |
| Sat 15 Aug · 09:43 | Mon 17 Aug · 08:05 | 2 nights | EUR 224 | 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, September 2026 is currently the cheapest month to fly from Miami to Chicago, with round trips from about EUR 120. Prices change — set an alert to catch the next drop.
More routes from Miami
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Flying to Chicago?
See all 8 departure cities with price alerts into Chicago O'Hare International Airport (ORD).
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