Miami to Chicago in October 2026
Round trips departing in October · Economy · Prices per person in USD
Prices updated
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when October fares drop below your price.October 2026 by departure day
Cheapest round trip leaving that day| Mon | Tue | Wed | Thu | Fri | Sat | Sun |
|---|---|---|---|---|---|---|
| 1 | 2 $396 | 3 | 4 | |||
| 5 | 6 | 7 | 8 | 9 | 10 | 11 |
| 12 | 13 | 14 $168 | 15 $311 | 16 $156 | 17 | 18 |
| 19 | 20 | 21 | 22 | 23 $180 | 24 | 25 |
| 26 | 27 | 28 | 29 | 30 | 31 |
Empty days: no round trip found for that departure date yet. Green = cheapest third of the month.
Cheapest dates in October 2026
Round trip, per person-
Oct 16 – 19 3 nights · leave Fri$156Frontier Airlines Nonstop · 3h 23mBook
-
Oct 14 – 18 4 nights · leave Wed$168Frontier Airlines Nonstop · 3h 23mBook
-
Oct 23 – 26 3 nights · leave Fri$180Frontier Airlines 2 stops · 4h 21mBook
-
Oct 16 – 18 2 nights · leave Fri$260Frontier Airlines Nonstop · 3h 23mBook
-
Oct 15 – 18 3 nights · leave Thu$311Frontier Airlines 1 stop · 4h 31mBook
-
Oct 2 – 6 4 nights · leave Fri$396Frontier Airlines 1 stop · 4h 17mBook
Prices change often. The booking site shows the final price before you pay.
Good to know for October
October vs other months
Cheapest round trip per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $156 (cheapest month) |
| November 2026 | $194 |
| December 2026 | $342 |
| January 2027 | $281 |
Miami to Chicago in October: questions
What's the cheapest date to fly from Miami to Chicago in October 2026?
Leaving Friday, October 16 and returning Monday, October 19 (3 nights) for $156 round trip on Frontier Airlines, the cheapest of the 6 date combinations we track that month.
How much is a round trip from Miami to Chicago in October 2026?
From $156. Half of the 6 date combinations we track are under $220. Prices are per person in USD and change often.
Is October a cheap month to fly from Miami to Chicago?
Yes. It's the cheapest of the 4 months ahead we have prices for.