Chicago to Miami 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 | 3 | 4 | |||
| 5 | 6 $249 | 7 | 8 | 9 $424 | 10 $256 | 11 |
| 12 $314 | 13 | 14 $149 | 15 $189 | 16 | 17 | 18 |
| 19 | 20 | 21 | 22 | 23 $205 | 24 | 25 |
| 26 | 27 $131 | 28 $131 | 29 $131 | 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 27 – Nov 4 8 nights · leave Tue$131Frontier Airlines 1 stop · 4h 17mBook
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Oct 28 – Nov 4 7 nights · leave Wed$131Frontier Airlines 1 stop · 4h 17mBook
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Oct 29 – Nov 3 5 nights · leave Thu$131Frontier Airlines 1 stop · 4h 12mBook
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Oct 27 – Nov 3 7 nights · leave Tue$136Frontier Airlines 1 stop · 4h 04mBook
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Oct 14 – 24 10 nights · leave Wed$149Frontier Airlines Nonstop · 3h 08mBook
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Oct 29 – Nov 5 7 nights · leave Thu$164Frontier Airlines 1 stop · 4h 12mBook
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Oct 29 – Nov 1 3 nights · leave Thu$172Frontier Airlines 1 stop · 3h 10mBook
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Oct 15 – 17 2 nights · leave Thu$189Frontier Airlines Nonstop · 3h 08mBook
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Oct 23 – 25 2 nights · leave Fri$205Frontier Airlines 1 stop · 4h 12mBook
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Oct 15 – 24 9 nights · leave Thu$208Frontier Airlines 1 stop · 5h 46mBook
Prices change often. The booking site shows the final price before you pay.
Cheapest by trip length
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 | $131 |
| November 2026 | $117 (cheapest month) |
| December 2026 | $179 |
| January 2027 | $216 |
| February 2027 | No fares found yet |
| March 2027 | No fares found yet |
| April 2027 | $431 |
Chicago to Miami in October: questions
What's the cheapest date to fly from Chicago to Miami in October 2026?
Leaving Tuesday, October 27 and returning Wednesday, November 4 (8 nights) for $131 round trip on Frontier Airlines, the cheapest of the 14 date combinations we track that month.
How much is a round trip from Chicago to Miami in October 2026?
From $131. Half of the 14 date combinations we track are under $181. Prices are per person in USD and change often.
Is October a cheap month to fly from Chicago to Miami?
It ranks 2 of 5 months we have prices for. The cheapest month is November 2026, from $117.