Chicago to Orlando 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 | 7 | 8 | 9 $291 | 10 | 11 |
| 12 | 13 | 14 | 15 | 16 $274 | 17 $255 | 18 |
| 19 | 20 | 21 | 22 | 23 | 24 | 25 |
| 26 | 27 | 28 $166 | 29 | 30 | 31 $185 |
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 28 – Nov 4 7 nights · leave Wed$166Allegiant Air Nonstop · 2h 30mBook
-
Oct 31 – Nov 4 4 nights · leave Sat$185Frontier Airlines 1 stop · 3h 57mBook
-
Oct 17 – 19 2 nights · leave Sat$255Frontier Airlines Nonstop · 2h 39mBook
-
Oct 16 – 19 3 nights · leave Fri$274Frontier Airlines Nonstop · 2h 39mBook
-
Oct 9 – 13 4 nights · leave Fri$291Frontier Airlines Nonstop · 2h 39mBook
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 | $166 (cheapest month) |
| November 2026 | $191 |
| December 2026 | $249 |
| January 2027 | $208 |
| February 2027 | No fares found yet |
| March 2027 | $306 |
Chicago to Orlando in October: questions
What's the cheapest date to fly from Chicago to Orlando in October 2026?
Leaving Wednesday, October 28 and returning Wednesday, November 4 (7 nights) for $166 round trip on Allegiant Air, the cheapest of the 5 date combinations we track that month.
How much is a round trip from Chicago to Orlando in October 2026?
From $166. Half of the 5 date combinations we track are under $255. Prices are per person in USD and change often.
Is October a cheap month to fly from Chicago to Orlando?
Yes. It's the cheapest of the 5 months ahead we have prices for.