Orlando to Chicago flights
Round trip · Economy · Prices per person in USD
Prices updated
Prices are low right now
$160 is $40 (20%) below the usual $200 for Orlando → Chicago.
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 Orlando → Chicago drops below your price.Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $160 (cheapest month) |
| November 2026 | $181 |
| December 2026 | $217 |
Cheapest dates in the next 4 months
Round trip, per person-
Oct 7 – 14 7 nights · leave Wed$160 −20% vs usual$160 −20% vs usual Book
Allegiant Air 1 stop · 2h 44m -
Nov 14 – 17 3 nights · leave Sat$181 −10% vs usual$181 −10% vs usual Book
Frontier Airlines 1 stop · 4h 02m -
Nov 25 – Dec 2 7 nights · leave Wed$189 −6% vs usual$189 −6% vs usual Book
Frontier Airlines 1 stop · 3h 01m
-
Dec 8 – 12 4 nights · leave Tue$217 +9% vs usual$217 +9% vs usual Book
Frontier Airlines 1 stop · 4h 05m
-
Oct 22 – 25 3 nights · leave Thu$224 +12% vs usual$224 +12% vs usual Book
Frontier Airlines 2 stops · 6h 38m
-
Oct 11 – 14 3 nights · leave Sun$317 +59% vs usual$317 +59% vs usual Book
Frontier Airlines Nonstop · 3h 11m
-
Oct 4 – 7 3 nights · leave Sun$321 +61% vs usual$321 +61% vs usual Book
Frontier Airlines Nonstop · 3h 08m
-
Nov 29 – Dec 9 10 nights · leave Sun$370 +85% vs usual$370 +85% vs usual Book
Frontier Airlines 1 stop · 4h 01m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
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Airport transfer to Chicago
Fixed prices from ORD on KiwitaxiTo see transfer prices here, turn on partner content in .
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Plan the rest of your trip
Chicago · Oct 7 – 14Travel insurance · EKTA Airport transfer · Kiwitaxi
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Good to know
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Orlando to Chicago: questions
How much is a flight from Orlando to Chicago?
The cheapest round trip we have found right now is $160, leaving October 7 and returning October 14. The usual price on this route is about $200, so this fare is 20% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Orlando to Chicago?
October 2026, with round trips from $160. The most expensive month in our data is December (from $217). Based on the 3 months ahead we have prices for.
Are there nonstop flights from Orlando to Chicago?
Yes. Nonstop from $317 round trip. 33% of the 9 date combinations we track are nonstop.
About this route
We track round-trip economy fares from Orlando (United States) to Chicago (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $160, departing October 7 and returning October 14, about 20% below the usual $200. Right now we're following 9 upcoming date combinations on this route. The cheapest month to fly in our data is October, from $160. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.