Orlando to Chicago flights
The cheapest round trip we found from Orlando to Chicago is $103 (Jan 14 – 18, 2027, Nonstop), 35% below the usual $159.
ORL to CHI · Round trip · Economy · Prices per person in USD · Price found (3 days ago)
Cheapest found
Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| November 2026 | $219 |
| December 2026 | $159 |
| January 2027 | $103 (cheapest month) |
Cheapest dates in the next 4 months
Round trip, per person-
Jan 14 – 18, 2027 4 nights · leave Thu$103 −35% vs usual$103 −35% vs usual Book
Allegiant Air Nonstop · 2h 55m -
Dec 8 – 15 7 nights · leave Tue$195 +23% vs usual$195 +23% vs usual Book
Frontier Airlines 1 stop · 4h 11m -
Nov 25 – Dec 2 7 nights · leave Wed$219 +38% vs usual$219 +38% vs usual Book
Allegiant Air 1 stop · 2h 51m
-
Dec 11 – 15 4 nights · leave Fri$221 +39% vs usual$221 +39% vs usual Book
Frontier Airlines 1 stop · 4h 06m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
One Go City pass for Shedd Aquarium, Skydeck Chicago, 360 CHICAGO and more
- All-Inclusive Pass Unlimited Visit as many attractions as you like for 1–5 days from $149 See pass
- Explorer Pass Pick 3–7 of 36 attractions from $109 See pass
- Essentials Pass A few top attractions, chosen as you go from $99 See pass
Go City prices checked Oct 23, 2026; the final price is on Go City. Partner links: we may earn a commission if you book, at no extra cost to you.
Plan the rest of your trip
Chicago · Jan 14 – 18, 2027Partner links: we may earn a commission if you book, at no extra cost to you.
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Orlando to Chicago: questions
How much does a flight from Orlando to Chicago cost?
The cheapest round trip we have found right now is $103, leaving January 14 and returning January 18. The usual price on this route is about $159, so this fare is 35% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Orlando to Chicago?
January 2027, with round trips from $103. The most expensive month in our data is November (from $219). Based on the 3 months ahead we have prices for.
Which airports do Orlando to Chicago flights use?
Orlando airports include Orlando International (MCO), Orlando Sanford International (SFB) and Orlando Executive (ORL). Chicago airports include O'Hare International (ORD), Chicago Midway International (MDW) and Chicago Rockford International (RFD). The prices on this page cover every airport in both cities (ORL and CHI are the city codes).
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 $103, departing January 14 and returning January 18 on a nonstop flight, about 35% below the usual $159. The cheapest month to fly in our data is January, from $103. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.