Round trip from
$130
16 Dec – 19 Dec · Frontier Airlines · direct
found today
Direct flights from
$130
16 Dec – 19 Dec · Frontier Airlines
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1587 km
Distance
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2 h 48 min
Shortest flight
-
67%
Direct flights
-
4
Airlines
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$46
One way from
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$130
Round trip from
The route at a glance
About 1587 km separate Orlando and Chicago; the quickest flight is 2 h 48 min and a typical one 3 h 6 min.
67% of the cheapest tickets are direct; Frontier Airlines carries 67% of them.
Most cheap flights leave from Orlando International Airport (14 km from the centre of Orlando).
Most land at O'Hare International Airport (25 km from the centre of Chicago).
A one-way ticket starts at $46, a round trip at $130.
Cheapest price by month
| Month | Round trip from |
|---|---|
| November 2026 | $146 |
| December 2026 | $130 |
| March 2027 | $377 |
Cheapest day to fly
The cheapest departure in the next two months is 6 November at $82.
Friday is the cheapest day of the week to fly.
| Mon | Tue | Wed | Thu | Fri | Sat | Sun |
|---|---|---|---|---|---|---|
| 4 $115 |
5 $141 |
6 $82 |
7 $106 |
8 $106 |
||
| 9 $106 |
10 $106 |
11 $106 |
12 $106 |
13 $129 |
14 $142 |
15 $142 |
| 16 $156 |
30 $116 |
31 $131 |
Cheaper More expensive
- $82 — Friday, Nov. 6, 2026
- $106 — Saturday, Nov. 7, 2026
- $106 — Sunday, Nov. 8, 2026
- $106 — Monday, Nov. 9, 2026
- $106 — Tuesday, Nov. 10, 2026
- $106 — Wednesday, Nov. 11, 2026
- $106 — Thursday, Nov. 12, 2026
- $115 — Wednesday, Nov. 4, 2026
- $116 — Wednesday, Dec. 30, 2026
- $129 — Friday, Nov. 13, 2026
- $131 — Thursday, Dec. 31, 2026
- $141 — Thursday, Nov. 5, 2026
- $142 — Saturday, Nov. 14, 2026
- $142 — Sunday, Nov. 15, 2026
- $156 — Monday, Nov. 16, 2026
Price trend, last 30 days
Over the last 30 days the fare moved between $119 and $207, averaging $143.
Today's price is 9% below that average — a good moment to book.
- 5 October — $119
- 10 October — $127
- 15 October — $161
- 20 October — $130
- 25 October — $130
- 30 October — $207
- 4 November — $130
Trip length and timing
The cheapest tickets are for stays of about 4 nights (the very cheapest: 3 nights), booked around 20 days ahead.
Airlines on this route
Airports used
Orlando
Trip essentials
Car rental in Chicago
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Mobile data in Chicago
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Airport transfer in Chicago
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Questions and answers
- What is the cheapest price for flights from Orlando to Chicago?
- The cheapest round-trip ticket found recently costs $130.
- Which month is the cheapest to fly from Orlando to Chicago?
- December 2026 is currently the cheapest month, with tickets from $130.
- Are there direct flights from Orlando to Chicago?
- Yes. Direct flights were found from $130.
- Which airlines fly from Orlando to Chicago?
- Airlines found on this route: American Airlines, Frontier Airlines, Allegiant Air, Southwest Airlines.
- How far is Chicago from Orlando?
- The distance is about 1587 km. A direct flight takes about 3 h 11 min.
- How long is the flight from Orlando to Chicago?
- The shortest flight takes 2 h 48 min; most take about 3 h 6 min.
- Which airports do flights from Orlando to Chicago use?
- Most depart from Orlando International Airport and arrive at O'Hare International Airport.
- What is the cheapest day of the week to fly from Orlando to Chicago?
- In the next two months, Friday departures are the cheapest; the single cheapest day is 6 November at $82.