Orlando to Chicago: what the flight costs
In the last 60 days we checked this route 6 times. The typical round trip was $295 per person and the lowest $270, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | $270 |
| Typical (median) | $295 |
| Price checks, 60 days | 6 |
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Trips we picked on this route
$295 $270 per person, round trip, taxes and fees included You save $25 (8%)
the typical fare on this route
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| Oct 12, 2026 | Oct 23–25, 2026 | $320 | F9 | with a stop | 10h 17m | Kiwi.com |
| Oct 12, 2026 | Oct 23–25, 2026 | $290 | Frontier | nonstop | 3h 11m | Google Flights |
| Oct 12, 2026 | Oct 16–18, 2026 | $310 | F9 | with a stop | 10h 17m | Kiwi.com |
| Oct 12, 2026 | Oct 16–18, 2026 | $270 | Frontier | nonstop | 3h 11m | Google Flights |
| Oct 12, 2026 | Oct 23–25, 2026 | $300 | F9 | nonstop | 3h 18m | Kiwi.com |
| Oct 12, 2026 | Oct 16–18, 2026 | $284 | F9 | nonstop | 3h 18m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about Orlando to Chicago
What does a round trip from Orlando to Chicago usually cost?
Over the last 60 days the typical price we found was $295 per person, taxes and fees included, across 6 checks; the lowest was $270.
When is the best time to fly from Orlando to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from Orlando to Chicago?
No, a government photo ID is enough for US citizens.