Cheap flights from Chicago to Orlando
Cheapest return fare right now: $150Nov 2 – Nov 6 · Frontier Airlines
- Direct flights
- Yes
- Typical flight time
- 2 h 39 min
- Price range seen
- $150 – $264
- Cheapest month (next 3 months)
- November 2026
Best dates
| Dates | Nights | Airline | Stops | From | Price | |
|---|---|---|---|---|---|---|
| Nov 2 – Nov 6 | 4 | Frontier Airlines | 1 | Chicago Midway | $150 | Book → |
| Nov 14 – Nov 16 | 3 | Frontier Airlines | 1 | Chicago O'Hare | $164 | Book → |
| Oct 31 – Nov 14 | 14 | Frontier Airlines | 1 | Chicago O'Hare | $175 | Book → |
| Nov 7 – Nov 9 | 2 | Frontier Airlines | Direct | Chicago O'Hare | $205 | Book → |
| Oct 13 – Oct 20 | 7 | Frontier Airlines | 1 | Chicago O'Hare | $254 | Book → |
| Nov 5 – Nov 9 | 4 | Frontier Airlines | 1 | Chicago O'Hare | $264 | Book → |
Prices checked on October 12, 2026.
Some links are affiliate links — we may earn a small commission at no extra cost to you.
Search flightsTravel guide: United States →Current flight deals from USA →
Plan your trip to United States
Flight delayed or cancelled? Claim up to €600
Check in two minutes whether you're owed compensation.
Some links are affiliate links — we may earn a small commission at no extra cost to you.
Other routes from Chicago
Weekly flight deals
Weekly flight deals from your country, every Sunday. Free, unsubscribe anytime.