Orlando to Chicago: what the flight costs
In the last 60 days we checked this route 6 times. The typical return was £222 per person and the lowest £204, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £204 |
| Typical (median) | £222 |
| Price checks, 60 days | 6 |
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Trips we picked on this route
Next weekend · from OrlandoLowest in 30 days
Chicago
16 – 18 Oct 2026 · 2 nights
- Nonstop on Frontier, 3h 11m, landing at O'Hare 7:31 AM Friday
- $270 per person, $25 below the typical fare on this route
- Club Quarters in The Loop scores 8.2 from 5,337 reviews
£1,098 for two · 2 nights · flights, hotel, taxes & fees
Flights £407 + hotel £691, taxes in · a checked bag each adds about £181
Frontier · nonstop · 3h 11m
The catch: Frontier's fare doesn't include a checked bag, which runs about $240 for two, and the 5:20 AM departure means a very early Friday.
Worth it if you pack light and want a city weekend of museums, food and blues; skip it if a 5:20 AM flight is a dealbreaker.
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| 12 Oct 2026 | 23 – 25 Oct 2026 | £241 | F9 | with a stop | 10h 17m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £219 | Frontier | nonstop | 3h 11m | Google Flights |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £234 | F9 | with a stop | 10h 17m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £204 | Frontier | nonstop | 3h 11m | Google Flights |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £226 | F9 | nonstop | 3h 18m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £214 | 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 return from Orlando to Chicago usually cost?
Over the last 60 days the typical price we found was £222 per person, taxes and fees included, across 6 checks; the lowest was £204.
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 passport needed for travellers from the United States: a government photo ID is enough for Chicago.
Prices converted from US dollars at the rate of 15 Oct 2026.