Jacksonville to Chicago: what the flight costs
In the last 60 days we checked this route 6 times. The typical return was £361 per person and the lowest £308, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £308 |
| Typical (median) | £361 |
| Price checks, 60 days | 6 |
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Trips we picked on this route
The weekend after · from JacksonvilleWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- Hilton Chicago in The Loop, 7.9 from 981 reviews, $522 for two nights
- Fare of $471 per person, $8 below the $479 median
- Highs of 55–71°F, with rain chances of 29% or less
£1,104 for two · 2 nights · flights, hotel, taxes & fees
Flights £710 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 12h 7m
The catch: The Frontier fare has one stop and takes 12h 7m to get there, and a checked bag is about $240 for two on top.
Worth it if you'll trade a long Friday of travel for the lower fare; skip it if layovers on a 2-night trip wear you out.
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 | £376 | MX + B6 | with a stop | 32h 15m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £355 | Frontier | with a stop | 12h 7m | Google Flights |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £369 | MX + F9 | with a stop | 30h 43m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £311 | Frontier | with a stop | 12h 7m | Google Flights |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £308 | F9 | with a stop | 16h 46m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £367 | MX + F9 | with a stop | 24h 44m | 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 Jacksonville to Chicago
What does a return from Jacksonville to Chicago usually cost?
Over the last 60 days the typical price we found was £361 per person, taxes and fees included, across 6 checks; the lowest was £308.
When is the best time to fly from Jacksonville 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 Jacksonville 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.