Chicago to Jacksonville (JAX) flight deals
Chicago to Jacksonville (JAX) from $244 round trip, Nov 10 to 17, 2026, American Airlines nonstop, airline price $257. Checked Oct 23, 2026.
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Fare examples by month
Round-trip totals · Economy · USD. Choose a month to see the dates.
| Month | Travelers / trip length | Axel | Airline fare |
|---|---|---|---|
| November 2026 | 1 adult · 7 days | $244–$452 | $257–$477 |
| December 2026 | 1 adult · 2–7 days | $244–$329 | $257–$348 |
| February 2027 | 1 adult · 4 days | $279 | $295 |
| March 2027 | 1 adult · 7 days | $390 | $411 |
More months: October 2026
Flights from Chicago · Chicago to United States flight deals
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Fares observed October 16 – 23, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
October 2026
1 adult · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Oct 30–Nov 6, 2026 · 7 days | Out: Frontier Airlines 2292 / 1550 · 1 stop (ATL) · 10h 52m · 06:16–18:08 local | From $264 · Save $14 | From $278 | Check Axel prices |
| MDW | Oct 30–Nov 6, 2026 · 7 days | Out: Southwest Airlines 4987 · Nonstop · 2h 20m · 14:55–18:15 local | From $433 · Save $25 | From $458 | Check Axel prices |
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November 2026
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 10–17, 2026 · 7 days | Out: American Airlines 1312 · Nonstop · 2h 26m · 19:20–22:46 local; Return: American Airlines 1329 · Nonstop · 3h 1m · 06:28–08:29 local | $244 · Save $13 | $257 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Nov 21–28, 2026 · 7 days | Out: United Airlines 3693 · Nonstop · 2h 42m · 20:00–23:42 local; Return: United Airlines 1733 · Nonstop · 2h 49m · 07:20–09:09 local | $452 · Save $25 | $477 | Customer link — Open these flights in Axel · Optional: check axel prices |
1 adult · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Nov 3–10, 2026 · 7 days | Out: Southwest Airlines 2886 / 3050 / 384 · 2 stops (ATL, DAL) · 7h 55m · 13:20–22:15 local | From $442 · Save $25 | From $467 | Check Axel prices |
| MDW | Nov 6–13, 2026 · 7 days | Out: Southwest Airlines 2178 · Nonstop · 2h 20m · 19:00–22:20 local | From $265 · Save $15 | From $280 | Check Axel prices |
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December 2026
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 19–26, 2026 · 7 days | Out: United Airlines 3475 · Nonstop · 2h 43m · 17:59–21:42 local; Return: United Airlines 1733 · Nonstop · 2h 51m · 07:09–09:00 local | $329 · Save $19 | $348 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 29–31, 2026 · 2 days | Out: American Airlines 1587 · Nonstop · 2h 32m · 19:01–22:33 local; Return: American Airlines 1887 · Nonstop · 2h 59m · 06:56–08:55 local | $244 · Save $13 | $257 | Customer link — Open these flights in Axel · Optional: check axel prices |
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February 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Feb 12–16, 2027 · 4 days | Out: United Airlines 1557 · Nonstop · 2h 33m · 17:55–21:28 local; Return: American Airlines 2100 · Nonstop · 2h 51m · 06:42–08:33 local | $279 · Save $16 | $295 | Customer link — Open these flights in Axel · Optional: check axel prices |
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March 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Mar 13–20, 2027 · 7 days | Out: American Airlines 2072 · Nonstop · 2h 27m · 18:24–21:51 local; Return: American Airlines 2100 · Nonstop · 2h 51m · 06:42–08:33 local | $390 · Save $21 | $411 | Customer link — Open these flights in Axel · Optional: check axel prices |
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The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Trip ideas from Chicago with Jacksonville (JAX)
- Florida vacations from Chicago: fly Nov 21 – Nov 28, 2026
- College football bowl and playoff trips from Chicago: fly Dec 29 – Dec 31, 2026
- Golf trips from Chicago
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Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Amelia Island has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Chicago to Jacksonville (JAX) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.