Chicago to Jacksonville (JAX) flight deals
Compare Chicago to Jacksonville (JAX) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
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Browse months: October 2026 · November 2026
Flights from Chicago · Chicago to United States flight deals
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Fares observed October 16, 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 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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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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Hotels in Amelia Island with Axel
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.