Jacksonville (JAX) to Chicago (MDW) · Jan 3, 2027 · return Jan 9, 2027

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Jan 3–9, 2027 · 6 nights · 2 adults, 1 room): 3★ The Willows Hotel, $578 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $663 total · 5★ Nobu Hotel Chicago, $2,091 total

All hotels in Chicago

Route overview: Jacksonville to Chicago (MDW) flight deals

2027-01-03 → 2027-01-09 · Axel-exclusive $323.35

• Southwest Airlines WN2264: JAX 2027-01-03 18:55:00 → MDW 2027-01-03 20:20:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-01-09 19:00:00 → JAX 2027-01-09 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-03 → 2027-01-09 · Axel-exclusive $206.28

• Frontier Airlines F91549 / F92291: JAX 2027-01-03 19:03:00 → MDW 2027-01-03 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-01-03 19:03:00 → ATL 2027-01-03 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-01-03 22:48:00 → MDW 2027-01-03 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-01-09 13:11:00 → JAX 2027-01-09 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-01-09 13:11:00 → ATL 2027-01-09 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-01-09 18:09:00 → JAX 2027-01-09 19:25:00.

2027-01-03 → 2027-01-09 · Axel-exclusive $367.95

• Delta Air Lines DL2333 / DL4677: JAX 2027-01-03 12:00:00 → MDW 2027-01-03 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
  • DL2333: JAX 2027-01-03 12:00:00 → DTW 2027-01-03 14:20:00; layover at DTW: 200 minutes.
  • DL4677: DTW 2027-01-03 17:40:00 → MDW 2027-01-03 18:01:00.
• Delta Air Lines DL2417 / DL2265: MDW 2027-01-09 13:02:00 → JAX 2027-01-09 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
  • DL2417: MDW 2027-01-09 13:02:00 → ATL 2027-01-09 16:01:00; layover at ATL: 212 minutes.
  • DL2265: ATL 2027-01-09 19:33:00 → JAX 2027-01-09 20:43:00.

2027-01-03 → 2027-01-09 · Axel-exclusive $323.35

• Southwest Airlines WN1979: JAX 2027-01-03 13:30:00 → MDW 2027-01-03 14:55:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN2946: MDW 2027-01-09 19:00:00 → JAX 2027-01-09 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-03 → 2027-01-09 · Axel-exclusive $313.75

• Southwest Airlines WN2265 / WN287: JAX 2027-01-03 06:00:00 → MDW 2027-01-03 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN2265: JAX 2027-01-03 06:00:00 → STL 2027-01-03 07:20:00; layover at STL: 215 minutes.
  • WN287: STL 2027-01-03 10:55:00 → MDW 2027-01-03 12:05:00.
• Southwest Airlines WN2946: MDW 2027-01-09 19:00:00 → JAX 2027-01-09 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-03 → 2027-01-09 · Axel-exclusive $313.75

• Southwest Airlines WN2253 / WN2062: JAX 2027-01-03 11:20:00 → MDW 2027-01-03 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
  • WN2253: JAX 2027-01-03 11:20:00 → BNA 2027-01-03 12:05:00; layover at BNA: 160 minutes.
  • WN2062: BNA 2027-01-03 14:45:00 → MDW 2027-01-03 16:15:00.
• Southwest Airlines WN2946: MDW 2027-01-09 19:00:00 → JAX 2027-01-09 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-03 → 2027-01-09 · Axel-exclusive $313.75

• Southwest Airlines WN2256 / WN1070: JAX 2027-01-03 08:00:00 → MDW 2027-01-03 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-01-03 08:00:00 → BWI 2027-01-03 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-01-03 11:05:00 → MDW 2027-01-03 12:15:00.
• Southwest Airlines WN2946: MDW 2027-01-09 19:00:00 → JAX 2027-01-09 22:15:00; nonstop; 135 minutes. Local airport times.

2027-01-03 → 2027-01-09 · Axel-exclusive $367.95

• Delta Air Lines DL2627 / DL1076: JAX 2027-01-03 18:59:00 → MDW 2027-01-03 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
  • DL2627: JAX 2027-01-03 18:59:00 → ATL 2027-01-03 20:19:00; layover at ATL: 61 minutes.
  • DL1076: ATL 2027-01-03 21:20:00 → MDW 2027-01-03 22:17:00.
• Delta Air Lines DL2417 / DL2265: MDW 2027-01-09 13:02:00 → JAX 2027-01-09 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
  • DL2417: MDW 2027-01-09 13:02:00 → ATL 2027-01-09 16:01:00; layover at ATL: 212 minutes.
  • DL2265: ATL 2027-01-09 19:33:00 → JAX 2027-01-09 20:43:00.

Explore this route

• All dates for this route
• Jan 2, 2027 · Return options
• Jan 4, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Jacksonville (JAX) to Chicago (MDW) · Jan 3, 2027 · return Jan 9, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Jacksonville to Chicago (MDW) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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