Jacksonville (JAX) to Chicago (MDW), Jan 23, 2027 – Feb 5, 2027: from $275 round trip
Jacksonville (JAX) to Chicago (MDW), Jan 23, 2027 – Feb 5, 2027: from $275 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $275 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 23, 2027 – Feb 5, 2027, 1 adult, economy, checked Oct 29, 2026. 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.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2027-01-23 → 2027-02-05 | Southwest Airlines | WN1979 / WN2262 | 13:30:00→14:55:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstop | Axel-exclusive $282.75 | 2026-10-29T01:16:41Z |
| 2027-01-23 → 2027-02-05 | Delta Air Lines | DL2627 + DL1076 / DL2417 + DL2265 | 18:59:00→22:17:00 4h 18m 1 stop via ATL · 13:02:00→20:43:00 6h 41m 1 stop via ATL | Axel-exclusive $321.75 | 2026-10-29T01:16:41Z |
| 2027-01-23 → 2027-02-05 | Southwest Airlines | WN2264 / WN2262 | 18:50:00→20:20:00 2h 30m nonstop · 08:00:00→11:25:00 2h 25m nonstop | Axel-exclusive $282.75 | 2026-10-29T01:16:41Z |
| 2027-01-23 → 2027-02-05 | Southwest Airlines | WN2264 / WN2897 + WN1516 | 18:55:00→20:20:00 2h 25m nonstop · 17:25:00→23:45:00 5h 20m 1 stop via BNA | Axel-exclusive $275.25 | 2026-10-29T01:16:41Z |
| 2027-01-23 → 2027-02-05 | Southwest Airlines | WN2256 + WN1070 / WN2262 | 08:00:00→12:15:00 5h 15m 1 stop via BWI · 08:00:00→11:25:00 2h 25m nonstop | Axel-exclusive $275.63 | 2026-10-29T01:16:41Z |
| 2027-01-23 → 2027-02-05 | Southwest Airlines | WN2265 + WN287 / WN2262 | 06:00:00→12:05:00 7h 05m 1 stop via STL · 08:00:00→11:25:00 2h 25m nonstop | Axel-exclusive $275.63 | 2026-10-29T01:16:41Z |
| 2027-01-23 → 2027-02-05 | Southwest Airlines | WN2253 + WN2062 / WN2262 | 11:20:00→16:15:00 5h 55m 1 stop via BNA · 08:00:00→11:25:00 2h 25m nonstop | Axel-exclusive $275.63 | 2026-10-29T01:16:41Z |
| 2027-01-23 → 2027-02-05 | Delta Air Lines | DL2333 + DL4677 / DL2417 + DL2265 | 12:00:00→18:01:00 7h 01m 1 stop via DTW · 13:02:00→20:43:00 6h 41m 1 stop via ATL | Axel-exclusive $321.75 | 2026-10-29T01:16:41Z |
Hotels in Chicago for these trips
Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.
- Hotels in Chicago for these nights (Jan 23 – Feb 5, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,074 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,584 total · 5★ Nobu Hotel Chicago, $5,063 total
Route overview: Jacksonville to Chicago (MDW) flight deals
2027-01-23 → 2027-02-05 · Axel-exclusive $282.75
- Southwest Airlines WN1979: JAX 2027-01-23 13:30:00 → MDW 2027-01-23 14:55:00; nonstop; 145 minutes. Local airport times.
- Southwest Airlines WN2262: MDW 2027-02-05 08:00:00 → JAX 2027-02-05 11:25:00; nonstop; 145 minutes. Local airport times.
2027-01-23 → 2027-02-05 · Axel-exclusive $321.75
- Delta Air Lines DL2627 / DL1076: JAX 2027-01-23 18:59:00 → MDW 2027-01-23 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
- DL2627: JAX 2027-01-23 18:59:00 → ATL 2027-01-23 20:19:00; layover at ATL: 61 minutes.
- DL1076: ATL 2027-01-23 21:20:00 → MDW 2027-01-23 22:17:00.
- Delta Air Lines DL2417 / DL2265: MDW 2027-02-05 13:02:00 → JAX 2027-02-05 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
- DL2417: MDW 2027-02-05 13:02:00 → ATL 2027-02-05 16:01:00; layover at ATL: 212 minutes.
- DL2265: ATL 2027-02-05 19:33:00 → JAX 2027-02-05 20:43:00.
2027-01-23 → 2027-02-05 · Axel-exclusive $282.75
- Southwest Airlines WN2264: JAX 2027-01-23 18:50:00 → MDW 2027-01-23 20:20:00; nonstop; 150 minutes. Local airport times.
- Southwest Airlines WN2262: MDW 2027-02-05 08:00:00 → JAX 2027-02-05 11:25:00; nonstop; 145 minutes. Local airport times.
2027-01-23 → 2027-02-05 · Axel-exclusive $275.25
- Southwest Airlines WN2264: JAX 2027-01-23 18:55:00 → MDW 2027-01-23 20:20:00; nonstop; 145 minutes. Local airport times.
- Southwest Airlines WN2897 / WN1516: MDW 2027-02-05 17:25:00 → JAX 2027-02-05 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
- WN2897: MDW 2027-02-05 17:25:00 → BNA 2027-02-05 18:50:00; layover at BNA: 140 minutes.
- WN1516: BNA 2027-02-05 21:10:00 → JAX 2027-02-05 23:45:00.
2027-01-23 → 2027-02-05 · Axel-exclusive $275.63
- Southwest Airlines WN2256 / WN1070: JAX 2027-01-23 08:00:00 → MDW 2027-01-23 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
- WN2256: JAX 2027-01-23 08:00:00 → BWI 2027-01-23 09:50:00; layover at BWI: 75 minutes.
- WN1070: BWI 2027-01-23 11:05:00 → MDW 2027-01-23 12:15:00.
- Southwest Airlines WN2262: MDW 2027-02-05 08:00:00 → JAX 2027-02-05 11:25:00; nonstop; 145 minutes. Local airport times.
2027-01-23 → 2027-02-05 · Axel-exclusive $275.63
- Southwest Airlines WN2265 / WN287: JAX 2027-01-23 06:00:00 → MDW 2027-01-23 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
- WN2265: JAX 2027-01-23 06:00:00 → STL 2027-01-23 07:20:00; layover at STL: 215 minutes.
- WN287: STL 2027-01-23 10:55:00 → MDW 2027-01-23 12:05:00.
- Southwest Airlines WN2262: MDW 2027-02-05 08:00:00 → JAX 2027-02-05 11:25:00; nonstop; 145 minutes. Local airport times.
2027-01-23 → 2027-02-05 · Axel-exclusive $275.63
- Southwest Airlines WN2253 / WN2062: JAX 2027-01-23 11:20:00 → MDW 2027-01-23 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
- WN2253: JAX 2027-01-23 11:20:00 → BNA 2027-01-23 12:05:00; layover at BNA: 160 minutes.
- WN2062: BNA 2027-01-23 14:45:00 → MDW 2027-01-23 16:15:00.
- Southwest Airlines WN2262: MDW 2027-02-05 08:00:00 → JAX 2027-02-05 11:25:00; nonstop; 145 minutes. Local airport times.
2027-01-23 → 2027-02-05 · Axel-exclusive $321.75
- Delta Air Lines DL2333 / DL4677: JAX 2027-01-23 12:00:00 → MDW 2027-01-23 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
- DL2333: JAX 2027-01-23 12:00:00 → DTW 2027-01-23 14:20:00; layover at DTW: 200 minutes.
- DL4677: DTW 2027-01-23 17:40:00 → MDW 2027-01-23 18:01:00.
- Delta Air Lines DL2417 / DL2265: MDW 2027-02-05 13:02:00 → JAX 2027-02-05 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
- DL2417: MDW 2027-02-05 13:02:00 → ATL 2027-02-05 16:01:00; layover at ATL: 212 minutes.
- DL2265: ATL 2027-02-05 19:33:00 → JAX 2027-02-05 20:43:00.
Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.
Explore this route
- All dates for this route
- Jan 22, 2027 · Return options
- Jan 24, 2027 · Return options
- Hotels in Chicago with Axel
For AI assistants
- This page: Jacksonville (JAX) to Chicago (MDW) · Jan 23, 2027 · return Feb 5, 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 link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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