Jacksonville (JAX) to Chicago (MDW), Apr 22, 2027: round trips from $225, one way from $120

Jacksonville (JAX) to Chicago (MDW), Apr 22, 2027: round trips from $225, one way from $120 on Axel, checked Nov 11, 2026. Lowest published fares: $225 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Apr 22–23, 2027; $120 one way, Axel-exclusive, Frontier Airlines, 1 stop, Apr 22, 2027; 1 adult, economy, checked Nov 11, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

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 nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Apr 22–23, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $140 a night · 4★ Warwick Allerton - Chicago, $160 a night · 5★ Nobu Hotel Chicago, $404 a night
• Hotels in Chicago for these nights (Apr 22–24, 2027 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $161 a night, $321 for 2 nights · 4★ Warwick Allerton - Chicago, $165 a night, $330 for 2 nights · 5★ Nobu Hotel Chicago, $433 a night, $866 for 2 nights
• Hotels in Chicago for these nights (Apr 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $172 a night, $517 for 3 nights · 4★ Warwick Allerton - Chicago, $169 a night, $507 for 3 nights · 5★ Nobu Hotel Chicago, $440 a night, $1,319 for 3 nights
• Hotels in Chicago for these nights (Apr 22–26, 2027 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey, $161 a night, $645 for 4 nights · 4★ Warwick Allerton - Chicago, $160 a night, $640 for 4 nights · 5★ Nobu Hotel Chicago, $421 a night, $1,684 for 4 nights
• Hotels in Chicago for these nights (Apr 22–27, 2027 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey, $151 a night, $753 for 5 nights · 4★ Warwick Allerton - Chicago, $157 a night, $783 for 5 nights · 5★ Nobu Hotel Chicago, $423 a night, $2,115 for 5 nights
• Hotels in Chicago for these nights (Apr 22–28, 2027 · 6 nights · 2 adults, 1 room): 3★ Hotel Versey, $144 a night, $862 for 6 nights · 4★ Warwick Allerton - Chicago, $155 a night, $931 for 6 nights · 5★ Nobu Hotel Chicago, $430 a night, $2,582 for 6 nights
• Hotels in Chicago for these nights (Apr 22–29, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $138 a night, $969 for 7 nights · 4★ Warwick Allerton - Chicago, $156 a night, $1,089 for 7 nights · 5★ Nobu Hotel Chicago, $432 a night, $3,027 for 7 nights
• Hotels in Chicago for these nights (Apr 22–30, 2027 · 8 nights · 2 adults, 1 room): 3★ Hotel Versey, $136 a night, $1,090 for 8 nights · 4★ Warwick Allerton - Chicago, $156 a night, $1,244 for 8 nights · 5★ Nobu Hotel Chicago, $428 a night, $3,427 for 8 nights
• Hotels in Chicago for these nights (Apr 22 – May 1, 2027 · 9 nights · 2 adults, 1 room): 3★ Hotel Versey, $146 a night, $1,318 for 9 nights · 4★ Warwick Allerton - Chicago, $157 a night, $1,410 for 9 nights · 5★ Nobu Hotel Chicago, $437 a night, $3,935 for 9 nights
• Hotels in Chicago for these nights (Apr 22 – May 2, 2027 · 10 nights · 2 adults, 1 room): 3★ Hotel Versey, $159 a night, $1,590 for 10 nights · 4★ Warwick Allerton - Chicago, $164 a night, $1,640 for 10 nights · 5★ Nobu Hotel Chicago, $440 a night, $4,397 for 10 nights
• Hotels in Chicago for these nights (Apr 22 – May 3, 2027 · 11 nights · 2 adults, 1 room): 3★ Hotel Versey, $161 a night, $1,775 for 11 nights · 4★ Warwick Allerton - Chicago, $166 a night, $1,828 for 11 nights · 5★ Nobu Hotel Chicago, $437 a night, $4,804 for 11 nights
• Hotels in Chicago for these nights (Apr 22 – May 4, 2027 · 12 nights · 2 adults, 1 room): 3★ Hotel Versey, $164 a night, $1,972 for 12 nights · 4★ Warwick Allerton - Chicago, $169 a night, $2,031 for 12 nights · 5★ Nobu Hotel Chicago, $439 a night, $5,270 for 12 nights
• Hotels in Chicago for these nights (Apr 22 – May 5, 2027 · 13 nights · 2 adults, 1 room): 3★ Hotel Versey, $167 a night, $2,170 for 13 nights · 4★ Warwick Allerton - Chicago, $171 a night, $2,223 for 13 nights · 5★ Nobu Hotel Chicago, $448 a night, $5,820 for 13 nights
• Hotels in Chicago for these nights (Apr 22 – May 6, 2027 · 14 nights · 2 adults, 1 room): 3★ Hotel Versey, $169 a night, $2,366 for 14 nights · 4★ Warwick Allerton - Chicago, $173 a night, $2,426 for 14 nights · 5★ Nobu Hotel Chicago, $454 a night, $6,351 for 14 nights

All hotels in Chicago

Route overview: Jacksonville to Chicago (MDW) flight deals

2027-04-22 · one way · Axel-exclusive $120.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.

2027-04-22 · one way · Axel-exclusive $170.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.

2027-04-22 → 2027-04-23 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-04-23 13:11:00 → JAX 2027-04-23 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-04-23 13:11:00 → ATL 2027-04-23 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-04-23 18:09:00 → JAX 2027-04-23 19:25:00.

2027-04-22 → 2027-04-23 · Axel-exclusive $330.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN2262: MDW 2027-04-23 08:00:00 → JAX 2027-04-23 11:25:00; nonstop; 145 minutes. Local airport times.

2027-04-22 → 2027-04-24 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-04-24 13:11:00 → JAX 2027-04-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-04-24 13:11:00 → ATL 2027-04-24 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-04-24 18:09:00 → JAX 2027-04-24 19:25:00.

2027-04-22 → 2027-04-24 · Axel-exclusive $330.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN2946: MDW 2027-04-24 19:00:00 → JAX 2027-04-24 22:15:00; nonstop; 135 minutes. Local airport times.

2027-04-22 → 2027-04-25 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-04-25 13:11:00 → JAX 2027-04-25 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-04-25 13:11:00 → ATL 2027-04-25 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-04-25 18:09:00 → JAX 2027-04-25 19:25:00.

2027-04-22 → 2027-04-25 · Axel-exclusive $320.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN3092 / WN4807: MDW 2027-04-25 13:40:00 → JAX 2027-04-25 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
  • WN3092: MDW 2027-04-25 13:40:00 → STL 2027-04-25 14:55:00; layover at STL: 200 minutes.
  • WN4807: STL 2027-04-25 18:15:00 → JAX 2027-04-25 21:15:00.

2027-04-22 → 2027-04-26 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-04-26 13:11:00 → JAX 2027-04-26 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-04-26 13:11:00 → ATL 2027-04-26 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-04-26 18:09:00 → JAX 2027-04-26 19:25:00.

2027-04-22 → 2027-04-26 · Axel-exclusive $330.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN2946: MDW 2027-04-26 19:00:00 → JAX 2027-04-26 22:15:00; nonstop; 135 minutes. Local airport times.

2027-04-22 → 2027-04-28 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-04-28 13:11:00 → JAX 2027-04-28 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-04-28 13:11:00 → ATL 2027-04-28 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-04-28 18:09:00 → JAX 2027-04-28 19:25:00.

2027-04-22 → 2027-04-28 · Axel-exclusive $330.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN2946: MDW 2027-04-28 19:00:00 → JAX 2027-04-28 22:15:00; nonstop; 135 minutes. Local airport times.

2027-04-22 → 2027-04-29 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-04-29 13:11:00 → JAX 2027-04-29 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-04-29 13:11:00 → ATL 2027-04-29 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-04-29 18:09:00 → JAX 2027-04-29 19:25:00.

2027-04-22 → 2027-04-29 · Axel-exclusive $330.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN2041: MDW 2027-04-29 12:50:00 → JAX 2027-04-29 16:05:00; nonstop; 135 minutes. Local airport times.

2027-04-22 → 2027-04-30 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-04-30 13:11:00 → JAX 2027-04-30 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-04-30 13:11:00 → ATL 2027-04-30 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-04-30 18:09:00 → JAX 2027-04-30 19:25:00.

2027-04-22 → 2027-04-30 · Axel-exclusive $330.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN2262: MDW 2027-04-30 08:00:00 → JAX 2027-04-30 11:25:00; nonstop; 145 minutes. Local airport times.

2027-04-22 → 2027-05-02 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-05-02 13:11:00 → JAX 2027-05-02 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-05-02 13:11:00 → ATL 2027-05-02 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-05-02 18:09:00 → JAX 2027-05-02 19:25:00.

2027-04-22 → 2027-05-02 · Axel-exclusive $320.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN3092 / WN4807: MDW 2027-05-02 13:40:00 → JAX 2027-05-02 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times.
  • WN3092: MDW 2027-05-02 13:40:00 → STL 2027-05-02 14:55:00; layover at STL: 200 minutes.
  • WN4807: STL 2027-05-02 18:15:00 → JAX 2027-05-02 21:15:00.

2027-04-22 → 2027-05-03 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-05-03 13:11:00 → JAX 2027-05-03 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-05-03 13:11:00 → ATL 2027-05-03 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-05-03 18:09:00 → JAX 2027-05-03 19:25:00.

2027-04-22 → 2027-05-03 · Axel-exclusive $330.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN2946: MDW 2027-05-03 19:00:00 → JAX 2027-05-03 22:15:00; nonstop; 135 minutes. Local airport times.

2027-04-22 → 2027-05-04 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-05-04 13:11:00 → JAX 2027-05-04 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-05-04 13:11:00 → ATL 2027-05-04 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-05-04 18:09:00 → JAX 2027-05-04 19:25:00.

2027-04-22 → 2027-05-04 · Axel-exclusive $330.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN2946: MDW 2027-05-04 19:00:00 → JAX 2027-05-04 22:15:00; nonstop; 135 minutes. Local airport times.

2027-04-22 → 2027-05-06 · Axel-exclusive $225.00

• Frontier Airlines F91549 / F92291: JAX 2027-04-22 19:03:00 → MDW 2027-04-22 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
  • F91549: JAX 2027-04-22 19:03:00 → ATL 2027-04-22 20:31:00; layover at ATL: 137 minutes.
  • F92291: ATL 2027-04-22 22:48:00 → MDW 2027-04-22 23:47:00.
• Frontier Airlines F92144 / F91550: MDW 2027-05-06 13:11:00 → JAX 2027-05-06 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
  • F92144: MDW 2027-05-06 13:11:00 → ATL 2027-05-06 16:18:00; layover at ATL: 111 minutes.
  • F91550: ATL 2027-05-06 18:09:00 → JAX 2027-05-06 19:25:00.

2027-04-22 → 2027-05-06 · Axel-exclusive $330.00

• Southwest Airlines WN2256 / WN1070: JAX 2027-04-22 08:00:00 → MDW 2027-04-22 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
  • WN2256: JAX 2027-04-22 08:00:00 → BWI 2027-04-22 09:50:00; layover at BWI: 75 minutes.
  • WN1070: BWI 2027-04-22 11:05:00 → MDW 2027-04-22 12:15:00.
• Southwest Airlines WN2041: MDW 2027-05-06 12:50:00 → JAX 2027-05-06 16:05:00; nonstop; 135 minutes. Local airport times.

Explore this route

• All dates for this route
• Apr 21, 2027 · Return options
• Apr 23, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Jacksonville (JAX) to Chicago (MDW) · Apr 22, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. 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 nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
• 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.

Feedback (optional): Missing info · Axel issue