Flights from Jacksonville to the Midwest for 3 days

Flights for your trip

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

2026-11-20 · one way · $155.00

• American Airlines AA4151: JAX 2026-11-20 12:39:00 → ORD 2026-11-20 14:30:00; nonstop; 171 minutes. Local airport times.

2026-11-20 · one way · $160.00

• United Airlines UA4718: JAX 2026-11-20 12:00:00 → ORD 2026-11-20 13:56:00; nonstop; 176 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $339.25

• American Airlines AA1329: JAX 2026-11-27 06:38:00 → ORD 2026-11-27 08:32:00; nonstop; 174 minutes. Local airport times.
• American Airlines AA3564: ORD 2026-12-04 13:43:00 → JAX 2026-12-04 17:17:00; nonstop; 154 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $350.75

• United Airlines UA4718: JAX 2026-11-20 12:00:00 → ORD 2026-11-20 13:56:00; nonstop; 176 minutes. Local airport times.
• United Airlines UA1113: ORD 2026-11-23 10:42:00 → JAX 2026-11-23 14:13:00; nonstop; 151 minutes. Local airport times.

2026-11-20 · one way · $100.00

• Frontier Airlines F92862 / F92113: JAX 2026-11-20 09:09:00 → ORD 2026-11-20 14:12:00; 1 stop(s) via PHL; 363 minutes. Local airport times.
  • F92862: JAX 2026-11-20 09:09:00 → PHL 2026-11-20 11:21:00; layover at PHL: 78 minutes.
  • F92113: PHL 2026-11-20 12:39:00 → ORD 2026-11-20 14:12:00.

2026-11-20 · one way · $160.00

• Delta Air Lines DL2333 / DL1084: JAX 2026-11-20 12:00:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 450 minutes. Local airport times.
  • DL2333: JAX 2026-11-20 12:00:00 → DTW 2026-11-20 14:20:00; layover at DTW: 216 minutes.
  • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.

2026-11-27 → 2026-12-04 · $276.00

• Frontier Airlines F91549 / F93397: JAX 2026-11-27 17:47:00 → ORD 2026-11-27 21:42:00; 1 stop(s) via ATL; 295 minutes. Local airport times.
  • F91549: JAX 2026-11-27 17:47:00 → ATL 2026-11-27 19:23:00; layover at ATL: 62 minutes.
  • F93397: ATL 2026-11-27 20:25:00 → ORD 2026-11-27 21:42:00.
• United Airlines UA460: ORD 2026-12-04 14:29:00 → JAX 2026-12-04 18:01:00; nonstop; 152 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $350.75

• Delta Air Lines DL3024 / DL2879: JAX 2026-11-20 14:27:00 → ORD 2026-11-20 19:05:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
  • DL3024: JAX 2026-11-20 14:27:00 → ATL 2026-11-20 15:42:00; layover at ATL: 123 minutes.
  • DL2879: ATL 2026-11-20 17:45:00 → ORD 2026-11-20 19:05:00.
• Delta Air Lines DL1477 / DL2315: ORD 2026-11-23 15:59:00 → JAX 2026-11-23 21:55:00; 1 stop(s) via ATL; 296 minutes. Local airport times.
  • DL1477: ORD 2026-11-23 15:59:00 → ATL 2026-11-23 18:54:00; layover at ATL: 111 minutes.
  • DL2315: ATL 2026-11-23 20:45:00 → JAX 2026-11-23 21:55:00.

2026-11-20 · one way · $155.00

• American Airlines AA1329: JAX 2026-11-20 06:38:00 → ORD 2026-11-20 08:32:00; nonstop; 174 minutes. Local airport times.

2026-11-20 · one way · $160.00

• United Airlines UA2414: JAX 2026-11-20 07:30:00 → ORD 2026-11-20 09:19:00; nonstop; 169 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $339.25

• American Airlines AA1329: JAX 2026-11-20 06:38:00 → ORD 2026-11-20 08:32:00; nonstop; 174 minutes. Local airport times.
• American Airlines AA3526: ORD 2026-11-23 13:33:00 → JAX 2026-11-23 17:04:00; nonstop; 151 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $339.25

• American Airlines AA4151: JAX 2026-11-20 12:39:00 → ORD 2026-11-20 14:30:00; nonstop; 171 minutes. Local airport times.
• American Airlines AA3526: ORD 2026-11-23 13:33:00 → JAX 2026-11-23 17:04:00; nonstop; 151 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $339.25

• American Airlines AA4151: JAX 2026-11-27 12:39:00 → ORD 2026-11-27 14:30:00; nonstop; 171 minutes. Local airport times.
• American Airlines AA3564: ORD 2026-12-04 13:43:00 → JAX 2026-12-04 17:17:00; nonstop; 154 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $350.75

• United Airlines UA4718: JAX 2026-11-27 12:00:00 → ORD 2026-11-27 13:56:00; nonstop; 176 minutes. Local airport times.
• United Airlines UA460: ORD 2026-12-04 14:29:00 → JAX 2026-12-04 18:01:00; nonstop; 152 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $350.75

• United Airlines UA2414: JAX 2026-11-27 07:30:00 → ORD 2026-11-27 09:19:00; nonstop; 169 minutes. Local airport times.
• United Airlines UA460: ORD 2026-12-04 14:29:00 → JAX 2026-12-04 18:01:00; nonstop; 152 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $350.75

• United Airlines UA2414: JAX 2026-11-20 07:30:00 → ORD 2026-11-20 09:19:00; nonstop; 169 minutes. Local airport times.
• United Airlines UA1113: ORD 2026-11-23 10:42:00 → JAX 2026-11-23 14:13:00; nonstop; 151 minutes. Local airport times.

2026-11-20 · one way · $100.00

• Frontier Airlines F91549 / F93397: JAX 2026-11-20 17:47:00 → ORD 2026-11-20 21:42:00; 1 stop(s) via ATL; 295 minutes. Local airport times.
  • F91549: JAX 2026-11-20 17:47:00 → ATL 2026-11-20 19:23:00; layover at ATL: 62 minutes.
  • F93397: ATL 2026-11-20 20:25:00 → ORD 2026-11-20 21:42:00.

2026-11-20 · one way · $145.00

• American Airlines AA1526 / AA1409: JAX 2026-11-20 05:00:00 → ORD 2026-11-20 08:59:00; 1 stop(s) via CLT; 299 minutes. Local airport times.
  • AA1526: JAX 2026-11-20 05:00:00 → CLT 2026-11-20 06:25:00; layover at CLT: 66 minutes.
  • AA1409: CLT 2026-11-20 07:31:00 → ORD 2026-11-20 08:59:00.

2026-11-20 · one way · $150.00

• United Airlines UA6170 / UA421: JAX 2026-11-20 19:10:00 → ORD 2026-11-21 00:01:00; 1 stop(s) via IAD; 351 minutes. Local airport times.
  • UA6170: JAX 2026-11-20 19:10:00 → IAD 2026-11-20 21:05:00; layover at IAD: 102 minutes.
  • UA421: IAD 2026-11-20 22:47:00 → ORD 2026-11-21 00:01:00.

2026-11-20 · one way · $160.00

• Delta Air Lines DL3024 / DL2879: JAX 2026-11-20 14:27:00 → ORD 2026-11-20 19:05:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
  • DL3024: JAX 2026-11-20 14:27:00 → ATL 2026-11-20 15:42:00; layover at ATL: 123 minutes.
  • DL2879: ATL 2026-11-20 17:45:00 → ORD 2026-11-20 19:05:00.

2026-11-27 → 2026-12-04 · $276.00

• Frontier Airlines F92862 / F92113: JAX 2026-11-27 09:09:00 → ORD 2026-11-27 14:12:00; 1 stop(s) via PHL; 363 minutes. Local airport times.
  • F92862: JAX 2026-11-27 09:09:00 → PHL 2026-11-27 11:21:00; layover at PHL: 78 minutes.
  • F92113: PHL 2026-11-27 12:39:00 → ORD 2026-11-27 14:12:00.
• United Airlines UA460: ORD 2026-12-04 14:29:00 → JAX 2026-12-04 18:01:00; nonstop; 152 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $286.75

• Frontier Airlines F92862 / F92113: JAX 2026-11-20 09:09:00 → ORD 2026-11-20 14:12:00; 1 stop(s) via PHL; 363 minutes. Local airport times.
  • F92862: JAX 2026-11-20 09:09:00 → PHL 2026-11-20 11:21:00; layover at PHL: 78 minutes.
  • F92113: PHL 2026-11-20 12:39:00 → ORD 2026-11-20 14:12:00.
• American Airlines AA3526: ORD 2026-11-23 13:33:00 → JAX 2026-11-23 17:04:00; nonstop; 151 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $286.75

• Frontier Airlines F91549 / F93397: JAX 2026-11-20 17:47:00 → ORD 2026-11-20 21:42:00; 1 stop(s) via ATL; 295 minutes. Local airport times.
  • F91549: JAX 2026-11-20 17:47:00 → ATL 2026-11-20 19:23:00; layover at ATL: 62 minutes.
  • F93397: ATL 2026-11-20 20:25:00 → ORD 2026-11-20 21:42:00.
• American Airlines AA3526: ORD 2026-11-23 13:33:00 → JAX 2026-11-23 17:04:00; nonstop; 151 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $329.50

• American Airlines AA1526 / AA1409: JAX 2026-11-27 05:00:00 → ORD 2026-11-27 08:59:00; 1 stop(s) via CLT; 299 minutes. Local airport times.
  • AA1526: JAX 2026-11-27 05:00:00 → CLT 2026-11-27 06:25:00; layover at CLT: 66 minutes.
  • AA1409: CLT 2026-11-27 07:31:00 → ORD 2026-11-27 08:59:00.
• American Airlines AA3564: ORD 2026-12-04 13:43:00 → JAX 2026-12-04 17:17:00; nonstop; 154 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $331.75

• American Airlines AA1329: JAX 2026-11-27 06:14:00 → ORD 2026-11-27 08:15:00; nonstop; 181 minutes. Local airport times.
• American Airlines AA1784 / AA2898: ORD 2026-12-04 06:41:00 → JAX 2026-12-04 12:43:00; 1 stop(s) via CLT; 302 minutes. Local airport times.
  • AA1784: ORD 2026-12-04 06:41:00 → CLT 2026-12-04 09:55:00; layover at CLT: 84 minutes.
  • AA2898: CLT 2026-12-04 11:19:00 → JAX 2026-12-04 12:43:00.

2026-11-20 → 2026-11-23 · $331.75

• American Airlines AA1526 / AA1409: JAX 2026-11-20 05:00:00 → ORD 2026-11-20 08:59:00; 1 stop(s) via CLT; 299 minutes. Local airport times.
  • AA1526: JAX 2026-11-20 05:00:00 → CLT 2026-11-20 06:25:00; layover at CLT: 66 minutes.
  • AA1409: CLT 2026-11-20 07:31:00 → ORD 2026-11-20 08:59:00.
• American Airlines AA3526: ORD 2026-11-23 13:33:00 → JAX 2026-11-23 17:04:00; nonstop; 151 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $337.75

• United Airlines UA6170 / UA421: JAX 2026-11-27 19:10:00 → ORD 2026-11-28 00:01:00; 1 stop(s) via IAD; 351 minutes. Local airport times.
  • UA6170: JAX 2026-11-27 19:10:00 → IAD 2026-11-27 21:05:00; layover at IAD: 102 minutes.
  • UA421: IAD 2026-11-27 22:47:00 → ORD 2026-11-28 00:01:00.
• United Airlines UA460: ORD 2026-12-04 14:29:00 → JAX 2026-12-04 18:01:00; nonstop; 152 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $340.75

• United Airlines UA6170 / UA421: JAX 2026-11-20 19:10:00 → ORD 2026-11-21 00:01:00; 1 stop(s) via IAD; 351 minutes. Local airport times.
  • UA6170: JAX 2026-11-20 19:10:00 → IAD 2026-11-20 21:05:00; layover at IAD: 102 minutes.
  • UA421: IAD 2026-11-20 22:47:00 → ORD 2026-11-21 00:01:00.
• United Airlines UA1113: ORD 2026-11-23 10:42:00 → JAX 2026-11-23 14:13:00; nonstop; 151 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $350.75

• Delta Air Lines DL3024 / DL2879: JAX 2026-11-27 14:27:00 → ORD 2026-11-27 19:05:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
  • DL3024: JAX 2026-11-27 14:27:00 → ATL 2026-11-27 15:42:00; layover at ATL: 123 minutes.
  • DL2879: ATL 2026-11-27 17:45:00 → ORD 2026-11-27 19:05:00.
• Delta Air Lines DL1477 / DL2315: ORD 2026-12-04 15:59:00 → JAX 2026-12-04 21:55:00; 1 stop(s) via ATL; 296 minutes. Local airport times.
  • DL1477: ORD 2026-12-04 15:59:00 → ATL 2026-12-04 18:54:00; layover at ATL: 111 minutes.
  • DL2315: ATL 2026-12-04 20:45:00 → JAX 2026-12-04 21:55:00.

2026-11-20 → 2026-11-23 · $350.75

• Delta Air Lines DL2333 / DL1084: JAX 2026-11-20 12:00:00 → ORD 2026-11-20 18:30:00; 1 stop(s) via DTW; 450 minutes. Local airport times.
  • DL2333: JAX 2026-11-20 12:00:00 → DTW 2026-11-20 14:20:00; layover at DTW: 216 minutes.
  • DL1084: DTW 2026-11-20 17:56:00 → ORD 2026-11-20 18:30:00.
• Delta Air Lines DL1477 / DL2315: ORD 2026-11-23 15:59:00 → JAX 2026-11-23 21:55:00; 1 stop(s) via ATL; 296 minutes. Local airport times.
  • DL1477: ORD 2026-11-23 15:59:00 → ATL 2026-11-23 18:54:00; layover at ATL: 111 minutes.
  • DL2315: ATL 2026-11-23 20:45:00 → JAX 2026-11-23 21:55:00.

More dates for this route

• Nov 20, 2026 → Nov 23, 2026
• Nov 27, 2026 → Dec 4, 2026
• Nov 20, 2026 · One way

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The Midwest for 3 days from other cities

Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.

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Where to stay: Where to stay in Chicago: the 10 best neighborhoods, ranked · Chicago hotels where a family of four can share one room

Hotels with an Axel review in Chicago: Claridge House Chicago, Tapestry Collection by Hilton · Freehand Chicago · Warwick Allerton - Chicago · The Chicago Hotel Collection - Wrigleyville · The Chicago Hotel Collection Magnificent Mile Hotel & Suites · All 154 reviewed hotels in Chicago

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