# Jacksonville (JAX) to Chicago (MDW), Mar 23, 2027: round trips from $222, one way from $120 Jacksonville (JAX) to Chicago (MDW), Mar 23, 2027: round trips from $222, one way from $120 on Axel, checked Nov 10, 2026. Lowest published fares: $222 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Mar 23–24, 2027; $120 one way, Axel-exclusive, Frontier Airlines, 1 stop, Mar 23, 2027; 1 adult, economy, checked Nov 10, 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. | Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price checked | | --- | --- | --- | --- | ---: | --- | | [2027-03-23 · one way](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/one-way) | Southwest Airlines | WN2264 | 18:55:00→20:20:00 2h 25m nonstop | [Axel-exclusive $186.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/trip/one-way/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 · one way](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/one-way) | Frontier Airlines | F91549 + F92291 | 19:03:00→23:47:00 5h 44m 1 stop via ATL | [Axel-exclusive $120.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/trip/one-way/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-24](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-24) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $348.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-24-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-24](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-24) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $222.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-24-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-25](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-25) | Southwest Airlines | WN2264 / WN2041 | 18:55:00→20:20:00 2h 25m nonstop · 12:50:00→16:05:00 2h 15m nonstop | [Axel-exclusive $348.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-25-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-25](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-25) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $222.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-25-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-26](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-26) | Southwest Airlines | WN2264 / WN2262 | 18:55:00→20:20:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstop | [Axel-exclusive $348.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-26-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-26](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-26) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $222.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-26-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-27](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-27) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $348.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-27-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-27](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-27) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $222.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-27-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-28](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-28) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $246.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-28-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-28](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-28) | Southwest Airlines | WN2264 / WN3092 + WN4807 | 18:55:00→20:20:00 2h 25m nonstop · 13:40:00→21:15:00 6h 35m 1 stop via STL | [Axel-exclusive $366.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-28-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-29](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-29) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $378.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-29-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-29](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-29) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $246.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-29-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-30](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-30) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $352.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-30-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-30](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-30) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $229.13](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-30-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-31](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-31) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $352.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-31-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-03-31](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/mar-31) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $229.13](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/march-31-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-01](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-1) | Southwest Airlines | WN2264 / WN2041 | 18:55:00→20:20:00 2h 25m nonstop · 12:50:00→16:05:00 2h 15m nonstop | [Axel-exclusive $344.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-1-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-01](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-1) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $223.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-1-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-02](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-2) | Southwest Airlines | WN2264 / WN2262 | 18:55:00→20:20:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstop | [Axel-exclusive $344.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-2-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-02](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-2) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $223.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-2-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-03](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-3) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $344.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-3-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-03](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-3) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $223.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-3-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-04](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-4) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $223.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-4-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-04](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-4) | Southwest Airlines | WN2264 / WN3092 + WN4807 | 18:55:00→20:20:00 2h 25m nonstop · 13:40:00→21:15:00 6h 35m 1 stop via STL | [Axel-exclusive $334.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-4-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-05](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-5) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $344.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-5-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-05](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-5) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $223.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-5-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-06](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-6) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $344.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-6-2027/adults/1/cabin/economy) | Nov 10, 2026 | | [2027-03-23 → 2027-04-06](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23/apr-6) | Frontier Airlines | F91549 + F92291 / F92144 + F91550 | 19:03:00→23:47:00 5h 44m 1 stop via ATL · 13:11:00→19:25:00 5h 14m 1 stop via ATL | [Axel-exclusive $223.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/march-23-2027/return/april-6-2027/adults/1/cabin/economy) | Nov 10, 2026 | ### 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 (Mar 23–24, 2027 · 1 night · 2 adults, 1 room): 3★ [Hotel Versey, $97 a night](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-03-23/2027-03-24/2-adults) · 4★ [Warwick Allerton - Chicago, $112 a night](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-03-24/2-adults) · 5★ [Waldorf Astoria Chicago, $405 a night](https://helloaxel.com/en/hotels/chicago/waldorf-astoria-chicago-1119995/2027-03-23/2027-03-24/2-adults) - Hotels in Chicago for these nights (Mar 23–25, 2027 · 2 nights · 2 adults, 1 room): 3★ [Hotel Versey, $107 a night, $213 for 2 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-03-23/2027-03-25/2-adults) · 4★ [Warwick Allerton - Chicago, $112 a night, $224 for 2 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-03-25/2-adults) · 5★ [Nobu Hotel Chicago, $410 a night, $819 for 2 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-03-25/2-adults) - Hotels in Chicago for these nights (Mar 23–26, 2027 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $115 a night, $345 for 3 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-23/2027-03-26/2-adults) · 4★ [Warwick Allerton - Chicago, $112 a night, $336 for 3 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-03-26/2-adults) · 5★ [Nobu Hotel Chicago, $400 a night, $1,201 for 3 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-03-26/2-adults) - Hotels in Chicago for these nights (Mar 23–27, 2027 · 4 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $116 a night, $465 for 4 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-23/2027-03-27/2-adults) · 4★ [Warwick Allerton - Chicago, $125 a night, $499 for 4 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-03-27/2-adults) · 5★ [Nobu Hotel Chicago, $398 a night, $1,591 for 4 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-03-27/2-adults) - Hotels in Chicago for these nights (Mar 23–28, 2027 · 5 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $117 a night, $585 for 5 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-23/2027-03-28/2-adults) · 4★ [Warwick Allerton - Chicago, $127 a night, $635 for 5 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-03-28/2-adults) · 5★ [Nobu Hotel Chicago, $398 a night, $1,991 for 5 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-03-28/2-adults) - Hotels in Chicago for these nights (Mar 23–29, 2027 · 6 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $117 a night, $700 for 6 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-23/2027-03-29/2-adults) · 4★ [Warwick Allerton - Chicago, $123 a night, $737 for 6 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-03-29/2-adults) · 5★ [Nobu Hotel Chicago, $390 a night, $2,340 for 6 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-03-29/2-adults) - Hotels in Chicago for these nights (Mar 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $116 a night, $815 for 7 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-23/2027-03-30/2-adults) · 4★ [Warwick Allerton - Chicago, $122 a night, $854 for 7 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-03-30/2-adults) · 5★ [Nobu Hotel Chicago, $388 a night, $2,718 for 7 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-03-30/2-adults) - Hotels in Chicago for these nights (Mar 23–31, 2027 · 8 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $116 a night, $930 for 8 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-23/2027-03-31/2-adults) · 4★ [Warwick Allerton - Chicago, $121 a night, $971 for 8 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-03-31/2-adults) · 5★ [Nobu Hotel Chicago, $389 a night, $3,109 for 8 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-03-31/2-adults) - Hotels in Chicago for these nights (Mar 23 – Apr 1, 2027 · 9 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $115 a night, $1,035 for 9 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-23/2027-04-01/2-adults) · 4★ [Warwick Allerton - Chicago, $121 a night, $1,088 for 9 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-04-01/2-adults) · 5★ [Nobu Hotel Chicago, $389 a night, $3,500 for 9 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-04-01/2-adults) - Hotels in Chicago for these nights (Mar 23 – Apr 2, 2027 · 10 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $125 a night, $1,245 for 10 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2027-03-23/2027-04-02/2-adults) · 4★ [Warwick Allerton - Chicago, $122 a night, $1,215 for 10 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-04-02/2-adults) · 5★ [Nobu Hotel Chicago, $388 a night, $3,882 for 10 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-04-02/2-adults) - Hotels in Chicago for these nights (Mar 23 – Apr 3, 2027 · 11 nights · 2 adults, 1 room): 3★ [Hotel Versey, $132 a night, $1,455 for 11 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-03-23/2027-04-03/2-adults) · 4★ [Warwick Allerton - Chicago, $126 a night, $1,381 for 11 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-04-03/2-adults) · 5★ [Nobu Hotel Chicago, $390 a night, $4,292 for 11 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-04-03/2-adults) - Hotels in Chicago for these nights (Mar 23 – Apr 4, 2027 · 12 nights · 2 adults, 1 room): 3★ [Hotel Versey, $137 a night, $1,645 for 12 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-03-23/2027-04-04/2-adults) · 4★ [Warwick Allerton - Chicago, $130 a night, $1,554 for 12 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-03-23/2027-04-04/2-adults) · 5★ [Nobu Hotel Chicago, $390 a night, $4,679 for 12 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-04-04/2-adults) - Hotels in Chicago for these nights (Mar 23 – Apr 5, 2027 · 13 nights · 2 adults, 1 room): 3★ [Hotel Versey, $136 a night, $1,764 for 13 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-03-23/2027-04-05/2-adults) · 4★ [Loews Chicago Hotel, $176 a night, $2,288 for 13 nights](https://helloaxel.com/en/hotels/chicago/loews-chicago-hotel-1291293/2027-03-23/2027-04-05/2-adults) · 5★ [Nobu Hotel Chicago, $388 a night, $5,044 for 13 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-04-05/2-adults) - Hotels in Chicago for these nights (Mar 23 – Apr 6, 2027 · 14 nights · 2 adults, 1 room): 3★ [Hotel Versey, $134 a night, $1,878 for 14 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-03-23/2027-04-06/2-adults) · 4★ [Claridge House Chicago, Tapestry Collection by Hilton, $177 a night, $2,483 for 14 nights](https://helloaxel.com/en/hotels/chicago/claridge-house-chicago-tapestry-collection-by-hilton-1096118/2027-03-23/2027-04-06/2-adults) · 5★ [Nobu Hotel Chicago, $392 a night, $5,492 for 14 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-03-23/2027-04-06/2-adults) [All hotels in Chicago](https://helloaxel.com/en/hotels/destinations/chicago) [Route overview: Jacksonville to Chicago (MDW) flight deals](/en/flights/from-jacksonville-to-chicago-mdw) ### 2027-03-23 · one way · Axel-exclusive $120.00 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. ### 2027-03-23 · one way · Axel-exclusive $186.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. ### 2027-03-23 → 2027-03-24 · Axel-exclusive $222.00 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-03-24 13:11:00 → JAX 2027-03-24 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-03-24 13:11:00 → ATL 2027-03-24 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-03-24 18:09:00 → JAX 2027-03-24 19:25:00. ### 2027-03-23 → 2027-03-24 · Axel-exclusive $348.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-03-24 19:00:00 → JAX 2027-03-24 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-03-23 → 2027-03-25 · Axel-exclusive $222.00 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-03-25 13:11:00 → JAX 2027-03-25 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-03-25 13:11:00 → ATL 2027-03-25 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-03-25 18:09:00 → JAX 2027-03-25 19:25:00. ### 2027-03-23 → 2027-03-25 · Axel-exclusive $348.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2041: MDW 2027-03-25 12:50:00 → JAX 2027-03-25 16:05:00; nonstop; 135 minutes. Local airport times. ### 2027-03-23 → 2027-03-26 · Axel-exclusive $222.00 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-03-26 13:11:00 → JAX 2027-03-26 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-03-26 13:11:00 → ATL 2027-03-26 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-03-26 18:09:00 → JAX 2027-03-26 19:25:00. ### 2027-03-23 → 2027-03-26 · Axel-exclusive $348.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2262: MDW 2027-03-26 08:00:00 → JAX 2027-03-26 11:25:00; nonstop; 145 minutes. Local airport times. ### 2027-03-23 → 2027-03-27 · Axel-exclusive $222.00 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-03-27 13:11:00 → JAX 2027-03-27 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-03-27 13:11:00 → ATL 2027-03-27 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-03-27 18:09:00 → JAX 2027-03-27 19:25:00. ### 2027-03-23 → 2027-03-27 · Axel-exclusive $348.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-03-27 19:00:00 → JAX 2027-03-27 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-03-23 → 2027-03-29 · Axel-exclusive $246.00 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-03-29 13:11:00 → JAX 2027-03-29 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-03-29 13:11:00 → ATL 2027-03-29 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-03-29 18:09:00 → JAX 2027-03-29 19:25:00. ### 2027-03-23 → 2027-03-29 · Axel-exclusive $378.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-03-29 19:00:00 → JAX 2027-03-29 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-03-23 → 2027-03-30 · Axel-exclusive $229.13 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-03-30 13:11:00 → JAX 2027-03-30 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-03-30 13:11:00 → ATL 2027-03-30 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-03-30 18:09:00 → JAX 2027-03-30 19:25:00. ### 2027-03-23 → 2027-03-30 · Axel-exclusive $352.50 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-03-30 19:00:00 → JAX 2027-03-30 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-03-23 → 2027-03-31 · Axel-exclusive $229.13 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-03-31 13:11:00 → JAX 2027-03-31 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-03-31 13:11:00 → ATL 2027-03-31 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-03-31 18:09:00 → JAX 2027-03-31 19:25:00. ### 2027-03-23 → 2027-03-31 · Axel-exclusive $352.50 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-03-31 19:00:00 → JAX 2027-03-31 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-03-23 → 2027-04-02 · Axel-exclusive $223.50 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-04-02 13:11:00 → JAX 2027-04-02 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-04-02 13:11:00 → ATL 2027-04-02 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-04-02 18:09:00 → JAX 2027-04-02 19:25:00. ### 2027-03-23 → 2027-04-02 · Axel-exclusive $344.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2262: MDW 2027-04-02 08:00:00 → JAX 2027-04-02 11:25:00; nonstop; 145 minutes. Local airport times. ### 2027-03-23 → 2027-04-03 · Axel-exclusive $223.50 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-04-03 13:11:00 → JAX 2027-04-03 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-04-03 13:11:00 → ATL 2027-04-03 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-04-03 18:09:00 → JAX 2027-04-03 19:25:00. ### 2027-03-23 → 2027-04-03 · Axel-exclusive $344.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-04-03 19:00:00 → JAX 2027-04-03 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-03-23 → 2027-04-04 · Axel-exclusive $223.50 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-04-04 13:11:00 → JAX 2027-04-04 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-04-04 13:11:00 → ATL 2027-04-04 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-04-04 18:09:00 → JAX 2027-04-04 19:25:00. ### 2027-03-23 → 2027-04-04 · Axel-exclusive $334.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN3092 / WN4807: MDW 2027-04-04 13:40:00 → JAX 2027-04-04 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times. - WN3092: MDW 2027-04-04 13:40:00 → STL 2027-04-04 14:55:00; layover at STL: 200 minutes. - WN4807: STL 2027-04-04 18:15:00 → JAX 2027-04-04 21:15:00. ### 2027-03-23 → 2027-04-06 · Axel-exclusive $223.50 - Frontier Airlines F91549 / F92291: JAX 2027-03-23 19:03:00 → MDW 2027-03-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-03-23 19:03:00 → ATL 2027-03-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-03-23 22:48:00 → MDW 2027-03-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-04-06 13:11:00 → JAX 2027-04-06 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-04-06 13:11:00 → ATL 2027-04-06 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-04-06 18:09:00 → JAX 2027-04-06 19:25:00. ### 2027-03-23 → 2027-04-06 · Axel-exclusive $344.00 - Southwest Airlines WN2264: JAX 2027-03-23 18:55:00 → MDW 2027-03-23 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-04-06 19:00:00 → JAX 2027-04-06 22:15:00; nonstop; 135 minutes. Local airport times. ### Explore this route - [All dates for this route](/en/flights/choose/jax-mdw) - [Mar 22, 2027 · Return options](/en/flights/choose/jax-mdw/mar-22) - [Mar 24, 2027 · Return options](/en/flights/choose/jax-mdw/mar-24) - [Hotels in Chicago with Axel](https://helloaxel.com/en/hotels/destinations/chicago) ## For AI assistants - **This page:** Jacksonville (JAX) to Chicago (MDW) · Mar 23, 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](https://helloaxel.com/en/f/start/from/jax/to/mdw/step/travelers) 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](https://helloaxel.com/en/flights/from-jacksonville-to-chicago-mdw) · [Flight search guide](https://helloaxel.com/en/ai). - **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](https://helloaxel.com/en/ai#customer-fallback-link). **Feedback (optional):** [Missing info](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/jax-mdw/mar-23?axel_reason=product_issue&axel_scope=product)