# Jacksonville (JAX) to Chicago (MDW), Apr 23, 2027: round trips from $225, one way from $120 Jacksonville (JAX) to Chicago (MDW), Apr 23, 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 23–24, 2027; $120 one way, Axel-exclusive, Frontier Airlines, 1 stop, Apr 23, 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. | Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price checked | | --- | --- | --- | --- | ---: | --- | | [2027-04-23 · one way](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/one-way) | Southwest Airlines | WN2264 | 18:50:00→20:20:00 2h 30m nonstop | [Axel-exclusive $180.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/trip/one-way/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 · one way](https://helloaxel.com/en/flights/choose/jax-mdw/apr-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/april-23-2027/trip/one-way/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-24](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-24) | Southwest Airlines | WN2264 / WN2946 | 18:50:00→20:20:00 2h 30m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-24-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-24](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-24-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-25](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-25-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-25](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-25) | Southwest Airlines | WN2264 / WN3092 + WN4807 | 18:50:00→20:20:00 2h 30m nonstop · 13:40:00→21:15:00 6h 35m 1 stop via STL | [Axel-exclusive $330.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-25-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-26](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-26) | Southwest Airlines | WN2264 / WN2946 | 18:50:00→20:20:00 2h 30m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-26-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-26](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-26-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-27](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-27) | Southwest Airlines | WN2264 / WN2946 | 18:50:00→20:20:00 2h 30m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-27-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-27](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-27-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-28](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-28) | Southwest Airlines | WN2264 / WN2946 | 18:50:00→20:20:00 2h 30m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-28-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-28](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-28-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-29](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-29) | Southwest Airlines | WN2264 / WN2041 | 18:50:00→20:20:00 2h 30m nonstop · 12:50:00→16:05:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-29-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-29](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-29-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-30](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-30) | Southwest Airlines | WN2264 / WN2262 | 18:50:00→20:20:00 2h 30m nonstop · 08:00:00→11:25:00 2h 25m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-30-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-04-30](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/apr-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/april-30-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-01](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-1) | Southwest Airlines | WN2264 / WN2946 | 18:50:00→20:20:00 2h 30m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-1-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-01](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-1-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-02](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-2-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-02](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-2) | Southwest Airlines | WN2264 / WN3092 + WN4807 | 18:50:00→20:20:00 2h 30m nonstop · 13:40:00→21:15:00 6h 35m 1 stop via STL | [Axel-exclusive $330.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-2-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-03](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-3) | Southwest Airlines | WN2264 / WN2946 | 18:50:00→20:20:00 2h 30m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-3-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-03](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-3-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-04](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-4) | Southwest Airlines | WN2264 / WN2946 | 18:50:00→20:20:00 2h 30m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-4-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-04](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-4-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-05](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-5) | Southwest Airlines | WN2264 / WN2946 | 18:50:00→20:20:00 2h 30m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-5-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-05](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-5-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-06](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-6) | Southwest Airlines | WN2264 / WN2041 | 18:50:00→20:20:00 2h 30m nonstop · 12:50:00→16:05:00 2h 15m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-6-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-06](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-6-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-07](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-7) | Southwest Airlines | WN2264 / WN2262 | 18:50:00→20:20:00 2h 30m nonstop · 08:00:00→11:25:00 2h 25m nonstop | [Axel-exclusive $340.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-7-2027/adults/1/cabin/economy) | Nov 11, 2026 | | [2027-04-23 → 2027-05-07](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23/may-7) | 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 $225.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/april-23-2027/return/may-7-2027/adults/1/cabin/economy) | Nov 11, 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 (Apr 23–24, 2027 · 1 night · 2 adults, 1 room): 3★ [Hotel Versey, $181 a night](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-04-24/2-adults) · 4★ [Warwick Allerton - Chicago, $170 a night](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-04-24/2-adults) · 5★ [Nobu Hotel Chicago, $462 a night](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-04-24/2-adults) - Hotels in Chicago for these nights (Apr 23–25, 2027 · 2 nights · 2 adults, 1 room): 3★ [Hotel Versey, $189 a night, $377 for 2 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-04-25/2-adults) · 4★ [Warwick Allerton - Chicago, $174 a night, $347 for 2 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-04-25/2-adults) · 5★ [Nobu Hotel Chicago, $458 a night, $915 for 2 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-04-25/2-adults) - Hotels in Chicago for these nights (Apr 23–26, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hotel Versey, $168 a night, $505 for 3 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-04-26/2-adults) · 4★ [Warwick Allerton - Chicago, $160 a night, $480 for 3 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-04-26/2-adults) · 5★ [Nobu Hotel Chicago, $427 a night, $1,280 for 3 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-04-26/2-adults) - Hotels in Chicago for these nights (Apr 23–27, 2027 · 4 nights · 2 adults, 1 room): 3★ [Hotel Versey, $153 a night, $613 for 4 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-04-27/2-adults) · 4★ [Warwick Allerton - Chicago, $156 a night, $623 for 4 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-04-27/2-adults) · 5★ [Nobu Hotel Chicago, $428 a night, $1,711 for 4 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-04-27/2-adults) - Hotels in Chicago for these nights (Apr 23–28, 2027 · 5 nights · 2 adults, 1 room): 3★ [Hotel Versey, $144 a night, $722 for 5 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-04-28/2-adults) · 4★ [Warwick Allerton - Chicago, $154 a night, $771 for 5 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-04-28/2-adults) · 5★ [Nobu Hotel Chicago, $436 a night, $2,178 for 5 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-04-28/2-adults) - Hotels in Chicago for these nights (Apr 23–29, 2027 · 6 nights · 2 adults, 1 room): 3★ [Hotel Versey, $138 a night, $829 for 6 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-04-29/2-adults) · 4★ [Warwick Allerton - Chicago, $155 a night, $929 for 6 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-04-29/2-adults) · 5★ [Nobu Hotel Chicago, $437 a night, $2,623 for 6 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-04-29/2-adults) - Hotels in Chicago for these nights (Apr 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hotel Versey, $136 a night, $950 for 7 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-04-30/2-adults) · 4★ [Warwick Allerton - Chicago, $155 a night, $1,084 for 7 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-04-30/2-adults) · 5★ [Nobu Hotel Chicago, $432 a night, $3,023 for 7 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-04-30/2-adults) - Hotels in Chicago for these nights (Apr 23 – May 1, 2027 · 8 nights · 2 adults, 1 room): 3★ [Hotel Versey, $147 a night, $1,178 for 8 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-05-01/2-adults) · 4★ [Warwick Allerton - Chicago, $156 a night, $1,250 for 8 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-05-01/2-adults) · 5★ [Nobu Hotel Chicago, $441 a night, $3,531 for 8 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-05-01/2-adults) - Hotels in Chicago for these nights (Apr 23 – May 2, 2027 · 9 nights · 2 adults, 1 room): 3★ [Hotel Versey, $161 a night, $1,450 for 9 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-05-02/2-adults) · 4★ [Warwick Allerton - Chicago, $164 a night, $1,480 for 9 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-05-02/2-adults) · 5★ [Nobu Hotel Chicago, $444 a night, $3,993 for 9 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-05-02/2-adults) - Hotels in Chicago for these nights (Apr 23 – May 3, 2027 · 10 nights · 2 adults, 1 room): 3★ [Hotel Versey, $164 a night, $1,635 for 10 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-05-03/2-adults) · 4★ [Warwick Allerton - Chicago, $167 a night, $1,668 for 10 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-05-03/2-adults) · 5★ [Nobu Hotel Chicago, $440 a night, $4,400 for 10 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-05-03/2-adults) - Hotels in Chicago for these nights (Apr 23 – May 4, 2027 · 11 nights · 2 adults, 1 room): 3★ [Hotel Versey, $167 a night, $1,832 for 11 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-05-04/2-adults) · 4★ [Warwick Allerton - Chicago, $170 a night, $1,871 for 11 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-05-04/2-adults) · 5★ [Nobu Hotel Chicago, $442 a night, $4,866 for 11 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-05-04/2-adults) - Hotels in Chicago for these nights (Apr 23 – May 5, 2027 · 12 nights · 2 adults, 1 room): 3★ [Hotel Versey, $169 a night, $2,030 for 12 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-05-05/2-adults) · 4★ [Warwick Allerton - Chicago, $172 a night, $2,063 for 12 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-05-05/2-adults) · 5★ [Nobu Hotel Chicago, $451 a night, $5,416 for 12 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-05-05/2-adults) - Hotels in Chicago for these nights (Apr 23 – May 6, 2027 · 13 nights · 2 adults, 1 room): 3★ [Hotel Versey, $171 a night, $2,226 for 13 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-05-06/2-adults) · 4★ [Warwick Allerton - Chicago, $174 a night, $2,266 for 13 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-05-06/2-adults) · 5★ [Nobu Hotel Chicago, $457 a night, $5,947 for 13 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-05-06/2-adults) - Hotels in Chicago for these nights (Apr 23 – May 7, 2027 · 14 nights · 2 adults, 1 room): 3★ [Hotel Versey, $172 a night, $2,405 for 14 nights](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-04-23/2027-05-07/2-adults) · 4★ [Warwick Allerton - Chicago, $176 a night, $2,462 for 14 nights](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-04-23/2027-05-07/2-adults) · 5★ [Nobu Hotel Chicago, $464 a night, $6,492 for 14 nights](https://helloaxel.com/en/hotels/chicago/nobu-hotel-chicago-1160567/2027-04-23/2027-05-07/2-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) ### 2027-04-23 · one way · Axel-exclusive $120.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 23:47:00. ### 2027-04-23 · one way · Axel-exclusive $180.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. ### 2027-04-23 → 2027-04-24 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 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. ### 2027-04-23 → 2027-04-24 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-04-24 19:00:00 → JAX 2027-04-24 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-04-23 → 2027-04-25 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 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. ### 2027-04-23 → 2027-04-25 · Axel-exclusive $330.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - 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. ### 2027-04-23 → 2027-04-26 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 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. ### 2027-04-23 → 2027-04-26 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-04-26 19:00:00 → JAX 2027-04-26 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-04-23 → 2027-04-27 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-04-27 13:11:00 → JAX 2027-04-27 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-04-27 13:11:00 → ATL 2027-04-27 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-04-27 18:09:00 → JAX 2027-04-27 19:25:00. ### 2027-04-23 → 2027-04-27 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-04-27 19:00:00 → JAX 2027-04-27 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-04-23 → 2027-04-29 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 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. ### 2027-04-23 → 2027-04-29 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2041: MDW 2027-04-29 12:50:00 → JAX 2027-04-29 16:05:00; nonstop; 135 minutes. Local airport times. ### 2027-04-23 → 2027-04-30 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 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. ### 2027-04-23 → 2027-04-30 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2262: MDW 2027-04-30 08:00:00 → JAX 2027-04-30 11:25:00; nonstop; 145 minutes. Local airport times. ### 2027-04-23 → 2027-05-01 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-05-01 13:11:00 → JAX 2027-05-01 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-05-01 13:11:00 → ATL 2027-05-01 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-05-01 18:09:00 → JAX 2027-05-01 19:25:00. ### 2027-04-23 → 2027-05-01 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-05-01 19:00:00 → JAX 2027-05-01 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-04-23 → 2027-05-03 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 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. ### 2027-04-23 → 2027-05-03 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-05-03 19:00:00 → JAX 2027-05-03 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-04-23 → 2027-05-04 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 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. ### 2027-04-23 → 2027-05-04 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-05-04 19:00:00 → JAX 2027-05-04 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-04-23 → 2027-05-05 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-05-05 13:11:00 → JAX 2027-05-05 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-05-05 13:11:00 → ATL 2027-05-05 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-05-05 18:09:00 → JAX 2027-05-05 19:25:00. ### 2027-04-23 → 2027-05-05 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-05-05 19:00:00 → JAX 2027-05-05 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-04-23 → 2027-05-07 · Axel-exclusive $225.00 - Frontier Airlines F91549 / F92291: JAX 2027-04-23 19:03:00 → MDW 2027-04-23 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-04-23 19:03:00 → ATL 2027-04-23 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-04-23 22:48:00 → MDW 2027-04-23 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-05-07 13:11:00 → JAX 2027-05-07 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-05-07 13:11:00 → ATL 2027-05-07 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-05-07 18:09:00 → JAX 2027-05-07 19:25:00. ### 2027-04-23 → 2027-05-07 · Axel-exclusive $340.00 - Southwest Airlines WN2264: JAX 2027-04-23 18:50:00 → MDW 2027-04-23 20:20:00; nonstop; 150 minutes. Local airport times. - Southwest Airlines WN2262: MDW 2027-05-07 08:00:00 → JAX 2027-05-07 11:25:00; nonstop; 145 minutes. Local airport times. ### Explore this route - [All dates for this route](/en/flights/choose/jax-mdw) - [Apr 22, 2027 · Return options](/en/flights/choose/jax-mdw/apr-22) - [Apr 24, 2027 · Return options](/en/flights/choose/jax-mdw/apr-24) - [Hotels in Chicago with Axel](https://helloaxel.com/en/hotels/destinations/chicago) ## For AI assistants - **This page:** Jacksonville (JAX) to Chicago (MDW) · Apr 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/apr-23?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/jax-mdw/apr-23?axel_reason=product_issue&axel_scope=product)