# Jacksonville (JAX) to Chicago (MDW), Feb 1, 2027: round trips from $185, one way from $100 Jacksonville (JAX) to Chicago (MDW), Feb 1, 2027: round trips from $185, one way from $100 on Axel, checked Oct 29, 2026. Lowest published fares: $185 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Feb 1–2, 2027; $100 one way, Axel-exclusive, Frontier Airlines, 1 stop, Feb 1, 2027; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply. **Prices by return date:** match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time 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 issuance times already shown here. | Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) | | --- | --- | --- | --- | ---: | --- | | [2027-02-01 · one way](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/one-way) | Southwest Airlines | WN2264 | 18:55:00→20:20:00 2h 25m nonstop | [Axel-exclusive $155.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/trip/one-way/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 · one way](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/one-way) | Frontier Airlines | F91549 + F92291 | 19:03:00→23:47:00 5h 44m 1 stop via ATL | [Axel-exclusive $100.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/trip/one-way/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-02](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-2) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-2-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-02](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-2-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-03](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-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 $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-3-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-03](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-3-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-04](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-4) | Southwest Airlines | WN2264 / WN2041 | 18:55:00→20:20:00 2h 25m nonstop · 12:50:00→16:05:00 2h 15m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-4-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-04](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-4-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-05](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-5) | Southwest Airlines | WN2264 / WN2262 | 18:55:00→20:20:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-5-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-05](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-5-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-06](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-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 $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-6-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-06](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-6-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-07](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-7-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-07](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-7) | 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 $282.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-7-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-08](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-8) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-8-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-08](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-8) | 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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-8-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-09](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-9) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-9-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-09](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-9) | 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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-9-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-10](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-10) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-10-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-10](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-10) | 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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-10-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-11](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-11) | Southwest Airlines | WN2264 / WN2041 | 18:55:00→20:20:00 2h 25m nonstop · 12:50:00→16:05:00 2h 15m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-11-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-11](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-11) | 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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-11-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-12](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-12) | Southwest Airlines | WN2264 / WN2262 | 18:55:00→20:20:00 2h 25m nonstop · 08:00:00→11:25:00 2h 25m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-12-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-12](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-12) | 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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-12-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-13](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-13) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-13-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-13](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-13) | 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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-13-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-14](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-14) | 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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-14-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-14](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-14) | 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 $282.50](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-14-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-15](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-15) | Southwest Airlines | WN2264 / WN2946 | 18:55:00→20:20:00 2h 25m nonstop · 19:00:00→22:15:00 2h 15m nonstop | [Axel-exclusive $290.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-15-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | | [2027-02-01 → 2027-02-15](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1/feb-15) | 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 $185.00](https://helloaxel.com/en/f/start/from/jax/to/mdw/depart/february-1-2027/return/february-15-2027/adults/1/cabin/economy) | 2026-10-29T01:16:41Z | ### Hotels in Chicago for these trips **Hotels:** under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates. - Hotels in Chicago for these nights (Feb 1–2, 2027 · 1 night · 2 adults, 1 room): 3★ [Hotel Versey, $69 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-02/2-adults) · 4★ [Warwick Allerton - Chicago, $89 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-02/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $258 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-02/2-adults) - Hotels in Chicago for these nights (Feb 1–3, 2027 · 2 nights · 2 adults, 1 room): 3★ [Hotel Versey, $143 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-03/2-adults) · 4★ [Warwick Allerton - Chicago, $183 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-03/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $520 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-03/2-adults) - Hotels in Chicago for these nights (Feb 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ [Hotel Versey, $216 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-04/2-adults) · 4★ [Warwick Allerton - Chicago, $272 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-04/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $782 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-04/2-adults) - Hotels in Chicago for these nights (Feb 1–5, 2027 · 4 nights · 2 adults, 1 room): 3★ [Hotel Versey, $290 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-05/2-adults) · 4★ [Warwick Allerton - Chicago, $358 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-05/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,044 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-05/2-adults) - Hotels in Chicago for these nights (Feb 1–6, 2027 · 5 nights · 2 adults, 1 room): 3★ [Hotel Versey, $392 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-06/2-adults) · 4★ [Warwick Allerton - Chicago, $450 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-06/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,308 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-06/2-adults) - Hotels in Chicago for these nights (Feb 1–7, 2027 · 6 nights · 2 adults, 1 room): 3★ [Hotel Versey, $505 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-07/2-adults) · 4★ [Warwick Allerton - Chicago, $539 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-07/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,570 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-07/2-adults) - Hotels in Chicago for these nights (Feb 1–8, 2027 · 7 nights · 2 adults, 1 room): 3★ [Hotel Versey, $588 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-08/2-adults) · 4★ [Warwick Allerton - Chicago, $631 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-08/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $1,843 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-08/2-adults) - Hotels in Chicago for these nights (Feb 1–9, 2027 · 8 nights · 2 adults, 1 room): 3★ [Hotel Versey, $671 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-09/2-adults) · 4★ [Warwick Allerton - Chicago, $717 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-09/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $2,105 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-09/2-adults) - Hotels in Chicago for these nights (Feb 1–10, 2027 · 9 nights · 2 adults, 1 room): 3★ [Hotel Versey, $752 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-10/2-adults) · 4★ [Warwick Allerton - Chicago, $813 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-10/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $2,363 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-10/2-adults) - Hotels in Chicago for these nights (Feb 1–11, 2027 · 10 nights · 2 adults, 1 room): 3★ [Hotel Versey, $836 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-11/2-adults) · 4★ [Warwick Allerton - Chicago, $913 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-11/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $2,630 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-11/2-adults) - Hotels in Chicago for these nights (Feb 1–12, 2027 · 11 nights · 2 adults, 1 room): 3★ [Hotel Versey, $919 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-12/2-adults) · 4★ [Warwick Allerton - Chicago, $1,008 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-12/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $2,888 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-12/2-adults) - Hotels in Chicago for these nights (Feb 1–13, 2027 · 12 nights · 2 adults, 1 room): 3★ [Hotel Versey, $1,048 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-13/2-adults) · 4★ [Warwick Allerton - Chicago, $1,124 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-13/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $3,155 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-13/2-adults) - Hotels in Chicago for these nights (Feb 1–14, 2027 · 13 nights · 2 adults, 1 room): 3★ [Hotel Versey, $1,213 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-14/2-adults) · 4★ [Warwick Allerton - Chicago, $1,283 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-14/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $3,417 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-14/2-adults) - Hotels in Chicago for these nights (Feb 1–15, 2027 · 14 nights · 2 adults, 1 room): 3★ [Hotel Versey, $1,311 total](https://helloaxel.com/en/hotels/chicago/hotel-versey-1098318/2027-02-01/2027-02-15/2-adults) · 4★ [Warwick Allerton - Chicago, $1,384 total](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2027-02-01/2027-02-15/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $3,679 total](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2027-02-01/2027-02-15/2-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) ### 2027-02-01 · one way · Axel-exclusive $100.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. ### 2027-02-01 · one way · Axel-exclusive $155.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. ### 2027-02-01 → 2027-02-02 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-02 13:11:00 → JAX 2027-02-02 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-02 13:11:00 → ATL 2027-02-02 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-02 18:09:00 → JAX 2027-02-02 19:25:00. ### 2027-02-01 → 2027-02-02 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-02-02 19:00:00 → JAX 2027-02-02 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-02-01 → 2027-02-03 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-03 13:11:00 → JAX 2027-02-03 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-03 13:11:00 → ATL 2027-02-03 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-03 18:09:00 → JAX 2027-02-03 19:25:00. ### 2027-02-01 → 2027-02-03 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-02-03 19:00:00 → JAX 2027-02-03 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-02-01 → 2027-02-04 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-04 13:11:00 → JAX 2027-02-04 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-04 13:11:00 → ATL 2027-02-04 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-04 18:09:00 → JAX 2027-02-04 19:25:00. ### 2027-02-01 → 2027-02-04 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2041: MDW 2027-02-04 12:50:00 → JAX 2027-02-04 16:05:00; nonstop; 135 minutes. Local airport times. ### 2027-02-01 → 2027-02-05 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-05 13:11:00 → JAX 2027-02-05 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-05 13:11:00 → ATL 2027-02-05 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-05 18:09:00 → JAX 2027-02-05 19:25:00. ### 2027-02-01 → 2027-02-05 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2262: MDW 2027-02-05 08:00:00 → JAX 2027-02-05 11:25:00; nonstop; 145 minutes. Local airport times. ### 2027-02-01 → 2027-02-07 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-07 13:11:00 → JAX 2027-02-07 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-07 13:11:00 → ATL 2027-02-07 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-07 18:09:00 → JAX 2027-02-07 19:25:00. ### 2027-02-01 → 2027-02-07 · Axel-exclusive $282.50 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN3092 / WN4807: MDW 2027-02-07 13:40:00 → JAX 2027-02-07 21:15:00; 1 stop(s) via STL; 395 minutes. Local airport times. - WN3092: MDW 2027-02-07 13:40:00 → STL 2027-02-07 14:55:00; layover at STL: 200 minutes. - WN4807: STL 2027-02-07 18:15:00 → JAX 2027-02-07 21:15:00. ### 2027-02-01 → 2027-02-08 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-08 13:11:00 → JAX 2027-02-08 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-08 13:11:00 → ATL 2027-02-08 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-08 18:09:00 → JAX 2027-02-08 19:25:00. ### 2027-02-01 → 2027-02-08 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-02-08 19:00:00 → JAX 2027-02-08 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-02-01 → 2027-02-09 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-09 13:11:00 → JAX 2027-02-09 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-09 13:11:00 → ATL 2027-02-09 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-09 18:09:00 → JAX 2027-02-09 19:25:00. ### 2027-02-01 → 2027-02-09 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-02-09 19:00:00 → JAX 2027-02-09 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-02-01 → 2027-02-11 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-11 13:11:00 → JAX 2027-02-11 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-11 13:11:00 → ATL 2027-02-11 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-11 18:09:00 → JAX 2027-02-11 19:25:00. ### 2027-02-01 → 2027-02-11 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2041: MDW 2027-02-11 12:50:00 → JAX 2027-02-11 16:05:00; nonstop; 135 minutes. Local airport times. ### 2027-02-01 → 2027-02-12 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-12 13:11:00 → JAX 2027-02-12 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-12 13:11:00 → ATL 2027-02-12 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-12 18:09:00 → JAX 2027-02-12 19:25:00. ### 2027-02-01 → 2027-02-12 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2262: MDW 2027-02-12 08:00:00 → JAX 2027-02-12 11:25:00; nonstop; 145 minutes. Local airport times. ### 2027-02-01 → 2027-02-13 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-13 13:11:00 → JAX 2027-02-13 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-13 13:11:00 → ATL 2027-02-13 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-13 18:09:00 → JAX 2027-02-13 19:25:00. ### 2027-02-01 → 2027-02-13 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-02-13 19:00:00 → JAX 2027-02-13 22:15:00; nonstop; 135 minutes. Local airport times. ### 2027-02-01 → 2027-02-15 · Axel-exclusive $185.00 - Frontier Airlines F91549 / F92291: JAX 2027-02-01 19:03:00 → MDW 2027-02-01 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times. - F91549: JAX 2027-02-01 19:03:00 → ATL 2027-02-01 20:31:00; layover at ATL: 137 minutes. - F92291: ATL 2027-02-01 22:48:00 → MDW 2027-02-01 23:47:00. - Frontier Airlines F92144 / F91550: MDW 2027-02-15 13:11:00 → JAX 2027-02-15 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times. - F92144: MDW 2027-02-15 13:11:00 → ATL 2027-02-15 16:18:00; layover at ATL: 111 minutes. - F91550: ATL 2027-02-15 18:09:00 → JAX 2027-02-15 19:25:00. ### 2027-02-01 → 2027-02-15 · Axel-exclusive $290.00 - Southwest Airlines WN2264: JAX 2027-02-01 18:55:00 → MDW 2027-02-01 20:20:00; nonstop; 145 minutes. Local airport times. - Southwest Airlines WN2946: MDW 2027-02-15 19:00:00 → JAX 2027-02-15 22:15:00; nonstop; 135 minutes. Local airport times. ### Explore this route - [All dates for this route](/en/flights/choose/jax-mdw) - [Jan 31, 2027 · Return options](/en/flights/choose/jax-mdw/jan-31) - [Feb 2, 2027 · Return options](/en/flights/choose/jax-mdw/feb-2) - [Hotels in Chicago with Axel](https://helloaxel.com/en/hotels/destinations/chicago) ## For AI assistants - **This page:** Jacksonville (JAX) to Chicago (MDW) · Feb 1, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates. - **Next:** each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); 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/feb-1?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/jax-mdw/feb-1?axel_reason=product_issue&axel_scope=product)