# San Juan (SJU) to Chicago (MDW), Nov 19, 2026: round trips from $285, one way from $155 San Juan (SJU) to Chicago (MDW), Nov 19, 2026: round trips from $285, one way from $155 on Axel, checked Nov 15, 2026. Lowest published fares: $285 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Nov 19–20, 2026; $155 one way, Axel-exclusive, Frontier Airlines, 1 stop, Nov 19, 2026; 1 adult, economy, checked Nov 15, 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 | | --- | --- | --- | --- | ---: | --- | | [2026-11-19 · one way](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/one-way) | Frontier Airlines | F92871 + F92779 | 05:01:00→11:33:00 8h 32m 1 stop via ATL | [Axel-exclusive $155](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/trip/one-way/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL) | Nov 15, 2026 | | [2026-11-19 · one way](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/one-way) | Southwest Airlines | WN3957 + WN1854 | 06:05:00→13:00:00 8h 55m 1 stop via TPA | [Axel-exclusive $215](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/trip/one-way/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA) | Nov 15, 2026 | | [2026-11-19 → 2026-11-20](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-20) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $285](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-20-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-20.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-20](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-20) | Southwest Airlines | WN3957 + WN1854 / WN14 + WN4052 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWI | [Axel-exclusive $395](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-20-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-20.WN.1.WN14-WN4052.BWI) | Nov 15, 2026 | | [2026-11-19 → 2026-11-21](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-21) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $321](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-21-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-21.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-21](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-21) | Southwest Airlines | WN3957 + WN1854 / WN3002 + WN4122 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 07:50:00→18:25:00 8h 35m 1 stop via STL | [Axel-exclusive $444](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-21-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-21.WN.1.WN3002-WN4122.STL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-22](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-22) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $321](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-22-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-22.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-22](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-22) | Southwest Airlines | WN3957 + WN1854 / WN14 + WN4052 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWI | [Axel-exclusive $444](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-22-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-22.WN.1.WN14-WN4052.BWI) | Nov 15, 2026 | | [2026-11-19 → 2026-11-23](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-23) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $321](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-23-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-23.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-23](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-23) | Southwest Airlines | WN3957 + WN1854 / WN14 + WN4052 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWI | [Axel-exclusive $444](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-23-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-23.WN.1.WN14-WN4052.BWI) | Nov 15, 2026 | | [2026-11-19 → 2026-11-24](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-24) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $321](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-24-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-24.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-24](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-24) | Southwest Airlines | WN3957 + WN1854 / WN3048 + WN3363 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 13:20:00→22:25:00 7h 05m 1 stop via TPA | [Axel-exclusive $444](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-24-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-24.WN.1.WN3048-WN3363.TPA) | Nov 15, 2026 | | [2026-11-19 → 2026-11-25](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-25) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $321](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-25-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-25.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-25](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-25) | Southwest Airlines | WN3957 + WN1854 / WN3048 + WN3363 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 13:20:00→22:25:00 7h 05m 1 stop via TPA | [Axel-exclusive $444](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-25-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-25.WN.1.WN3048-WN3363.TPA) | Nov 15, 2026 | | [2026-11-19 → 2026-11-26](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-26) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $321](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-26-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-26.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-26](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-26) | Southwest Airlines | WN3957 + WN1854 / WN14 + WN4052 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWI | [Axel-exclusive $444](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-26-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-26.WN.1.WN14-WN4052.BWI) | Nov 15, 2026 | | [2026-11-19 → 2026-11-27](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-27) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $321](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-27-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-27.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-27](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-27) | Southwest Airlines | WN3957 + WN1854 / WN14 + WN4052 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWI | [Axel-exclusive $444](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-27-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-27.WN.1.WN14-WN4052.BWI) | Nov 15, 2026 | | [2026-11-19 → 2026-11-28](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-28) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $321](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-28-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-28.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-28](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-28) | Southwest Airlines | WN3957 + WN1854 / WN3002 + WN4122 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 07:50:00→18:25:00 8h 35m 1 stop via STL | [Axel-exclusive $444](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-28-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-28.WN.1.WN3002-WN4122.STL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-29](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-29) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $321](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-29-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-29.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-29](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-29) | Southwest Airlines | WN3957 + WN1854 / WN14 + WN4052 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWI | [Axel-exclusive $444](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-29-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-29.WN.1.WN14-WN4052.BWI) | Nov 15, 2026 | | [2026-11-19 → 2026-11-30](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-30) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $285](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-30-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-11-30.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-11-30](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/nov-30) | Southwest Airlines | WN3957 + WN1854 / WN14 + WN4052 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWI | [Axel-exclusive $395](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/november-30-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-11-30.WN.1.WN14-WN4052.BWI) | Nov 15, 2026 | | [2026-11-19 → 2026-12-01](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/dec-1) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $285](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/december-1-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-12-01.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-12-01](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/dec-1) | Southwest Airlines | WN3957 + WN1854 / WN3048 + WN3363 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 13:20:00→22:25:00 7h 05m 1 stop via TPA | [Axel-exclusive $395](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/december-1-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-12-01.WN.1.WN3048-WN3363.TPA) | Nov 15, 2026 | | [2026-11-19 → 2026-12-02](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/dec-2) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $285](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/december-2-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-12-02.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-12-02](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/dec-2) | Southwest Airlines | WN3957 + WN1854 / WN3048 + WN3363 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 13:20:00→22:25:00 7h 05m 1 stop via TPA | [Axel-exclusive $395](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/december-2-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-12-02.WN.1.WN3048-WN3363.TPA) | Nov 15, 2026 | | [2026-11-19 → 2026-12-03](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/dec-3) | Frontier Airlines | F92871 + F92779 / F92144 + F92300 | 05:01:00→11:33:00 8h 32m 1 stop via ATL · 13:11:00→23:44:00 8h 33m 1 stop via ATL | [Axel-exclusive $285](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/december-3-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.F9.1.F92871-F92779.ATL%7EMDW-SJU.2026-12-03.F9.1.F92144-F92300.ATL) | Nov 15, 2026 | | [2026-11-19 → 2026-12-03](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19/dec-3) | Southwest Airlines | WN3957 + WN1854 / WN14 + WN4052 | 06:05:00→13:00:00 8h 55m 1 stop via TPA · 14:30:00→01:00:00 8h 30m 1 stop via BWI | [Axel-exclusive $395](https://helloaxel.com/en/f/start/from/sju/to/mdw/depart/november-19-2026/return/december-3-2026/adults/1/cabin/economy?example_flight=SJU-MDW.2026-11-19.WN.1.WN3957-WN1854.TPA%7EMDW-SJU.2026-12-03.WN.1.WN14-WN4052.BWI) | Nov 15, 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 (Nov 19–20, 2026 · 1 night · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $108 a night](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-20/2-adults) · 4★ [Warwick Allerton - Chicago, $123 a night](https://helloaxel.com/en/hotels/chicago/warwick-allerton-chicago-1114033/2026-11-19/2026-11-20/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $314 a night](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-20/2-adults) - Hotels in Chicago for these nights (Nov 19–21, 2026 · 2 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $157 a night, $314 for 2 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-21/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $166 a night, $331 for 2 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-21/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $306 a night, $611 for 2 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-21/2-adults) - Hotels in Chicago for these nights (Nov 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $171 a night, $512 for 3 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-22/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $179 a night, $536 for 3 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-22/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $288 a night, $864.50 for 3 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-22/2-adults) - Hotels in Chicago for these nights (Nov 19–23, 2026 · 4 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $155 a night, $621 for 4 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-23/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $163 a night, $653 for 4 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-23/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $269 a night, $1,074.50 for 4 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-23/2-adults) - Hotels in Chicago for these nights (Nov 19–24, 2026 · 5 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $146 a night, $730 for 5 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-24/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $154 a night, $770 for 5 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-24/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $257 a night, $1,284.50 for 5 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-24/2-adults) - Hotels in Chicago for these nights (Nov 19–25, 2026 · 6 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $140 a night, $839 for 6 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-25/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $148 a night, $890 for 6 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-25/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $248 a night, $1,487.50 for 6 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-25/2-adults) - Hotels in Chicago for these nights (Nov 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $134 a night, $940 for 7 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-26/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $145 a night, $1,018 for 7 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-26/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $243 a night, $1,697.50 for 7 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-26/2-adults) - Hotels in Chicago for these nights (Nov 19–27, 2026 · 8 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $135 a night, $1,077 for 8 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-27/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $143 a night, $1,140 for 8 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-27/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $237 a night, $1,896.50 for 8 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-27/2-adults) - Hotels in Chicago for these nights (Nov 19–28, 2026 · 9 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $138 a night, $1,244 for 9 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-28/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $145 a night, $1,305 for 9 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-28/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $244 a night, $2,199.50 for 9 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-28/2-adults) - Hotels in Chicago for these nights (Nov 19–29, 2026 · 10 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $139 a night, $1,387 for 10 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-29/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $149 a night, $1,491 for 10 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-29/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $250 a night, $2,496.50 for 10 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-29/2-adults) - Hotels in Chicago for these nights (Nov 19–30, 2026 · 11 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $136 a night, $1,501 for 11 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-11-30/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $150 a night, $1,652 for 11 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-11-30/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $255 a night, $2,805.50 for 11 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-11-30/2-adults) - Hotels in Chicago for these nights (Nov 19 – Dec 1, 2026 · 12 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $135 a night, $1,615 for 12 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-12-01/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $152 a night, $1,819 for 12 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-12-01/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $260 a night, $3,122.50 for 12 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-12-01/2-adults) - Hotels in Chicago for these nights (Nov 19 – Dec 2, 2026 · 13 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $135 a night, $1,755 for 13 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-12-02/2-adults) · 4★ [Millennium Hotel Knickerbocker Chicago, $152 a night, $1,977 for 13 nights](https://helloaxel.com/en/hotels/chicago/millennium-hotel-knickerbocker-chicago-1046970/2026-11-19/2026-12-02/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $264 a night, $3,431.50 for 13 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-12-02/2-adults) - Hotels in Chicago for these nights (Nov 19 – Dec 3, 2026 · 14 nights · 2 adults, 1 room): 3★ [The Chicago Hotel Collection River North, $134 a night, $1,874 for 14 nights](https://helloaxel.com/en/hotels/chicago/the-chicago-hotel-collection-river-north-1389180/2026-11-19/2026-12-03/2-adults) · 4★ [Hotel Lincoln, $152 a night, $2,129 for 14 nights](https://helloaxel.com/en/hotels/chicago/hotel-lincoln-1100857/2026-11-19/2026-12-03/2-adults) · 5★ [Sofitel Chicago Magnificent Mile, $266 a night, $3,728.50 for 14 nights](https://helloaxel.com/en/hotels/chicago/sofitel-chicago-magnificent-mile-1279364/2026-11-19/2026-12-03/2-adults) [All hotels in Chicago](https://helloaxel.com/en/hotels/destinations/chicago) [Route overview: San Juan to Chicago (MDW) flight deals](/en/flights/from-san-juan-to-chicago-mdw) ### 2026-11-19 · one way · Axel-exclusive $155 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. ### 2026-11-19 · one way · Axel-exclusive $215 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. ### 2026-11-19 → 2026-11-20 · Axel-exclusive $285 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-11-20 13:11:00 → SJU 2026-11-20 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-11-20 13:11:00 → ATL 2026-11-20 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-11-20 19:06:00 → SJU 2026-11-20 23:44:00. ### 2026-11-19 → 2026-11-20 · Axel-exclusive $395 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN14 / WN4052: MDW 2026-11-20 14:30:00 → SJU 2026-11-21 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times. - WN14: MDW 2026-11-20 14:30:00 → BWI 2026-11-20 17:15:00; layover at BWI: 160 minutes. - WN4052: BWI 2026-11-20 19:55:00 → SJU 2026-11-21 01:00:00. ### 2026-11-19 → 2026-11-21 · Axel-exclusive $321 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-11-21 13:11:00 → SJU 2026-11-21 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-11-21 13:11:00 → ATL 2026-11-21 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-11-21 19:06:00 → SJU 2026-11-21 23:44:00. ### 2026-11-19 → 2026-11-21 · Axel-exclusive $444 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN3002 / WN4122: MDW 2026-11-21 07:50:00 → SJU 2026-11-21 18:25:00; 1 stop(s) via STL; 515 minutes. Local airport times. - WN3002: MDW 2026-11-21 07:50:00 → STL 2026-11-21 09:10:00; layover at STL: 175 minutes. - WN4122: STL 2026-11-21 12:05:00 → SJU 2026-11-21 18:25:00. ### 2026-11-19 → 2026-11-22 · Axel-exclusive $321 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-11-22 13:11:00 → SJU 2026-11-22 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-11-22 13:11:00 → ATL 2026-11-22 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-11-22 19:06:00 → SJU 2026-11-22 23:44:00. ### 2026-11-19 → 2026-11-22 · Axel-exclusive $444 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN14 / WN4052: MDW 2026-11-22 14:30:00 → SJU 2026-11-23 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times. - WN14: MDW 2026-11-22 14:30:00 → BWI 2026-11-22 17:15:00; layover at BWI: 160 minutes. - WN4052: BWI 2026-11-22 19:55:00 → SJU 2026-11-23 01:00:00. ### 2026-11-19 → 2026-11-23 · Axel-exclusive $321 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-11-23 13:11:00 → SJU 2026-11-23 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-11-23 13:11:00 → ATL 2026-11-23 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-11-23 19:06:00 → SJU 2026-11-23 23:44:00. ### 2026-11-19 → 2026-11-23 · Axel-exclusive $444 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN14 / WN4052: MDW 2026-11-23 14:30:00 → SJU 2026-11-24 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times. - WN14: MDW 2026-11-23 14:30:00 → BWI 2026-11-23 17:15:00; layover at BWI: 160 minutes. - WN4052: BWI 2026-11-23 19:55:00 → SJU 2026-11-24 01:00:00. ### 2026-11-19 → 2026-11-25 · Axel-exclusive $321 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-11-25 13:11:00 → SJU 2026-11-25 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-11-25 13:11:00 → ATL 2026-11-25 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-11-25 19:06:00 → SJU 2026-11-25 23:44:00. ### 2026-11-19 → 2026-11-25 · Axel-exclusive $444 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN3048 / WN3363: MDW 2026-11-25 13:20:00 → SJU 2026-11-25 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times. - WN3048: MDW 2026-11-25 13:20:00 → TPA 2026-11-25 16:55:00; layover at TPA: 80 minutes. - WN3363: TPA 2026-11-25 18:15:00 → SJU 2026-11-25 22:25:00. ### 2026-11-19 → 2026-11-26 · Axel-exclusive $321 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-11-26 13:11:00 → SJU 2026-11-26 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-11-26 13:11:00 → ATL 2026-11-26 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-11-26 19:06:00 → SJU 2026-11-26 23:44:00. ### 2026-11-19 → 2026-11-26 · Axel-exclusive $444 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN14 / WN4052: MDW 2026-11-26 14:30:00 → SJU 2026-11-27 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times. - WN14: MDW 2026-11-26 14:30:00 → BWI 2026-11-26 17:15:00; layover at BWI: 160 minutes. - WN4052: BWI 2026-11-26 19:55:00 → SJU 2026-11-27 01:00:00. ### 2026-11-19 → 2026-11-27 · Axel-exclusive $321 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-11-27 13:11:00 → SJU 2026-11-27 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-11-27 13:11:00 → ATL 2026-11-27 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-11-27 19:06:00 → SJU 2026-11-27 23:44:00. ### 2026-11-19 → 2026-11-27 · Axel-exclusive $444 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN14 / WN4052: MDW 2026-11-27 14:30:00 → SJU 2026-11-28 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times. - WN14: MDW 2026-11-27 14:30:00 → BWI 2026-11-27 17:15:00; layover at BWI: 160 minutes. - WN4052: BWI 2026-11-27 19:55:00 → SJU 2026-11-28 01:00:00. ### 2026-11-19 → 2026-11-29 · Axel-exclusive $321 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-11-29 13:11:00 → SJU 2026-11-29 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-11-29 13:11:00 → ATL 2026-11-29 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-11-29 19:06:00 → SJU 2026-11-29 23:44:00. ### 2026-11-19 → 2026-11-29 · Axel-exclusive $444 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN14 / WN4052: MDW 2026-11-29 14:30:00 → SJU 2026-11-30 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times. - WN14: MDW 2026-11-29 14:30:00 → BWI 2026-11-29 17:15:00; layover at BWI: 160 minutes. - WN4052: BWI 2026-11-29 19:55:00 → SJU 2026-11-30 01:00:00. ### 2026-11-19 → 2026-11-30 · Axel-exclusive $285 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-11-30 13:11:00 → SJU 2026-11-30 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-11-30 13:11:00 → ATL 2026-11-30 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-11-30 19:06:00 → SJU 2026-11-30 23:44:00. ### 2026-11-19 → 2026-11-30 · Axel-exclusive $395 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN14 / WN4052: MDW 2026-11-30 14:30:00 → SJU 2026-12-01 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times. - WN14: MDW 2026-11-30 14:30:00 → BWI 2026-11-30 17:15:00; layover at BWI: 160 minutes. - WN4052: BWI 2026-11-30 19:55:00 → SJU 2026-12-01 01:00:00. ### 2026-11-19 → 2026-12-01 · Axel-exclusive $285 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-12-01 13:11:00 → SJU 2026-12-01 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-12-01 13:11:00 → ATL 2026-12-01 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-12-01 19:06:00 → SJU 2026-12-01 23:44:00. ### 2026-11-19 → 2026-12-01 · Axel-exclusive $395 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN3048 / WN3363: MDW 2026-12-01 13:20:00 → SJU 2026-12-01 22:25:00; 1 stop(s) via TPA; 425 minutes. Local airport times. - WN3048: MDW 2026-12-01 13:20:00 → TPA 2026-12-01 16:55:00; layover at TPA: 80 minutes. - WN3363: TPA 2026-12-01 18:15:00 → SJU 2026-12-01 22:25:00. ### 2026-11-19 → 2026-12-03 · Axel-exclusive $285 - Frontier Airlines F92871 / F92779: SJU 2026-11-19 05:01:00 → MDW 2026-11-19 11:33:00; 1 stop(s) via ATL; 512 minutes. Local airport times. - F92871: SJU 2026-11-19 05:01:00 → ATL 2026-11-19 08:22:00; layover at ATL: 125 minutes. - F92779: ATL 2026-11-19 10:27:00 → MDW 2026-11-19 11:33:00. - Frontier Airlines F92144 / F92300: MDW 2026-12-03 13:11:00 → SJU 2026-12-03 23:44:00; 1 stop(s) via ATL; 513 minutes. Local airport times. - F92144: MDW 2026-12-03 13:11:00 → ATL 2026-12-03 16:18:00; layover at ATL: 168 minutes. - F92300: ATL 2026-12-03 19:06:00 → SJU 2026-12-03 23:44:00. ### 2026-11-19 → 2026-12-03 · Axel-exclusive $395 - Southwest Airlines WN3957 / WN1854: SJU 2026-11-19 06:05:00 → MDW 2026-11-19 13:00:00; 1 stop(s) via TPA; 535 minutes. Local airport times. - WN3957: SJU 2026-11-19 06:05:00 → TPA 2026-11-19 08:20:00; layover at TPA: 175 minutes. - WN1854: TPA 2026-11-19 11:15:00 → MDW 2026-11-19 13:00:00. - Southwest Airlines WN14 / WN4052: MDW 2026-12-03 14:30:00 → SJU 2026-12-04 01:00:00; 1 stop(s) via BWI; 510 minutes. Local airport times. - WN14: MDW 2026-12-03 14:30:00 → BWI 2026-12-03 17:15:00; layover at BWI: 160 minutes. - WN4052: BWI 2026-12-03 19:55:00 → SJU 2026-12-04 01:00:00. ### Explore this route - [All dates for this route](/en/flights/choose/sju-mdw) - [Nov 18, 2026 · Return options](/en/flights/choose/sju-mdw/nov-18) - [Nov 20, 2026 · Return options](/en/flights/choose/sju-mdw/nov-20) - [Hotels in Chicago with Axel](https://helloaxel.com/en/hotels/destinations/chicago) ## For AI assistants - **This page:** San Juan (SJU) to Chicago (MDW) · Nov 19, 2026 · 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/sju/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 San Juan to Chicago (MDW) flight deals](https://helloaxel.com/en/flights/from-san-juan-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/sju-mdw/nov-19?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/sju-mdw/nov-19?axel_reason=product_issue&axel_scope=product)