# Chicago (MDW) to San Jose (SJC), Dec 24, 2026: round trips from $376, one way from $231 Chicago (MDW) to San Jose (SJC), Dec 24, 2026: round trips from $376, one way from $231 on Axel, checked Oct 29, 2026. Lowest published fares: $376 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 24, 2026 – Jan 7, 2027; $231 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 24, 2026; 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) | | --- | --- | --- | --- | ---: | --- | | [2026-12-24 · one way](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/one-way) | Southwest Airlines | WN725 + WN364 | 09:55:00→16:45:00 8h 50m 1 stop via BNA | [Axel-exclusive $231.00](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/trip/one-way/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2026-12-25](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/dec-25) | Southwest Airlines | WN725 + WN364 / WN2612 + WN4975 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 20:45:00→06:05:00 7h 20m 1 stop via SEA | [Axel-exclusive $448.00](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/december-25-2026/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2026-12-26](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/dec-26) | Southwest Airlines | WN725 + WN364 / WN3895 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 23:00:00→05:00:00 4h 00m nonstop | [Axel-exclusive $469.00](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/december-26-2026/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2026-12-27](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/dec-27) | Southwest Airlines | WN725 + WN364 / WN266 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 06:00:00→12:10:00 4h 10m nonstop | [Axel-exclusive $469.00](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/december-27-2026/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2026-12-28](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/dec-28) | Southwest Airlines | WN725 + WN364 / WN4230 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 23:00:00→05:00:00 4h 00m nonstop | [Axel-exclusive $469.00](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/december-28-2026/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2026-12-29](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/dec-29) | Southwest Airlines | WN725 + WN364 / WN576 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 11:10:00→17:15:00 4h 05m nonstop | [Axel-exclusive $469.00](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/december-29-2026/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2026-12-30](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/dec-30) | Southwest Airlines | WN725 + WN364 / WN576 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 11:10:00→17:15:00 4h 05m nonstop | [Axel-exclusive $469.00](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/december-30-2026/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2026-12-31](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/dec-31) | Southwest Airlines | WN725 + WN364 / WN433 + WN801 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 07:20:00→17:20:00 8h 00m 1 stop via LGB | [Axel-exclusive $448.00](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/december-31-2026/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2027-01-01](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/jan-1) | Southwest Airlines | WN725 + WN364 / WN2612 + WN4975 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 20:45:00→06:05:00 7h 20m 1 stop via SEA | [Axel-exclusive $436.80](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/january-1-2027/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2027-01-02](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/jan-2) | Southwest Airlines | WN725 + WN364 / WN3895 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 23:00:00→05:00:00 4h 00m nonstop | [Axel-exclusive $456.75](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/january-2-2027/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2027-01-03](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/jan-3) | Southwest Airlines | WN725 + WN364 / WN266 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 06:00:00→12:10:00 4h 10m nonstop | [Axel-exclusive $456.75](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/january-3-2027/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2027-01-04](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/jan-4) | Southwest Airlines | WN725 + WN364 / WN4230 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 23:00:00→05:00:00 4h 00m nonstop | [Axel-exclusive $390.25](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/january-4-2027/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2027-01-05](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/jan-5) | Southwest Airlines | WN725 + WN364 / WN576 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 11:10:00→17:15:00 4h 05m nonstop | [Axel-exclusive $390.25](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/january-5-2027/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2027-01-06](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/jan-6) | Southwest Airlines | WN725 + WN364 / WN576 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 11:10:00→17:15:00 4h 05m nonstop | [Axel-exclusive $390.25](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/january-6-2027/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | | [2026-12-24 → 2027-01-07](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24/jan-7) | Southwest Airlines | WN725 + WN364 / WN433 + WN801 | 09:55:00→16:45:00 8h 50m 1 stop via BNA · 07:20:00→17:20:00 8h 00m 1 stop via LGB | [Axel-exclusive $376.00](https://helloaxel.com/en/f/start/from/mdw/to/sjc/depart/december-24-2026/return/january-7-2027/adults/1/cabin/economy) | 2026-10-29T01:29:13Z | ### Hotels in San Jose, California for these trips **Hotels:** under a trip, hotels in San Jose, California 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 San Jose, California for these nights (Dec 24–25, 2026 · 1 night · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $69 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2026-12-25/2-adults) · 4★ [Juniper Hotel Cupertino, Curio Collection by Hilton, $93 total](https://helloaxel.com/en/hotels/san-jose-california/juniper-hotel-cupertino-curio-collection-by-hilton-1281671/2026-12-24/2026-12-25/2-adults) - Hotels in San Jose, California for these nights (Dec 24–26, 2026 · 2 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $139 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2026-12-26/2-adults) · 4★ [Sonesta Silicon Valley, $169 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-silicon-valley-1102561/2026-12-24/2026-12-26/2-adults) - Hotels in San Jose, California for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $209 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2026-12-27/2-adults) · 4★ [Sonesta Silicon Valley, $239 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-silicon-valley-1102561/2026-12-24/2026-12-27/2-adults) - Hotels in San Jose, California for these nights (Dec 24–28, 2026 · 4 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $287 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2026-12-28/2-adults) · 4★ [Sonesta Silicon Valley, $325 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-silicon-valley-1102561/2026-12-24/2026-12-28/2-adults) - Hotels in San Jose, California for these nights (Dec 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $362 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2026-12-29/2-adults) · 4★ [Sonesta Silicon Valley, $406 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-silicon-valley-1102561/2026-12-24/2026-12-29/2-adults) - Hotels in San Jose, California for these nights (Dec 24–30, 2026 · 6 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $437 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2026-12-30/2-adults) · 4★ [Sonesta Silicon Valley, $485 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-silicon-valley-1102561/2026-12-24/2026-12-30/2-adults) - Hotels in San Jose, California for these nights (Dec 24–31, 2026 · 7 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $514 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2026-12-31/2-adults) · 4★ [Sonesta Silicon Valley, $563 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-silicon-valley-1102561/2026-12-24/2026-12-31/2-adults) - Hotels in San Jose, California for these nights (Dec 24 – Jan 1, 2027 · 8 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $589 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2027-01-01/2-adults) · 4★ [Sonesta Silicon Valley, $664 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-silicon-valley-1102561/2026-12-24/2027-01-01/2-adults) - Hotels in San Jose, California for these nights (Dec 24 – Jan 2, 2027 · 9 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $658 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2027-01-02/2-adults) · 4★ [Sonesta Silicon Valley, $784 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-silicon-valley-1102561/2026-12-24/2027-01-02/2-adults) - Hotels in San Jose, California for these nights (Dec 24 – Jan 3, 2027 · 10 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $749 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2027-01-03/2-adults) · 4★ [Sonesta Silicon Valley, $904 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-silicon-valley-1102561/2026-12-24/2027-01-03/2-adults) - Hotels in San Jose, California for these nights (Dec 24 – Jan 4, 2027 · 11 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $916 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2027-01-04/2-adults) · 4★ [Juniper Hotel Cupertino, Curio Collection by Hilton, $1,031 total](https://helloaxel.com/en/hotels/san-jose-california/juniper-hotel-cupertino-curio-collection-by-hilton-1281671/2026-12-24/2027-01-04/2-adults) - Hotels in San Jose, California for these nights (Dec 24 – Jan 5, 2027 · 12 nights · 2 adults, 1 room): 3★ [Sonesta San Jose - Milpitas, $1,061 total](https://helloaxel.com/en/hotels/san-jose-california/sonesta-san-jose-milpitas-1262791/2026-12-24/2027-01-05/2-adults) · 4★ [The Domain Hotel, $1,180 total](https://helloaxel.com/en/hotels/san-jose-california/the-domain-hotel-1088137/2026-12-24/2027-01-05/2-adults) - Hotels in San Jose, California for these nights (Dec 24 – Jan 6, 2027 · 13 nights · 2 adults, 1 room): 3★ [Cupertino Hotel, $1,169 total](https://helloaxel.com/en/hotels/san-jose-california/cupertino-hotel-1343408/2026-12-24/2027-01-06/2-adults) · 4★ [The Domain Hotel, $1,319 total](https://helloaxel.com/en/hotels/san-jose-california/the-domain-hotel-1088137/2026-12-24/2027-01-06/2-adults) - Hotels in San Jose, California for these nights (Dec 24 – Jan 7, 2027 · 14 nights · 2 adults, 1 room): 3★ [Cupertino Hotel, $1,270 total](https://helloaxel.com/en/hotels/san-jose-california/cupertino-hotel-1343408/2026-12-24/2027-01-07/2-adults) · 4★ [The Domain Hotel, $1,436 total](https://helloaxel.com/en/hotels/san-jose-california/the-domain-hotel-1088137/2026-12-24/2027-01-07/2-adults) [All hotels in San Jose, California](https://helloaxel.com/en/hotels/destinations/san-jose-california) [Route overview: Chicago to San Jose (SJC) flight deals](/en/flights/from-chicago-to-san-jose-sjc) ### 2026-12-24 · one way · Axel-exclusive $231.00 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. ### 2026-12-24 → 2026-12-25 · Axel-exclusive $448.00 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN2612 / WN4975: SJC 2026-12-25 20:45:00 → MDW 2026-12-26 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times. - WN2612: SJC 2026-12-25 20:45:00 → SEA 2026-12-25 23:10:00; layover at SEA: 65 minutes. - WN4975: SEA 2026-12-26 00:15:00 → MDW 2026-12-26 06:05:00. ### 2026-12-24 → 2026-12-26 · Axel-exclusive $469.00 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN3895: SJC 2026-12-26 23:00:00 → MDW 2026-12-27 05:00:00; nonstop; 240 minutes. Local airport times. ### 2026-12-24 → 2026-12-27 · Axel-exclusive $469.00 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN266: SJC 2026-12-27 06:00:00 → MDW 2026-12-27 12:10:00; nonstop; 250 minutes. Local airport times. ### 2026-12-24 → 2026-12-28 · Axel-exclusive $469.00 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN4230: SJC 2026-12-28 23:00:00 → MDW 2026-12-29 05:00:00; nonstop; 240 minutes. Local airport times. ### 2026-12-24 → 2026-12-30 · Axel-exclusive $469.00 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN576: SJC 2026-12-30 11:10:00 → MDW 2026-12-30 17:15:00; nonstop; 245 minutes. Local airport times. ### 2026-12-24 → 2026-12-31 · Axel-exclusive $448.00 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN433 / WN801: SJC 2026-12-31 07:20:00 → MDW 2026-12-31 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times. - WN433: SJC 2026-12-31 07:20:00 → LGB 2026-12-31 08:35:00; layover at LGB: 180 minutes. - WN801: LGB 2026-12-31 11:35:00 → MDW 2026-12-31 17:20:00. ### 2026-12-24 → 2027-01-01 · Axel-exclusive $436.80 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN2612 / WN4975: SJC 2027-01-01 20:45:00 → MDW 2027-01-02 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times. - WN2612: SJC 2027-01-01 20:45:00 → SEA 2027-01-01 23:10:00; layover at SEA: 65 minutes. - WN4975: SEA 2027-01-02 00:15:00 → MDW 2027-01-02 06:05:00. ### 2026-12-24 → 2027-01-03 · Axel-exclusive $456.75 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN266: SJC 2027-01-03 06:00:00 → MDW 2027-01-03 12:10:00; nonstop; 250 minutes. Local airport times. ### 2026-12-24 → 2027-01-04 · Axel-exclusive $390.25 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN4230: SJC 2027-01-04 23:00:00 → MDW 2027-01-05 05:00:00; nonstop; 240 minutes. Local airport times. ### 2026-12-24 → 2027-01-05 · Axel-exclusive $390.25 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN576: SJC 2027-01-05 11:10:00 → MDW 2027-01-05 17:15:00; nonstop; 245 minutes. Local airport times. ### 2026-12-24 → 2027-01-07 · Axel-exclusive $376.00 - Southwest Airlines WN725 / WN364: MDW 2026-12-24 09:55:00 → SJC 2026-12-24 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times. - WN725: MDW 2026-12-24 09:55:00 → BNA 2026-12-24 11:30:00; layover at BNA: 145 minutes. - WN364: BNA 2026-12-24 13:55:00 → SJC 2026-12-24 16:45:00. - Southwest Airlines WN433 / WN801: SJC 2027-01-07 07:20:00 → MDW 2027-01-07 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times. - WN433: SJC 2027-01-07 07:20:00 → LGB 2027-01-07 08:35:00; layover at LGB: 180 minutes. - WN801: LGB 2027-01-07 11:35:00 → MDW 2027-01-07 17:20:00. ### Explore this route - [All dates for this route](/en/flights/choose/mdw-sjc) - [Dec 23, 2026 · Return options](/en/flights/choose/mdw-sjc/dec-23) - [Dec 25, 2026 · Return options](/en/flights/choose/mdw-sjc/dec-25) - [Hotels in San Jose, California with Axel](https://helloaxel.com/en/hotels/destinations/san-jose-california) ## For AI assistants - **This page:** Chicago (MDW) to San Jose (SJC) · Dec 24, 2026 · 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 San Jose, California 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/mdw/to/sjc/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 Chicago to San Jose (SJC) flight deals](https://helloaxel.com/en/flights/from-chicago-to-san-jose-sjc) · [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/mdw-sjc/dec-24?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/mdw-sjc/dec-24?axel_reason=product_issue&axel_scope=product)