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.

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 · 4★ Juniper Hotel Cupertino, Curio Collection by Hilton, $93 total
• 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 · 4★ Sonesta Silicon Valley, $169 total
• 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 · 4★ Sonesta Silicon Valley, $239 total
• 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 · 4★ Sonesta Silicon Valley, $325 total
• 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 · 4★ Sonesta Silicon Valley, $406 total
• 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 · 4★ Sonesta Silicon Valley, $485 total
• 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 · 4★ Sonesta Silicon Valley, $563 total
• 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 · 4★ Sonesta Silicon Valley, $664 total
• 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 · 4★ Sonesta Silicon Valley, $784 total
• 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 · 4★ Sonesta Silicon Valley, $904 total
• 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 · 4★ Juniper Hotel Cupertino, Curio Collection by Hilton, $1,031 total
• 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 · 4★ The Domain Hotel, $1,180 total
• Hotels in San Jose, California for these nights (Dec 24 – Jan 6, 2027 · 13 nights · 2 adults, 1 room): 3★ Cupertino Hotel, $1,188 total · 4★ The Domain Hotel, $1,319 total
• Hotels in San Jose, California for these nights (Dec 24 – Jan 7, 2027 · 14 nights · 2 adults, 1 room): 3★ Cupertino Hotel, $1,289 total · 4★ The Domain Hotel, $1,436 total

All hotels in San Jose, California

Route overview: Chicago to San Jose (SJC) flight deals

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
• Dec 23, 2026 · Return options
• Dec 25, 2026 · Return options
• Hotels in San Jose, California with Axel

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.
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