Chicago (MDW) to San Jose (SJC), Nov 25, 2026: round trips from $396, one way from $243

Chicago (MDW) to San Jose (SJC), Nov 25, 2026: round trips from $396, one way from $243 on Axel, checked Nov 11, 2026. Lowest published fares: $396 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 25, 2026 – Dec 3, 2026; $243 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 25, 2026; 1 adult, economy, checked Nov 11, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

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 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 San Jose, California for these nights (Nov 25–26, 2026 · 1 night · 2 adults, 1 room): 3★ Maple Tree Inn, $82 a night · 4★ Juniper Hotel Cupertino, Curio Collection by Hilton, $86 a night
• Hotels in San Jose, California for these nights (Nov 25–27, 2026 · 2 nights · 2 adults, 1 room): 3★ Sonesta San Jose - Milpitas, $80 a night, $160 for 2 nights · 4★ Juniper Hotel Cupertino, Curio Collection by Hilton, $86 a night, $172 for 2 nights
• Hotels in San Jose, California for these nights (Nov 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ Sonesta San Jose - Milpitas, $80 a night, $241 for 3 nights · 4★ Juniper Hotel Cupertino, Curio Collection by Hilton, $86 a night, $258 for 3 nights
• Hotels in San Jose, California for these nights (Nov 25–29, 2026 · 4 nights · 2 adults, 1 room): 3★ Sonesta San Jose - Milpitas, $79 a night, $314 for 4 nights · 4★ Juniper Hotel Cupertino, Curio Collection by Hilton, $86 a night, $342 for 4 nights
• Hotels in San Jose, California for these nights (Nov 25–30, 2026 · 5 nights · 2 adults, 1 room): 3★ Wild Palms, a JdV by Hyatt Hotel, $88 a night, $440 for 5 nights · 4★ Sonesta Silicon Valley, $100 a night, $498 for 5 nights
• Hotels in San Jose, California for these nights (Nov 25 – Dec 1, 2026 · 6 nights · 2 adults, 1 room): 3★ Sonesta San Jose - Milpitas, $98 a night, $587 for 6 nights · 4★ Sonesta Silicon Valley, $112 a night, $672 for 6 nights
• Hotels in San Jose, California for these nights (Nov 25 – Dec 2, 2026 · 7 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $101 a night, $707 for 7 nights · 4★ The Domain Hotel, $111 a night, $777 for 7 nights
• Hotels in San Jose, California for these nights (Nov 25 – Dec 3, 2026 · 8 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $103 a night, $825 for 8 nights · 4★ The Domain Hotel, $106 a night, $850 for 8 nights
• Hotels in San Jose, California for these nights (Nov 25 – Dec 4, 2026 · 9 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $103 a night, $924 for 9 nights · 4★ The Domain Hotel, $105 a night, $944 for 9 nights
• Hotels in San Jose, California for these nights (Nov 25 – Dec 5, 2026 · 10 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $101 a night, $1,011 for 10 nights · 4★ The Domain Hotel, $104 a night, $1,036 for 10 nights
• Hotels in San Jose, California for these nights (Nov 25 – Dec 6, 2026 · 11 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $100 a night, $1,095 for 11 nights · 4★ The Domain Hotel, $103 a night, $1,138 for 11 nights
• Hotels in San Jose, California for these nights (Nov 25 – Dec 7, 2026 · 12 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $100 a night, $1,194 for 12 nights · 4★ The Domain Hotel, $103 a night, $1,235 for 12 nights
• Hotels in San Jose, California for these nights (Nov 25 – Dec 8, 2026 · 13 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $100 a night, $1,297 for 13 nights · 4★ The Domain Hotel, $103 a night, $1,342 for 13 nights
• Hotels in San Jose, California for these nights (Nov 25 – Dec 9, 2026 · 14 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $100 a night, $1,404 for 14 nights · 4★ The Domain Hotel, $104 a night, $1,452 for 14 nights

All hotels in San Jose, California

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

2026-11-25 · one way · Axel-exclusive $243.00

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.

2026-11-25 → 2026-11-26 · Axel-exclusive $452.25

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3877 / WN776: SJC 2026-11-26 13:40:00 → MDW 2026-11-26 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-26 13:40:00 → DEN 2026-11-26 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00.

2026-11-25 → 2026-11-27 · Axel-exclusive $452.25

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN2612 / WN4975: SJC 2026-11-27 20:45:00 → MDW 2026-11-28 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2026-11-27 20:45:00 → SEA 2026-11-27 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2026-11-28 00:15:00 → MDW 2026-11-28 06:05:00.

2026-11-25 → 2026-11-28 · Axel-exclusive $472.50

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3895: SJC 2026-11-28 23:00:00 → MDW 2026-11-29 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-25 → 2026-11-29 · Axel-exclusive $472.50

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN266: SJC 2026-11-29 06:00:00 → MDW 2026-11-29 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-25 → 2026-12-01 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3895: SJC 2026-12-01 23:00:00 → MDW 2026-12-02 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-25 → 2026-12-03 · Axel-exclusive $396.25

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3877 / WN776: SJC 2026-12-03 13:40:00 → MDW 2026-12-03 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-12-03 13:40:00 → DEN 2026-12-03 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-12-03 18:05:00 → MDW 2026-12-03 21:30:00.

2026-11-25 → 2026-12-05 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3895: SJC 2026-12-05 23:00:00 → MDW 2026-12-06 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-25 → 2026-12-06 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN266: SJC 2026-12-06 06:00:00 → MDW 2026-12-06 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-25 → 2026-12-07 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN4230: SJC 2026-12-07 23:00:00 → MDW 2026-12-08 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-25 → 2026-12-09 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-25 09:55:00 → SJC 2026-11-25 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN576: SJC 2026-12-09 11:10:00 → MDW 2026-12-09 17:15:00; nonstop; 245 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 24, 2026 · Return options
• Nov 26, 2026 · Return options
• Hotels in San Jose, California with Axel

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• This page: Chicago (MDW) to San Jose (SJC) · Nov 25, 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 San Jose, California 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.
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