Chicago (MDW) to San Jose (SJC), Nov 15, 2026: round trips from $335, one way from $180

Chicago (MDW) to San Jose (SJC), Nov 15, 2026: round trips from $335, one way from $180 on Axel, checked Nov 13, 2026. Lowest published fares: $335 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 15–19, 2026; $180 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 15, 2026; 1 adult, economy, checked Nov 13, 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 15–16, 2026 · 1 night · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $109 a night · 4★ Sonesta Silicon Valley, $91 a night
• Hotels in San Jose, California for these nights (Nov 15–17, 2026 · 2 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $126 a night, $251 for 2 nights · 4★ Sonesta Silicon Valley, $133 a night, $265 for 2 nights
• Hotels in San Jose, California for these nights (Nov 15–18, 2026 · 3 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $135 a night, $404 for 3 nights · 4★ The Domain Hotel, $160 a night, $479 for 3 nights
• Hotels in San Jose, California for these nights (Nov 15–19, 2026 · 4 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $136 a night, $544 for 4 nights · 4★ The Domain Hotel, $163 a night, $650 for 4 nights
• Hotels in San Jose, California for these nights (Nov 15–20, 2026 · 5 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $132 a night, $661 for 5 nights · 4★ The Domain Hotel, $155 a night, $777 for 5 nights
• Hotels in San Jose, California for these nights (Nov 15–21, 2026 · 6 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $127 a night, $761 for 6 nights · 4★ The Domain Hotel, $145 a night, $871 for 6 nights
• Hotels in San Jose, California for these nights (Nov 15–22, 2026 · 7 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $121 a night, $848 for 7 nights · 4★ The Domain Hotel, $138 a night, $966 for 7 nights
• Hotels in San Jose, California for these nights (Nov 15–23, 2026 · 8 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $118 a night, $941 for 8 nights · 4★ The Domain Hotel, $134 a night, $1,074 for 8 nights
• Hotels in San Jose, California for these nights (Nov 15–24, 2026 · 9 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $115 a night, $1,039 for 9 nights · 4★ The Domain Hotel, $130 a night, $1,174 for 9 nights
• Hotels in San Jose, California for these nights (Nov 15–25, 2026 · 10 nights · 2 adults, 1 room): 3★ Maple Tree Inn, $115 a night, $1,149 for 10 nights · 4★ Sonesta Silicon Valley, $127 a night, $1,271 for 10 nights
• Hotels in San Jose, California for these nights (Nov 15–26, 2026 · 11 nights · 2 adults, 1 room): 3★ Maple Tree Inn, $112 a night, $1,231 for 11 nights · 4★ Sonesta Silicon Valley, $124 a night, $1,363 for 11 nights
• Hotels in San Jose, California for these nights (Nov 15–27, 2026 · 12 nights · 2 adults, 1 room): 3★ Maple Tree Inn, $110 a night, $1,314 for 12 nights · 4★ Sonesta Silicon Valley, $121 a night, $1,451 for 12 nights
• Hotels in San Jose, California for these nights (Nov 15–28, 2026 · 13 nights · 2 adults, 1 room): 3★ Maple Tree Inn, $107 a night, $1,394 for 13 nights · 4★ Sonesta Silicon Valley, $118 a night, $1,529 for 13 nights
• Hotels in San Jose, California for these nights (Nov 15–29, 2026 · 14 nights · 2 adults, 1 room): 3★ Maple Tree Inn, $106 a night, $1,479 for 14 nights · 4★ Sonesta Silicon Valley, $118 a night, $1,658 for 14 nights

All hotels in San Jose, California

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

2026-11-15 · one way · Axel-exclusive $180

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

2026-11-15 → 2026-11-16 · Axel-exclusive $350

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN4230: SJC 2026-11-16 23:00:00 → MDW 2026-11-17 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-15 → 2026-11-17 · Axel-exclusive $350

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN1973: SJC 2026-11-17 06:00:00 → MDW 2026-11-17 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-15 → 2026-11-18 · Axel-exclusive $350

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN1973: SJC 2026-11-18 06:00:00 → MDW 2026-11-18 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-15 → 2026-11-19 · Axel-exclusive $335

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3877 / WN776: SJC 2026-11-19 13:40:00 → MDW 2026-11-19 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-19 13:40:00 → DEN 2026-11-19 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-19 18:05:00 → MDW 2026-11-19 21:30:00.

2026-11-15 → 2026-11-21 · Axel-exclusive $411

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3895: SJC 2026-11-21 23:00:00 → MDW 2026-11-22 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-15 → 2026-11-22 · Axel-exclusive $411

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN266: SJC 2026-11-22 06:00:00 → MDW 2026-11-22 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-15 → 2026-11-23 · Axel-exclusive $411

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN4230: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-15 → 2026-11-25 · Axel-exclusive $411

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN266: SJC 2026-11-25 06:00:00 → MDW 2026-11-25 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-15 → 2026-11-26 · Axel-exclusive $391

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 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.

2026-11-15 → 2026-11-27 · Axel-exclusive $391

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 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.

2026-11-15 → 2026-11-29 · Axel-exclusive $411

• Southwest Airlines WN3035: MDW 2026-11-15 09:55:00 → SJC 2026-11-15 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.

Explore this route

• All dates for this route
• Nov 14, 2026 · Return options
• Nov 16, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Nov 15, 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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