Chicago (MDW) to San Jose (SJC), Nov 29, 2026: round trips from $396, one way from $243

Chicago (MDW) to San Jose (SJC), Nov 29, 2026: round trips from $396, one way from $243 on Axel, checked Nov 10, 2026. Lowest published fares: $396 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 29, 2026 – Dec 3, 2026; $243 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 29, 2026; 1 adult, economy, checked Nov 10, 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 29–30, 2026 · 1 night · 2 adults, 1 room): 3★ Wild Palms, a JdV by Hyatt Hotel, $88 a night · 4★ Sonesta Silicon Valley, $111 a night
• Hotels in San Jose, California for these nights (Nov 29 – Dec 1, 2026 · 2 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $108 a night, $215 for 2 nights · 4★ The Domain Hotel, $123 a night, $246 for 2 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 2, 2026 · 3 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $109 a night, $326 for 3 nights · 4★ The Domain Hotel, $116 a night, $347 for 3 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 3, 2026 · 4 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $108 a night, $432 for 4 nights · 4★ The Domain Hotel, $105 a night, $420 for 4 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 4, 2026 · 5 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $106 a night, $531 for 5 nights · 4★ The Domain Hotel, $103 a night, $514 for 5 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 5, 2026 · 6 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $103 a night, $618 for 6 nights · 4★ The Domain Hotel, $101 a night, $606 for 6 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 6, 2026 · 7 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $100 a night, $702 for 7 nights · 4★ The Domain Hotel, $101 a night, $708 for 7 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 7, 2026 · 8 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $100 a night, $801 for 8 nights · 4★ The Domain Hotel, $101 a night, $805 for 8 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 8, 2026 · 9 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $100 a night, $904 for 9 nights · 4★ The Domain Hotel, $101 a night, $912 for 9 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 9, 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, $102 a night, $1,022 for 10 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 10, 2026 · 11 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $102 a night, $1,118 for 11 nights · 4★ The Domain Hotel, $102 a night, $1,123 for 11 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 11, 2026 · 12 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $102 a night, $1,218 for 12 nights · 4★ The Domain Hotel, $101 a night, $1,215 for 12 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 12, 2026 · 13 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $101 a night, $1,312 for 13 nights · 4★ The Domain Hotel, $101 a night, $1,312 for 13 nights
• Hotels in San Jose, California for these nights (Nov 29 – Dec 13, 2026 · 14 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $100 a night, $1,406 for 14 nights · 4★ The Domain Hotel, $102 a night, $1,429 for 14 nights

All hotels in San Jose, California

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

2026-11-29 · one way · Axel-exclusive $243.00

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

2026-11-29 → 2026-11-30 · Axel-exclusive $472.50

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN4230: SJC 2026-11-30 23:00:00 → MDW 2026-12-01 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-29 → 2026-12-01 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 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.

2026-11-29 → 2026-12-02 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 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.

2026-11-29 → 2026-12-03 · Axel-exclusive $396.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 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.

2026-11-29 → 2026-12-05 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 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.

2026-11-29 → 2026-12-06 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 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.

2026-11-29 → 2026-12-07 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 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.

2026-11-29 → 2026-12-09 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 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.

2026-11-29 → 2026-12-10 · Axel-exclusive $396.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN433 / WN801: SJC 2026-12-10 07:20:00 → MDW 2026-12-10 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2026-12-10 07:20:00 → LGB 2026-12-10 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2026-12-10 11:35:00 → MDW 2026-12-10 17:20:00.

2026-11-29 → 2026-12-11 · Axel-exclusive $396.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN2612 / WN4975: SJC 2026-12-11 20:45:00 → MDW 2026-12-12 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2026-12-11 20:45:00 → SEA 2026-12-11 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2026-12-12 00:15:00 → MDW 2026-12-12 06:05:00.

2026-11-29 → 2026-12-13 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-29 09:55:00 → SJC 2026-11-29 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN266: SJC 2026-12-13 06:00:00 → MDW 2026-12-13 12:10:00; nonstop; 250 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 28, 2026 · Return options
• Nov 30, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Nov 29, 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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