Chicago (MDW) to San Jose (SJC), Nov 26, 2026: round trips from $376, one way from $223

Chicago (MDW) to San Jose (SJC), Nov 26, 2026: round trips from $376, one way from $223 on Axel, checked Nov 11, 2026. Lowest published fares: $376 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 26, 2026 – Dec 3, 2026; $223 one way, Axel-exclusive, Southwest Airlines, 1 stop, Nov 26, 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 26–27, 2026 · 1 night · 2 adults, 1 room): 3★ Sonesta San Jose - Milpitas, $78 a night · 4★ Juniper Hotel Cupertino, Curio Collection by Hilton, $86 a night
• Hotels in San Jose, California for these nights (Nov 26–28, 2026 · 2 nights · 2 adults, 1 room): 3★ Sonesta San Jose - Milpitas, $80 a night, $159 for 2 nights · 4★ Sonesta Silicon Valley, $83 a night, $166 for 2 nights
• Hotels in San Jose, California for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ Sonesta San Jose - Milpitas, $77 a night, $232 for 3 nights · 4★ Juniper Hotel Cupertino, Curio Collection by Hilton, $85 a night, $256 for 3 nights
• Hotels in San Jose, California for these nights (Nov 26–30, 2026 · 4 nights · 2 adults, 1 room): 3★ Wild Palms, a JdV by Hyatt Hotel, $88 a night, $352 for 4 nights · 4★ Sonesta Silicon Valley, $102 a night, $406 for 4 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 1, 2026 · 5 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $97 a night, $485 for 5 nights · 4★ The Domain Hotel, $113 a night, $566 for 5 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 2, 2026 · 6 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $101 a night, $603 for 6 nights · 4★ The Domain Hotel, $111 a night, $667 for 6 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 3, 2026 · 7 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $103 a night, $721 for 7 nights · 4★ The Domain Hotel, $106 a night, $740 for 7 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 4, 2026 · 8 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Milpitas, $104 a night, $829 for 8 nights · 4★ The Domain Hotel, $104 a night, $834 for 8 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 5, 2026 · 9 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $103 a night, $923 for 9 nights · 4★ The Domain Hotel, $103 a night, $926 for 9 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 6, 2026 · 10 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $101 a night, $1,007 for 10 nights · 4★ The Domain Hotel, $103 a night, $1,028 for 10 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 7, 2026 · 11 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $101 a night, $1,106 for 11 nights · 4★ The Domain Hotel, $102 a night, $1,125 for 11 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 8, 2026 · 12 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $101 a night, $1,209 for 12 nights · 4★ The Domain Hotel, $103 a night, $1,232 for 12 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 9, 2026 · 13 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $101 a night, $1,316 for 13 nights · 4★ The Domain Hotel, $103 a night, $1,342 for 13 nights
• Hotels in San Jose, California for these nights (Nov 26 – Dec 10, 2026 · 14 nights · 2 adults, 1 room): 3★ Larkspur Landing Extended Stay Suites Campbell, $102 a night, $1,423 for 14 nights · 4★ The Domain Hotel, $103 a night, $1,443 for 14 nights

All hotels in San Jose, California

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

2026-11-26 · one way · Axel-exclusive $222.75

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.

2026-11-26 → 2026-11-27 · Axel-exclusive $432.00

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• 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.

2026-11-26 → 2026-11-28 · Axel-exclusive $452.25

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• Southwest Airlines WN3895: SJC 2026-11-28 23:00:00 → MDW 2026-11-29 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-26 → 2026-11-29 · Axel-exclusive $452.25

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• Southwest Airlines WN266: SJC 2026-11-29 06:00:00 → MDW 2026-11-29 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-26 → 2026-11-30 · Axel-exclusive $452.25

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• Southwest Airlines WN4230: SJC 2026-11-30 23:00:00 → MDW 2026-12-01 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-26 → 2026-12-02 · Axel-exclusive $391.00

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-26 → 2026-12-03 · Axel-exclusive $376.00

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• 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.

2026-11-26 → 2026-12-04 · Axel-exclusive $376.00

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• Southwest Airlines WN2612 / WN4975: SJC 2026-12-04 20:45:00 → MDW 2026-12-05 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2026-12-04 20:45:00 → SEA 2026-12-04 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2026-12-05 00:15:00 → MDW 2026-12-05 06:05:00.

2026-11-26 → 2026-12-06 · Axel-exclusive $391.00

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• Southwest Airlines WN266: SJC 2026-12-06 06:00:00 → MDW 2026-12-06 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-26 → 2026-12-07 · Axel-exclusive $391.00

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• Southwest Airlines WN4230: SJC 2026-12-07 23:00:00 → MDW 2026-12-08 05:00:00; nonstop; 240 minutes. Local airport times.

2026-11-26 → 2026-12-08 · Axel-exclusive $391.00

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• Southwest Airlines WN576: SJC 2026-12-08 11:10:00 → MDW 2026-12-08 17:15:00; nonstop; 245 minutes. Local airport times.

2026-11-26 → 2026-12-10 · Axel-exclusive $376.00

• Southwest Airlines WN725 / WN364: MDW 2026-11-26 09:55:00 → SJC 2026-11-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-26 09:55:00 → BNA 2026-11-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-26 13:55:00 → SJC 2026-11-26 16:45:00.
• 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.

Explore this route

• All dates for this route
• Nov 25, 2026 · Return options
• Nov 27, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Nov 26, 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.
• Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); 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 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 · Flight search guide.
• 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.

Feedback (optional): Missing info · Axel issue