Chicago (MDW) to San Diego (SAN), Nov 18–23, 2026: from $396 round trip

Chicago (MDW) to San Diego (SAN), Nov 18–23, 2026: from $396 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $396 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 18–23, 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.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Hotels in Oceanside, California for these trips

Hotels: under a trip, hotels in Oceanside, 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 Oceanside, California for these nights (Nov 18–23, 2026 · 5 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt

All hotels in Oceanside, California

Route overview: Chicago to San Diego (SAN) flight deals

2026-11-18 → 2026-11-23 · Axel-exclusive $411.25

• Southwest Airlines WN1456: MDW 2026-11-18 10:20:00 → SAN 2026-11-18 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN674: SAN 2026-11-23 06:30:00 → MDW 2026-11-23 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-18 → 2026-11-23 · Axel-exclusive $411.25

• Southwest Airlines WN4415: MDW 2026-11-18 15:15:00 → SAN 2026-11-18 17:35:00; nonstop; 260 minutes. Local airport times.
• Southwest Airlines WN674: SAN 2026-11-23 06:30:00 → MDW 2026-11-23 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-18 → 2026-11-23 · Axel-exclusive $396.25

• Southwest Airlines WN1354 / WN225: MDW 2026-11-18 13:20:00 → SAN 2026-11-18 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2026-11-18 13:20:00 → CMH 2026-11-18 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2026-11-18 16:45:00 → SAN 2026-11-18 18:35:00.
• Southwest Airlines WN674: SAN 2026-11-23 06:30:00 → MDW 2026-11-23 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-18 → 2026-11-23 · Axel-exclusive $396.25

• Southwest Airlines WN2995 / WN2447: MDW 2026-11-18 05:05:00 → SAN 2026-11-18 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
  • WN2995: MDW 2026-11-18 05:05:00 → PHX 2026-11-18 07:55:00; layover at PHX: 85 minutes.
  • WN2447: PHX 2026-11-18 09:20:00 → SAN 2026-11-18 09:40:00.
• Southwest Airlines WN674: SAN 2026-11-23 06:30:00 → MDW 2026-11-23 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-18 → 2026-11-23 · Axel-exclusive $396.25

• Southwest Airlines WN153 / WN167: MDW 2026-11-18 15:45:00 → SAN 2026-11-18 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
  • WN153: MDW 2026-11-18 15:45:00 → ABQ 2026-11-18 17:55:00; layover at ABQ: 115 minutes.
  • WN167: ABQ 2026-11-18 19:50:00 → SAN 2026-11-18 20:50:00.
• Southwest Airlines WN674: SAN 2026-11-23 06:30:00 → MDW 2026-11-23 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-18 → 2026-11-23 · Axel-exclusive $396.25

• Southwest Airlines WN4606 / WN1780: MDW 2026-11-18 14:35:00 → SAN 2026-11-18 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • WN4606: MDW 2026-11-18 14:35:00 → DEN 2026-11-18 16:15:00; layover at DEN: 70 minutes.
  • WN1780: DEN 2026-11-18 17:25:00 → SAN 2026-11-18 18:45:00.
• Southwest Airlines WN674: SAN 2026-11-23 06:30:00 → MDW 2026-11-23 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-18 → 2026-11-23 · Axel-exclusive $396.25

• Southwest Airlines WN725 / WN1079: MDW 2026-11-18 09:55:00 → SAN 2026-11-18 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
  • WN725: MDW 2026-11-18 09:55:00 → BNA 2026-11-18 11:30:00; layover at BNA: 60 minutes.
  • WN1079: BNA 2026-11-18 12:30:00 → SAN 2026-11-18 14:55:00.
• Southwest Airlines WN674: SAN 2026-11-23 06:30:00 → MDW 2026-11-23 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-18 → 2026-11-23 · Axel-exclusive $396.25

• Southwest Airlines WN4395 / WN3167: MDW 2026-11-18 10:15:00 → SAN 2026-11-18 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
  • WN4395: MDW 2026-11-18 10:15:00 → HOU 2026-11-18 12:50:00; layover at HOU: 95 minutes.
  • WN3167: HOU 2026-11-18 14:25:00 → SAN 2026-11-18 15:50:00.
• Southwest Airlines WN674: SAN 2026-11-23 06:30:00 → MDW 2026-11-23 12:30:00; nonstop; 240 minutes. Local airport times.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Nov 17, 2026 · Return options
• Nov 19, 2026 · Return options
• Hotels in Oceanside, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Diego (SAN) · Nov 18, 2026 · return Nov 23, 2026: 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 Oceanside, 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.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own 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 Diego (SAN) 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.

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