Chicago (MDW) to San Diego (SAN) · Dec 30, 2026 · return Jan 5, 2027

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: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Oceanside, California for these nights (Dec 30 – Jan 5, 2027 · 6 nights · 2 adults, 1 room): 3★ Holiday Inn Oceanside Camp Pendleton Area by IHG, $785 total · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt, $1,958 total

All hotels in Oceanside, California

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

2026-12-30 → 2027-01-05 · Axel-exclusive $411.25

• Southwest Airlines WN1456: MDW 2026-12-30 10:10:00 → SAN 2026-12-30 12:35:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN2962: SAN 2027-01-05 16:05:00 → MDW 2027-01-05 22:00:00; nonstop; 235 minutes. Local airport times.

2026-12-30 → 2027-01-05 · Axel-exclusive $411.25

• Southwest Airlines WN1987: MDW 2026-12-30 21:15:00 → SAN 2026-12-30 23:55:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN2962: SAN 2027-01-05 16:05:00 → MDW 2027-01-05 22:00:00; nonstop; 235 minutes. Local airport times.

2026-12-30 → 2027-01-05 · Axel-exclusive $390.25

• Southwest Airlines WN4606 / WN1780: MDW 2026-12-30 14:35:00 → SAN 2026-12-30 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • WN4606: MDW 2026-12-30 14:35:00 → DEN 2026-12-30 16:15:00; layover at DEN: 70 minutes.
  • WN1780: DEN 2026-12-30 17:25:00 → SAN 2026-12-30 18:45:00.
• Southwest Airlines WN2962: SAN 2027-01-05 16:05:00 → MDW 2027-01-05 22:00:00; nonstop; 235 minutes. Local airport times.

2026-12-30 → 2027-01-05 · Axel-exclusive $390.25

• Southwest Airlines WN725 / WN1079: MDW 2026-12-30 09:55:00 → SAN 2026-12-30 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
  • WN725: MDW 2026-12-30 09:55:00 → BNA 2026-12-30 11:30:00; layover at BNA: 60 minutes.
  • WN1079: BNA 2026-12-30 12:30:00 → SAN 2026-12-30 14:55:00.
• Southwest Airlines WN2962: SAN 2027-01-05 16:05:00 → MDW 2027-01-05 22:00:00; nonstop; 235 minutes. Local airport times.

2026-12-30 → 2027-01-05 · Axel-exclusive $390.25

• Southwest Airlines WN4395 / WN3167: MDW 2026-12-30 10:15:00 → SAN 2026-12-30 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
  • WN4395: MDW 2026-12-30 10:15:00 → HOU 2026-12-30 12:50:00; layover at HOU: 95 minutes.
  • WN3167: HOU 2026-12-30 14:25:00 → SAN 2026-12-30 15:50:00.
• Southwest Airlines WN2962: SAN 2027-01-05 16:05:00 → MDW 2027-01-05 22:00:00; nonstop; 235 minutes. Local airport times.

2026-12-30 → 2027-01-05 · Axel-exclusive $390.25

• Southwest Airlines WN153 / WN167: MDW 2026-12-30 15:45:00 → SAN 2026-12-30 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
  • WN153: MDW 2026-12-30 15:45:00 → ABQ 2026-12-30 17:55:00; layover at ABQ: 115 minutes.
  • WN167: ABQ 2026-12-30 19:50:00 → SAN 2026-12-30 20:50:00.
• Southwest Airlines WN2962: SAN 2027-01-05 16:05:00 → MDW 2027-01-05 22:00:00; nonstop; 235 minutes. Local airport times.

2026-12-30 → 2027-01-05 · Axel-exclusive $390.25

• Southwest Airlines WN2995 / WN2447: MDW 2026-12-30 05:05:00 → SAN 2026-12-30 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
  • WN2995: MDW 2026-12-30 05:05:00 → PHX 2026-12-30 07:55:00; layover at PHX: 85 minutes.
  • WN2447: PHX 2026-12-30 09:20:00 → SAN 2026-12-30 09:40:00.
• Southwest Airlines WN2962: SAN 2027-01-05 16:05:00 → MDW 2027-01-05 22:00:00; nonstop; 235 minutes. Local airport times.

2026-12-30 → 2027-01-05 · Axel-exclusive $390.25

• Southwest Airlines WN1354 / WN225: MDW 2026-12-30 13:20:00 → SAN 2026-12-30 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2026-12-30 13:20:00 → CMH 2026-12-30 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2026-12-30 16:45:00 → SAN 2026-12-30 18:35:00.
• Southwest Airlines WN2962: SAN 2027-01-05 16:05:00 → MDW 2027-01-05 22:00:00; nonstop; 235 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 29, 2026 · Return options
• Dec 31, 2026 · Return options
• Hotels in Oceanside, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Diego (SAN) · Dec 30, 2026 · return Jan 5, 2027: 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: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• 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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