Chicago (MDW) to San Diego (SAN) · Jan 13, 2027 · return Jan 18, 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 (Jan 13–18, 2027 · 5 nights · 2 adults, 1 room): 3★ Holiday Inn Oceanside Camp Pendleton Area by IHG, $780 total · 4★ MISSION PACIFIC BEACH RESORT, part of JdV by Hyatt, $1,738 total

All hotels in Oceanside, California

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

2027-01-13 → 2027-01-18 · Axel-exclusive $332.50

• Southwest Airlines WN1456: MDW 2027-01-13 10:10:00 → SAN 2027-01-13 12:35:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN1981: SAN 2027-01-18 12:00:00 → MDW 2027-01-18 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-13 → 2027-01-18 · Axel-exclusive $332.50

• Southwest Airlines WN1987: MDW 2027-01-13 21:15:00 → SAN 2027-01-13 23:55:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN1981: SAN 2027-01-18 12:00:00 → MDW 2027-01-18 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-13 → 2027-01-18 · Axel-exclusive $318.25

• Southwest Airlines WN2995 / WN2447: MDW 2027-01-13 05:05:00 → SAN 2027-01-13 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
  • WN2995: MDW 2027-01-13 05:05:00 → PHX 2027-01-13 07:55:00; layover at PHX: 85 minutes.
  • WN2447: PHX 2027-01-13 09:20:00 → SAN 2027-01-13 09:40:00.
• Southwest Airlines WN1981: SAN 2027-01-18 12:00:00 → MDW 2027-01-18 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-13 → 2027-01-18 · Axel-exclusive $318.25

• Southwest Airlines WN4606 / WN1780: MDW 2027-01-13 14:35:00 → SAN 2027-01-13 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • WN4606: MDW 2027-01-13 14:35:00 → DEN 2027-01-13 16:15:00; layover at DEN: 70 minutes.
  • WN1780: DEN 2027-01-13 17:25:00 → SAN 2027-01-13 18:45:00.
• Southwest Airlines WN1981: SAN 2027-01-18 12:00:00 → MDW 2027-01-18 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-13 → 2027-01-18 · Axel-exclusive $318.25

• Southwest Airlines WN4395 / WN3167: MDW 2027-01-13 10:15:00 → SAN 2027-01-13 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
  • WN4395: MDW 2027-01-13 10:15:00 → HOU 2027-01-13 12:50:00; layover at HOU: 95 minutes.
  • WN3167: HOU 2027-01-13 14:25:00 → SAN 2027-01-13 15:50:00.
• Southwest Airlines WN1981: SAN 2027-01-18 12:00:00 → MDW 2027-01-18 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-13 → 2027-01-18 · Axel-exclusive $318.25

• Southwest Airlines WN153 / WN167: MDW 2027-01-13 15:45:00 → SAN 2027-01-13 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
  • WN153: MDW 2027-01-13 15:45:00 → ABQ 2027-01-13 17:55:00; layover at ABQ: 115 minutes.
  • WN167: ABQ 2027-01-13 19:50:00 → SAN 2027-01-13 20:50:00.
• Southwest Airlines WN1981: SAN 2027-01-18 12:00:00 → MDW 2027-01-18 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-13 → 2027-01-18 · Axel-exclusive $318.25

• Southwest Airlines WN725 / WN1079: MDW 2027-01-13 09:55:00 → SAN 2027-01-13 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
  • WN725: MDW 2027-01-13 09:55:00 → BNA 2027-01-13 11:30:00; layover at BNA: 60 minutes.
  • WN1079: BNA 2027-01-13 12:30:00 → SAN 2027-01-13 14:55:00.
• Southwest Airlines WN1981: SAN 2027-01-18 12:00:00 → MDW 2027-01-18 17:55:00; nonstop; 235 minutes. Local airport times.

2027-01-13 → 2027-01-18 · Axel-exclusive $318.25

• Southwest Airlines WN1354 / WN225: MDW 2027-01-13 13:20:00 → SAN 2027-01-13 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
  • WN1354: MDW 2027-01-13 13:20:00 → CMH 2027-01-13 15:25:00; layover at CMH: 80 minutes.
  • WN225: CMH 2027-01-13 16:45:00 → SAN 2027-01-13 18:35:00.
• Southwest Airlines WN1981: SAN 2027-01-18 12:00:00 → MDW 2027-01-18 17:55:00; nonstop; 235 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 12, 2027 · Return options
• Jan 14, 2027 · Return options
• Hotels in Oceanside, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Diego (SAN) · Jan 13, 2027 · return Jan 18, 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.
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