Chicago (MDW) to San Diego (SAN), Nov 21, 2026: round trips from $411, one way from $250

Chicago (MDW) to San Diego (SAN), Nov 21, 2026: round trips from $411, one way from $250 on Axel, checked Oct 29, 2026. Lowest published fares: $411 round trip, Axel-exclusive, Southwest Airlines, nonstop, Nov 21, 2026 – Dec 1, 2026; $250 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 21, 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time 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 issuance times already shown here.

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 21–22, 2026 · 1 night · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21–23, 2026 · 2 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21–24, 2026 · 3 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21–25, 2026 · 4 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21–26, 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
• Hotels in Oceanside, California for these nights (Nov 21–27, 2026 · 6 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21–29, 2026 · 8 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21–30, 2026 · 9 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21 – Dec 1, 2026 · 10 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21 – Dec 2, 2026 · 11 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21 – Dec 3, 2026 · 12 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21 – Dec 4, 2026 · 13 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt
• Hotels in Oceanside, California for these nights (Nov 21 – Dec 5, 2026 · 14 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

2026-11-21 · one way · Axel-exclusive $249.75

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.

2026-11-21 → 2026-11-22 · Axel-exclusive $472.50

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN1011: SAN 2026-11-22 22:40:00 → MDW 2026-11-23 04:25:00; nonstop; 225 minutes. Local airport times.

2026-11-21 → 2026-11-23 · Axel-exclusive $472.50

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 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.

2026-11-21 → 2026-11-24 · Axel-exclusive $472.50

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN1981: SAN 2026-11-24 12:00:00 → MDW 2026-11-24 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-11-25 · Axel-exclusive $472.50

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN126: SAN 2026-11-25 11:25:00 → MDW 2026-11-25 17:25:00; nonstop; 240 minutes. Local airport times.

2026-11-21 → 2026-11-27 · Axel-exclusive $472.50

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN1156: SAN 2026-11-27 11:45:00 → MDW 2026-11-27 17:40:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-11-28 · Axel-exclusive $472.50

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN634: SAN 2026-11-28 08:15:00 → MDW 2026-11-28 14:15:00; nonstop; 240 minutes. Local airport times.

2026-11-21 → 2026-11-29 · Axel-exclusive $472.50

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN1011: SAN 2026-11-29 22:40:00 → MDW 2026-11-30 04:25:00; nonstop; 225 minutes. Local airport times.

2026-11-21 → 2026-12-01 · Axel-exclusive $411.25

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN1981: SAN 2026-12-01 12:00:00 → MDW 2026-12-01 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-12-02 · Axel-exclusive $411.25

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN126: SAN 2026-12-02 11:25:00 → MDW 2026-12-02 17:25:00; nonstop; 240 minutes. Local airport times.

2026-11-21 → 2026-12-03 · Axel-exclusive $411.25

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN1981: SAN 2026-12-03 12:00:00 → MDW 2026-12-03 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-21 → 2026-12-05 · Axel-exclusive $411.25

• Southwest Airlines WN1456: MDW 2026-11-21 10:20:00 → SAN 2026-11-21 12:45:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN634: SAN 2026-12-05 08:15:00 → MDW 2026-12-05 14:15:00; nonstop; 240 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 20, 2026 · Return options
• Nov 22, 2026 · Return options
• Hotels in Oceanside, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Diego (SAN) · Nov 21, 2026 · choose your return date: 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.
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