San Diego (SAN) to Chicago (ORD) · Dec 14, 2026 · return Dec 28, 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 Chicago for these trips

Hotels: under a trip, hotels in Chicago 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 Chicago for these nights (Dec 14–28, 2026 · 14 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,543 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,784 total · 5★ Nobu Hotel Chicago, $4,578 total

All hotels in Chicago

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

2026-12-14 → 2026-12-28 · Axel-exclusive $414.00

• Alaska Airlines AS1446: SAN 2026-12-14 07:00:00 → ORD 2026-12-14 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2026-12-28 14:13:00 → SAN 2026-12-28 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $420.00

• American Airlines AA1494: SAN 2026-12-14 22:45:00 → ORD 2026-12-15 04:49:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA1543: ORD 2026-12-28 15:12:00 → SAN 2026-12-28 17:45:00; nonstop; 273 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $432.00

• United Airlines UA540: SAN 2026-12-14 22:30:00 → ORD 2026-12-15 04:42:00; nonstop; 252 minutes. Local airport times.
• United Airlines UA1875: ORD 2026-12-28 16:05:00 → SAN 2026-12-28 18:43:00; nonstop; 278 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $240.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-14 16:16:00 → ORD 2026-12-15 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-14 16:16:00 → DEN 2026-12-14 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-14 20:59:00 → ORD 2026-12-15 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2026-12-28 06:21:00 → SAN 2026-12-28 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2026-12-28 06:21:00 → LAS 2026-12-28 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2026-12-28 10:15:00 → SAN 2026-12-28 11:37:00.

2026-12-14 → 2026-12-28 · Axel-exclusive $414.00

• Alaska Airlines AS1493: SAN 2026-12-14 17:38:00 → ORD 2026-12-14 23:59:00; nonstop; 261 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2026-12-28 14:13:00 → SAN 2026-12-28 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $420.00

• American Airlines AA2343: SAN 2026-12-14 10:14:00 → ORD 2026-12-14 16:29:00; nonstop; 255 minutes. Local airport times.
• American Airlines AA1543: ORD 2026-12-28 15:12:00 → SAN 2026-12-28 17:45:00; nonstop; 273 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $432.00

• United Airlines UA1779: SAN 2026-12-14 14:26:00 → ORD 2026-12-14 20:40:00; nonstop; 254 minutes. Local airport times.
• United Airlines UA1875: ORD 2026-12-28 16:05:00 → SAN 2026-12-28 18:43:00; nonstop; 278 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $402.50

• American Airlines AA2438 / AA2221: SAN 2026-12-14 15:13:00 → ORD 2026-12-14 23:59:00; 1 stop(s) via DFW; 406 minutes. Local airport times.
  • AA2438: SAN 2026-12-14 15:13:00 → DFW 2026-12-14 20:30:00; layover at DFW: 60 minutes.
  • AA2221: DFW 2026-12-14 21:30:00 → ORD 2026-12-14 23:59:00.
• American Airlines AA1543: ORD 2026-12-28 15:12:00 → SAN 2026-12-28 17:45:00; nonstop; 273 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $404.00

• Alaska Airlines AS1342 / AA1277: SAN 2026-12-14 09:27:00 → ORD 2026-12-14 18:14:00; 1 stop(s) via DEN; 407 minutes. Local airport times.
  • AS1342: SAN 2026-12-14 09:27:00 → DEN 2026-12-14 12:56:00; layover at DEN: 99 minutes.
  • AA1277: DEN 2026-12-14 14:35:00 → ORD 2026-12-14 18:14:00.
• Alaska Airlines AS1447: ORD 2026-12-28 14:13:00 → SAN 2026-12-28 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $404.00

• Alaska Airlines AS2291 / AA3010: SAN 2026-12-14 14:59:00 → ORD 2026-12-14 23:40:00; 1 stop(s) via LAS; 401 minutes. Local airport times.
  • AS2291: SAN 2026-12-14 14:59:00 → LAS 2026-12-14 16:23:00; layover at LAS: 103 minutes.
  • AA3010: LAS 2026-12-14 18:06:00 → ORD 2026-12-14 23:40:00.
• Alaska Airlines AS1447: ORD 2026-12-28 14:13:00 → SAN 2026-12-28 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $404.00

• Alaska Airlines AS2297 / AA1333: SAN 2026-12-14 21:11:00 → ORD 2026-12-15 05:22:00; 1 stop(s) via PHX; 371 minutes. Local airport times.
  • AS2297: SAN 2026-12-14 21:11:00 → PHX 2026-12-14 23:37:00; layover at PHX: 68 minutes.
  • AA1333: PHX 2026-12-15 00:45:00 → ORD 2026-12-15 05:22:00.
• Alaska Airlines AS1447: ORD 2026-12-28 14:13:00 → SAN 2026-12-28 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $414.50

• United Airlines UA1329 / UA1946: SAN 2026-12-14 06:20:00 → ORD 2026-12-14 14:43:00; 1 stop(s) via LAX; 383 minutes. Local airport times.
  • UA1329: SAN 2026-12-14 06:20:00 → LAX 2026-12-14 07:25:00; layover at LAX: 60 minutes.
  • UA1946: LAX 2026-12-14 08:25:00 → ORD 2026-12-14 14:43:00.
• United Airlines UA1875: ORD 2026-12-28 16:05:00 → SAN 2026-12-28 18:43:00; nonstop; 278 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 13, 2026 · Return options
• Dec 15, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Diego (SAN) to Chicago (ORD) · Dec 14, 2026 · return Dec 28, 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 Chicago 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.
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