San Diego (SAN) to Chicago (ORD) · Dec 27, 2026 · return Dec 30, 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 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $295 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $357 total · 5★ Nobu Hotel Chicago, $1,008 total

All hotels in Chicago

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

2026-12-27 → 2026-12-30 · Axel-exclusive $483.00

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 18:54:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1470: ORD 2026-12-30 07:27:00 → SAN 2026-12-30 10:12:00; nonstop; 285 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $490.00

• American Airlines AA621: SAN 2026-12-27 11:34:00 → ORD 2026-12-27 17:47:00; nonstop; 253 minutes. Local airport times.
• American Airlines AA2657: ORD 2026-12-30 21:00:00 → SAN 2026-12-30 23:36:00; nonstop; 276 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $504.00

• United Airlines UA1710: SAN 2026-12-27 10:44:00 → ORD 2026-12-27 17:00:00; nonstop; 256 minutes. Local airport times.
• United Airlines UA2384: ORD 2026-12-30 12:40:00 → SAN 2026-12-30 15:14:00; nonstop; 274 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $280.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2026-12-30 06:21:00 → SAN 2026-12-30 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2026-12-30 06:21:00 → LAS 2026-12-30 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2026-12-30 10:15:00 → SAN 2026-12-30 11:37:00.

2026-12-27 → 2026-12-30 · Axel-exclusive $483.00

• Alaska Airlines AS1446: SAN 2026-12-27 07:00:00 → ORD 2026-12-27 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1470: ORD 2026-12-30 07:27:00 → SAN 2026-12-30 10:12:00; nonstop; 285 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $490.00

• American Airlines AA3111: SAN 2026-12-27 22:33:00 → ORD 2026-12-28 04:37:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA2657: ORD 2026-12-30 21:00:00 → SAN 2026-12-30 23:36:00; nonstop; 276 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $504.00

• United Airlines UA540: SAN 2026-12-27 22:30:00 → ORD 2026-12-28 04:42:00; nonstop; 252 minutes. Local airport times.
• United Airlines UA2384: ORD 2026-12-30 12:40:00 → SAN 2026-12-30 15:14:00; nonstop; 274 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $465.50

• American Airlines AA2438 / AA2221: SAN 2026-12-27 15:13:00 → ORD 2026-12-27 23:59:00; 1 stop(s) via DFW; 406 minutes. Local airport times.
  • AA2438: SAN 2026-12-27 15:13:00 → DFW 2026-12-27 20:30:00; layover at DFW: 60 minutes.
  • AA2221: DFW 2026-12-27 21:30:00 → ORD 2026-12-27 23:59:00.
• American Airlines AA2657: ORD 2026-12-30 21:00:00 → SAN 2026-12-30 23:36:00; nonstop; 276 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $469.00

• Alaska Airlines AS1342 / AA1277: SAN 2026-12-27 09:27:00 → ORD 2026-12-27 18:14:00; 1 stop(s) via DEN; 407 minutes. Local airport times.
  • AS1342: SAN 2026-12-27 09:27:00 → DEN 2026-12-27 12:56:00; layover at DEN: 99 minutes.
  • AA1277: DEN 2026-12-27 14:35:00 → ORD 2026-12-27 18:14:00.
• Alaska Airlines AS1470: ORD 2026-12-30 07:27:00 → SAN 2026-12-30 10:12:00; nonstop; 285 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $469.00

• Alaska Airlines AS2291 / AA3010: SAN 2026-12-27 14:59:00 → ORD 2026-12-27 23:40:00; 1 stop(s) via LAS; 401 minutes. Local airport times.
  • AS2291: SAN 2026-12-27 14:59:00 → LAS 2026-12-27 16:23:00; layover at LAS: 103 minutes.
  • AA3010: LAS 2026-12-27 18:06:00 → ORD 2026-12-27 23:40:00.
• Alaska Airlines AS1470: ORD 2026-12-30 07:27:00 → SAN 2026-12-30 10:12:00; nonstop; 285 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $469.00

• Alaska Airlines AS2297 / AA1333: SAN 2026-12-27 21:11:00 → ORD 2026-12-28 05:22:00; 1 stop(s) via PHX; 371 minutes. Local airport times.
  • AS2297: SAN 2026-12-27 21:11:00 → PHX 2026-12-27 23:37:00; layover at PHX: 68 minutes.
  • AA1333: PHX 2026-12-28 00:45:00 → ORD 2026-12-28 05:22:00.
• Alaska Airlines AS1470: ORD 2026-12-30 07:27:00 → SAN 2026-12-30 10:12:00; nonstop; 285 minutes. Local airport times.

2026-12-27 → 2026-12-30 · Axel-exclusive $479.50

• United Airlines UA1329 / UA1946: SAN 2026-12-27 06:20:00 → ORD 2026-12-27 14:43:00; 1 stop(s) via LAX; 383 minutes. Local airport times.
  • UA1329: SAN 2026-12-27 06:20:00 → LAX 2026-12-27 07:25:00; layover at LAX: 60 minutes.
  • UA1946: LAX 2026-12-27 08:25:00 → ORD 2026-12-27 14:43:00.
• United Airlines UA2384: ORD 2026-12-30 12:40:00 → SAN 2026-12-30 15:14:00; nonstop; 274 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 26, 2026 · Return options
• Dec 28, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Diego (SAN) to Chicago (ORD) · Dec 27, 2026 · return Dec 30, 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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