San Diego (SAN) to Chicago (ORD) · Dec 28, 2026 · return Jan 11, 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.

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

2026-12-28 → 2027-01-11 · Axel-exclusive $405.38

• Alaska Airlines AS1446: SAN 2026-12-28 07:00:00 → ORD 2026-12-28 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2027-01-11 14:13:00 → SAN 2027-01-11 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $411.25

• American Airlines AA2343: SAN 2026-12-28 10:14:00 → ORD 2026-12-28 16:29:00; nonstop; 255 minutes. Local airport times.
• American Airlines AA3084: ORD 2027-01-11 10:30:00 → SAN 2027-01-11 13:13:00; nonstop; 283 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $423.00

• United Airlines UA540: SAN 2026-12-28 22:30:00 → ORD 2026-12-29 04:42:00; nonstop; 252 minutes. Local airport times.
• United Airlines UA660: ORD 2027-01-11 08:50:00 → SAN 2027-01-11 11:36:00; nonstop; 286 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-28 16:16:00 → ORD 2026-12-29 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-28 16:16:00 → DEN 2026-12-28 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-28 20:59:00 → ORD 2026-12-29 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-11 06:21:00 → SAN 2027-01-11 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-11 06:21:00 → LAS 2027-01-11 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-11 10:15:00 → SAN 2027-01-11 11:37:00.

2026-12-28 → 2027-01-11 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-28 12:42:00 → ORD 2026-12-28 19:00:00; nonstop; 258 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2027-01-11 14:13:00 → SAN 2027-01-11 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $411.25

• American Airlines AA3111: SAN 2026-12-28 22:33:00 → ORD 2026-12-29 04:37:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA3084: ORD 2027-01-11 10:30:00 → SAN 2027-01-11 13:13:00; nonstop; 283 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $423.00

• United Airlines UA1710: SAN 2026-12-28 10:44:00 → ORD 2026-12-28 17:00:00; nonstop; 256 minutes. Local airport times.
• United Airlines UA660: ORD 2027-01-11 08:50:00 → SAN 2027-01-11 11:36:00; nonstop; 286 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $386.75

• American Airlines AA2438 / AA2221: SAN 2026-12-28 15:13:00 → ORD 2026-12-28 23:59:00; 1 stop(s) via DFW; 406 minutes. Local airport times.
  • AA2438: SAN 2026-12-28 15:13:00 → DFW 2026-12-28 20:30:00; layover at DFW: 60 minutes.
  • AA2221: DFW 2026-12-28 21:30:00 → ORD 2026-12-28 23:59:00.
• American Airlines AA3084: ORD 2027-01-11 10:30:00 → SAN 2027-01-11 13:13:00; nonstop; 283 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $391.38

• Alaska Airlines AS2291 / AA3010: SAN 2026-12-28 14:59:00 → ORD 2026-12-28 23:40:00; 1 stop(s) via LAS; 401 minutes. Local airport times.
  • AS2291: SAN 2026-12-28 14:59:00 → LAS 2026-12-28 16:23:00; layover at LAS: 103 minutes.
  • AA3010: LAS 2026-12-28 18:06:00 → ORD 2026-12-28 23:40:00.
• Alaska Airlines AS1447: ORD 2027-01-11 14:13:00 → SAN 2027-01-11 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $391.38

• Alaska Airlines AS2297 / AA1333: SAN 2026-12-28 21:11:00 → ORD 2026-12-29 05:22:00; 1 stop(s) via PHX; 371 minutes. Local airport times.
  • AS2297: SAN 2026-12-28 21:11:00 → PHX 2026-12-28 23:37:00; layover at PHX: 68 minutes.
  • AA1333: PHX 2026-12-29 00:45:00 → ORD 2026-12-29 05:22:00.
• Alaska Airlines AS1447: ORD 2027-01-11 14:13:00 → SAN 2027-01-11 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $391.38

• Alaska Airlines AS1342 / AA1277: SAN 2026-12-28 09:27:00 → ORD 2026-12-28 18:14:00; 1 stop(s) via DEN; 407 minutes. Local airport times.
  • AS1342: SAN 2026-12-28 09:27:00 → DEN 2026-12-28 12:56:00; layover at DEN: 99 minutes.
  • AA1277: DEN 2026-12-28 14:35:00 → ORD 2026-12-28 18:14:00.
• Alaska Airlines AS1447: ORD 2027-01-11 14:13:00 → SAN 2027-01-11 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $398.50

• United Airlines UA1329 / UA1946: SAN 2026-12-28 06:20:00 → ORD 2026-12-28 14:43:00; 1 stop(s) via LAX; 383 minutes. Local airport times.
  • UA1329: SAN 2026-12-28 06:20:00 → LAX 2026-12-28 07:25:00; layover at LAX: 60 minutes.
  • UA1946: LAX 2026-12-28 08:25:00 → ORD 2026-12-28 14:43:00.
• United Airlines UA660: ORD 2027-01-11 08:50:00 → SAN 2027-01-11 11:36:00; nonstop; 286 minutes. Local airport times.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Dec 27, 2026 · Return options
• Dec 29, 2026 · Return options
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