San Diego (SAN) to Chicago (ORD) · Dec 16, 2026 · return Dec 20, 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 16–20, 2026 · 4 nights · 2 adults, 1 room): 3★ The Willows Hotel, $455 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $508 total · 5★ Nobu Hotel Chicago, $1,414 total

All hotels in Chicago

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

2026-12-16 → 2026-12-20 · Axel-exclusive $414.00

• Alaska Airlines AS1446: SAN 2026-12-16 07:00:00 → ORD 2026-12-16 13:15:00; nonstop; 255 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2026-12-20 14:17:00 → SAN 2026-12-20 17:02:00; nonstop; 285 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $420.00

• American Airlines AA3111: SAN 2026-12-16 22:33:00 → ORD 2026-12-17 04:37:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA2343: ORD 2026-12-20 06:45:00 → SAN 2026-12-20 09:24:00; nonstop; 279 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $432.00

• United Airlines UA540: SAN 2026-12-16 22:30:00 → ORD 2026-12-17 04:42:00; nonstop; 252 minutes. Local airport times.
• United Airlines UA2472: ORD 2026-12-20 20:13:00 → SAN 2026-12-20 22:55:00; nonstop; 282 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $240.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-16 16:16:00 → ORD 2026-12-17 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-16 16:16:00 → DEN 2026-12-16 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-16 20:59:00 → ORD 2026-12-17 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2026-12-20 06:21:00 → SAN 2026-12-20 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2026-12-20 06:21:00 → LAS 2026-12-20 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2026-12-20 10:15:00 → SAN 2026-12-20 11:37:00.

2026-12-16 → 2026-12-20 · Axel-exclusive $414.00

• Alaska Airlines AS1478: SAN 2026-12-16 12:42:00 → ORD 2026-12-16 19:00:00; nonstop; 258 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2026-12-20 14:17:00 → SAN 2026-12-20 17:02:00; nonstop; 285 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $420.00

• American Airlines AA2343: SAN 2026-12-16 10:14:00 → ORD 2026-12-16 16:29:00; nonstop; 255 minutes. Local airport times.
• American Airlines AA2343: ORD 2026-12-20 06:45:00 → SAN 2026-12-20 09:24:00; nonstop; 279 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $432.00

• United Airlines UA1779: SAN 2026-12-16 14:23:00 → ORD 2026-12-16 20:37:00; nonstop; 254 minutes. Local airport times.
• United Airlines UA2472: ORD 2026-12-20 20:13:00 → SAN 2026-12-20 22:55:00; nonstop; 282 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $402.50

• American Airlines AA2438 / AA2221: SAN 2026-12-16 15:13:00 → ORD 2026-12-16 23:59:00; 1 stop(s) via DFW; 406 minutes. Local airport times.
  • AA2438: SAN 2026-12-16 15:13:00 → DFW 2026-12-16 20:30:00; layover at DFW: 60 minutes.
  • AA2221: DFW 2026-12-16 21:30:00 → ORD 2026-12-16 23:59:00.
• American Airlines AA2343: ORD 2026-12-20 06:45:00 → SAN 2026-12-20 09:24:00; nonstop; 279 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $404.00

• Alaska Airlines AS2297 / AA1333: SAN 2026-12-16 21:11:00 → ORD 2026-12-17 05:22:00; 1 stop(s) via PHX; 371 minutes. Local airport times.
  • AS2297: SAN 2026-12-16 21:11:00 → PHX 2026-12-16 23:37:00; layover at PHX: 68 minutes.
  • AA1333: PHX 2026-12-17 00:45:00 → ORD 2026-12-17 05:22:00.
• Alaska Airlines AS1447: ORD 2026-12-20 14:17:00 → SAN 2026-12-20 17:02:00; nonstop; 285 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $404.00

• Alaska Airlines AS2291 / AA3010: SAN 2026-12-16 14:59:00 → ORD 2026-12-16 23:40:00; 1 stop(s) via LAS; 401 minutes. Local airport times.
  • AS2291: SAN 2026-12-16 14:59:00 → LAS 2026-12-16 16:23:00; layover at LAS: 103 minutes.
  • AA3010: LAS 2026-12-16 18:06:00 → ORD 2026-12-16 23:40:00.
• Alaska Airlines AS1447: ORD 2026-12-20 14:17:00 → SAN 2026-12-20 17:02:00; nonstop; 285 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $404.00

• Alaska Airlines AS1342 / AA1277: SAN 2026-12-16 09:27:00 → ORD 2026-12-16 18:14:00; 1 stop(s) via DEN; 407 minutes. Local airport times.
  • AS1342: SAN 2026-12-16 09:27:00 → DEN 2026-12-16 12:56:00; layover at DEN: 99 minutes.
  • AA1277: DEN 2026-12-16 14:35:00 → ORD 2026-12-16 18:14:00.
• Alaska Airlines AS1447: ORD 2026-12-20 14:17:00 → SAN 2026-12-20 17:02:00; nonstop; 285 minutes. Local airport times.

2026-12-16 → 2026-12-20 · Axel-exclusive $414.50

• United Airlines UA1329 / UA1946: SAN 2026-12-16 06:20:00 → ORD 2026-12-16 14:43:00; 1 stop(s) via LAX; 383 minutes. Local airport times.
  • UA1329: SAN 2026-12-16 06:20:00 → LAX 2026-12-16 07:25:00; layover at LAX: 60 minutes.
  • UA1946: LAX 2026-12-16 08:25:00 → ORD 2026-12-16 14:43:00.
• United Airlines UA2472: ORD 2026-12-20 20:13:00 → SAN 2026-12-20 22:55:00; nonstop; 282 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 15, 2026 · Return options
• Dec 17, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Diego (SAN) to Chicago (ORD) · Dec 16, 2026 · return Dec 20, 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.
• 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.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Diego to Chicago (ORD) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

Feedback (optional): Missing info · Axel issue