San Diego (SAN) to Chicago (ORD) · Jan 26, 2027 · return Feb 1, 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.

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 (Jan 26 – Feb 1, 2027 · 6 nights · 2 adults, 1 room): 3★ The Willows Hotel, $651 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $856 total · 5★ Nobu Hotel Chicago, $2,175 total

All hotels in Chicago

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

2027-01-26 → 2027-02-01 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-26 07:00:00 → ORD 2027-01-26 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2027-02-01 14:13:00 → SAN 2027-02-01 17:00:00; nonstop; 287 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $332.50

• American Airlines AA2081: SAN 2027-01-26 07:21:00 → ORD 2027-01-26 13:37:00; nonstop; 256 minutes. Local airport times.
• American Airlines AA3084: ORD 2027-02-01 10:30:00 → SAN 2027-02-01 13:13:00; nonstop; 283 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $342.00

• United Airlines UA540: SAN 2027-01-26 22:30:00 → ORD 2027-01-27 04:42:00; nonstop; 252 minutes. Local airport times.
• United Airlines UA660: ORD 2027-02-01 08:50:00 → SAN 2027-02-01 11:36:00; nonstop; 286 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-26 16:16:00 → ORD 2027-01-27 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-26 16:16:00 → DEN 2027-01-26 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-26 20:59:00 → ORD 2027-01-27 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-02-01 06:21:00 → SAN 2027-02-01 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-02-01 06:21:00 → LAS 2027-02-01 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-02-01 10:15:00 → SAN 2027-02-01 11:37:00.

2027-01-26 → 2027-02-01 · Axel-exclusive $327.76

• Alaska Airlines AS1478: SAN 2027-01-26 12:32:00 → ORD 2027-01-26 18:54:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2027-02-01 14:13:00 → SAN 2027-02-01 17:00:00; nonstop; 287 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $332.50

• American Airlines AA3111: SAN 2027-01-26 22:33:00 → ORD 2027-01-27 04:37:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA3084: ORD 2027-02-01 10:30:00 → SAN 2027-02-01 13:13:00; nonstop; 283 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $342.00

• United Airlines UA2343: SAN 2027-01-26 06:50:00 → ORD 2027-01-26 13:08:00; nonstop; 258 minutes. Local airport times.
• United Airlines UA660: ORD 2027-02-01 08:50:00 → SAN 2027-02-01 11:36:00; nonstop; 286 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $315.88

• American Airlines AA2438 / AA2221: SAN 2027-01-26 15:13:00 → ORD 2027-01-26 23:59:00; 1 stop(s) via DFW; 406 minutes. Local airport times.
  • AA2438: SAN 2027-01-26 15:13:00 → DFW 2027-01-26 20:30:00; layover at DFW: 60 minutes.
  • AA2221: DFW 2027-01-26 21:30:00 → ORD 2027-01-26 23:59:00.
• American Airlines AA3084: ORD 2027-02-01 10:30:00 → SAN 2027-02-01 13:13:00; nonstop; 283 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $318.26

• Alaska Airlines AS2297 / AA1333: SAN 2027-01-26 21:11:00 → ORD 2027-01-27 05:22:00; 1 stop(s) via PHX; 371 minutes. Local airport times.
  • AS2297: SAN 2027-01-26 21:11:00 → PHX 2027-01-26 23:37:00; layover at PHX: 68 minutes.
  • AA1333: PHX 2027-01-27 00:45:00 → ORD 2027-01-27 05:22:00.
• Alaska Airlines AS1447: ORD 2027-02-01 14:13:00 → SAN 2027-02-01 17:00:00; nonstop; 287 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $318.26

• Alaska Airlines AS2291 / AA3010: SAN 2027-01-26 14:59:00 → ORD 2027-01-26 23:40:00; 1 stop(s) via LAS; 401 minutes. Local airport times.
  • AS2291: SAN 2027-01-26 14:59:00 → LAS 2027-01-26 16:23:00; layover at LAS: 103 minutes.
  • AA3010: LAS 2027-01-26 18:06:00 → ORD 2027-01-26 23:40:00.
• Alaska Airlines AS1447: ORD 2027-02-01 14:13:00 → SAN 2027-02-01 17:00:00; nonstop; 287 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $318.26

• Alaska Airlines AS1342 / AA1277: SAN 2027-01-26 09:27:00 → ORD 2027-01-26 18:14:00; 1 stop(s) via DEN; 407 minutes. Local airport times.
  • AS1342: SAN 2027-01-26 09:27:00 → DEN 2027-01-26 12:56:00; layover at DEN: 99 minutes.
  • AA1277: DEN 2027-01-26 14:35:00 → ORD 2027-01-26 18:14:00.
• Alaska Airlines AS1447: ORD 2027-02-01 14:13:00 → SAN 2027-02-01 17:00:00; nonstop; 287 minutes. Local airport times.

2027-01-26 → 2027-02-01 · Axel-exclusive $325.38

• United Airlines UA1329 / UA1946: SAN 2027-01-26 06:20:00 → ORD 2027-01-26 14:43:00; 1 stop(s) via LAX; 383 minutes. Local airport times.
  • UA1329: SAN 2027-01-26 06:20:00 → LAX 2027-01-26 07:25:00; layover at LAX: 60 minutes.
  • UA1946: LAX 2027-01-26 08:25:00 → ORD 2027-01-26 14:43:00.
• United Airlines UA660: ORD 2027-02-01 08:50:00 → SAN 2027-02-01 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
• Jan 25, 2027 · Return options
• Jan 27, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Diego (SAN) to Chicago (ORD) · Jan 26, 2027 · return Feb 1, 2027: 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.
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