San Diego (SAN) to Chicago (ORD), Jan 21–22, 2027: from $190 round trip

San Diego (SAN) to Chicago (ORD), Jan 21–22, 2027: from $190 round trip on Axel, checked Nov 12, 2026. Lowest published fare: $190 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 21–22, 2027, 1 adult, economy, checked Nov 12, 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 link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Jan 21–22, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $73 a night · 4★ Warwick Allerton - Chicago, $89 a night · 5★ Sofitel Chicago Magnificent Mile, $236 a night

All hotels in Chicago

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

2027-01-21 → 2027-01-22 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-21 07:00:00 → ORD 2027-01-21 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1479: ORD 2027-01-22 19:58:00 → SAN 2027-01-22 22:49:00; nonstop; 291 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $332.50

• American Airlines AA2081: SAN 2027-01-21 06:15:00 → ORD 2027-01-21 12:30:00; nonstop; 255 minutes. Local airport times.
• American Airlines AA3064: ORD 2027-01-22 21:21:00 → SAN 2027-01-22 23:59:00; nonstop; 278 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $342.00

• United Airlines UA540: SAN 2027-01-21 22:30:00 → ORD 2027-01-22 04:42:00; nonstop; 252 minutes. Local airport times.
• United Airlines UA2428: ORD 2027-01-22 07:00:00 → SAN 2027-01-22 09:35:00; nonstop; 275 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-21 16:16:00 → ORD 2027-01-22 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-21 16:16:00 → DEN 2027-01-21 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-21 20:59:00 → ORD 2027-01-22 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-22 06:21:00 → SAN 2027-01-22 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-22 06:21:00 → LAS 2027-01-22 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-22 10:15:00 → SAN 2027-01-22 11:37:00.

2027-01-21 → 2027-01-22 · Axel-exclusive $327.76

• Alaska Airlines AS1493: SAN 2027-01-21 17:37:00 → ORD 2027-01-21 23:59:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1479: ORD 2027-01-22 19:58:00 → SAN 2027-01-22 22:49:00; nonstop; 291 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $332.50

• American Airlines AA3111: SAN 2027-01-21 22:33:00 → ORD 2027-01-22 04:37:00; nonstop; 244 minutes. Local airport times.
• American Airlines AA3064: ORD 2027-01-22 21:21:00 → SAN 2027-01-22 23:59:00; nonstop; 278 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $342.00

• United Airlines UA1710: SAN 2027-01-21 10:30:00 → ORD 2027-01-21 16:44:00; nonstop; 254 minutes. Local airport times.
• United Airlines UA2428: ORD 2027-01-22 07:00:00 → SAN 2027-01-22 09:35:00; nonstop; 275 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $315.88

• American Airlines AA2438 / AA2221: SAN 2027-01-21 15:13:00 → ORD 2027-01-21 23:59:00; 1 stop(s) via DFW; 406 minutes. Local airport times.
  • AA2438: SAN 2027-01-21 15:13:00 → DFW 2027-01-21 20:30:00; layover at DFW: 60 minutes.
  • AA2221: DFW 2027-01-21 21:30:00 → ORD 2027-01-21 23:59:00.
• American Airlines AA3064: ORD 2027-01-22 21:21:00 → SAN 2027-01-22 23:59:00; nonstop; 278 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $318.26

• Alaska Airlines AS2291 / AA3010: SAN 2027-01-21 14:59:00 → ORD 2027-01-21 23:40:00; 1 stop(s) via LAS; 401 minutes. Local airport times.
  • AS2291: SAN 2027-01-21 14:59:00 → LAS 2027-01-21 16:23:00; layover at LAS: 103 minutes.
  • AA3010: LAS 2027-01-21 18:06:00 → ORD 2027-01-21 23:40:00.
• Alaska Airlines AS1479: ORD 2027-01-22 19:58:00 → SAN 2027-01-22 22:49:00; nonstop; 291 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $318.26

• Alaska Airlines AS2297 / AA1333: SAN 2027-01-21 21:11:00 → ORD 2027-01-22 05:22:00; 1 stop(s) via PHX; 371 minutes. Local airport times.
  • AS2297: SAN 2027-01-21 21:11:00 → PHX 2027-01-21 23:37:00; layover at PHX: 68 minutes.
  • AA1333: PHX 2027-01-22 00:45:00 → ORD 2027-01-22 05:22:00.
• Alaska Airlines AS1479: ORD 2027-01-22 19:58:00 → SAN 2027-01-22 22:49:00; nonstop; 291 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $318.26

• Alaska Airlines AS1342 / AA1277: SAN 2027-01-21 09:27:00 → ORD 2027-01-21 18:14:00; 1 stop(s) via DEN; 407 minutes. Local airport times.
  • AS1342: SAN 2027-01-21 09:27:00 → DEN 2027-01-21 12:56:00; layover at DEN: 99 minutes.
  • AA1277: DEN 2027-01-21 14:35:00 → ORD 2027-01-21 18:14:00.
• Alaska Airlines AS1479: ORD 2027-01-22 19:58:00 → SAN 2027-01-22 22:49:00; nonstop; 291 minutes. Local airport times.

2027-01-21 → 2027-01-22 · Axel-exclusive $325.38

• United Airlines UA1329 / UA1946: SAN 2027-01-21 06:20:00 → ORD 2027-01-21 14:43:00; 1 stop(s) via LAX; 383 minutes. Local airport times.
  • UA1329: SAN 2027-01-21 06:20:00 → LAX 2027-01-21 07:25:00; layover at LAX: 60 minutes.
  • UA1946: LAX 2027-01-21 08:25:00 → ORD 2027-01-21 14:43:00.
• United Airlines UA2428: ORD 2027-01-22 07:00:00 → SAN 2027-01-22 09:35:00; nonstop; 275 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 20, 2027 · Return options
• Jan 22, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Diego (SAN) to Chicago (ORD) · Jan 21, 2027 · return Jan 22, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
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