San Diego (SAN) to Chicago (ORD), Dec 28, 2026: round trips from $235, one way from $147

San Diego (SAN) to Chicago (ORD), Dec 28, 2026: round trips from $235, one way from $147 on Axel, checked Nov 10, 2026. Lowest published fares: $235 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Dec 28, 2026 – Jan 4, 2027; $147 one way, Axel-exclusive, Frontier Airlines, 1 stop, Dec 28, 2026; 1 adult, economy, checked Nov 10, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

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 (Dec 28–29, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $83 a night · 4★ Warwick Allerton - Chicago, $96 a night · 5★ Sofitel Chicago Magnificent Mile, $206 a night
• Hotels in Chicago for these nights (Dec 28–30, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $84 a night, $168 for 2 nights · 4★ Warwick Allerton - Chicago, $95 a night, $190 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $207 a night, $413 for 2 nights
• Hotels in Chicago for these nights (Dec 28–31, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $92 a night, $275 for 3 nights · 4★ Warwick Allerton - Chicago, $95 a night, $284 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $205 a night, $616 for 3 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 1, 2027 · 4 nights · 2 adults, 1 room): 3★ The Willows Hotel, $116 a night, $463 for 4 nights · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $120 a night, $480 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $267 a night, $1,066 for 4 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 2, 2027 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel, $121 a night, $603 for 5 nights · 4★ Warwick Allerton - Chicago, $117 a night, $587 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $254 a night, $1,269 for 5 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 3, 2027 · 6 nights · 2 adults, 1 room): 3★ The Willows Hotel, $122 a night, $732 for 6 nights · 4★ Warwick Allerton - Chicago, $115 a night, $691 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $247 a night, $1,479 for 6 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 4, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $117 a night, $819 for 7 nights · 4★ Warwick Allerton - Chicago, $111 a night, $780 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $244 a night, $1,709 for 7 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 5, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $112 a night, $894 for 8 nights · 4★ Warwick Allerton - Chicago, $109 a night, $868 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $240 a night, $1,919 for 8 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 6, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $108 a night, $969 for 9 nights · 4★ Warwick Allerton - Chicago, $107 a night, $964 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $236 a night, $2,125 for 9 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 7, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $105 a night, $1,052 for 10 nights · 4★ Warwick Allerton - Chicago, $105 a night, $1,049 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $234 a night, $2,335 for 10 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 8, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $102 a night, $1,127 for 11 nights · 4★ Warwick Allerton - Chicago, $104 a night, $1,141 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $230 a night, $2,534 for 11 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 9, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $101 a night, $1,210 for 12 nights · 4★ Warwick Allerton - Chicago, $103 a night, $1,230 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $232 a night, $2,784 for 12 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 10, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $99 a night, $1,285 for 13 nights · 4★ Warwick Allerton - Chicago, $102 a night, $1,326 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $234 a night, $3,042 for 13 nights
• Hotels in Chicago for these nights (Dec 28 – Jan 11, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $97 a night, $1,360 for 14 nights · 4★ Warwick Allerton - Chicago, $101 a night, $1,411 for 14 nights · 5★ Sofitel Chicago Magnificent Mile, $233 a night, $3,261 for 14 nights

All hotels in Chicago

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

2026-12-28 · one way · Axel-exclusive $147.00

• 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.

2026-12-28 · one way · Axel-exclusive $252.00

• Alaska Airlines AS1446: SAN 2026-12-28 07:00:00 → ORD 2026-12-28 13:19:00; nonstop; 259 minutes. Local airport times.

2026-12-28 → 2026-12-29 · Axel-exclusive $280.00

• 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 2026-12-29 06:21:00 → SAN 2026-12-29 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2026-12-29 06:21:00 → LAS 2026-12-29 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2026-12-29 10:15:00 → SAN 2026-12-29 11:37:00.

2026-12-28 → 2026-12-29 · Axel-exclusive $483.00

• 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 2026-12-29 14:13:00 → SAN 2026-12-29 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-28 → 2026-12-30 · Axel-exclusive $280.00

• 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 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.

2026-12-28 → 2026-12-30 · Axel-exclusive $483.00

• 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 AS1470: ORD 2026-12-30 07:27:00 → SAN 2026-12-30 10:12:00; nonstop; 285 minutes. Local airport times.

2026-12-28 → 2026-12-31 · Axel-exclusive $280.00

• 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 2026-12-31 06:21:00 → SAN 2026-12-31 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2026-12-31 06:21:00 → LAS 2026-12-31 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2026-12-31 10:15:00 → SAN 2026-12-31 11:37:00.

2026-12-28 → 2026-12-31 · Axel-exclusive $483.00

• 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 AS1479: ORD 2026-12-31 19:58:00 → SAN 2026-12-31 22:49:00; nonstop; 291 minutes. Local airport times.

2026-12-28 → 2027-01-01 · Axel-exclusive $273.00

• 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 2027-01-01 06:21:00 → SAN 2027-01-01 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-01 06:21:00 → LAS 2027-01-01 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-01 10:15:00 → SAN 2027-01-01 11:37:00.

2026-12-28 → 2027-01-01 · Axel-exclusive $470.93

• 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 AS1479: ORD 2027-01-01 19:58:00 → SAN 2027-01-01 22:49:00; nonstop; 291 minutes. Local airport times.

2026-12-28 → 2027-01-03 · Axel-exclusive $273.00

• 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 2027-01-03 06:21:00 → SAN 2027-01-03 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-03 06:21:00 → LAS 2027-01-03 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-03 10:15:00 → SAN 2027-01-03 11:37:00.

2026-12-28 → 2027-01-03 · Axel-exclusive $470.93

• 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 AS1479: ORD 2027-01-03 19:58:00 → SAN 2027-01-03 22:45:00; nonstop; 287 minutes. Local airport times.

2026-12-28 → 2027-01-04 · 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 2027-01-04 06:21:00 → SAN 2027-01-04 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-04 06:21:00 → LAS 2027-01-04 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-04 10:15:00 → SAN 2027-01-04 11:37:00.

2026-12-28 → 2027-01-04 · 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 2027-01-04 14:13:00 → SAN 2027-01-04 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-28 → 2027-01-05 · 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 2027-01-05 06:21:00 → SAN 2027-01-05 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-05 06:21:00 → LAS 2027-01-05 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-05 10:15:00 → SAN 2027-01-05 11:37:00.

2026-12-28 → 2027-01-05 · 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 2027-01-05 14:13:00 → SAN 2027-01-05 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-28 → 2027-01-07 · 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 2027-01-07 06:21:00 → SAN 2027-01-07 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-07 06:21:00 → LAS 2027-01-07 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-07 10:15:00 → SAN 2027-01-07 11:37:00.

2026-12-28 → 2027-01-07 · 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 AS1479: ORD 2027-01-07 19:58:00 → SAN 2027-01-07 22:49:00; nonstop; 291 minutes. Local airport times.

2026-12-28 → 2027-01-08 · 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 2027-01-08 06:21:00 → SAN 2027-01-08 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-08 06:21:00 → LAS 2027-01-08 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-08 10:15:00 → SAN 2027-01-08 11:37:00.

2026-12-28 → 2027-01-08 · 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 AS1479: ORD 2027-01-08 19:58:00 → SAN 2027-01-08 22:49:00; nonstop; 291 minutes. Local airport times.

2026-12-28 → 2027-01-09 · 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 2027-01-09 06:21:00 → SAN 2027-01-09 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-09 06:21:00 → LAS 2027-01-09 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-09 10:15:00 → SAN 2027-01-09 11:37:00.

2026-12-28 → 2027-01-09 · 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 AS1479: ORD 2027-01-09 19:58:00 → SAN 2027-01-09 22:45:00; nonstop; 287 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 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.

Explore this route

• All dates for this route
• Dec 27, 2026 · Return options
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• Hotels in Chicago with Axel

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• This page: San Diego (SAN) to Chicago (ORD) · Dec 28, 2026 · choose your return date: 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.
• Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
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