San Diego (SAN) to Chicago (ORD), Dec 29, 2026: round trips from $235, one way from $147

San Diego (SAN) to Chicago (ORD), Dec 29, 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 29, 2026 – Jan 4, 2027; $147 one way, Axel-exclusive, Frontier Airlines, 1 stop, Dec 29, 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 29–30, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $85 a night · 4★ Warwick Allerton - Chicago, $94 a night · 5★ Sofitel Chicago Magnificent Mile, $207 a night
• Hotels in Chicago for these nights (Dec 29–31, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $96 a night, $192 for 2 nights · 4★ Warwick Allerton - Chicago, $94 a night, $188 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $205 a night, $410 for 2 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 1, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $124 a night, $372 for 3 nights · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $122 a night, $365 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $287 a night, $860 for 3 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 2, 2027 · 4 nights · 2 adults, 1 room): 3★ The Willows Hotel, $128 a night, $512 for 4 nights · 4★ Warwick Allerton - Chicago, $123 a night, $491 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $266 a night, $1,063 for 4 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 3, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $128 a night, $640 for 5 nights · 4★ Warwick Allerton - Chicago, $119 a night, $595 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $255 a night, $1,273 for 5 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 4, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $119 a night, $715 for 6 nights · 4★ Warwick Allerton - Chicago, $114 a night, $684 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $251 a night, $1,503 for 6 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 5, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $113 a night, $790 for 7 nights · 4★ Warwick Allerton - Chicago, $110 a night, $772 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $245 a night, $1,713 for 7 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 6, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $108 a night, $865 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 29 – Jan 7, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $105 a night, $948 for 9 nights · 4★ Warwick Allerton - Chicago, $106 a night, $953 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $237 a night, $2,129 for 9 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 8, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $102 a night, $1,023 for 10 nights · 4★ Warwick Allerton - Chicago, $105 a night, $1,045 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $233 a night, $2,328 for 10 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 9, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $101 a night, $1,106 for 11 nights · 4★ Warwick Allerton - Chicago, $103 a night, $1,134 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $234 a night, $2,578 for 11 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 10, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $98 a night, $1,181 for 12 nights · 4★ Warwick Allerton - Chicago, $103 a night, $1,230 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $236 a night, $2,836 for 12 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 11, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $97 a night, $1,256 for 13 nights · 4★ Warwick Allerton - Chicago, $101 a night, $1,315 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $235 a night, $3,055 for 13 nights
• Hotels in Chicago for these nights (Dec 29 – Jan 12, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $96 a night, $1,341 for 14 nights · 4★ Warwick Allerton - Chicago, $100 a night, $1,400 for 14 nights · 5★ Sofitel Chicago Magnificent Mile, $236 a night, $3,309 for 14 nights

All hotels in Chicago

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

2026-12-29 · one way · Axel-exclusive $147.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 00:26:00.

2026-12-29 · one way · Axel-exclusive $252.00

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 minutes. Local airport times.

2026-12-29 → 2026-12-30 · Axel-exclusive $280.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 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.

2026-12-29 → 2026-12-30 · Axel-exclusive $483.00

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 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.

2026-12-29 → 2026-12-31 · Axel-exclusive $280.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 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.

2026-12-29 → 2026-12-31 · Axel-exclusive $483.00

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 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.

2026-12-29 → 2027-01-01 · Axel-exclusive $273.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 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.

2026-12-29 → 2027-01-01 · Axel-exclusive $470.93

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 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.

2026-12-29 → 2027-01-02 · Axel-exclusive $273.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-02 06:21:00 → SAN 2027-01-02 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-02 06:21:00 → LAS 2027-01-02 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-02 10:15:00 → SAN 2027-01-02 11:37:00.

2026-12-29 → 2027-01-02 · Axel-exclusive $470.93

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1479: ORD 2027-01-02 19:58:00 → SAN 2027-01-02 22:45:00; nonstop; 287 minutes. Local airport times.

2026-12-29 → 2027-01-04 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 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.

2026-12-29 → 2027-01-04 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 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.

2026-12-29 → 2027-01-05 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 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.

2026-12-29 → 2027-01-05 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 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.

2026-12-29 → 2027-01-06 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-06 06:21:00 → SAN 2027-01-06 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-06 06:21:00 → LAS 2027-01-06 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-06 10:15:00 → SAN 2027-01-06 11:37:00.

2026-12-29 → 2027-01-06 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1470: ORD 2027-01-06 07:27:00 → SAN 2027-01-06 10:12:00; nonstop; 285 minutes. Local airport times.

2026-12-29 → 2027-01-08 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 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.

2026-12-29 → 2027-01-08 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 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.

2026-12-29 → 2027-01-09 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 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.

2026-12-29 → 2027-01-09 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 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.

2026-12-29 → 2027-01-10 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-10 06:21:00 → SAN 2027-01-10 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-10 06:21:00 → LAS 2027-01-10 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-10 10:15:00 → SAN 2027-01-10 11:37:00.

2026-12-29 → 2027-01-10 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1479: ORD 2027-01-10 19:58:00 → SAN 2027-01-10 22:45:00; nonstop; 287 minutes. Local airport times.

2026-12-29 → 2027-01-12 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-29 16:16:00 → ORD 2026-12-30 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-29 16:16:00 → DEN 2026-12-29 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-29 20:59:00 → ORD 2026-12-30 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-12 06:21:00 → SAN 2027-01-12 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-12 06:21:00 → LAS 2027-01-12 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-12 10:15:00 → SAN 2027-01-12 11:37:00.

2026-12-29 → 2027-01-12 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-29 12:32:00 → ORD 2026-12-29 18:54:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2027-01-12 14:13:00 → SAN 2027-01-12 17:00:00; nonstop; 287 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 28, 2026 · Return options
• Dec 30, 2026 · Return options
• Hotels in Chicago with Axel

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• This page: San Diego (SAN) to Chicago (ORD) · Dec 29, 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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