San Diego (SAN) to Chicago (ORD), Dec 27, 2026: round trips from $235, one way from $147

San Diego (SAN) to Chicago (ORD), Dec 27, 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 27, 2026 – Jan 4, 2027; $147 one way, Axel-exclusive, Frontier Airlines, 1 stop, Dec 27, 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 27–28, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $89 a night · 4★ Warwick Allerton - Chicago, $96 a night · 5★ Sofitel Chicago Magnificent Mile, $210 a night
• Hotels in Chicago for these nights (Dec 27–29, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $86 a night, $172 for 2 nights · 4★ Warwick Allerton - Chicago, $96 a night, $192 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $208 a night, $416 for 2 nights
• Hotels in Chicago for these nights (Dec 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $86 a night, $257 for 3 nights · 4★ Warwick Allerton - Chicago, $95 a night, $286 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $208 a night, $623 for 3 nights
• Hotels in Chicago for these nights (Dec 27–31, 2026 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey, $91 a night, $364 for 4 nights · 4★ Warwick Allerton - Chicago, $95 a night, $380 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $207 a night, $826 for 4 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 1, 2027 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel, $113 a night, $567 for 5 nights · 4★ Warwick Allerton - Chicago, $117 a night, $583 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $255 a night, $1,276 for 5 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 2, 2027 · 6 nights · 2 adults, 1 room): 3★ The Willows Hotel, $118 a night, $707 for 6 nights · 4★ Warwick Allerton - Chicago, $114 a night, $683 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $247 a night, $1,479 for 6 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 3, 2027 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $119 a night, $831 for 7 nights · 4★ Warwick Allerton - Chicago, $112 a night, $787 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $241 a night, $1,689 for 7 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 4, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $115 a night, $917 for 8 nights · 4★ Warwick Allerton - Chicago, $110 a night, $876 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $240 a night, $1,919 for 8 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 5, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $110 a night, $992 for 9 nights · 4★ Warwick Allerton - Chicago, $107 a night, $964 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $237 a night, $2,129 for 9 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 6, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $107 a night, $1,067 for 10 nights · 4★ Warwick Allerton - Chicago, $106 a night, $1,060 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $234 a night, $2,335 for 10 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 7, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $105 a night, $1,150 for 11 nights · 4★ Warwick Allerton - Chicago, $104 a night, $1,145 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $231 a night, $2,545 for 11 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 8, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $102 a night, $1,225 for 12 nights · 4★ Warwick Allerton - Chicago, $103 a night, $1,237 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $229 a night, $2,744 for 12 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 9, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $101 a night, $1,308 for 13 nights · 4★ Warwick Allerton - Chicago, $102 a night, $1,326 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $230 a night, $2,994 for 13 nights
• Hotels in Chicago for these nights (Dec 27 – Jan 10, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $99 a night, $1,383 for 14 nights · 4★ Warwick Allerton - Chicago, $102 a night, $1,422 for 14 nights · 5★ Sofitel Chicago Magnificent Mile, $232 a night, $3,252 for 14 nights

All hotels in Chicago

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

2026-12-27 · one way · Axel-exclusive $147.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 00:26:00.

2026-12-27 · one way · Axel-exclusive $252.00

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 18:54:00; nonstop; 262 minutes. Local airport times.

2026-12-27 → 2026-12-28 · Axel-exclusive $280.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2026-12-28 06:21:00 → SAN 2026-12-28 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2026-12-28 06:21:00 → LAS 2026-12-28 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2026-12-28 10:15:00 → SAN 2026-12-28 11:37:00.

2026-12-27 → 2026-12-28 · Axel-exclusive $483.00

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 18:54:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2026-12-28 14:13:00 → SAN 2026-12-28 17:00:00; nonstop; 287 minutes. Local airport times.

2026-12-27 → 2026-12-29 · Axel-exclusive $280.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2026-12-29 · Axel-exclusive $483.00

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 18:54:00; nonstop; 262 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.

2026-12-27 → 2026-12-30 · Axel-exclusive $280.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2026-12-30 · Axel-exclusive $483.00

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 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.

2026-12-27 → 2026-12-31 · Axel-exclusive $280.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2026-12-31 · Axel-exclusive $483.00

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 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.

2026-12-27 → 2027-01-02 · Axel-exclusive $273.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2027-01-02 · Axel-exclusive $470.93

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 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.

2026-12-27 → 2027-01-03 · Axel-exclusive $273.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2027-01-03 · Axel-exclusive $470.93

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 18:54:00; nonstop; 262 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.

2026-12-27 → 2027-01-04 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2027-01-04 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 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.

2026-12-27 → 2027-01-06 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2027-01-06 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 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.

2026-12-27 → 2027-01-07 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2027-01-07 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 18:54:00; nonstop; 262 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.

2026-12-27 → 2027-01-08 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2027-01-08 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 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.

2026-12-27 → 2027-01-10 · Axel-exclusive $235.00

• Frontier Airlines F92422 / F93174: SAN 2026-12-27 16:16:00 → ORD 2026-12-28 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2026-12-27 16:16:00 → DEN 2026-12-27 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2026-12-27 20:59:00 → ORD 2026-12-28 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.

2026-12-27 → 2027-01-10 · Axel-exclusive $405.38

• Alaska Airlines AS1478: SAN 2026-12-27 12:32:00 → ORD 2026-12-27 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.

Explore this route

• All dates for this route
• Dec 26, 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 27, 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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