San Diego (SAN) to Chicago (ORD), Jan 3, 2027: round trips from $228, one way from $140

San Diego (SAN) to Chicago (ORD), Jan 3, 2027: round trips from $228, one way from $140 on Axel, checked Nov 10, 2026. Lowest published fares: $228 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 3–4, 2027; $140 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 3, 2027; 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 (Jan 3–4, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 a night · 4★ Warwick Allerton - Chicago, $89 a night · 5★ Sofitel Chicago Magnificent Mile, $230 a night
• Hotels in Chicago for these nights (Jan 3–5, 2027 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $70 a night, $140 for 2 nights · 4★ Warwick Allerton - Chicago, $89 a night, $177 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $220 a night, $440 for 2 nights
• Hotels in Chicago for these nights (Jan 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $71 a night, $214 for 3 nights · 4★ Warwick Allerton - Chicago, $91 a night, $273 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $215 a night, $646 for 3 nights
• Hotels in Chicago for these nights (Jan 3–7, 2027 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey, $72 a night, $287 for 4 nights · 4★ Warwick Allerton - Chicago, $90 a night, $358 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $214 a night, $856 for 4 nights
• Hotels in Chicago for these nights (Jan 3–8, 2027 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey, $72 a night, $361 for 5 nights · 4★ Warwick Allerton - Chicago, $90 a night, $450 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $211 a night, $1,055 for 5 nights
• Hotels in Chicago for these nights (Jan 3–9, 2027 · 6 nights · 2 adults, 1 room): 3★ Hotel Versey, $77 a night, $463 for 6 nights · 4★ Warwick Allerton - Chicago, $90 a night, $539 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $218 a night, $1,305 for 6 nights
• Hotels in Chicago for these nights (Jan 3–10, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $77 a night, $541 for 7 nights · 4★ Warwick Allerton - Chicago, $91 a night, $635 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $223 a night, $1,563 for 7 nights
• Hotels in Chicago for these nights (Jan 3–11, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $77 a night, $616 for 8 nights · 4★ Warwick Allerton - Chicago, $90 a night, $720 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $223 a night, $1,782 for 8 nights
• Hotels in Chicago for these nights (Jan 3–12, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $701 for 9 nights · 4★ Warwick Allerton - Chicago, $89 a night, $805 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $226 a night, $2,036 for 9 nights
• Hotels in Chicago for these nights (Jan 3–13, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $776 for 10 nights · 4★ Warwick Allerton - Chicago, $89 a night, $892 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $229 a night, $2,290 for 10 nights
• Hotels in Chicago for these nights (Jan 3–14, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $77 a night, $851 for 11 nights · 4★ Warwick Allerton - Chicago, $89 a night, $980 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $231 a night, $2,544 for 11 nights
• Hotels in Chicago for these nights (Jan 3–15, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $77 a night, $926 for 12 nights · 4★ Warwick Allerton - Chicago, $89 a night, $1,069 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $230 a night, $2,758 for 12 nights
• Hotels in Chicago for these nights (Jan 3–16, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $1,009 for 13 nights · 4★ Warwick Allerton - Chicago, $89 a night, $1,160 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $229 a night, $2,973 for 13 nights
• Hotels in Chicago for these nights (Jan 3–17, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $77 a night, $1,084 for 14 nights · 4★ Warwick Allerton - Chicago, $90 a night, $1,256 for 14 nights · 5★ Sofitel Chicago Magnificent Mile, $228 a night, $3,192 for 14 nights

All hotels in Chicago

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

2027-01-03 · one way · Axel-exclusive $139.65

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 00:26:00.

2027-01-03 · one way · Axel-exclusive $239.40

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; nonstop; 262 minutes. Local airport times.

2027-01-03 → 2027-01-04 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 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.

2027-01-03 → 2027-01-04 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; 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.

2027-01-03 → 2027-01-05 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 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.

2027-01-03 → 2027-01-05 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; 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.

2027-01-03 → 2027-01-06 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 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.

2027-01-03 → 2027-01-06 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; 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.

2027-01-03 → 2027-01-07 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 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.

2027-01-03 → 2027-01-07 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; 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.

2027-01-03 → 2027-01-09 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 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.

2027-01-03 → 2027-01-09 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; 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.

2027-01-03 → 2027-01-10 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 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.

2027-01-03 → 2027-01-10 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; 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.

2027-01-03 → 2027-01-11 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 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.

2027-01-03 → 2027-01-11 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; nonstop; 262 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.

2027-01-03 → 2027-01-13 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-13 06:21:00 → SAN 2027-01-13 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-13 06:21:00 → LAS 2027-01-13 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-13 10:15:00 → SAN 2027-01-13 11:37:00.

2027-01-03 → 2027-01-13 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1470: ORD 2027-01-13 07:27:00 → SAN 2027-01-13 10:12:00; nonstop; 285 minutes. Local airport times.

2027-01-03 → 2027-01-14 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-14 06:21:00 → SAN 2027-01-14 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-14 06:21:00 → LAS 2027-01-14 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-14 10:15:00 → SAN 2027-01-14 11:37:00.

2027-01-03 → 2027-01-14 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1479: ORD 2027-01-14 19:58:00 → SAN 2027-01-14 22:49:00; nonstop; 291 minutes. Local airport times.

2027-01-03 → 2027-01-15 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-15 06:21:00 → SAN 2027-01-15 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-15 06:21:00 → LAS 2027-01-15 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-15 10:15:00 → SAN 2027-01-15 11:37:00.

2027-01-03 → 2027-01-15 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1479: ORD 2027-01-15 19:58:00 → SAN 2027-01-15 22:49:00; nonstop; 291 minutes. Local airport times.

2027-01-03 → 2027-01-17 · Axel-exclusive $228.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-03 16:16:00 → ORD 2027-01-04 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-03 16:16:00 → DEN 2027-01-03 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-03 20:59:00 → ORD 2027-01-04 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-17 06:21:00 → SAN 2027-01-17 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-17 06:21:00 → LAS 2027-01-17 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-17 10:15:00 → SAN 2027-01-17 11:37:00.

2027-01-03 → 2027-01-17 · Axel-exclusive $393.31

• Alaska Airlines AS1493: SAN 2027-01-03 17:37:00 → ORD 2027-01-03 23:59:00; nonstop; 262 minutes. Local airport times.
• Alaska Airlines AS1479: ORD 2027-01-17 19:58:00 → SAN 2027-01-17 22:45:00; nonstop; 287 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 2, 2027 · Return options
• Jan 4, 2027 · Return options
• Hotels in Chicago with Axel

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• This page: San Diego (SAN) to Chicago (ORD) · Jan 3, 2027 · 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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