San Diego (SAN) to Chicago (ORD), Jan 8, 2027: round trips from $190, one way from $100

San Diego (SAN) to Chicago (ORD), Jan 8, 2027: round trips from $190, one way from $100 on Axel, checked Oct 29, 2026. Lowest published fares: $190 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 8–9, 2027; $100 one way, Axel-exclusive, Frontier Airlines, 1 stop, Jan 8, 2027; 1 adult, economy, checked Oct 29, 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, issued at the time 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 issuance times 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 8–9, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $83 a night · 4★ Warwick Allerton - Chicago, $89 a night · 5★ Sofitel Chicago Magnificent Mile, $250 a night
• Hotels in Chicago for these nights (Jan 8–10, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $158 for 2 nights · 4★ Warwick Allerton - Chicago, $93 a night, $185 for 2 nights · 5★ Sofitel Chicago Magnificent Mile, $254 a night, $508 for 2 nights
• Hotels in Chicago for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $233 for 3 nights · 4★ Warwick Allerton - Chicago, $90 a night, $270 for 3 nights · 5★ Sofitel Chicago Magnificent Mile, $242 a night, $727 for 3 nights
• Hotels in Chicago for these nights (Jan 8–12, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $80 a night, $318 for 4 nights · 4★ Warwick Allerton - Chicago, $89 a night, $355 for 4 nights · 5★ Sofitel Chicago Magnificent Mile, $245 a night, $981 for 4 nights
• Hotels in Chicago for these nights (Jan 8–13, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $79 a night, $393 for 5 nights · 4★ Warwick Allerton - Chicago, $88 a night, $442 for 5 nights · 5★ Sofitel Chicago Magnificent Mile, $247 a night, $1,235 for 5 nights
• Hotels in Chicago for these nights (Jan 8–14, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $468 for 6 nights · 4★ Warwick Allerton - Chicago, $88 a night, $530 for 6 nights · 5★ Sofitel Chicago Magnificent Mile, $248 a night, $1,489 for 6 nights
• Hotels in Chicago for these nights (Jan 8–15, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $543 for 7 nights · 4★ Warwick Allerton - Chicago, $88 a night, $619 for 7 nights · 5★ Sofitel Chicago Magnificent Mile, $243 a night, $1,703 for 7 nights
• Hotels in Chicago for these nights (Jan 8–16, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $626 for 8 nights · 4★ Warwick Allerton - Chicago, $89 a night, $710 for 8 nights · 5★ Sofitel Chicago Magnificent Mile, $240 a night, $1,918 for 8 nights
• Hotels in Chicago for these nights (Jan 8–17, 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, $90 a night, $806 for 9 nights · 5★ Sofitel Chicago Magnificent Mile, $237 a night, $2,137 for 9 nights
• Hotels in Chicago for these nights (Jan 8–18, 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, $90 a night, $896 for 10 nights · 5★ Sofitel Chicago Magnificent Mile, $236 a night, $2,360 for 10 nights
• Hotels in Chicago for these nights (Jan 8–19, 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, $90 a night, $988 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $238 a night, $2,614 for 11 nights
• Hotels in Chicago for these nights (Jan 8–20, 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, $1,072 for 12 nights · 5★ Sofitel Chicago Magnificent Mile, $239 a night, $2,867 for 12 nights
• Hotels in Chicago for these nights (Jan 8–21, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $1,011 for 13 nights · 4★ Warwick Allerton - Chicago, $89 a night, $1,157 for 13 nights · 5★ Sofitel Chicago Magnificent Mile, $237 a night, $3,077 for 13 nights
• Hotels in Chicago for these nights (Jan 8–22, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $78 a night, $1,094 for 14 nights · 4★ Warwick Allerton - Chicago, $89 a night, $1,246 for 14 nights · 5★ Sofitel Chicago Magnificent Mile, $237 a night, $3,313 for 14 nights

All hotels in Chicago

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

2027-01-08 · one way · Axel-exclusive $99.75

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 00:26:00.

2027-01-08 · one way · Axel-exclusive $171.00

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 13:19:00; nonstop; 259 minutes. Local airport times.

2027-01-08 → 2027-01-09 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 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.

2027-01-08 → 2027-01-09 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 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.

2027-01-08 → 2027-01-10 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 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.

2027-01-08 → 2027-01-10 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 13:19:00; nonstop; 259 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.

2027-01-08 → 2027-01-11 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 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.

2027-01-08 → 2027-01-11 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 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.

2027-01-08 → 2027-01-12 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 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.

2027-01-08 → 2027-01-12 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 13:19:00; nonstop; 259 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.

2027-01-08 → 2027-01-14 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 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.

2027-01-08 → 2027-01-14 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 13:19:00; nonstop; 259 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.

2027-01-08 → 2027-01-15 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 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.

2027-01-08 → 2027-01-15 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 13:19:00; nonstop; 259 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.

2027-01-08 → 2027-01-16 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-16 06:21:00 → SAN 2027-01-16 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-16 06:21:00 → LAS 2027-01-16 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-16 10:15:00 → SAN 2027-01-16 11:37:00.

2027-01-08 → 2027-01-16 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1479: ORD 2027-01-16 19:58:00 → SAN 2027-01-16 22:45:00; nonstop; 287 minutes. Local airport times.

2027-01-08 → 2027-01-18 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-18 06:21:00 → SAN 2027-01-18 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-18 06:21:00 → LAS 2027-01-18 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-18 10:15:00 → SAN 2027-01-18 11:37:00.

2027-01-08 → 2027-01-18 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2027-01-18 14:13:00 → SAN 2027-01-18 17:00:00; nonstop; 287 minutes. Local airport times.

2027-01-08 → 2027-01-19 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-19 06:21:00 → SAN 2027-01-19 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-19 06:21:00 → LAS 2027-01-19 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-19 10:15:00 → SAN 2027-01-19 11:37:00.

2027-01-08 → 2027-01-19 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2027-01-19 14:13:00 → SAN 2027-01-19 17:00:00; nonstop; 287 minutes. Local airport times.

2027-01-08 → 2027-01-20 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 00:26:00.
• Frontier Airlines F92145 / F91326: ORD 2027-01-20 06:21:00 → SAN 2027-01-20 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
  • F92145: ORD 2027-01-20 06:21:00 → LAS 2027-01-20 08:34:00; layover at LAS: 101 minutes.
  • F91326: LAS 2027-01-20 10:15:00 → SAN 2027-01-20 11:37:00.

2027-01-08 → 2027-01-20 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1470: ORD 2027-01-20 07:27:00 → SAN 2027-01-20 10:12:00; nonstop; 285 minutes. Local airport times.

2027-01-08 → 2027-01-22 · Axel-exclusive $190.00

• Frontier Airlines F92422 / F93174: SAN 2027-01-08 16:16:00 → ORD 2027-01-09 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
  • F92422: SAN 2027-01-08 16:16:00 → DEN 2027-01-08 19:50:00; layover at DEN: 69 minutes.
  • F93174: DEN 2027-01-08 20:59:00 → ORD 2027-01-09 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.

2027-01-08 → 2027-01-22 · Axel-exclusive $327.76

• Alaska Airlines AS1446: SAN 2027-01-08 07:00:00 → ORD 2027-01-08 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.

Explore this route

• All dates for this route
• Jan 7, 2027 · Return options
• Jan 9, 2027 · Return options
• Hotels in Chicago with Axel

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• This page: San Diego (SAN) to Chicago (ORD) · Jan 8, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. 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 the time its price was issued); 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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