San Diego (SAN) to Chicago (ORD), Dec 20–31, 2026: from $314 round trip

San Diego (SAN) to Chicago (ORD), Dec 20–31, 2026: from $314 round trip on Axel, checked Nov 12, 2026. Lowest published fare: $314 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Dec 20–31, 2026, 1 adult, economy, checked Nov 12, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

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 20–31, 2026 · 11 nights · 2 adults, 1 room): 3★ Hotel Versey, $99 a night, $1,085 for 11 nights · 4★ Freehand Chicago, $72 a night, $787 for 11 nights · 5★ Sofitel Chicago Magnificent Mile, $206 a night, $2,264 for 11 nights

All hotels in Chicago

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

2026-12-20 → 2026-12-31 · Axel-exclusive $386.80

• American Airlines AA2081: SAN 2026-12-20 07:21:00 → ORD 2026-12-20 13:37:00; nonstop; 256 minutes. Local airport times.
• American Airlines AA2343: ORD 2026-12-31 06:45:00 → SAN 2026-12-31 09:24:00; nonstop; 279 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $386.80

• United Airlines UA2343: SAN 2026-12-20 06:50:00 → ORD 2026-12-20 13:08:00; nonstop; 258 minutes. Local airport times.
• United Airlines UA2384: ORD 2026-12-31 12:40:00 → SAN 2026-12-31 15:14:00; nonstop; 274 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $386.80

• Alaska Airlines AS1446: SAN 2026-12-20 07:00:00 → ORD 2026-12-20 13:19:00; nonstop; 259 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2026-12-31 14:17:00 → SAN 2026-12-31 17:02:00; nonstop; 285 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $313.96

• Frontier Airlines F92818 / F93174: SAN 2026-12-20 06:36:00 → ORD 2026-12-21 00:26:00; 1 stop(s) via DEN; 950 minutes. Local airport times.
  • F92818: SAN 2026-12-20 06:36:00 → DEN 2026-12-20 10:10:00; layover at DEN: 649 minutes.
  • F93174: DEN 2026-12-20 20:59:00 → ORD 2026-12-21 00:26:00.
• Frontier Airlines F91483 / F92711: ORD 2026-12-31 07:00:00 → SAN 2026-12-31 23:58:00; 1 stop(s) via DEN; 1138 minutes. Local airport times.
  • F91483: ORD 2026-12-31 07:00:00 → DEN 2026-12-31 09:04:00; layover at DEN: 805 minutes.
  • F92711: DEN 2026-12-31 22:29:00 → SAN 2026-12-31 23:58:00.

2026-12-20 → 2026-12-31 · Axel-exclusive $694.82

• JetBlue Airways B62120 / B6811: SAN 2026-12-20 21:39:00 → ORD 2026-12-21 13:49:00; 1 stop(s) via BOS; 850 minutes. Local airport times.
  • B62120: SAN 2026-12-20 21:39:00 → BOS 2026-12-21 06:01:00; layover at BOS: 344 minutes.
  • B6811: BOS 2026-12-21 11:45:00 → ORD 2026-12-21 13:49:00.
• JetBlue Airways B61012 / B6919: ORD 2026-12-31 19:55:00 → SAN 2027-01-01 10:34:00; 1 stop(s) via BOS; 999 minutes. Local airport times.
  • B61012: ORD 2026-12-31 19:55:00 → BOS 2026-12-31 23:21:00; layover at BOS: 459 minutes.
  • B6919: BOS 2027-01-01 07:00:00 → SAN 2027-01-01 10:34:00.

2026-12-20 → 2026-12-31 · Axel-exclusive $793.54

• Sun Country Airlines SY408 / SY259: SAN 2026-12-20 18:22:00 → ORD 2026-12-21 09:48:00; 1 stop(s) via MSP; 806 minutes. Local airport times.
  • SY408: SAN 2026-12-20 18:22:00 → MSP 2026-12-20 23:59:00; layover at MSP: 481 minutes.
  • SY259: MSP 2026-12-21 08:00:00 → ORD 2026-12-21 09:48:00.
• Sun Country Airlines SY260 / SY407: ORD 2026-12-31 11:53:00 → SAN 2026-12-31 17:12:00; 1 stop(s) via MSP; 439 minutes. Local airport times.
  • SY260: ORD 2026-12-31 11:53:00 → MSP 2026-12-31 13:39:00; layover at MSP: 96 minutes.
  • SY407: MSP 2026-12-31 15:15:00 → SAN 2026-12-31 17:12:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Dec 19, 2026 · Return options
• Dec 21, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Diego (SAN) to Chicago (ORD) · Dec 20, 2026 · return Dec 31, 2026: 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 priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Diego to Chicago (ORD) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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