San Diego (SAN) to Chicago (ORD), Jan 20, 2027 – Feb 2, 2027: from $314 round trip

San Diego (SAN) to Chicago (ORD), Jan 20, 2027 – Feb 2, 2027: from $314 round trip on Axel, checked Nov 12, 2026. Lowest published fare: $314 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 20, 2027 – Feb 2, 2027, 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 (Jan 20 – Feb 2, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $80 a night, $1,040 for 13 nights · 4★ Freehand Chicago, $74 a night, $964 for 13 nights · 5★ Nobu Hotel Chicago, $393 a night, $5,111 for 13 nights

All hotels in Chicago

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

2027-01-20 → 2027-02-02 · Axel-exclusive $386.80

• American Airlines AA2717: SAN 2027-01-20 07:36:00 → ORD 2027-01-20 13:52:00; nonstop; 256 minutes. Local airport times.
• American Airlines AA831: ORD 2027-02-02 16:59:00 → SAN 2027-02-02 19:36:00; nonstop; 277 minutes. Local airport times.

2027-01-20 → 2027-02-02 · Axel-exclusive $386.80

• Alaska Airlines AS1446: SAN 2027-01-20 07:00:00 → ORD 2027-01-20 13:15:00; nonstop; 255 minutes. Local airport times.
• Alaska Airlines AS1447: ORD 2027-02-02 14:13:00 → SAN 2027-02-02 16:51:00; nonstop; 278 minutes. Local airport times.

2027-01-20 → 2027-02-02 · Axel-exclusive $386.80

• United Airlines UA2343: SAN 2027-01-20 06:50:00 → ORD 2027-01-20 13:08:00; nonstop; 258 minutes. Local airport times.
• United Airlines UA660: ORD 2027-02-02 08:45:00 → SAN 2027-02-02 11:21:00; nonstop; 276 minutes. Local airport times.

2027-01-20 → 2027-02-02 · Axel-exclusive $313.96

• Frontier Airlines F91326 / F93648: SAN 2027-01-20 20:37:00 → ORD 2027-01-21 06:10:00; 1 stop(s) via LAS; 453 minutes. Local airport times.
  • F91326: SAN 2027-01-20 20:37:00 → LAS 2027-01-20 22:06:00; layover at LAS: 139 minutes.
  • F93648: LAS 2027-01-21 00:25:00 → ORD 2027-01-21 06:10:00.
• Frontier Airlines F93171 / F92817: ORD 2027-02-02 06:21:00 → SAN 2027-02-02 16:31:00; 1 stop(s) via DEN; 730 minutes. Local airport times.
  • F93171: ORD 2027-02-02 06:21:00 → DEN 2027-02-02 08:21:00; layover at DEN: 405 minutes.
  • F92817: DEN 2027-02-02 15:06:00 → SAN 2027-02-02 16:31:00.

2027-01-20 → 2027-02-02 · Axel-exclusive $694.82

• JetBlue Airways B62120 / B6811: SAN 2027-01-20 21:39:00 → ORD 2027-01-21 13:49:00; 1 stop(s) via BOS; 850 minutes. Local airport times.
  • B62120: SAN 2027-01-20 21:39:00 → BOS 2027-01-21 06:01:00; layover at BOS: 344 minutes.
  • B6811: BOS 2027-01-21 11:45:00 → ORD 2027-01-21 13:49:00.
• JetBlue Airways B61012 / B6919: ORD 2027-02-02 14:55:00 → SAN 2027-02-03 09:50:00; 1 stop(s) via BOS; 1255 minutes. Local airport times.
  • B61012: ORD 2027-02-02 14:55:00 → BOS 2027-02-02 18:17:00; layover at BOS: 714 minutes.
  • B6919: BOS 2027-02-03 06:11:00 → SAN 2027-02-03 09:50:00.

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
• Jan 19, 2027 · Return options
• Jan 21, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Diego (SAN) to Chicago (ORD) · Jan 20, 2027 · return Feb 2, 2027: 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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