San Jose (SJC) to Chicago (ORD), Sep 17–20, 2027: from $435 round trip
San Jose (SJC) to Chicago (ORD), Sep 17–20, 2027: from $435 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $435 round trip, Axel-exclusive, Alaska Airlines / American Airlines, 1 stop, Sep 17–20, 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.
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.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2027-09-17 → 2027-09-20 | United Airlines | UA2382 / UA1840 | 23:00:00→05:17:00 4h 17m nonstop · 19:45:00→22:45:00 5h 00m nonstop | Axel-exclusive $494.00 | 2026-10-29T01:22:11Z |
| 2027-09-17 → 2027-09-20 | Alaska Airlines / American Airlines | AS653 + AS1478 / AA3111 + AS672 | 09:54:00→19:00:00 7h 06m 1 stop via SAN · 16:45:00→22:56:00 8h 11m 1 stop via SAN | Axel-exclusive $434.63 | 2026-10-29T01:22:11Z |
| 2027-09-17 → 2027-09-20 | American Airlines | AA3257 + AA1528 / AA3111 + AS672 | 13:05:00→21:58:00 6h 53m 1 stop via PHX · 16:45:00→22:56:00 8h 11m 1 stop via SAN | Axel-exclusive $441.76 | 2026-10-29T01:22:11Z |
| 2027-09-17 → 2027-09-20 | Delta Air Lines | DL2904 + DL1178 / DL756 + DL3883 | 22:40:00→08:34:00 7h 54m 1 stop via ATL · 14:25:00→19:25:00 7h 00m 1 stop via LAX | Axel-exclusive $460.76 | 2026-10-29T01:22:11Z |
| 2027-09-17 → 2027-09-20 | United Airlines | UA1082 / UA1840 | 14:11:00→20:30:00 4h 19m nonstop · 19:45:00→22:45:00 5h 00m nonstop | Axel-exclusive $494.00 | 2026-10-29T01:22:11Z |
| 2027-09-17 → 2027-09-20 | Alaska Airlines / American Airlines | AS1859 + AA2664 / AA3111 + AS672 | 20:24:00→05:01:00 6h 37m 1 stop via LAX · 16:45:00→22:56:00 8h 11m 1 stop via SAN | Axel-exclusive $434.63 | 2026-10-29T01:22:11Z |
| 2027-09-17 → 2027-09-20 | Delta Air Lines | DL1254 + DL2413 / DL756 + DL3883 | 13:39:00→22:27:00 6h 48m 1 stop via SLC · 14:25:00→19:25:00 7h 00m 1 stop via LAX | Axel-exclusive $460.76 | 2026-10-29T01:22:11Z |
| 2027-09-17 → 2027-09-20 | United Airlines | UA2013 + UA1651 / UA1840 | 08:45:00→18:38:00 7h 53m 1 stop via DEN · 19:45:00→22:45:00 5h 00m nonstop | Axel-exclusive $467.88 | 2026-10-29T01:22:11Z |
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 lowest saved total among the shortlisted hotels in that star tier for those dates.
- Hotels in Chicago for these nights (Sep 17–20, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Route overview: San Francisco Bay Area to Chicago (ORD) flight deals
2027-09-17 → 2027-09-20 · Axel-exclusive $494.00
- United Airlines UA2382: SJC 2027-09-17 23:00:00 → ORD 2027-09-18 05:17:00; nonstop; 257 minutes. Local airport times.
- United Airlines UA1840: ORD 2027-09-20 19:45:00 → SJC 2027-09-20 22:45:00; nonstop; 300 minutes. Local airport times.
2027-09-17 → 2027-09-20 · Axel-exclusive $434.63
- Alaska Airlines AS653 / AS1478: SJC 2027-09-17 09:54:00 → ORD 2027-09-17 19:00:00; 1 stop(s) via SAN; 426 minutes. Local airport times.
- AS653: SJC 2027-09-17 09:54:00 → SAN 2027-09-17 11:19:00; layover at SAN: 83 minutes.
- AS1478: SAN 2027-09-17 12:42:00 → ORD 2027-09-17 19:00:00.
- American Airlines AA3111 / AS672: ORD 2027-09-20 16:45:00 → SJC 2027-09-20 22:56:00; 1 stop(s) via SAN; 491 minutes. Local airport times.
- AA3111: ORD 2027-09-20 16:45:00 → SAN 2027-09-20 19:18:00; layover at SAN: 121 minutes.
- AS672: SAN 2027-09-20 21:19:00 → SJC 2027-09-20 22:56:00.
2027-09-17 → 2027-09-20 · Axel-exclusive $441.76
- American Airlines AA3257 / AA1528: SJC 2027-09-17 13:05:00 → ORD 2027-09-17 21:58:00; 1 stop(s) via PHX; 413 minutes. Local airport times.
- AA3257: SJC 2027-09-17 13:05:00 → PHX 2027-09-17 15:05:00; layover at PHX: 81 minutes.
- AA1528: PHX 2027-09-17 16:26:00 → ORD 2027-09-17 21:58:00.
- American Airlines AA3111 / AS672: ORD 2027-09-20 16:45:00 → SJC 2027-09-20 22:56:00; 1 stop(s) via SAN; 491 minutes. Local airport times.
- AA3111: ORD 2027-09-20 16:45:00 → SAN 2027-09-20 19:18:00; layover at SAN: 121 minutes.
- AS672: SAN 2027-09-20 21:19:00 → SJC 2027-09-20 22:56:00.
2027-09-17 → 2027-09-20 · Axel-exclusive $460.76
- Delta Air Lines DL2904 / DL1178: SJC 2027-09-17 22:40:00 → ORD 2027-09-18 08:34:00; 1 stop(s) via ATL; 474 minutes. Local airport times.
- DL2904: SJC 2027-09-17 22:40:00 → ATL 2027-09-18 06:10:00; layover at ATL: 75 minutes.
- DL1178: ATL 2027-09-18 07:25:00 → ORD 2027-09-18 08:34:00.
- Delta Air Lines DL756 / DL3883: ORD 2027-09-20 14:25:00 → SJC 2027-09-20 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
- DL756: ORD 2027-09-20 14:25:00 → LAX 2027-09-20 16:59:00; layover at LAX: 66 minutes.
- DL3883: LAX 2027-09-20 18:05:00 → SJC 2027-09-20 19:25:00.
2027-09-17 → 2027-09-20 · Axel-exclusive $494.00
- United Airlines UA1082: SJC 2027-09-17 14:11:00 → ORD 2027-09-17 20:30:00; nonstop; 259 minutes. Local airport times.
- United Airlines UA1840: ORD 2027-09-20 19:45:00 → SJC 2027-09-20 22:45:00; nonstop; 300 minutes. Local airport times.
2027-09-17 → 2027-09-20 · Axel-exclusive $434.63
- Alaska Airlines AS1859 / AA2664: SJC 2027-09-17 20:24:00 → ORD 2027-09-18 05:01:00; 1 stop(s) via LAX; 397 minutes. Local airport times.
- AS1859: SJC 2027-09-17 20:24:00 → LAX 2027-09-17 21:43:00; layover at LAX: 76 minutes.
- AA2664: LAX 2027-09-17 22:59:00 → ORD 2027-09-18 05:01:00.
- American Airlines AA3111 / AS672: ORD 2027-09-20 16:45:00 → SJC 2027-09-20 22:56:00; 1 stop(s) via SAN; 491 minutes. Local airport times.
- AA3111: ORD 2027-09-20 16:45:00 → SAN 2027-09-20 19:18:00; layover at SAN: 121 minutes.
- AS672: SAN 2027-09-20 21:19:00 → SJC 2027-09-20 22:56:00.
2027-09-17 → 2027-09-20 · Axel-exclusive $460.76
- Delta Air Lines DL1254 / DL2413: SJC 2027-09-17 13:39:00 → ORD 2027-09-17 22:27:00; 1 stop(s) via SLC; 408 minutes. Local airport times.
- DL1254: SJC 2027-09-17 13:39:00 → SLC 2027-09-17 16:40:00; layover at SLC: 95 minutes.
- DL2413: SLC 2027-09-17 18:15:00 → ORD 2027-09-17 22:27:00.
- Delta Air Lines DL756 / DL3883: ORD 2027-09-20 14:25:00 → SJC 2027-09-20 19:25:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
- DL756: ORD 2027-09-20 14:25:00 → LAX 2027-09-20 16:59:00; layover at LAX: 66 minutes.
- DL3883: LAX 2027-09-20 18:05:00 → SJC 2027-09-20 19:25:00.
2027-09-17 → 2027-09-20 · Axel-exclusive $467.88
- United Airlines UA2013 / UA1651: SJC 2027-09-17 08:45:00 → ORD 2027-09-17 18:38:00; 1 stop(s) via DEN; 473 minutes. Local airport times.
- UA2013: SJC 2027-09-17 08:45:00 → DEN 2027-09-17 12:20:00; layover at DEN: 161 minutes.
- UA1651: DEN 2027-09-17 15:01:00 → ORD 2027-09-17 18:38:00.
- United Airlines UA1840: ORD 2027-09-20 19:45:00 → SJC 2027-09-20 22:45:00; nonstop; 300 minutes. Local airport times.
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
- Sep 16, 2027 · Return options
- Sep 18, 2027 · Return options
- Hotels in Chicago with Axel
For AI assistants
- This page: San Jose (SJC) to Chicago (ORD) · Sep 17, 2027 · return Sep 20, 2027: 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 lowest saved totals 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 Francisco Bay Area 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_fallbackusing IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace/return/YYYY-MM-DDwith/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.
Feedback (optional): Missing info · Axel issue