Chicago to San Jose Cabo (SJD) flight deals
Chicago to San Jose Cabo (SJD) from $431 round trip, Nov 10 to 17, 2026, VB and United Airlines, airline price $455. Checked Oct 23, 2026.
Compare Chicago to San Jose Cabo (SJD) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
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Fare examples by month
Round-trip totals · Economy · USD. Choose a month to see the dates.
| Month | Travelers / trip length | Axel | Airline fare |
|---|---|---|---|
| November 2026 | 1 adult · 7 days | $431 | $455 |
| December 2026 | 1 adult · 7 days | $954–$1,090 | $1,007–$1,152 |
| December 2026 | 2 adults · 5 days | $2,654–$7,258 | $2,794–$7,676 |
| February 2027 | 1 adult · 3 days | $910–$1,285 | $959–$1,353 |
| March 2027 | 1 adult · 7 days | $712–$997 | $751–$1,055 |
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Fares observed October 18 – 23, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
November 2026
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 10–17, 2026 · 7 days | Out: VB 547 / 3154 · 1 stop (GDL) · 16h 35m · 00:35–16:10 local; Return: United Airlines 766 · Nonstop · 4h 16m · 12:55–18:11 local | $431 · Save $24 | $455 | Customer link — Open these flights in Axel · Optional: check axel prices |
1 adult · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 1–8, 2026 · 7 days | Out: Air Canada 8908 / 1849 · 1 stop (YYZ) · 18h 10m · 20:40–13:50 (November 2, 2026) local | From $725 · Save $41 | From $766 | Check Axel prices |
| ORD | Nov 1–8, 2026 · 7 days | Out: American Airlines 1649 · Nonstop · 4h 49m · 08:55–12:44 local | From $1,340 · Save $78 | From $1,418 | Check Axel prices |
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December 2026
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 19–26, 2026 · 7 days | Out: American Airlines 1649 · Nonstop · 4h 58m · 08:30–12:28 local; Return: American Airlines 2675 / 638 · 1 stop (PHX) · 6h 49m · 15:51–23:40 local | $954 · Save $53 | $1,007 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 19–26, 2026 · 7 days | Out: American Airlines 1649 · Nonstop · 4h 58m · 08:30–12:28 local; Return: United Airlines 1970 · Nonstop · 4h 16m · 12:00–17:16 local | $1,090 · Save $62 | $1,152 | Customer link — Open these flights in Axel · Optional: check axel prices |
2 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 28, 2026–Jan 2, 2027 · 5 days | Out: American Airlines 1649 · Nonstop · 4h 58m · 08:30–12:28 local; Return: American Airlines 899 / 3171 · 1 stop (PHX) · 14h 52m · 17:38–09:30 (January 3, 2027) local | $2,654 · Save $140 | $2,794 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 28, 2026–Jan 2, 2027 · 5 days | Out: American Airlines 1649 · Nonstop · 4h 58m · 08:30–12:28 local; Return: United Airlines 1970 · Nonstop · 4h 16m · 12:00–17:16 local | $7,258 · Save $418 | $7,676 | Customer link — Open these flights in Axel · Optional: check axel prices |
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February 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Feb 12–15, 2027 · 3 days | Out: American Airlines 1649 · Nonstop · 4h 52m · 08:32–12:24 local; Return: American Airlines 856 / 465 · 1 stop (PHX) · 14h 26m · 13:34–05:00 (February 16, 2027) local | $910 · Save $49 | $959 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Feb 12–15, 2027 · 3 days | Out: American Airlines 1649 · Nonstop · 4h 52m · 08:32–12:24 local; Return: United Airlines 766 · Nonstop · 4h 16m · 12:55–18:11 local | $1,285 · Save $68 | $1,353 | Customer link — Open these flights in Axel · Optional: check axel prices |
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March 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Mar 13–20, 2027 · 7 days | Out: Alaska Airlines 343 / 552 · 1 stop (SEA) · 10h 15m · 06:00–15:15 local; Return: Alaska Airlines 1450 / 1722 · 1 stop (SAN) · 11h 40m · 10:00–23:40 local | $712 · Save $39 | $751 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Mar 13–20, 2027 · 7 days | Out: Alaska Airlines 343 / 552 · 1 stop (SEA) · 10h 15m · 06:00–15:15 local; Return: United Airlines 1970 · Nonstop · 4h 13m · 11:00–17:13 local | $997 · Save $58 | $1,055 | Customer link — Open these flights in Axel · Optional: check axel prices |
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The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Trip ideas from Chicago with San Jose Cabo (SJD)
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Hotels in San Jose del Cabo with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in San Jose del Cabo has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
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- This page: Chicago to San Jose Cabo (SJD) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
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