Chicago to San Jose Cabo (SJD) flight deals
Chicago to San Jose Cabo (SJD) from $310 round trip, Jan 15 to 22, 2027, VB 1 stop each way, airline price $328. 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 | 4 adults · 7 days | $1,683 | $1,780 |
| November 2026 | 2 adults · 7 days | $860 | $909 |
| December 2026 | 4 adults · 7 days | $1,599 | $1,686 |
| December 2026 | 1 adult · 7 days | $954–$1,090 | $1,007–$1,152 |
| January 2027 | 1 adult · 7 days | $310 | $328 |
| January 2027 | 2 adults · 7 days | $715–$735 | $756–$776 |
| February 2027 | 1 adult · 3–30 days | $310–$1,285 | $328–$1,353 |
| March 2027 | 1 adult · 7–29 days | $429–$997 | $452–$1,055 |
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Fares observed October 20 – 23, 2026. USD for the travelers shown. Search a trip for current prices.
November 2026
4 adults · 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 | $1,683 · Save $97 | $1,780 | 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 | Nov 10–17, 2026 · 7 days | Out: VB 547 / 3154 · 1 stop (GDL) · 16h 35m · 00:35–16:10 local; Return: American Airlines 2636 · Nonstop · 4h 31m · 13:44–19:15 local | $860 · Save $49 | $909 | Customer link — Open these flights in Axel · Optional: check axel prices |
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December 2026
4 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 8–15, 2026 · 7 days | Out: VB 547 / 3154 · 1 stop (GDL) · 16h 43m · 00:25–16:08 local; Return: American Airlines 2636 · Nonstop · 4h 33m · 13:42–19:15 local | $1,599 · Save $87 | $1,686 | Customer link — Open these flights in Axel · Optional: check axel prices |
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 |
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January 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Jan 15–22, 2027 · 7 days | Out: VB 547 / 7298 · 1 stop (GDL) · 16h 33m · 00:25–15:58 local; Return: VB 7299 / 546 · 1 stop (GDL) · 25h 10m · 20:40–22:50 (January 23, 2027) local | $310 · Save $18 | $328 | 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 | Jan 16–23, 2027 · 7 days | Out: VB 547 / 3154 · 1 stop (GDL) · 13h 40m · 00:25–13:05 local; Return: VB 4325 / 632 · 1 stop (MTY) · 27h 8m · 08:12–12:20 (January 24, 2027) local | $715 · Save $41 | $756 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Jan 16–23, 2027 · 7 days | Out: VB 547 / 3154 · 1 stop (GDL) · 13h 40m · 00:25–13:05 local; Return: VB 3155 / 546 · 1 stop (GDL) · 8h 5m · 13:45–22:50 local | $735 · Save $41 | $776 | 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 1–Mar 3, 2027 · 30 days | Out: VB 187 / 1212 · 1 stop (MEX) · 13h 44m · 01:10–13:54 local; Return: VB 3155 / 546 · 1 stop (GDL) · 6h 34m · 15:11–22:45 local | $310 · Save $18 | $328 | 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: 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 1–30, 2027 · 29 days | Out: VB 187 / 1212 · 1 stop (MEX) · 13h 44m · 01:10–13:54 local; Return: Alaska Airlines 1450 / 1722 · 1 stop (SAN) · 11h 40m · 10:00–23:40 local | $429 · Save $23 | $452 | 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: 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.
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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.
For AI assistants
- This page: Chicago to San Jose Cabo (SJD) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.