Chicago to San Jose (SJO) flight deals
Chicago to San Jose (SJO) from $402 round trip, Feb 1 to Mar 3, 2027 (airline price $424), seen Oct 23.
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Fare examples by month
Round-trip totals · Economy · USD, saved from earlier searches. Each month opens its day-by-day date picker for live prices.
| Month | Travelers / trip length | Axel | Airline fare |
|---|---|---|---|
| November 2026 | 4 adults · 7 days | $1,881 | $1,982 |
| November 2026 | 1 adult · 7 days | $460 | $484 |
| December 2026 | 4 adults · 7 days | $1,923 | $2,026 |
| December 2026 | 1 adult · 24 days | $1,319–$2,799 | $1,396–$2,951 |
| January 2027 | 1 adult · 29 days | $449 | $473 |
| February 2027 | 1 adult · 30 days | $402–$1,724 | $424–$1,820 |
| March 2027 | 1 adult · 29 days | $446–$704 | $472–$744 |
Flights from Chicago · Chicago to Central America flight deals
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Fares observed October 17 – 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
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: United Airlines 1856 / 1222 · 1 stop (EWR) · 9h 14m · 10:39–19:53 local; Return: United Airlines 1649 / 2431 · 1 stop (EWR) · 9h 33m · 23:28–09:01 (November 18, 2026) local | $1,881 · Save $101 | $1,982 | 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 | Nov 10–17, 2026 · 7 days | Out: United Airlines 1856 / 1222 · 1 stop (EWR) · 9h 14m · 10:39–19:53 local; Return: United Airlines 1649 / 2431 · 1 stop (EWR) · 9h 33m · 23:28–09:01 (November 18, 2026) local | $460 · Save $24 | $484 | Customer link — Open these flights in Axel · Optional: check axel prices |
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December 2026
2 adults · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Dec 25, 2026–Jan 3, 2027 · 9 days | Out: Southwest Airlines 2964 / 181 · 1 stop (MCO) · 7h 55m · 05:20–13:15 local | From $3,507 · Save $194 | From $3,701 | Check Axel prices |
| MDW | Dec 27–29, 2026 · 2 days | Out: Delta Air Lines 1285 / 1931 · 1 stop (ATL) · 15h 46m · 06:00–21:46 local | From $3,097 · Save $179 | From $3,276 | Check Axel prices |
| MDW | Dec 27–29, 2026 · 2 days | Out: Delta Air Lines 1285 / 1937 · 1 stop (ATL) · 6h 59m · 06:00–12:59 local | From $4,493 · Save $256 | From $4,749 | Check Axel prices |
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: Avianca 263 / 696 · 1 stop (BOG) · 10h 20m · 22:30–08:50 (December 9, 2026) local; Return: Avianca 640 / 630 · 1 stop (GUA) · 7h 20m · 05:35–12:55 local | $1,923 · Save $103 | $2,026 | 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 10, 2026–Jan 3, 2027 · 24 days | Out: Copa Airlines 236 / 116 · 1 stop (PTY) · 9h 18m · 07:35–16:53 local; Return: Copa Airlines 839 / 228 · 1 stop (PTY) · 18h 44m · 18:02–12:46 (January 4, 2027) local | $1,319 · Save $77 | $1,396 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 10, 2026–Jan 3, 2027 · 24 days | Out: Copa Airlines 236 / 116 · 1 stop (PTY) · 9h 18m · 07:35–16:53 local; Return: United Airlines 1952 · Nonstop · 5h 32m · 13:25–18:57 local | $2,799 · Save $152 | $2,951 | 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 4–Feb 2, 2027 · 29 days | Out: United Airlines 564 / 1660 · 1 stop (IAH) · 17h 2m · 05:30–22:32 local; Return: United Airlines 1172 / 547 · 1 stop (IAH) · 8h 55m · 01:15–10:10 local | $449 · Save $24 | $473 | 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: Avianca 263 / 696 · 1 stop (BOG) · 10h 20m · 22:30–08:50 (February 2, 2027) local; Return: Avianca 697 / 262 · 1 stop (BOG) · 11h 0m · 09:30–20:30 local | $402 · Save $22 | $424 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Feb 1–Mar 3, 2027 · 30 days | Out: Avianca 263 / 696 · 1 stop (BOG) · 10h 20m · 22:30–08:50 (February 2, 2027) local; Return: Copa Airlines 343 / 4235 · 1 stop (PTY) · 9h 2m · 14:42–23:44 local | $1,724 · Save $96 | $1,820 | 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: Avianca 263 / 696 · 1 stop (BOG) · 10h 20m · 22:30–08:50 (March 2, 2027) local; Return: Avianca 699 / 262 · 1 stop (BOG) · 28h 20m · 16:00–21:20 (March 31, 2027) local | $446 · Save $26 | $472 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Mar 1–30, 2027 · 29 days | Out: Avianca 263 / 696 · 1 stop (BOG) · 10h 20m · 22:30–08:50 (March 2, 2027) local; Return: Avianca 604 / 2106 · 1 stop (MIA) · 9h 46m · 07:45–18:31 local | $704 · Save $40 | $744 | Customer link — Open these flights in Axel · Optional: check axel prices |
2 adults · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Mar 25–28, 2027 · 3 days | Out: United Airlines 1135 · Nonstop · 5h 13m · 07:02–11:15 local | From $1,745 · Save $97 | From $1,842 | 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 (SJO)
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For AI assistants
- This page: Chicago to San Jose (SJO) 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.