Chicago to San Jose (SJO) flight deals
Chicago to San Jose (SJO) from $1,319 round trip, Dec 10, 2026 to Jan 3, 2027 (airline price $1,396), seen Oct 20.
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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 |
|---|---|---|---|
| December 2026 | 1 adult · 24 days | $1,319–$2,799 | $1,396–$2,951 |
| December 2026 | 2 adults · 11 days | $2,194–$7,391 | $2,313–$7,805 |
More months: March 2027
Flights from Chicago · Chicago to Central America flight deals
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Fares observed October 17 – 20, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
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 |
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 |
2 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 20–31, 2026 · 11 days | Out: Avianca 631 / 641 · 1 stop (GUA) · 8h 55m · 14:20–23:15 local; Return: Avianca 693 / 262 · 1 stop (BOG) · 18h 40m · 01:50–20:30 local | $2,194 · Save $119 | $2,313 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 20–31, 2026 · 11 days | Out: Avianca 631 / 641 · 1 stop (GUA) · 8h 55m · 14:20–23:15 local; Return: United Airlines 1952 · Nonstop · 5h 32m · 13:25–18:57 local | $7,391 · Save $414 | $7,805 | Customer link — Open these flights in Axel · Optional: check axel prices |
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March 2027
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 |
| ORD | Mar 26–Apr 4, 2027 · 9 days | Out: Copa Airlines 229 / 162 · 1 stop (PTY) · 7h 39m · 15:13–21:52 local | From $1,652 · Save $93 | From $1,745 | Check Axel prices |
| ORD | Mar 26–Apr 4, 2027 · 9 days | Out: United Airlines 1135 · Nonstop · 5h 13m · 07:02–11:15 local | From $2,705 · Save $147 | From $2,852 | 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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Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Costa Rica 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 (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.