Chicago to Guanacaste (LIR) flight deals
Chicago to Guanacaste (LIR) from $376 round trip, Nov 10 to 17, 2026, Air Canada 1 stop each way, airline price $396. Checked Oct 23, 2026.
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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 | $1,516–$1,558 | $1,603–$1,643 |
| November 2026 | 1 adult · 7 days | $376–$390 | $396–$411 |
| December 2026 | 2 adults · 4–7 days | $694–$2,423 | $733–$2,556 |
| December 2026 | 1 adult · 7 days | $1,006–$3,476 | $1,062–$3,667 |
| January 2027 | 1 adult · 29 days | $507 | $536 |
| January 2027 | 2 adults · 7 days | $1,285 | $1,353 |
| February 2027 | 1 adult · 30 days | $507–$524 | $536–$552 |
| February 2027 | 2 adults · 7 days | $1,402–$1,766 | $1,481–$1,861 |
| March 2027 | 1 adult · 2–29 days | $639–$788 | $673–$833 |
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: Air Canada 508 / 1873 · 1 stop (YYZ) · 21h 40m · 16:30–14:10 (November 11, 2026) local; Return: Air Canada 1872 / 501 · 1 stop (YYZ) · 18h 13m · 15:10–09:23 (November 18, 2026) local | $1,516 · Save $87 | $1,603 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Nov 10–17, 2026 · 7 days | Out: Air Canada 508 / 1873 · 1 stop (YYZ) · 21h 40m · 16:30–14:10 (November 11, 2026) local; Return: Air Canada 1872 / 1540 · 1 stop (YYZ) · 16h 44m · 15:10–07:54 (November 18, 2026) local | $1,558 · Save $85 | $1,643 | 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: Air Canada 508 / 1873 · 1 stop (YYZ) · 21h 40m · 16:30–14:10 (November 11, 2026) local; Return: Air Canada 1862 / 8481 · 1 stop (YUL) · 23h 42m · 15:20–15:02 (November 18, 2026) local | $376 · Save $20 | $396 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Nov 10–17, 2026 · 7 days | Out: Air Canada 508 / 1873 · 1 stop (YYZ) · 21h 40m · 16:30–14:10 (November 11, 2026) local; Return: Air Canada 1872 / 1540 · 1 stop (YYZ) · 16h 44m · 15:10–07:54 (November 18, 2026) local | $390 · Save $21 | $411 | Customer link — Open these flights in Axel · Optional: check axel prices |
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December 2026
2 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: Air Canada 8484 / 1863 · 1 stop (YUL) · 22h 35m · 15:45–14:20 (December 9, 2026) local; Return: Air Canada 1862 / 8477 · 1 stop (YUL) · 19h 47m · 15:20–11:07 (December 16, 2026) local | $694 · Save $39 | $733 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 8–15, 2026 · 7 days | Out: Air Canada 8484 / 1863 · 1 stop (YUL) · 22h 35m · 15:45–14:20 (December 9, 2026) local; Return: Air Canada 1872 / 2775 · 1 stop (YYZ) · 16h 44m · 15:10–07:54 (December 16, 2026) local | $723 · Save $39 | $762 | Customer link — Open these flights in Axel · Optional: check axel prices |
| MDW | Dec 27–31, 2026 · 4 days | Out: Southwest Airlines 4789 / 691 · 1 stop (HOU) · 8h 0m · 05:10–13:10 local; Return: Delta Air Lines 1784 / 1063 · 1 stop (ATL) · 17h 48m · 15:25–09:13 (January 1, 2027) local | $2,403 · Save $128 | $2,531 | Customer link — Open these flights in Axel · Optional: check axel prices |
| MDW | Dec 27–31, 2026 · 4 days | Out: Southwest Airlines 4789 / 691 · 1 stop (HOU) · 8h 0m · 05:10–13:10 local; Return: Southwest Airlines 567 / 2383 · 1 stop (HOU) · 9h 5m · 14:05–23:10 local | $2,423 · Save $133 | $2,556 | 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 |
|---|---|---|---|---|---|
| MDW | Dec 25–29, 2026 · 4 days | Out: Southwest Airlines 2867 / 691 · 1 stop (HOU) · 7h 20m · 06:30–13:50 local | From $2,141 · Save $120 | From $2,261 | 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 2984 / 1377 · 1 stop (MIA) · 7h 31m · 05:00–12:31 local; Return: American Airlines 404 / 1452 · 1 stop (PHL) · 9h 47m · 14:02–23:49 local | $1,006 · Save $56 | $1,062 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 19–26, 2026 · 7 days | Out: American Airlines 2984 / 1377 · 1 stop (MIA) · 7h 31m · 05:00–12:31 local; Return: United Airlines 1121 · Nonstop · 5h 23m · 12:30–17:53 local | $3,476 · Save $191 | $3,667 | 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 1120 · Nonstop · 5h 17m · 10:03–15:20 local; Return: United Airlines 1516 / 787 · 1 stop (IAH) · 8h 39m · 14:20–22:59 local | $507 · Save $29 | $536 | 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: American Airlines 3178 / 887 · 1 stop (CLT) · 15h 24m · 21:00–12:24 (January 17, 2027) local; Return: American Airlines 1338 / 2818 · 1 stop (MIA) · 8h 15m · 13:39–21:54 local | $1,285 · Save $68 | $1,353 | 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: United Airlines 1120 · Nonstop · 5h 10m · 07:46–12:56 local; Return: United Airlines 1516 / 1486 · 1 stop (IAH) · 17h 29m · 14:20–07:49 (March 4, 2027) local | $507 · Save $29 | $536 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Feb 1–Mar 3, 2027 · 30 days | Out: United Airlines 1120 · Nonstop · 5h 10m · 07:46–12:56 local; Return: United Airlines 1265 / 787 · 1 stop (IAH) · 12h 44m · 08:45–21:29 local | $524 · Save $28 | $552 | 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 | Feb 13–20, 2027 · 7 days | Out: American Airlines 3297 / 415 · 1 stop (DFW) · 14h 39m · 22:11–12:50 (February 14, 2027) local; Return: United Airlines 1918 / 1787 · 1 stop (DEN) · 10h 53m · 13:00–23:53 local | $1,402 · Save $79 | $1,481 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Feb 13–20, 2027 · 7 days | Out: American Airlines 3297 / 415 · 1 stop (DFW) · 14h 39m · 22:11–12:50 (February 14, 2027) local; Return: American Airlines 1132 · Nonstop · 5h 35m · 14:37–20:12 local | $1,766 · Save $95 | $1,861 | 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: American Airlines 2984 / 1377 · 1 stop (MIA) · 7h 24m · 05:00–12:24 local; Return: United Airlines 1446 / 2164 · 1 stop (EWR) · 16h 7m · 16:30–09:37 (March 31, 2027) local | $639 · Save $34 | $673 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Mar 1–30, 2027 · 29 days | Out: American Airlines 2984 / 1377 · 1 stop (MIA) · 7h 24m · 05:00–12:24 local; Return: American Airlines 3332 · Nonstop · 5h 40m · 14:41–21:21 local | $788 · Save $45 | $833 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Mar 5–7, 2027 · 2 days | Out: United Airlines 1120 · Nonstop · 5h 10m · 07:46–12:56 local; Return: United Airlines 1121 · Nonstop · 5h 23m · 14:06–19:29 local | $683 · Save $39 | $722 | 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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- This page: Chicago to Guanacaste (LIR) 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.