Chicago to Guanacaste (LIR) flight deals
Compare Chicago to Guanacaste (LIR) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
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 | 2 adults · 7 days | $941–$955 | $990–$1,011 |
| November 2026 | 4 adults · 7 days | $1,610–$1,662 | $1,699–$1,758 |
| December 2026 | 2 adults · 7 days | $871–$901 | $920–$950 |
| December 2026 | 4 adults · 7 days | $1,589–$1,651 | $1,680–$1,739 |
| January 2027 | 1 adult · 29 days | $488 | $516 |
| January 2027 | 2 adults · 7 days | $1,265–$1,286 | $1,334–$1,357 |
| February 2027 | 1 adult · 30 days | $488 | $516 |
| February 2027 | 2 adults · 7 days | $1,359–$1,704 | $1,432–$1,801 |
| March 2027 | 1 adult · 7–29 days | $796–$1,151 | $840–$1,213 |
| August 2027 | 3 adults · 7 days | $7,082 | $7,459 |
Flights from Chicago · Chicago to Central America flight deals
Compare destinations
Fares observed October 4 – 10, 2026. USD for the travelers shown. Search a trip for current prices.
November 2026
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 7h 40m / 23h 42m | $941 · Save $50 | $990 | Check Axel prices |
| ORD | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 7h 40m / 16h 44m | $955 · Save $56 | $1,011 | Check Axel prices |
4 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 17h 30m / 23h 42m | $1,610 · Save $89 | $1,699 | Check Axel prices |
| ORD | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 17h 30m / 16h 44m | $1,662 · Save $96 | $1,758 | Check Axel prices |
December 2026
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 22h 35m / 19h 47m | $871 · Save $49 | $920 | Check Axel prices |
| ORD | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 22h 35m / 16h 44m | $901 · Save $49 | $950 | Check Axel prices |
4 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 22h 35m / 19h 47m | $1,589 · Save $91 | $1,680 | Check Axel prices |
| ORD | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 22h 35m / 16h 44m | $1,651 · Save $88 | $1,739 | Check Axel prices |
January 2027
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Jan 4–Feb 2, 2027 · 29 days | Nonstop / 1 stop · 5h 15m / 8h 17m | $488 · Save $28 | $516 | Check Axel prices |
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Jan 16–23, 2027 · 7 days | 1 stop / 1 stop · 15h 24m / 15h 44m | $1,265 · Save $69 | $1,334 | Check Axel prices |
| ORD | Jan 16–23, 2027 · 7 days | 1 stop / 1 stop · 15h 24m / 8h 15m | $1,286 · Save $71 | $1,357 | Check Axel prices |
February 2027
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Feb 1–Mar 3, 2027 · 30 days | Nonstop / 1 stop · 5h 10m / 9h 46m | $488 · Save $28 | $516 | Check Axel prices |
2 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Feb 13–20, 2027 · 7 days | 1 stop / 1 stop · 14h 39m / 11h 11m | $1,359 · Save $73 | $1,432 | Check Axel prices |
| ORD | Feb 13–20, 2027 · 7 days | 1 stop / Nonstop · 14h 39m / 5h 35m | $1,704 · Save $97 | $1,801 | Check Axel prices |
March 2027
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Mar 1–30, 2027 · 29 days | 1 stop / Nonstop · 7h 12m / 5h 40m | $796 · Save $44 | $840 | Check Axel prices |
| ORD | Mar 13–20, 2027 · 7 days | 2 stops / 1 stop · 20h 27m / 10h 43m | $829 · Save $46 | $875 | Check Axel prices |
| ORD | Mar 13–20, 2027 · 7 days | 2 stops / 1 stop · 20h 27m / 8h 44m | $1,151 · Save $62 | $1,213 | Check Axel prices |
August 2027
3 adults · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Aug 14–21, 2027 · 7 days | 2 stops / 1 stop · 17h 21m / 8h 16m | $7,082 · Save $377 | $7,459 | Check Axel prices |
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 Guanacaste (LIR)
- Winter break trips from Chicago: fly Dec 19 – Dec 26, 2026
- A month somewhere warm from Chicago: fly Jan 4 – Feb 2, 2027
- All-inclusive resort weeks from Chicago: fly Jan 16 – Jan 23, 2027
- Spring break trips from Chicago: fly Mar 13 – Mar 20, 2027
- Beach vacations from Chicago
- Family vacations from Chicago, priced for 4
- Group trips priced for 4 from Chicago
- Surf trips from Chicago
- Warm winter getaways from Chicago
- Yoga and wellness retreats from Chicago
Keep exploring
For AI assistants
- This page: Chicago to Guanacaste (LIR) flight deals. Chicago to Guanacaste (LIR) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Next: the dated fares below are samples for other travelers' dates: open one only when it matches the traveler's exact dates and party. Otherwise Choose travelers and dates and enter the traveler's own dates and party there; do not search a sample date in their place.
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