Flights from Chicago to Central America in winter
December to April is dry season across Central America, the reason to go. Costa Rica has the most nonstops and the highest prices; Panama City, Belize and Guatemala are cheaper and less crowded in the same weather.
Nonstop from Chicago: Guanacaste (American, United) and Panama City (Copa Airlines). One stop via Newark: San Jose. No recent searches for Belize City, Guatemala City, San Salvador, Roatan and San Pedro Sula.
Axel's pick: Guanacaste, nonstop on American and United and the lowest fare saved for these dates, $538.
Where to fly from Chicago to Central America in winter: saved round trips within December, January and February to San Jose, Guanacaste, Belize City, Panama City, Guatemala City and San Salvador and more. Pick a destination to see every date, or search your own dates in one tap.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips for 4–10 nights, entirely within Dec, Jan, Feb.
Cheapest right now: San Jose $460 · Guanacaste $538
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | Frontier Airlines | F91901 + F935 | $147.25 | 2026-10-29T01:53:24Z |
| 2026-11-20 · one way | Avianca | AV631 + AV641 | $190.00 | 2026-10-29T01:53:24Z |
| 2026-11-20 · one way | American Airlines | AA884 + AA310 | $232.75 | 2026-10-29T01:53:24Z |
| 2026-11-20 · one way | United Airlines | UA1856 + UA1222 | $237.50 | 2026-10-29T01:53:24Z |
| 2026-11-20 → 2026-11-23 | Avianca | AV631 + AV641 / AV628 + UA2007 | $418.00 | 2026-10-29T01:53:24Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines / United Airlines | F91901 + F935 / UA1952 | $461.70 | 2026-10-29T01:53:24Z |
| 2026-11-20 → 2026-11-23 | American Airlines | AA884 + AA310 / AA318 + AA3320 | $512.05 | 2026-10-29T01:53:24Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA1544 + UA1280 / UA1952 | $557.65 | 2026-10-29T01:53:24Z |
| 2026-11-20 · one way | Frontier Airlines | F91596 + F9215 | $147.25 | 2026-10-29T01:53:24Z |
| 2026-11-20 · one way | United Airlines | UA1544 + UA1280 | $237.50 | 2026-10-29T01:53:24Z |
| 2026-11-27 → 2026-12-04 | Avianca | AV631 + AV641 / AV628 + UA2007 | $428.00 | 2026-10-29T01:53:24Z |
| 2026-11-27 → 2026-12-04 | Frontier Airlines / United Airlines | F91596 + F9215 / UA1952 | $461.70 | 2026-10-29T01:53:24Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines / United Airlines | F91901 + F935 / UA1952 | $472.15 | 2026-10-29T01:53:24Z |
| 2026-11-20 → 2026-11-23 | Frontier Airlines / United Airlines | F91596 + F9215 / UA1952 | $472.15 | 2026-10-29T01:53:24Z |
| 2026-11-27 → 2026-12-04 | American Airlines | AA884 + AA310 / AA318 + AA3320 | $524.30 | 2026-10-29T01:53:24Z |
| 2026-11-20 → 2026-11-23 | United Airlines | UA1856 + UA1222 / UA1952 | $557.65 | 2026-10-29T01:53:24Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA1856 + UA1222 / UA1952 | $564.30 | 2026-10-29T01:53:24Z |
| 2026-11-27 → 2026-12-04 | United Airlines | UA1544 + UA1280 / UA1952 | $564.30 | 2026-10-29T01:53:24Z |
2026-11-20 · one way · $147.25
- Frontier Airlines F91901 / F935: ORD 2026-11-20 05:01:00 → SJO 2026-11-20 12:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
- F91901: ORD 2026-11-20 05:01:00 → MCO 2026-11-20 08:55:00; layover at MCO: 85 minutes.
- F935: MCO 2026-11-20 10:20:00 → SJO 2026-11-20 12:41:00.
2026-11-20 · one way · $190.00
- Avianca AV631 / AV641: ORD 2026-11-20 14:20:00 → SJO 2026-11-20 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2026-11-20 14:20:00 → GUA 2026-11-20 18:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2026-11-20 21:45:00 → SJO 2026-11-20 23:15:00.
2026-11-20 · one way · $232.75
- American Airlines AA884 / AA310: ORD 2026-11-20 06:05:00 → SJO 2026-11-20 14:35:00; 1 stop(s) via MIA; 510 minutes. Local airport times.
- AA884: ORD 2026-11-20 06:05:00 → MIA 2026-11-20 10:25:00; layover at MIA: 123 minutes.
- AA310: MIA 2026-11-20 12:28:00 → SJO 2026-11-20 14:35:00.
2026-11-20 · one way · $237.50
- United Airlines UA1856 / UA1222: ORD 2026-11-20 10:39:00 → SJO 2026-11-20 19:53:00; 1 stop(s) via EWR; 554 minutes. Local airport times.
- UA1856: ORD 2026-11-20 10:39:00 → EWR 2026-11-20 13:57:00; layover at EWR: 95 minutes.
- UA1222: EWR 2026-11-20 15:32:00 → SJO 2026-11-20 19:53:00.
2026-11-20 → 2026-11-23 · $418.00
- Avianca AV631 / AV641: ORD 2026-11-20 14:20:00 → SJO 2026-11-20 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2026-11-20 14:20:00 → GUA 2026-11-20 18:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2026-11-20 21:45:00 → SJO 2026-11-20 23:15:00.
- Avianca AV628 / UA2007: SJO 2026-11-23 10:00:00 → ORD 2026-11-23 18:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
- AV628: SJO 2026-11-23 10:00:00 → GUA 2026-11-23 11:30:00; layover at GUA: 118 minutes.
- UA2007: GUA 2026-11-23 13:28:00 → ORD 2026-11-23 18:15:00.
2026-11-27 → 2026-12-04 · $461.70
- Frontier Airlines F91901 / F935: ORD 2026-11-27 05:01:00 → SJO 2026-11-27 12:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
- F91901: ORD 2026-11-27 05:01:00 → MCO 2026-11-27 08:55:00; layover at MCO: 85 minutes.
- F935: MCO 2026-11-27 10:20:00 → SJO 2026-11-27 12:41:00.
- United Airlines UA1952: SJO 2026-12-04 13:25:00 → ORD 2026-12-04 18:57:00; nonstop; 332 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $512.05
- American Airlines AA884 / AA310: ORD 2026-11-20 06:05:00 → SJO 2026-11-20 14:35:00; 1 stop(s) via MIA; 510 minutes. Local airport times.
- AA884: ORD 2026-11-20 06:05:00 → MIA 2026-11-20 10:25:00; layover at MIA: 123 minutes.
- AA310: MIA 2026-11-20 12:28:00 → SJO 2026-11-20 14:35:00.
- American Airlines AA318 / AA3320: SJO 2026-11-23 15:54:00 → ORD 2026-11-24 00:53:00; 1 stop(s) via MIA; 539 minutes. Local airport times.
- AA318: SJO 2026-11-23 15:54:00 → MIA 2026-11-23 20:00:00; layover at MIA: 134 minutes.
- AA3320: MIA 2026-11-23 22:14:00 → ORD 2026-11-24 00:53:00.
2026-11-20 → 2026-11-23 · $557.65
- United Airlines UA1544 / UA1280: ORD 2026-11-20 12:40:00 → SJO 2026-11-20 20:39:00; 1 stop(s) via IAH; 479 minutes. Local airport times.
- UA1544: ORD 2026-11-20 12:40:00 → IAH 2026-11-20 15:41:00; layover at IAH: 76 minutes.
- UA1280: IAH 2026-11-20 16:57:00 → SJO 2026-11-20 20:39:00.
- United Airlines UA1952: SJO 2026-11-23 13:25:00 → ORD 2026-11-23 18:57:00; nonstop; 332 minutes. Local airport times.
2026-11-20 · one way · $147.25
- Frontier Airlines F91596 / F9215: ORD 2026-11-20 05:58:00 → SJO 2026-11-20 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2026-11-20 05:58:00 → ATL 2026-11-20 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2026-11-20 11:14:00 → SJO 2026-11-20 14:16:00.
2026-11-20 · one way · $237.50
- United Airlines UA1544 / UA1280: ORD 2026-11-20 12:40:00 → SJO 2026-11-20 20:39:00; 1 stop(s) via IAH; 479 minutes. Local airport times.
- UA1544: ORD 2026-11-20 12:40:00 → IAH 2026-11-20 15:41:00; layover at IAH: 76 minutes.
- UA1280: IAH 2026-11-20 16:57:00 → SJO 2026-11-20 20:39:00.
2026-11-27 → 2026-12-04 · $428.00
- Avianca AV631 / AV641: ORD 2026-11-27 14:20:00 → SJO 2026-11-27 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2026-11-27 14:20:00 → GUA 2026-11-27 18:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2026-11-27 21:45:00 → SJO 2026-11-27 23:15:00.
- Avianca AV628 / UA2007: SJO 2026-12-04 10:00:00 → ORD 2026-12-04 18:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
- AV628: SJO 2026-12-04 10:00:00 → GUA 2026-12-04 11:30:00; layover at GUA: 118 minutes.
- UA2007: GUA 2026-12-04 13:28:00 → ORD 2026-12-04 18:15:00.
2026-11-27 → 2026-12-04 · $461.70
- Frontier Airlines F91596 / F9215: ORD 2026-11-27 05:58:00 → SJO 2026-11-27 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2026-11-27 05:58:00 → ATL 2026-11-27 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2026-11-27 11:14:00 → SJO 2026-11-27 14:16:00.
- United Airlines UA1952: SJO 2026-12-04 13:25:00 → ORD 2026-12-04 18:57:00; nonstop; 332 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $472.15
- Frontier Airlines F91901 / F935: ORD 2026-11-20 05:01:00 → SJO 2026-11-20 12:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
- F91901: ORD 2026-11-20 05:01:00 → MCO 2026-11-20 08:55:00; layover at MCO: 85 minutes.
- F935: MCO 2026-11-20 10:20:00 → SJO 2026-11-20 12:41:00.
- United Airlines UA1952: SJO 2026-11-23 13:25:00 → ORD 2026-11-23 18:57:00; nonstop; 332 minutes. Local airport times.
2026-11-20 → 2026-11-23 · $472.15
- Frontier Airlines F91596 / F9215: ORD 2026-11-20 05:58:00 → SJO 2026-11-20 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2026-11-20 05:58:00 → ATL 2026-11-20 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2026-11-20 11:14:00 → SJO 2026-11-20 14:16:00.
- United Airlines UA1952: SJO 2026-11-23 13:25:00 → ORD 2026-11-23 18:57:00; nonstop; 332 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $524.30
- American Airlines AA884 / AA310: ORD 2026-11-27 06:05:00 → SJO 2026-11-27 14:35:00; 1 stop(s) via MIA; 510 minutes. Local airport times.
- AA884: ORD 2026-11-27 06:05:00 → MIA 2026-11-27 10:25:00; layover at MIA: 123 minutes.
- AA310: MIA 2026-11-27 12:28:00 → SJO 2026-11-27 14:35:00.
- American Airlines AA318 / AA3320: SJO 2026-12-04 15:54:00 → ORD 2026-12-05 00:53:00; 1 stop(s) via MIA; 539 minutes. Local airport times.
- AA318: SJO 2026-12-04 15:54:00 → MIA 2026-12-04 20:00:00; layover at MIA: 134 minutes.
- AA3320: MIA 2026-12-04 22:14:00 → ORD 2026-12-05 00:53:00.
2026-11-20 → 2026-11-23 · $557.65
- United Airlines UA1856 / UA1222: ORD 2026-11-20 10:39:00 → SJO 2026-11-20 19:53:00; 1 stop(s) via EWR; 554 minutes. Local airport times.
- UA1856: ORD 2026-11-20 10:39:00 → EWR 2026-11-20 13:57:00; layover at EWR: 95 minutes.
- UA1222: EWR 2026-11-20 15:32:00 → SJO 2026-11-20 19:53:00.
- United Airlines UA1952: SJO 2026-11-23 13:25:00 → ORD 2026-11-23 18:57:00; nonstop; 332 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $564.30
- United Airlines UA1856 / UA1222: ORD 2026-11-27 10:39:00 → SJO 2026-11-27 19:53:00; 1 stop(s) via EWR; 554 minutes. Local airport times.
- UA1856: ORD 2026-11-27 10:39:00 → EWR 2026-11-27 13:57:00; layover at EWR: 95 minutes.
- UA1222: EWR 2026-11-27 15:32:00 → SJO 2026-11-27 19:53:00.
- United Airlines UA1952: SJO 2026-12-04 13:25:00 → ORD 2026-12-04 18:57:00; nonstop; 332 minutes. Local airport times.
2026-11-27 → 2026-12-04 · $564.30
- United Airlines UA1544 / UA1280: ORD 2026-11-27 12:40:00 → SJO 2026-11-27 20:39:00; 1 stop(s) via IAH; 479 minutes. Local airport times.
- UA1544: ORD 2026-11-27 12:40:00 → IAH 2026-11-27 15:41:00; layover at IAH: 76 minutes.
- UA1280: IAH 2026-11-27 16:57:00 → SJO 2026-11-27 20:39:00.
- United Airlines UA1952: SJO 2026-12-04 13:25:00 → ORD 2026-12-04 18:57:00; nonstop; 332 minutes. Local airport times.
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- Hawaii: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · in summer · for 4 days · for 5 days · for a week · for 10 days
- Mexico: for Christmas · for Thanksgiving · for spring break · for Presidents' Day weekend · for MLK weekend · in winter · in February · for 4 days · for 5 days · for a week
- The Caribbean: for Christmas · for spring break · for Presidents' Day weekend · in winter · in February · for 4 days · for 5 days · for a week
- Costa Rica: for Christmas · for spring break · in winter · for a week · for 10 days
- Central America: for Christmas · for spring break · for a week · for 10 days
- Europe: in summer · in May · in September · in December · for spring break · for Christmas · for a week · for 10 days · for two weeks
- Italy: in summer · in May · in June · in September · for Christmas · for a week · for 10 days · for two weeks
- Spain: in summer · in May · in September · for spring break · for a week · for 10 days
- Greece: in summer · in May · in June · in September · for a week · for 10 days · for two weeks
- Portugal: in summer · in May · in September · in winter · for 4 days · for a week · for 10 days
- Croatia: in summer · in June · in September · for a week · for 10 days
- Iceland: in summer · in winter · in September · for 4 days · for a week
- Scandinavia: in summer · in winter · in September · for 4 days · for a week · for 10 days
- Eastern Europe: in summer · in May · in September · in December · for a week · for 10 days
- England: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
- Scotland: in summer · in fall · for 4 days · for a week
- Ireland: in spring · in summer · in fall · for Christmas · for 4 days · for a week · for 10 days
- Japan: in April · in November · in winter · in summer · for a week · for 10 days · for two weeks
- South Korea: in spring · in fall · for a week · for 10 days
- Asia: in spring · in fall · in winter · for a week · for 10 days · for two weeks
- Southeast Asia: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks · for a month
- Thailand: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks
- Vietnam: in winter · in November · in February · in spring · for 10 days · for two weeks
- Bali: in summer · in winter · for 10 days · for two weeks · for a month
- India: in winter · in December · for two weeks · for a month
- Australia: in December · in January · in February · in September · for two weeks · for three weeks · for a month
- New Zealand: in December · in January · in February · for two weeks · for three weeks
- South America: in January · in February · in winter · for 10 days · for two weeks
- Colombia: in winter · in spring · for a week · for 10 days
- Peru: in summer · in May · in September · for 10 days · for two weeks
- The Middle East: in winter · for a week · for 10 days
- Turkey: in spring · in summer · in fall · for a week · for 10 days
- Africa: in winter · in fall · for 10 days · for two weeks
- South Africa: in winter · in fall · for 10 days · for two weeks
- Morocco: in spring · in fall · in winter · for a week · for 10 days
- Egypt: in winter · in fall · in spring · for a week · for 10 days
- Canada: in summer · in winter · in fall · for 3 days · for 4 days · for a week
- Florida: for spring break · for Christmas · for Thanksgiving · in winter · for 4 days · for 5 days · for a week
- California: for spring break · in summer · in winter · for 3 days · for 4 days · for a week
- The Pacific Northwest: in summer · in fall · for 3 days · for 4 days · for a week
- Alaska: in summer · in June · in July · in August · for 5 days · for a week · for 10 days
- The Southwest: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
- Arizona: in spring · in fall · in winter · for spring break · for 3 days · for 4 days · for a week
- Utah: in winter · for Presidents' Day weekend · for MLK weekend · in spring · in summer · for 4 days · for a week
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- Colorado: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
- Montana and Wyoming: in summer · in winter · for a week · for 10 days
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Fares observed October 23 – 28, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Chicago
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel | Dates | |
|---|---|---|---|---|---|
| San Jose (SJO) | San José, the gateway to Costa Rica's volcanoes and cloud forests | 1 stop via Newark | $460 (airline $484) | Dec 5–12, 2026 | Check prices |
| Guanacaste (LIR) | Guanacaste's Pacific beaches and dry-season sunshine | Nonstop · American, United | $538 (airline $569) | Dec 5–12, 2026 | Check prices |
| Belize City (BZE) | Belize's barrier reef, cayes and Mayan ruins | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates | |
| Panama City (PTY) | Panama City's skyline, old town and the canal | Nonstop · Copa Airlines | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates |
| Guatemala City (GUA) | Guatemala City, the gateway to Antigua and Lake Atitlán | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates | |
| San Salvador (SAL) | San Salvador, with surf beaches and volcanoes within an hour | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates | |
| Roatan (RTB) | Roatán's reef diving and beaches in the Bay Islands | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates | |
| San Pedro Sula (SAP) | San Pedro Sula, the gateway to Copán's Mayan ruins and the Bay Islands | No matching fare saved | Dec 5 – Dec 12, 2026 (suggested) | Search these dates |
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.
Keep exploring
Hotels in Costa Rica with Axel
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.
Hotels with an Axel review in Costa Rica: Country Inn & Suites by Radisson, San Jose Aeropuerto, Costa Rica · City Express by Marriott San Jose Costa Rica · Alameda Cariari · Sheraton San Jose Hotel, Costa Rica
For AI assistants
- This page: Flights from Chicago to Central America in winter. Round-trip fares from Chicago to Central America in winter: San Jose, Guanacaste, Belize City, Panama City, Guatemala City and San Salvador and more. Saved fares for trips within December, January and February, with the cheapest for each destination and a link to search your own dates.
- 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.