Flights from Chicago to Central America for 10 days (Dec 4–13, 2026)
No published fare for Fri Dec 4 – Sun Dec 13, 2026 from Chicago yet; the lowest published fares for the months ahead follow.
Ten days is two sides of one country or two neighbours: Costa Rica's Pacific coast and cloud forest, Belize's cayes and the Mayan ruins, or Guatemala's Antigua and Lake Atitlán with Belize's reef. Dry season, December to April, is the time.
Nonstop from Chicago: Guanacaste (American, United). No recent searches for San Jose, Belize City, Panama City, Guatemala City, San Salvador, Roatan and San Pedro Sula.
Axel's pick: Guanacaste, nonstop on American and United on 24 of the 46 departure dates searched recently, the most of any.
Where to fly from Chicago to Central America for 10 days: round trips of 9 to 11 nights 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 Ten days in December (Dec 4 – Dec 13, 2026) and Ten days in March (Mar 5 – Mar 14, 2027).
Flights for the months ahead
Lowest published fares for the months ahead: $366 round trip, Axel-exclusive, Avianca, 1 stop, Sep 3–6, 2027; $155 one way, Axel-exclusive, Frontier Airlines, 1 stop, Dec 1, 2026; 144 priced flights on 72 exact dates, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.
Chicago (ORD) to San Jose (SJO): November 2026
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | Frontier Airlines / Copa Airlines | Up to 1 stop each way | Axel-exclusive $415.15 |
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $418.00 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $418.00 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $472.15 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $456.00 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $501.60 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $176.70 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $228.00 |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 | Frontier Airlines / Copa Airlines | Up to 1 stop each way | Axel-exclusive $444.60 |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $456.00 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | Frontier Airlines / Copa Airlines | Up to 1 stop each way | Axel-exclusive $444.60 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $456.00 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $418.00 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $447.45 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $428.00 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $461.70 |
Chicago (ORD) to San Jose (SJO): December 2026
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $155.00 |
| Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $200.00 |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $415.00 |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $155.00 |
| Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $200.00 |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $415.00 |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $490.00 |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $568.25 |
| Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $155.00 |
| Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $200.00 |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $490.00 |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $532.00 |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $490.00 |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $568.25 |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $580.00 |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $638.00 |
| Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $224.75 |
| Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $290.00 |
| Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $580.00 |
| Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $601.75 |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $580.00 |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $601.75 |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $570.00 |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $623.75 |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $570.00 |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $623.75 |
| Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $217.00 |
| Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $280.00 |
| Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $560.00 |
| Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $616.00 |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 | Avianca | Up to 1 stop each way | Axel-exclusive $560.00 |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $581.00 |
Chicago (ORD) to San Jose (SJO): January 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $560.00 |
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $616.00 |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $480.00 |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $502.00 |
| Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $155.00 |
| Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $200.00 |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $415.00 |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $155.00 |
| Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $200.00 |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $415.00 |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $155.00 |
| Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $200.00 |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $415.00 |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $155.00 |
| Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $200.00 |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $415.00 |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
Chicago (ORD) to San Jose (SJO): February 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | Frontier Airlines | Up to 1 stop each way | Axel-exclusive $155.00 |
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $200.00 |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 | Frontier Airlines / Delta Air Lines | Up to 1 stop each way | Axel-exclusive $415.00 |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $430.00 |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $482.75 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $460.00 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $506.00 |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $400.00 |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $440.00 |
Chicago (ORD) to San Jose (SJO): March 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $482.00 |
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $550.35 |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $544.00 |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $598.40 |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $564.40 |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $625.60 |
Chicago (ORD) to San Jose (SJO): April 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $430.00 |
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $475.00 |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $430.00 |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $475.00 |
Chicago (ORD) to San Jose (SJO): May 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $408.50 |
| May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $451.25 |
| May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $408.50 |
| May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $451.25 |
| May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $408.50 |
| May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $451.25 |
Chicago (ORD) to San Jose (SJO): June 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $430.00 |
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $475.00 |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $430.00 |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $475.00 |
Chicago (ORD) to San Jose (SJO): July 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $494.50 |
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 | Frontier Airlines / American Airlines | Up to 1 stop each way | Axel-exclusive $494.50 |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $430.00 |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $475.00 |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $430.00 |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $475.00 |
Chicago (ORD) to San Jose (SJO): August 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $408.50 |
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $451.25 |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $408.50 |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $451.25 |
Chicago (ORD) to San Jose (SJO): September 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $365.50 |
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $403.75 |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $365.50 |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $403.75 |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $365.50 |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $403.75 |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027 | Avianca | Up to 1 stop each way | Axel-exclusive $376.25 |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027 | Frontier Airlines / United Airlines | Up to 1 stop each way | Axel-exclusive $419.00 |
Route overview: Chicago to San Jose (SJO) flight deals
2026-11-19 → 2026-11-22 · Axel-exclusive $415.15
- Frontier Airlines F91901 / F935: ORD 2026-11-19 05:01:00 → SJO 2026-11-19 12:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
- F91901: ORD 2026-11-19 05:01:00 → MCO 2026-11-19 08:55:00; layover at MCO: 85 minutes.
- F935: MCO 2026-11-19 10:20:00 → SJO 2026-11-19 12:41:00.
- Copa Airlines CM461 / CM228: SJO 2026-11-22 03:59:00 → ORD 2026-11-22 12:46:00; 1 stop(s) via PTY; 527 minutes. Local airport times.
- CM461: SJO 2026-11-22 03:59:00 → PTY 2026-11-22 06:23:00; layover at PTY: 105 minutes.
- CM228: PTY 2026-11-22 08:08:00 → ORD 2026-11-22 12:46:00.
2026-11-19 → 2026-11-22 · Axel-exclusive $418.00
- Avianca AV263 / AV696: ORD 2026-11-19 22:30:00 → SJO 2026-11-20 08:50:00; 1 stop(s) via BOG; 620 minutes. Local airport times.
- AV263: ORD 2026-11-19 22:30:00 → BOG 2026-11-20 05:30:00; layover at BOG: 115 minutes.
- AV696: BOG 2026-11-20 07:25:00 → SJO 2026-11-20 08:50:00.
- Avianca AV697 / AV262: SJO 2026-11-22 09:30:00 → ORD 2026-11-22 20:30:00; 1 stop(s) via BOG; 660 minutes. Local airport times.
- AV697: SJO 2026-11-22 09:30:00 → BOG 2026-11-22 12:45:00; layover at BOG: 125 minutes.
- AV262: BOG 2026-11-22 14:50:00 → ORD 2026-11-22 20:30:00.
2026-11-24 · one way · Axel-exclusive $176.70
- Frontier Airlines F91901 / F935: ORD 2026-11-24 05:01:00 → SJO 2026-11-24 12:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
- F91901: ORD 2026-11-24 05:01:00 → MCO 2026-11-24 08:55:00; layover at MCO: 85 minutes.
- F935: MCO 2026-11-24 10:20:00 → SJO 2026-11-24 12:41:00.
2026-11-24 · one way · Axel-exclusive $228.00
- Avianca AV631 / AV641: ORD 2026-11-24 14:20:00 → SJO 2026-11-24 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2026-11-24 14:20:00 → GUA 2026-11-24 18:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2026-11-24 21:45:00 → SJO 2026-11-24 23:15:00.
2026-11-28 → 2026-12-05 · Axel-exclusive $428.00
- Avianca AV631 / AV641: ORD 2026-11-28 14:20:00 → SJO 2026-11-28 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2026-11-28 14:20:00 → GUA 2026-11-28 18:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2026-11-28 21:45:00 → SJO 2026-11-28 23:15:00.
- Avianca AV628 / UA2007: SJO 2026-12-05 10:00:00 → ORD 2026-12-05 18:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
- AV628: SJO 2026-12-05 10:00:00 → GUA 2026-12-05 11:30:00; layover at GUA: 118 minutes.
- UA2007: GUA 2026-12-05 13:28:00 → ORD 2026-12-05 18:15:00.
2026-11-28 → 2026-12-05 · Axel-exclusive $461.70
- Frontier Airlines F91596 / F9215: ORD 2026-11-28 05:58:00 → SJO 2026-11-28 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2026-11-28 05:58:00 → ATL 2026-11-28 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2026-11-28 11:14:00 → SJO 2026-11-28 14:16:00.
- United Airlines UA1952: SJO 2026-12-05 13:55:00 → ORD 2026-12-05 19:28:00; nonstop; 333 minutes. Local airport times.
2026-12-12 → 2026-12-19 · Axel-exclusive $490.00
- Avianca AV631 / AV641: ORD 2026-12-12 14:20:00 → SJO 2026-12-12 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2026-12-12 14:20:00 → GUA 2026-12-12 18:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2026-12-12 21:45:00 → SJO 2026-12-12 23:15:00.
- Avianca AV628 / UA2007: SJO 2026-12-19 10:00:00 → ORD 2026-12-19 18:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
- AV628: SJO 2026-12-19 10:00:00 → GUA 2026-12-19 11:30:00; layover at GUA: 118 minutes.
- UA2007: GUA 2026-12-19 13:28:00 → ORD 2026-12-19 18:15:00.
2026-12-12 → 2026-12-19 · Axel-exclusive $568.25
- Frontier Airlines F91596 / F9215: ORD 2026-12-12 05:58:00 → SJO 2026-12-12 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2026-12-12 05:58:00 → ATL 2026-12-12 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2026-12-12 11:14:00 → SJO 2026-12-12 14:16:00.
- United Airlines UA1952: SJO 2026-12-19 13:25:00 → ORD 2026-12-19 18:57:00; nonstop; 332 minutes. Local airport times.
2026-12-25 → 2026-12-28 · Axel-exclusive $570.00
- Avianca AV263 / AV696: ORD 2026-12-25 22:30:00 → SJO 2026-12-26 08:50:00; 1 stop(s) via BOG; 620 minutes. Local airport times.
- AV263: ORD 2026-12-25 22:30:00 → BOG 2026-12-26 05:30:00; layover at BOG: 115 minutes.
- AV696: BOG 2026-12-26 07:25:00 → SJO 2026-12-26 08:50:00.
- Avianca AV697 / AV262: SJO 2026-12-28 09:30:00 → ORD 2026-12-28 20:30:00; 1 stop(s) via BOG; 660 minutes. Local airport times.
- AV697: SJO 2026-12-28 09:30:00 → BOG 2026-12-28 12:45:00; layover at BOG: 125 minutes.
- AV262: BOG 2026-12-28 14:50:00 → ORD 2026-12-28 20:30:00.
2026-12-25 → 2026-12-28 · Axel-exclusive $623.75
- Frontier Airlines F91901 / F935: ORD 2026-12-25 05:01:00 → SJO 2026-12-25 12:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
- F91901: ORD 2026-12-25 05:01:00 → MCO 2026-12-25 08:55:00; layover at MCO: 85 minutes.
- F935: MCO 2026-12-25 10:20:00 → SJO 2026-12-25 12:41:00.
- United Airlines UA1952: SJO 2026-12-28 13:25:00 → ORD 2026-12-28 18:57:00; nonstop; 332 minutes. Local airport times.
2027-01-07 → 2027-01-10 · Axel-exclusive $415.00
- Frontier Airlines F91596 / F9215: ORD 2027-01-07 05:58:00 → SJO 2027-01-07 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2027-01-07 05:58:00 → ATL 2027-01-07 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2027-01-07 11:14:00 → SJO 2027-01-07 14:16:00.
- Delta Air Lines DL1794 / DL2738: SJO 2027-01-10 07:00:00 → ORD 2027-01-10 17:06:00; 1 stop(s) via ATL; 606 minutes. Local airport times.
- DL1794: SJO 2027-01-10 07:00:00 → ATL 2027-01-10 12:05:00; layover at ATL: 225 minutes.
- DL2738: ATL 2027-01-10 15:50:00 → ORD 2027-01-10 17:06:00.
2027-01-07 → 2027-01-10 · Axel-exclusive $530.00
- United Airlines UA1544 / UA1280: ORD 2027-01-07 12:40:00 → SJO 2027-01-07 20:39:00; 1 stop(s) via IAH; 479 minutes. Local airport times.
- UA1544: ORD 2027-01-07 12:40:00 → IAH 2027-01-07 15:41:00; layover at IAH: 76 minutes.
- UA1280: IAH 2027-01-07 16:57:00 → SJO 2027-01-07 20:39:00.
- United Airlines UA1952: SJO 2027-01-10 13:25:00 → ORD 2027-01-10 18:57:00; nonstop; 332 minutes. Local airport times.
2027-01-21 → 2027-01-24 · Axel-exclusive $400.00
- Avianca AV631 / AV641: ORD 2027-01-21 14:20:00 → SJO 2027-01-21 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2027-01-21 14:20:00 → GUA 2027-01-21 18:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2027-01-21 21:45:00 → SJO 2027-01-21 23:15:00.
- Avianca AV628 / UA2007: SJO 2027-01-24 10:00:00 → ORD 2027-01-24 18:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
- AV628: SJO 2027-01-24 10:00:00 → GUA 2027-01-24 11:30:00; layover at GUA: 118 minutes.
- UA2007: GUA 2027-01-24 13:28:00 → ORD 2027-01-24 18:15:00.
2027-01-21 → 2027-01-24 · Axel-exclusive $415.00
- Frontier Airlines F91596 / F9215: ORD 2027-01-21 05:58:00 → SJO 2027-01-21 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2027-01-21 05:58:00 → ATL 2027-01-21 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2027-01-21 11:14:00 → SJO 2027-01-21 14:16:00.
- Delta Air Lines DL1794 / DL2738: SJO 2027-01-24 07:00:00 → ORD 2027-01-24 17:06:00; 1 stop(s) via ATL; 606 minutes. Local airport times.
- DL1794: SJO 2027-01-24 07:00:00 → ATL 2027-01-24 12:05:00; layover at ATL: 225 minutes.
- DL2738: ATL 2027-01-24 15:50:00 → ORD 2027-01-24 17:06:00.
2027-02-04 → 2027-02-07 · Axel-exclusive $400.00
- Avianca AV631 / AV641: ORD 2027-02-04 14:20:00 → SJO 2027-02-04 23:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2027-02-04 14:20:00 → GUA 2027-02-04 18:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2027-02-04 21:45:00 → SJO 2027-02-04 23:15:00.
- Avianca AV628 / UA2007: SJO 2027-02-07 10:00:00 → ORD 2027-02-07 18:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
- AV628: SJO 2027-02-07 10:00:00 → GUA 2027-02-07 11:30:00; layover at GUA: 118 minutes.
- UA2007: GUA 2027-02-07 13:28:00 → ORD 2027-02-07 18:15:00.
2027-02-04 → 2027-02-07 · Axel-exclusive $415.00
- Frontier Airlines F91596 / F9215: ORD 2027-02-04 05:58:00 → SJO 2027-02-04 14:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2027-02-04 05:58:00 → ATL 2027-02-04 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2027-02-04 11:14:00 → SJO 2027-02-04 14:16:00.
- Delta Air Lines DL1794 / DL2738: SJO 2027-02-07 07:00:00 → ORD 2027-02-07 17:06:00; 1 stop(s) via ATL; 606 minutes. Local airport times.
- DL1794: SJO 2027-02-07 07:00:00 → ATL 2027-02-07 12:05:00; layover at ATL: 225 minutes.
- DL2738: ATL 2027-02-07 15:50:00 → ORD 2027-02-07 17:06:00.
2027-03-19 → 2027-03-22 · Axel-exclusive $482.00
- Avianca AV263 / AV696: ORD 2027-03-19 22:30:00 → SJO 2027-03-20 07:50:00; 1 stop(s) via BOG; 620 minutes. Local airport times.
- AV263: ORD 2027-03-19 22:30:00 → BOG 2027-03-20 04:30:00; layover at BOG: 115 minutes.
- AV696: BOG 2027-03-20 06:25:00 → SJO 2027-03-20 07:50:00.
- Avianca AV697 / AV262: SJO 2027-03-22 09:30:00 → ORD 2027-03-22 21:30:00; 1 stop(s) via BOG; 660 minutes. Local airport times.
- AV697: SJO 2027-03-22 09:30:00 → BOG 2027-03-22 12:45:00; layover at BOG: 125 minutes.
- AV262: BOG 2027-03-22 14:50:00 → ORD 2027-03-22 21:30:00.
2027-03-19 → 2027-03-22 · Axel-exclusive $550.35
- Frontier Airlines F91901 / F935: ORD 2027-03-19 05:01:00 → SJO 2027-03-19 11:41:00; 1 stop(s) via MCO; 460 minutes. Local airport times.
- F91901: ORD 2027-03-19 05:01:00 → MCO 2027-03-19 08:55:00; layover at MCO: 85 minutes.
- F935: MCO 2027-03-19 10:20:00 → SJO 2027-03-19 11:41:00.
- United Airlines UA1952: SJO 2027-03-22 13:25:00 → ORD 2027-03-22 19:57:00; nonstop; 332 minutes. Local airport times.
2027-05-15 → 2027-05-22 · Axel-exclusive $408.50
- Avianca AV631 / AV641: ORD 2027-05-15 14:20:00 → SJO 2027-05-15 22:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2027-05-15 14:20:00 → GUA 2027-05-15 17:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2027-05-15 20:45:00 → SJO 2027-05-15 22:15:00.
- Avianca AV628 / UA2007: SJO 2027-05-22 10:00:00 → ORD 2027-05-22 19:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
- AV628: SJO 2027-05-22 10:00:00 → GUA 2027-05-22 11:30:00; layover at GUA: 118 minutes.
- UA2007: GUA 2027-05-22 13:28:00 → ORD 2027-05-22 19:15:00.
2027-05-15 → 2027-05-22 · Axel-exclusive $451.25
- Frontier Airlines F91596 / F9215: ORD 2027-05-15 05:58:00 → SJO 2027-05-15 13:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2027-05-15 05:58:00 → ATL 2027-05-15 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2027-05-15 11:14:00 → SJO 2027-05-15 13:16:00.
- United Airlines UA1952: SJO 2027-05-22 13:25:00 → ORD 2027-05-22 19:57:00; nonstop; 332 minutes. Local airport times.
2027-07-10 → 2027-07-17 · Axel-exclusive $430.00
- Avianca AV631 / AV641: ORD 2027-07-10 14:20:00 → SJO 2027-07-10 22:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2027-07-10 14:20:00 → GUA 2027-07-10 17:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2027-07-10 20:45:00 → SJO 2027-07-10 22:15:00.
- Avianca AV628 / UA2007: SJO 2027-07-17 10:00:00 → ORD 2027-07-17 19:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
- AV628: SJO 2027-07-17 10:00:00 → GUA 2027-07-17 11:30:00; layover at GUA: 118 minutes.
- UA2007: GUA 2027-07-17 13:28:00 → ORD 2027-07-17 19:15:00.
2027-07-10 → 2027-07-17 · Axel-exclusive $475.00
- Frontier Airlines F91596 / F9215: ORD 2027-07-10 05:58:00 → SJO 2027-07-10 13:16:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
- F91596: ORD 2027-07-10 05:58:00 → ATL 2027-07-10 09:27:00; layover at ATL: 107 minutes.
- F9215: ATL 2027-07-10 11:14:00 → SJO 2027-07-10 13:16:00.
- United Airlines UA1952: SJO 2027-07-17 13:25:00 → ORD 2027-07-17 19:57:00; nonstop; 332 minutes. Local airport times.
2027-09-25 → 2027-10-02 · Axel-exclusive $376.25
- Avianca AV631 / AV641: ORD 2027-09-25 14:20:00 → SJO 2027-09-25 22:15:00; 1 stop(s) via GUA; 535 minutes. Local airport times.
- AV631: ORD 2027-09-25 14:20:00 → GUA 2027-09-25 17:50:00; layover at GUA: 175 minutes.
- AV641: GUA 2027-09-25 20:45:00 → SJO 2027-09-25 22:15:00.
- Avianca AV628 / UA2007: SJO 2027-10-02 10:00:00 → ORD 2027-10-02 19:15:00; 1 stop(s) via GUA; 495 minutes. Local airport times.
- AV628: SJO 2027-10-02 10:00:00 → GUA 2027-10-02 11:30:00; layover at GUA: 118 minutes.
- UA2007: GUA 2027-10-02 13:28:00 → ORD 2027-10-02 19:15:00.
2027-09-25 → 2027-10-02 · Axel-exclusive $455.00
- American Airlines AA884 / AA310: ORD 2027-09-25 06:05:00 → SJO 2027-09-25 13:35:00; 1 stop(s) via MIA; 510 minutes. Local airport times.
- AA884: ORD 2027-09-25 06:05:00 → MIA 2027-09-25 10:25:00; layover at MIA: 123 minutes.
- AA310: MIA 2027-09-25 12:28:00 → SJO 2027-09-25 13:35:00.
- American Airlines AA378 / AA2999: SJO 2027-10-02 00:43:00 → ORD 2027-10-02 11:05:00; 1 stop(s) via DFW; 562 minutes. Local airport times.
- AA378: SJO 2027-10-02 00:43:00 → DFW 2027-10-02 06:10:00; layover at DFW: 137 minutes.
- AA2999: DFW 2027-10-02 08:27:00 → ORD 2027-10-02 11:05:00.
More dates for this route
- Nov 19, 2026 · Return options
- Nov 27, 2026 · Return options
- Dec 8, 2026 · Return options
- Dec 19, 2026 · Return options
- Dec 29, 2026 · Return options
- Jan 8, 2027 · Return options
- Jan 19, 2027 · Return options
- Jan 30, 2027 · Return options
- Feb 19, 2027 · Return options
- May 14, 2027 · Return options
- Jul 9, 2027 · Return options
- Sep 25, 2027 · Return options
- Hotels in Costa Rica with Axel
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- 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 · in winter · for a week
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- Croatia: in summer · in June · in September · for a week · for 10 days
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- 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
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- South America: in January · in February · in winter · for 10 days · for two weeks
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- 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
- The Rockies: in summer · in winter · for Presidents' Day weekend · for MLK weekend · for spring break · for 4 days · for a week
- 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
- Texas: in spring · in fall · for 3 days · for 4 days
- The Northeast: in fall · in summer · for Thanksgiving · for Christmas · for spring break · for 3 days · for 4 days · for a week
- New England: in fall · in summer · for 3 days · for 4 days · for a week
- The Southeast: in spring · in fall · for 3 days · for 4 days
- Anywhere: for Thanksgiving · for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · for Easter weekend · for Memorial Day weekend · for July 4th weekend · for Labor Day weekend · in November · in December · in January · in February · in March · in April · in May · in June · in July · in August · in September · for 4 days · for a week · for two weeks
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-exclusive | Dates | |
|---|---|---|---|---|---|
| San Jose (SJO) | San José, the gateway to Costa Rica's volcanoes and cloud forests | No matching fare saved | Dec 4 – Dec 13, 2026 (suggested) | Search these dates | |
| Guanacaste (LIR) | Guanacaste's Pacific beaches and dry-season sunshine | Nonstop · American, United | No matching fare saved | Dec 4 – Dec 13, 2026 (suggested) | Search these dates |
| Belize City (BZE) | Belize's barrier reef, cayes and Mayan ruins | No matching fare saved | Dec 4 – Dec 13, 2026 (suggested) | Search these dates | |
| Panama City (PTY) | Panama City's skyline, old town and the canal | No matching fare saved | Dec 4 – Dec 13, 2026 (suggested) | Search these dates | |
| Guatemala City (GUA) | Guatemala City, the gateway to Antigua and Lake Atitlán | No matching fare saved | Dec 4 – Dec 13, 2026 (suggested) | Search these dates | |
| San Salvador (SAL) | San Salvador, with surf beaches and volcanoes within an hour | No matching fare saved | Dec 4 – Dec 13, 2026 (suggested) | Search these dates | |
| Roatan (RTB) | Roatán's reef diving and beaches in the Bay Islands | No matching fare saved | Dec 4 – Dec 13, 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 4 – Dec 13, 2026 (suggested) | Search these dates |
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.
Hotel details in Costa Rica: Country Inn & Suites by Radisson, San Jose Aeropuerto, Costa Rica · City Express by Marriott San Jose Costa Rica · Alameda Cariari · Berlor Airport Inn · Buena Vista Chic Hotel · All 21 hotels in Costa Rica
For AI assistants
- This page: Flights from Chicago to Central America for 10 days. Round-trip fares from Chicago to Central America for 10 days: San Jose, Guanacaste, Belize City, Panama City, Guatemala City and San Salvador and more, for stays of 9 to 11 nights. The cheapest saved fare 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.