Other Destinations
Flights from Other Cities
New York (LGA) to Chicago (ORD) in October from $44
From $44
New York (Any) to Chicago (ORD) in October from $49
From $49
Miami (MIA) to Chicago (ORD) in October from $84
From $84
Philadelphia (PHL) to Chicago (ORD) in October from $85
From $85
Miami (MIA) to Chicago (ORD) in October from $93
From $93
Tampa (TPA) to Chicago (ORD) in October from $94
From $94
✈️ Flight Guide: San Jose (SJO) → Chicago (ORD)
Complete travel information for your October journey
October is part of Costa Rica's green season, which means frequent afternoon and evening showers around San José. Travelers departing from Juan Santamaría International Airport (SJO) should expect wetter roads and slightly longer ground transfer times to and from downtown San José. Nonstop SJO–O'Hare International Airport (ORD) flights may be seasonal; check airline schedules in October and book early to secure direct options. For cheaper October fares, target mid-week departures, sign up for fare alerts, and consider flexible dates. CTAs: Compare nonstop and connecting SJO to ORD flights now and book early to lock in best prices for October travel.
Departing from San Jose (SJO) FAQs
In October, traffic and occasional heavy rains can slow travel to Juan Santamaría International Airport (SJO). The fastest options are private airport shuttles and taxis (about 20–35 minutes from central San José), while shared shuttles and public buses are the most budget-friendly but can take longer. Plan extra time in October for wet-road delays and check live traffic before departing.
Direct SJO to O'Hare (ORD) service is offered seasonally and varies by carrier; United Airlines has historically provided non-stop service on this route. In October, check airline schedules because direct flights may be reduced or shifted to peak travel dates. Use airline websites or flight search engines to confirm nonstop availability for your travel dates.
October is in Costa Rica's rainy (green) season, so pack a compact rain jacket, quick-dry layers, and waterproof shoes when leaving from Juan Santamaría International Airport (SJO). Allow extra time for transfers, and consider travel insurance that covers weather-related delays. Airports typically remain operational, but ground transfers to hotels or beach destinations can be slower.
Yes—Juan Santamaría International Airport (SJO) serves as the primary gateway for Pacific destinations like Manuel Antonio, Jaco, and Tamarindo as well as routes to the Central Valley and Caribbean-adjacent areas via ground transfers or short domestic flights. Book early-morning departures for same-day connections and consider domestic carriers for quick internal hops. October ground travel times may be longer due to rains, so plan accordingly.
Juan Santamaría International Airport (SJO) provides essential traveler services including restaurants, duty-free shops, currency exchange, and several lounges (some operated by airlines or independent companies). Lounges may have seasonal hours and access rules, so check availability before your October departure. Expect typical Central American airport amenities and reliable ground transportation options.
For international travel from Juan Santamaría International Airport (SJO) to O'Hare International Airport (ORD), arrive at least 2–3 hours before departure. In October, factor in potential rain-related delays and holiday-weekend surges; arriving 3 hours early gives extra time for check-in and security. If flying nonstop or during peak windows, confirm recommended check-in times with your airline.
October arrivals at O'Hare International Airport (ORD) mean crisp fall air and high demand around event weekends like the Chicago Marathon and film festival. Use the CTA Blue Line for a fast trip to downtown Chicago or consider rideshares and airport shuttles for door-to-door service. If you’re coming from Juan Santamaría International Airport (SJO), plan for customs and potential jet-lag adjustments; carry layered clothing for Chicago's variable October temperatures. CTA and Metra options also make ORD a good gateway to Milwaukee, Aurora, and suburban business centers. CTA: Book your O'Hare transfers and check local events when planning your October itinerary.
Arriving at Chicago (ORD) FAQs
From O'Hare International Airport (ORD) you can take the CTA 'L' Blue Line direct to downtown Chicago (about 45 minutes), taxis, app-based rideshares, or airport shuttles. In October, cool weather can affect traffic but the Blue Line remains a reliable option for avoiding road congestion. Reserve airport transfers in advance for the best fares and quicker exits from the terminal.
October in Chicago is fall season—temperatures typically range from the mid-40s to mid-60s °F (about 7–18 °C) and can be windy. Pack layered clothing, a warm jacket, and a compact umbrella for unpredictable rain or wind. If arriving from warm Costa Rica at O'Hare International Airport (ORD), plan to layer up immediately upon landing.
Arriving from Juan Santamaría International Airport (SJO), you'll clear U.S. Customs and Border Protection at O'Hare International Airport (ORD). Carry required travel documents, be prepared for possible secondary inspection, and declare all goods as required. In October there are no routine extra health screenings, but check current CDC and CBP guidance before travel.
O'Hare International Airport (ORD) serves as a major hub for accessing Chicago neighborhoods and nearby major cities such as Milwaukee, Aurora, Naperville, and Rockford, as well as tourist destinations like the Magnificent Mile, Navy Pier, and suburban conference centers. Many travelers also use ORD as a gateway to the greater Midwest region, so consider car rentals or Metra/Amtrak connections for onward travel.
For late-night arrivals at O'Hare International Airport (ORD), pre-book a hotel shuttle or rideshare and check CTA schedules because public transit frequencies can be reduced overnight. October nights are cooler—dress warmly when arranging transfers or waiting outside. If you arrive late, confirm terminal pickup points and have alternate transportation options just in case.
1.0.2510.29
October Events & Festivals — Travel from Juan Santamaría (SJO) to O'Hare (ORD)
Chicago (near O'Hare International Airport (ORD)): October often features the Bank of America Chicago Marathon, the Chicago International Film Festival, and numerous fall food and Halloween events—expect higher accommodation demand around race weekend. San José/Costa Rica (near Juan Santamaría International Airport (SJO)): October is quieter for major festivals but is prime green-season time for coffee harvest tours, wildlife viewing, and cultural events in smaller towns; domestic ecotourism experiences are popular. CTA: Check event dates before booking SJO–ORD flights in October to avoid premium fares and secure accommodations early.
Best Time to Fly SJO to ORD — When to Book for October Travel
For October travel, the best time to book SJO → ORD flights is generally 6–10 weeks in advance to catch shoulder-season discounts. Target mid-week departures (Tuesday–Thursday) to reduce fares while avoiding peak event weekends in Chicago, such as marathon dates. If you prefer nonstop travel, book early since direct seasonal seats can sell out. CTA: Compare flexible date prices today and lock in an October itinerary that fits your schedule.
Direct vs Connecting Flights: SJO to ORD — Which Should You Choose in October?
Direct flights from Juan Santamaría International Airport (SJO) to O'Hare International Airport (ORD) save time and reduce the risk of missed connections, typically shaving several hours off a one-stop itinerary. However, nonstop fares in October can be higher or seasonally limited; connecting itineraries via hubs like PTY, IAH, MIA, or ATL often offer significant savings. Choose nonstop for convenience and short trips; choose a connection if price is the priority or if you want to break the journey in a hub city. CTA: Compare nonstop and connecting itineraries side-by-side for your October travel dates and weigh cost vs. convenience.
Airline Comparison for SJO → ORD: United, Copa, American, Delta (October)
United Airlines: Often offers seasonal nonstop service between Juan Santamaría International Airport (SJO) and O'Hare International Airport (ORD), making United a top choice for speed and direct routing. Copa Airlines: Strong for one-stop connections via Panama (PTY) with competitive fares and consistent schedules. American Airlines and Delta: Typically require single connections through Miami (MIA), Dallas (DFW), or Atlanta (ATL), offering robust frequent-flyer benefits and multiple daily options. Budget carriers and local operators may offer cheap connecting routes but watch baggage and seat fees. CTA: Compare total price including baggage fees and preferred schedules to pick the best airline for your October journey.
Seasonal Travel Tips for Flying SJO to ORD in October
Pack for two climates when traveling from Juan Santamaría International Airport (SJO) to O'Hare International Airport (ORD) in October: lightweight rain gear and insect repellant for Costa Rica, plus warm layers and a wind-resistant jacket for Chicago. Book refundable or changeable fares when possible because October rainy-season weather can cause domestic delays in Costa Rica; consider travel insurance that covers weather disruptions. Allow at least 2–3 hours at SJO for international check-in and allocate additional buffer for ground transfers. CTA: Review your airline's change policy and buy flexible fare options for peace of mind on October travel.
Flight Time & Schedule Guide: Juan Santamaría (SJO) to O'Hare (ORD)
Typical nonstop flights between Juan Santamaría International Airport (SJO) and O'Hare International Airport (ORD) take roughly 5 hours 30 minutes to 6 hours, depending on wind and routing. Many itineraries in October are one-stop with connections in Panama City (PTY), Houston (IAH), Miami (MIA), Atlanta (ATL), or Dallas (DFW). Early-morning and late-evening departures from SJO are common for international services, while ORD offers all-day arrivals and departures to accommodate connections. CTA: Check specific airline schedules for your October dates and confirm total travel time including layovers.
How to Find Cheap Flights from Juan Santamaría (SJO) to O'Hare (ORD) in October
To find cheap flights from Juan Santamaría International Airport (SJO) to O'Hare International Airport (ORD) in October, search 6–10 weeks before travel and compare mid-week departures for the lowest fares. Consider one-stop itineraries via Panama (PTY), Houston (IAH), Miami (MIA), or Dallas (DFW) to unlock savings, and set fare alerts to catch sale windows. Use flexible date search and mix-and-match one-way tickets if needed; check baggage fees and total trip cost before booking. CTA: Use a fare alert or price calendar to compare SJO–ORD October deals and book when you see a price dip.