Best Flights starting from $3,628
from$3,628premium_economy
Kailua-Kona (KOA)
Sun, Oct 18
Roundtrip
Chicago (ORD)
Fri, Oct 23
from$3,630premium_economy
Kailua-Kona (KOA)
Tue, Oct 13
Roundtrip
Chicago (ORD)
Sun, Oct 18
from$4,049premium_economy
Kailua-Kona (KOA)
Sat, Oct 17
Roundtrip
Chicago (ORD)
Thu, Oct 22
from$4,053premium_economy
Kailua-Kona (KOA)
Wed, Oct 14
Roundtrip
Chicago (ORD)
Mon, Oct 19
from$4,053premium_economy
Kailua-Kona (KOA)
Thu, Oct 15
Roundtrip
Chicago (ORD)
Tue, Oct 20
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Other Destinations
Kailua-Kona (KOA) to Los Angeles (LAX) in October from $189
From $189
Kailua-Kona (KOA) to Phoenix (PHX) in November from $180
From $180
Kailua-Kona (KOA) to San Francisco (SFO) in November from $277
From $277
Kailua-Kona (KOA) to Honolulu (HNL) in January from $70
From $70
Kailua-Kona (KOA) to Bucharest (Any) in February from $539
From $539
Kailua-Kona (KOA) to Tokyo (HND) in February from $2,550
From $2,550
Flights from Other Cities
Tampa (TPA) to Chicago (ORD) in October from $22
From $22
Atlanta (Any) to Chicago (ORD) in October from $41
From $41
New York (LGA) to Chicago (ORD) in October from $44
From $44
New York (Any) to Chicago (ORD) in October from $49
From $49
Denver (DEN) to Chicago (ORD) in October from $80
From $80
Miami (MIA) to Chicago (ORD) in October from $84
From $84
✈️ Flight Guide: Kailua-Kona (KOA) → Chicago (ORD)
Complete travel information for your October journey
October at Kona International Airport at Keahole (KOA) is an ideal time to depart for the mainland: you’ll find fewer visitors than peak winter months and often lower fares on Kona to Chicago flights. Expect most itineraries to route through West Coast hubs (LAX, SFO, SEA) with total travel time typically between 9 and 12 hours depending on connections. Pack light layers for Chicago fall weather and confirm transfers if you have tight layovers. To secure the best October deals, set price alerts, consider midweek departures, and book 6–12 weeks ahead. CTA: Compare flights KOA to ORD and book your October trip today.
Departing from Kailua-Kona (KOA) FAQs
October is a shoulder season for Kona International Airport at Keahole (KOA) with generally pleasant weather and fewer tourists than winter months. Expect on-time performance to be good, but check your airline for schedule changes and arrive 90 minutes before domestic departures. Use this month to find better airfare on your Kona to Chicago flights and book midweek for lower prices.
Most KOA to ORD itineraries in October are one-stop connections via West Coast hubs such as Los Angeles (LAX), San Francisco (SFO), or Seattle (SEA). Nonstop options are rare and usually seasonal; check carriers like United or Hawaiian Airlines for occasional nonstop schedules. If you prefer nonstop travel, monitor airline routes and book ASAP when a nonstop appears.
For October travel, book KOA to ORD tickets about 6–12 weeks in advance for the best balance of price and availability. Since October is a shoulder season, last-minute deals sometimes appear mid-month, but booking earlier secures better schedules and connection choices. Use price alerts and flexible dates to capture promos on Hawaii to Chicago flights.
From Kona International Airport at Keahole (KOA), you can take shuttle services, taxis, ride-shares (Uber/Lyft), car rentals, or scheduled hotel transfers. Car rental counters are on-site and recommended for exploring the Kona coast and nearby destinations like Waikoloa and Volcano National Park. Book rentals in advance for October, when weekend demand can spike around short local events.
Pack for a transition from warm Kona weather to cooler Chicago fall temperatures—bring a lightweight jacket for arrival. Follow TSA rules: liquids in 3.4 oz containers, and check airline carry-on size limits. October can bring holiday-season fare fluctuations, so verify checked bag fees and potential weight limits for connections through mainland hubs.
October is near the end of the Central Pacific hurricane season, so while major storms are uncommon at KOA, occasional tropical weather or localized heavy rain can cause delays. Airlines often rebook passengers proactively for significant weather; track your flight and sign up for airline alerts. Consider travel insurance if you’re concerned about weather disruptions on a KOA to ORD itinerary.
Arriving at O'Hare International Airport (ORD) in October puts you in prime position to experience Chicago’s fall colors and signature events. Expect cooler weather than Kona and plan transport into downtown Chicago or suburbs like Naperville and Evanston by CTA Blue Line, Metra, or pre-booked shuttle. Event weekends (e.g., the Chicago Marathon) can increase demand for rideshares and hotels—reserve early. For speedy transfers, allow 60–90 minutes for baggage and terminal changes, and consider off-peak arrival times. CTA: Book your Kona to Chicago arrival transfer to ORD today.
Arriving at Chicago (ORD) FAQs
When arriving at O'Hare International Airport (ORD) in October, expect cooler fall temperatures and increased airport activity due to seasonal business travel and events like the Chicago Marathon (early October). Allow extra time for immigration (if applicable on separate itineraries), baggage claim, and transportation into downtown Chicago or suburbs. Check CTA and Metra options for budget-friendly transit into the city.
O'Hare International Airport (ORD) serves downtown Chicago (The Loop), neighborhoods like Lincoln Park and River North, and nearby suburban destinations such as Schaumburg, Naperville, Oak Brook, and Evanston. ORD is also a gateway to regional cities including Milwaukee and Rockford via connecting flights or ground transport. Plan transit times—rush hour can significantly add to travel time to the Loop in October.
Yes—early October often hosts the Bank of America Chicago Marathon and multiple fall festivals which increase hotel and transit demand near downtown. Special events can cause surges in taxi and ride-share wait times at O'Hare International Airport (ORD). For smoother arrival in October, pre-book airport shuttles or car services and consider off-peak arrival times.
Allow 45–90 minutes for baggage claim and customs if your itinerary routes through an international point; for domestic connections, plan on at least 60–90 minutes between flights during October peak windows. O'Hare International Airport (ORD) has multiple terminals—verify arrival terminal and use the free airport transit to transfer between terminals efficiently. If you have tight connections, request assistance at arrival or choose flights with longer layovers when booking.
O'Hare International Airport (ORD) offers CTA Blue Line service to downtown, Metra and Pace bus connections, ride-shares, taxis, and on-site parking. For October arrivals during event weekends, CTA and express shuttles can be faster than taxi lines; consider pre-booked airport parking or off-site lots for multi-day stays. Always check CTA schedules and real-time updates on event days.
October in Chicago brings crisp fall weather and occasional rain; early snow is rare but possible late in the month. Keep a light jacket or layering options for immediate comfort after your Hawaii flight. Monitor forecasts before departure from Kona and upon approach to O'Hare International Airport (ORD) since seasonal winds or storms can affect arrival times.
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October Events & Festivals — From Kona (KOA) Departure to Chicago (ORD) Arrival
October brings notable events that can affect flights and hotels on the KOA to ORD route. On Hawaii’s Big Island, smaller community events and seasonal agricultural activities may increase local transport demand around Kona International Airport (KOA). In Chicago, the Bank of America Chicago Marathon (typically early October), Oktoberfest celebrations, and fall cultural festivals drive higher demand at O'Hare International Airport (ORD) and downtown hotels. If your October travel coincides with major events, book flights and ground transport early and consider arriving a day earlier to avoid event-day congestion.
Best Time to Fly KOA to ORD — October Travel Recommendations
For October, the best time to fly KOA to ORD is midweek—Tuesdays through Thursdays—when fares tend to be lower and airport crowds lighter. Early morning departures from KOA or late-night red-eyes to mainland hubs often reduce prices and can simplify connections, arriving in Chicago early afternoon or late evening. Avoid weekend travel and major event weekends in Chicago (like Marathon weekend) if you want lower rates and smoother ground transit. Book 6–12 weeks in advance for the best combination of price and seat availability.
Direct vs Connecting Flights — KOA to ORD October Choices
Nonstop flights are fastest when available, cutting travel time and reducing the risk of missed connections; however, nonstop KOA to ORD services are rare and often seasonal. Connecting flights via LAX, SFO, SEA, or PHX are the most common in October and typically offer lower fares and more schedule flexibility. If prioritizing comfort, choose a single long layover instead of multiple short connections and allow at least 90 minutes for tight transfers. For cost-sensitive travelers, a one-stop itinerary is usually the best balance of price and total travel time.
Airline Comparison for KOA to ORD — October Schedules & Service
United Airlines often offers the most competitive KOA to ORD itineraries via its West Coast hubs and O'Hare hub, with multiple daily connection options. Hawaiian Airlines specializes in Hawaii-origin service and may offer convenient single-stop routings via Los Angeles or Daniel K. Inouye International Airport (HNL) with Hawaiian hospitality onboard. Alaska Airlines provides reliable West Coast connections through Seattle and Portland. Compare ticket prices, carry-on and checked baggage rules, seat selection fees, and loyalty program benefits—United MileagePlus, HawaiianMiles, and Alaska Mileage Plan—before booking. CTA: Compare KOA to ORD airline options and pick the best fit for your October travel.
Seasonal Travel Tips for KOA to ORD in October — Weather, Packing & Logistics
October is a transitional month—departing warm Kona and arriving to cool Chicago fall weather—so pack versatile layers, a light waterproof jacket, and comfortable shoes for walking downtown. October is still within the extended Pacific hurricane season, though significant storms affecting Kona are uncommon; monitor forecasts and sign up for airline flight alerts. For smoother OCT travel: pre-book airport transfers at O'Hare, allow longer connection times for one-stop itineraries, and check bag restrictions to avoid fees. CTA: Prepare for October travel from KOA to ORD—check weather and book transfers now.
KOA to ORD Flight Time & Schedules — October Guide
Direct nonstop service between Kona International Airport at Keahole (KOA) and O'Hare International Airport (ORD) is uncommon; most October itineraries include one stop at West Coast hubs such as Los Angeles (LAX), San Francisco (SFO), Seattle (SEA), or Phoenix (PHX). Typical airborne time is roughly 8–9 hours of flight time total; include layovers and you should plan for 9–12+ hours door-to-door. Red-eye options from KOA to mainland hubs can help maximize daytime in Chicago and sometimes reduce fares. Verify schedules with airlines, as October can have slight timetable adjustments after summer peak periods.
Cheap Flights KOA to ORD in October — Tips & Deals
To secure cheap flights from Kona International Airport at Keahole (KOA) to O'Hare International Airport (ORD) in October, search flexible dates and midweek departures—Tuesdays and Wednesdays often yield the lowest fares. Book at least 6–12 weeks before travel; however, keep an eye on airline flash sales and shoulder-season promos that drop closer to departure. Use multi-airline connections via LAX, SFO, or SEA for lower-price itineraries and consider red-eye departures from KOA to mainland hubs to save money. Sign up for fare alerts, compare aggregate search engines, and redeem miles if available. CTA: Compare cheap KOA to ORD flights and set your fare alerts today.