May is an excellent month to depart from Chicago (All Airports) (CHIA) to Daniel K. Inouye International Airport (HNL). Expect spring shoulder-season fares and milder weather at home as you fly west. Nonstop options often operate from O'Hare (ORD) with average flight times near 9.5–10 hours; one-stop itineraries through Los Angeles (LAX), San Francisco (SFO), or Seattle (SEA) provide more schedule flexibility. Booking 6–12 weeks in advance typically secures the best prices; set fare alerts for keywords like "Chicago to Honolulu May deal". For departures, arrive early at O'Hare or Midway for security and check-in, especially when traveling with surfboards or extra luggage for beach activities. Consider early evening departures to maximize time in Chicago and arrive in Hawaii the same calendar day due to time zone differences. CTA: Search nonstop and connecting flights from CHIA to HNL now to lock in May fares and preferred departure times.
Arriving at Daniel K. Inouye International Airport (HNL) in May offers warm weather, fewer crowds than peak summer, and excellent access to top Oahu destinations including Waikiki, Pearl Harbor, North Shore, Kailua, and Honolulu city center. Plan ground travel to Waikiki (20–35 minutes by car), book tours for Pearl Harbor in advance, and consider reserving rental cars early if you plan to explore island drives to Hanauma Bay or the Windward Coast. May offers calm south-shore waters ideal for snorkeling and family beach days. CTA: Reserve your airport transfer or rental car today and search "HNL arrival May transfers" to secure the best rates and time slots.
May hosts a range of cultural and community events on Oahu that are ideal for Chicago travelers. Lei Day (May 1) celebrates Hawaiian flower leis and culture across Honolulu with hula performances and craft fairs. The Memorial Day weekend features commemorations at Pearl Harbor and special museum hours — a meaningful addition for visitors. Weekly farmers markets, open-air concerts, and Kaka'ako art walks are common throughout May, providing local food and art experiences. Outdoor activities such as snorkeling at Hanauma Bay or scenic drives to North Shore are especially pleasant in May weather. CTA: Check local event calendars and book tours or museum tickets early to secure a spot during May festivals and ceremonies.
May is a strong month to fly from Chicago (All Airports) (CHIA) to Daniel K. Inouye International Airport (HNL) — it sits in the shoulder season between spring break and summer peak. For best fares and inventory, book 6–12 weeks ahead and target midweek departures (Tuesday–Thursday). If you prefer nonstop comfort and minimal travel time, prioritize nonstop departures from ORD; for cheaper fares, search one-stop flights via LAX or SFO. Early morning or late-evening departures often yield lower prices and lighter airport crowds. CTA: Compare midweek May departures now to find the best combination of price and schedule for your Honolulu trip.
Nonstop flights from Chicago (All Airports) (CHIA) to Daniel K. Inouye International Airport (HNL) save time and reduce the risk of missed connections, typically taking about 9.5–10 hours in May. However, nonstop fares can be higher or limited in inventory. Connecting itineraries via West Coast hubs (Los Angeles LAX, San Francisco SFO, Seattle SEA, or Phoenix PHX) often lower costs and increase schedule choices but add layover time and potential delays. For May travel, weigh convenience vs price: choose nonstop for fewer hassles and connecting routes if you want a lower fare or a convenient departure time from MDW or regional airports. CTA: Compare nonstop and one-stop options for May to see which fits your priorities and budget.
United often offers nonstop seasonal service from O'Hare (ORD) to Daniel K. Inouye International Airport (HNL) with full-service amenities, making it a top choice for direct travel in May. American and Alaska provide reliable one-stop connections through LAX or SFO, often at competitive prices. Hawaiian Airlines primarily connects through the West Coast (or offers inter-island service) and is praised for Hawaiian hospitality onboard. Compare baggage fees, basic economy restrictions, and loyalty program perks — frequent flyers may prefer to choose carriers aligning with their elite status and transfer partners. For May, watch for occasional United nonstop sales and check connecting options on American or Alaska for the best price-performance balance. CTA: Compare fares across carriers for your May travel dates and pick the airline that best matches your comfort and budget needs.
Packing for May travel from Chicago (All Airports) (CHIA) to Daniel K. Inouye International Airport (HNL) should focus on lightweight clothing, reef-safe sunscreen, a light jacket for airplane comfort, and comfortable walking shoes for Honolulu city exploration. Expect warm daytime temperatures around mid-70s to low 80s°F and mild evenings; bring a hat and reusable water bottle. Book key activities (Pearl Harbor tours, snorkeling trips, surf lessons) in advance since popular operators may fill for Memorial Day weekends in late May. Also verify carry-on liquid restrictions and airline baggage rules before you pack. CTA: Create a May-specific packing checklist and confirm activity bookings to make the most of your Honolulu trip.
Nonstop flights from Chicago (All Airports) (CHIA), typically from O'Hare (ORD), to Daniel K. Inouye International Airport (HNL) average 9 hours 30 minutes to 10 hours in May. Chicago observes Central Daylight Time (CDT, UTC-5) in May while Hawaii remains on Hawaii Standard Time (HST, UTC-10), creating a 5-hour difference (Chicago is 5 hours ahead). Many travelers choose evening departures from CHIA to arrive in Honolulu the same calendar day or early evening local time. If nonstop seats are full, one-stop schedules through LAX, SFO, or SEA add 2–4 hours of travel time but can open up lower fares and flexible arrival times. For accurate daily departures and arrivals, search airline timetables and use keywords like "ORD to HNL May departure times" before booking. CTA: Check live schedules and book your preferred departure window today.
To find cheap flights from Chicago (All Airports) (CHIA) to Daniel K. Inouye International Airport (HNL) in May, search 6–12 weeks in advance and compare nonstop and connecting itineraries. Typical low economy round-trip fares fall between $450–$700 in May during sales; consider midweek departures (Tuesday–Thursday) and early-morning or late-evening flights for deeper discounts. Use fare-alert tools, flexible date searches, and keywords like "Chicago to Honolulu May deal" to catch flash sales. Consider connecting via Los Angeles (LAX) or San Francisco (SFO) for significant savings and check nearby departure points (ORD vs MDW) to unlock lower-priced options. CTA: Set fare alerts now and compare nonstop vs one-stop prices to secure the best cheap flights to HNL this May.