Submit feedbackSubmit feedbackMay is a favorable month to fly from Ancona (All Airports) (ANCA) to O'Hare International Airport (ORD) because spring shoulder-season fares and pleasant weather converge to create attractive travel windows. Expect most itineraries to route through Rome, Milan, Frankfurt or Amsterdam with total travel times typically between 12–18 hours depending on layovers. For budget-conscious travelers, monitor 6–8 week booking windows and set price alerts for ANCA to ORD cheap flights in May; mid-week departures often yield lower fares. Pack a light jacket for cool Chicago evenings and confirm connection times if your itinerary includes multiple carriers. Nearby Italian cities commonly used as gateways include Bologna, Milan, Rome, Venice, and Florence—consider starting your journey in a larger hub to access more transatlantic options. Book now to secure competitive May rates and check real-time schedules with the selected carrier.
Direct nonstop flights between Ancona (All Airports) (ANCA) and O'Hare International Airport (ORD) are rare year-round. In May, most itineraries require one or two connections through major European hubs such as Rome Fiumicino (FCO), Milan Malpensa (MXP), Frankfurt (FRA) or Amsterdam (AMS). For faster travel, search for one-stop itineraries with a single European layover to minimize total journey time.
Total travel time from Ancona (All Airports) (ANCA) to O'Hare International Airport (ORD) in May generally ranges from 12 to 20+ hours depending on the number and length of layovers. Shorter itineraries often connect through Milan (MXP) or Rome (FCO) with a single transit; longer multi-stop routings via Frankfurt or Amsterdam can extend travel time. Always check layover minimum connection times and seasonal schedule changes when booking.
Average round-trip fares in May for ANCA → ORD tend to fall in the €450–€900 range when booked 6–8 weeks in advance, with cheaper deals possible during flash sales. Prices vary by airline, routing, and how early you book; flying mid-week and avoiding peak holiday dates can reduce costs. Use price alerts and flexible date searches to capture low-fare windows.
Baggage allowances depend on the operating carrier: legacy carriers typically include one checked bag in economy on international itineraries, while low-cost carriers may charge separately. For May transatlantic travel via European partners, confirm both carry-on and checked baggage allowances and fees at booking, and always check connecting carrier policies if you have multiple airlines on the same ticket. Pack important items and medications in carry-on in case of checked baggage delays.
For international departures from Ancona (All Airports) (ANCA) in May, arrive at least 2 to 3 hours before your scheduled departure to allow time for check-in, security screening, and any seasonal staffing variations. If you have a long-haul connection or are checking a bag, err on the side of extra time during busy May weekends and around public holidays. Confirm specific airline check-in deadlines and factor in local transit times.
Ancona (All Airports) (ANCA) is well linked to nearby major cities such as Bologna, Milan, Rome, Venice and Florence by regional trains, intercity buses, and highways. In May you’ll find regular train and coach services to the airport; pre-booked airport shuttles and private transfers are good options if you're carrying heavy luggage. Plan connections in advance—especially if you need to travel from Milan or Rome on the same day as your flight—to avoid tight layovers.
Arriving at O'Hare International Airport (ORD) in May from Ancona (All Airports) (ANCA) is generally smooth, provided you prepare for immigration and ground transit. May sees pleasant spring weather in Chicago but occasional storms, so build buffer time for customs and baggage claim. For fastest access to downtown Chicago use the CTA Blue Line; if you’re visiting nearby suburbs like Evanston, Naperville or Aurora, regional trains and shuttle services operate regularly. Check the airline and CBP guidance for the latest entry requirements and download the airline app for real-time gate and baggage updates. For a stress-free arrival, pre-book a rideshare or shuttle and have U.S. entry documents ready on your phone or printed.
Upon arrival at O'Hare International Airport (ORD), expect customs and immigration processing for international passengers arriving from Ancona (All Airports) (ANCA). Processing times vary by time of day; in May, early morning and late evening arrivals can be busier. Have your passport, ESTA/visa documentation, and customs declaration forms ready, and consider enrolling in mobile passport control options if eligible to speed up entry.
From O'Hare International Airport (ORD), you can reach downtown Chicago by the CTA Blue Line train (about 45–50 minutes), airport shuttles, taxi, rideshare, or private transfer; travel time can be longer during peak May events. The Blue Line is often the fastest budget option, while taxis and rideshares offer door-to-door service but may be affected by traffic. If you’re visiting nearby cities like Evanston, Naperville or Aurora, regional trains and express bus services are available.
Timing your ANCA→ORD trip in May can let you enjoy local cultural events on both ends. In the Ancona and Marche region, May often features spring maritime festivals, local food markets and 'Festa del Mare' weekend events celebrating seafood and coastal culture—ideal for a pre-departure cultural stop. In Chicago, May brings outdoor festivals, Memorial Day parades, spring food markets and the early music festival circuit; watch for neighborhood street fairs and waterfront activities. These events can increase hotel and flight demand—book early if you plan to attend. CTA: Check event dates and book your ANCA to ORD May flights now to secure travel during popular festival weekends.
May is a prime shoulder-season month to fly from Ancona (All Airports) (ANCA) to O'Hare International Airport (ORD). Spring weather in both regions is generally pleasant, demand is lower than summer peak, and airlines often deploy added frequencies—creating a balance of availability and competitive fares. Best booking windows are usually 6–8 weeks in advance for the best mix of price and flight choice; however, for specific holiday weekends or festival dates in Chicago, book earlier. For budget travelers, consider flying mid-week and taking advantage of connecting hubs that offer cheaper transatlantic legs.
Because Ancona (All Airports) (ANCA) is a regional gateway, direct flights to O'Hare International Airport (ORD) are uncommon, making connecting itineraries the norm in May. Connecting flights via Rome, Milan, Frankfurt, Amsterdam or Paris give you more frequent schedule options and competitive pricing. Pros of connecting: more departure windows, lower fares, and access to multiple carriers. Cons: longer total travel time and potential for missed connections—especially if booked as separate tickets. To reduce risk, book single-ticket itineraries through one alliance or verify minimum connection times, and choose layovers of at least 90–120 minutes for transatlantic segments in May.
Typical routings from Ancona (All Airports) (ANCA) to O'Hare International Airport (ORD) in May use a combination of short-haul partners and major transatlantic carriers. Examples: ITA Airways or regional carriers to Rome (FCO) or Milan (MXP) followed by a transatlantic partner like United Airlines or another Star Alliance member; or KLM via Amsterdam (AMS) or Air France via Paris (CDG) under SkyTeam partnerships. Lufthansa via Frankfurt (FRA) is another common option with efficient European connections. Compare total journey time, baggage inclusion, loyalty benefits, and change/cancellation flexibility when choosing. CTA: Compare itineraries now to select the optimal carrier for your May trip.
May travel from Ancona (All Airports) (ANCA) to O'Hare International Airport (ORD) benefits from spring temperatures and fewer winter disruptions, but pack layers: light sweaters, a waterproof jacket for possible Midwest showers, and adaptors for European plugs if needed en route. Confirm passport validity and visa/ESTA status well before departure, and download airline apps for real-time gate and baggage alerts. For smoother connections, allow 90–120 minutes for European-to-transatlantic transfers and prioritize single-ticket itineraries. CTA: Prepare your May trip checklist now and verify travel documents before booking ANCA→ORD flights.
Typical total travel times from Ancona (All Airports) (ANCA) to O'Hare International Airport (ORD) in May range from approximately 12 hours (fast one-stop via Milan or Rome plus transatlantic sector) to 20+ hours for multi-stop routings. Common connection airports are Rome Fiumicino (FCO), Milan Malpensa (MXP), Frankfurt (FRA), Amsterdam Schiphol (AMS) and Paris Charles de Gaulle (CDG). Recommended minimum connection times are 60–90 minutes for intra-Schengen to Schengen transfers and 2 hours for transatlantic handoffs; if international checked baggage transfers are involved, allow additional buffer. Flight schedules in May typically expand as carriers add seasonal frequencies—check updated timetables and aim for single-ticket itineraries to protect connections.
To find cheap flights from Ancona (All Airports) (ANCA) to O'Hare International Airport (ORD) in May, start by searching 6–8 weeks before your departure for the optimal balance of price and availability. Use flexible date searches and consider departing mid-week (Tuesday–Thursday) to lower fares. Compare one-stop itineraries through major European hubs like Rome, Milan, Frankfurt and Amsterdam—sometimes adding a cheap short-haul flight to a larger hub yields significant savings on the transatlantic leg. Sign up for airline newsletters and set price alerts for ANCA to ORD cheap flights; consider refundable or flexible fares if prices are volatile. CTA: Compare fares now and activate nightly price alerts for ANCA→ORD flights in May.
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Book your economy class flight from Anchorage (Any) to Chicago (ORD)and save money on your travel. Compare all flight options to find the best deal for your may trip.
Starting from $169
Book your economy class flight from Anchorage (Any) to Chicago (ORD)and save money on your travel. Compare all flight options to find the best deal for your may trip.
Starting from $169
Book your economy class flight from Anchorage (Any) to Chicago (ORD)and save money on your travel. Compare all flight options to find the best deal for your may trip.
Starting from $169
Book your economy class flight from Anchorage (Any) to Chicago (ORD)and save money on your travel. Compare all flight options to find the best deal for your may trip.
Starting from $169
Book your economy class flight from Anchorage (Any) to Chicago (ORD)and save money on your travel. Compare all flight options to find the best deal for your may trip.
Planning a trip from Anchorage (Any) to Chicago (ORD) in may? SlickTrip helps you find the cheapest economy class flights with our comprehensive flight comparison tool. Whether you prefer direct flights for convenience or multi-stop flights for savings, we have options for every budget and schedule.
May is generally a stable travel month at O'Hare International Airport (ORD) with fewer severe weather disruptions than winter, but spring storms can still cause delays. Construction-related gate or concourse changes occasionally occur—check airport advisories and your airline's status updates before departure and upon arrival. Allow buffer time for connections and ground transportation during busy holiday weekends and events.
O'Hare International Airport (ORD) offers convenient access to Chicago and surrounding major destinations such as Evanston, Naperville, Aurora, Gary (Indiana), and Milwaukee (via train or shuttle). May is ideal for exploring Chicago’s parks and lakefront, or for short trips to nearby suburbs and cultural sites. Use regional transit options or rental cars for day trips to these cities.
As of this May travel guidance, most countries (including the U.S.) have relaxed routine COVID-19 entry testing and quarantine mandates, but requirements can change. Check the U.S. CDC guidance, airline notices, and Italian government advisories before travel. Carry proof of vaccination or negative tests if still required by carriers or transit hubs, and pack masks and hand sanitizer for airport and public transit use.
Whether you collect checked baggage at a connection depends on how your itinerary is ticketed and U.S. entry rules: on many itineraries you may be required to clear customs at the first U.S. entry point, which could be ORD or another airport. If your checked luggage is ticketed through to ORD and you have a single ticket, it typically transfers automatically, but you will retrieve it if ORD is your first U.S. stop or if required for customs. Confirm baggage transfer details with your airline when booking.
