Submit feedbackComplete travel information for your May journey
Departure planning from Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ) in May should focus on flexible booking, checking seasonal carrier schedules, and monitoring spring weather. May is a shoulder-season month where fares often dip before summer; search early-morning and midweek options for the best “cheap flights Chicago to Toronto” fares. ORD offers robust ground transport—CTA Blue Line, shuttle services, and interstate connections—making it easy to time your arrival. For business and leisure travelers, May brings pleasant temperatures in Chicago but occasional rain; pack a light waterproof layer and confirm baggage and entry document requirements for Canada. Book nonstop ORD to YYZ flights where possible to reduce risk of May-weather-related connections, and sign up for airline alerts for gate or schedule changes.
A nonstop flight from Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ) typically takes about 1 hour and 45 minutes to 2 hours. May schedules often include multiple daily direct flights from major carriers, but total travel time can vary with taxiing, air traffic, and weather conditions. Check carrier schedules for precise departure and arrival times.
For budget-conscious travelers flying from Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ) in May, midweek flights (Tuesdays and Wednesdays) and early-morning departures usually offer the lowest fares. Booking 3–8 weeks ahead and using flexible-date search tools for May can reveal the best deals. Consider nearby airports (e.g., Midway) and nearby destination options like Toronto Hamilton or Niagara Falls for potential savings.
Yes. Because Toronto Pearson International Airport (YYZ) is in Canada, U.S. citizens departing from Chicago O'Hare International Airport (ORD) must present a valid passport or other approved travel document for international travel. Passports must be valid for the duration required by Canadian entry rules; always verify current requirements before your May departure.
Travelers departing from Chicago O'Hare International Airport (ORD) can use the CTA Blue Line train, airport shuttle services, rideshares, taxis, and regional buses to reach downtown Chicago. In May, expect moderate traffic; allow extra time for morning or rush-hour departures when heading to ORD. Many hotels near O'Hare offer shuttle service which is convenient for early flights to Toronto Pearson International Airport (YYZ).
In May, Chicago O'Hare International Airport (ORD) can experience occasional spring thunderstorms that may cause short-notice delays or air traffic flow restrictions. Construction projects affecting certain terminals occasionally continue into May; check the airport’s official advisories and your airline’s notifications for real-time updates. Arrive at least 2–3 hours before international departures to Toronto Pearson International Airport (YYZ).
From Chicago O'Hare International Airport (ORD), travelers often connect from or to nearby major cities such as Milwaukee, Indianapolis, Detroit, Madison, and even Cleveland when planning multi-city trips to Toronto Pearson International Airport (YYZ). These cities are commonly served by regional and legacy carriers offering coordinated itineraries in May. Use multi-city search to find the best routing and prices.
Arriving at Toronto Pearson International Airport (YYZ) in May means pleasant spring weather and active tourism season. For travelers coming from Chicago O'Hare International Airport (ORD), expect streamlined customs processing if paperwork is in order and ArriveCAN is used where applicable. May is ideal for exploring nearby destinations—downtown Toronto, the Distillery District, Mississauga waterfront, Brampton parks, and a short trip to Niagara Falls—so plan ground transport in advance. Take advantage of the UP Express or prebook ride services to save time and money. Keep an eye on seasonal events (festivals and patio openings) and check YYZ flight status and baggage claim updates for a smooth arrival.
Arriving at Toronto Pearson International Airport (YYZ) from Chicago O'Hare International Airport (ORD) requires going through Canada Border Services Agency (CBSA) processing. In May, lines can vary; use the ArriveCAN app and have your passport and any supporting travel documentation ready to speed processing. Many international arrivals can use automated kiosks, but be prepared for manual inspection if requested.
From Toronto Pearson International Airport (YYZ), you can take the UP Express train to Union Station in downtown Toronto, regional GO Transit buses, local Mississauga and Brampton transit services, taxis, and rideshares. In May, UP Express runs frequent services and road traffic is generally milder than summer; allow 30–60 minutes to reach downtown depending on your transport choice. For Hamilton or Niagara Falls, consider regional GO or private shuttle services.
May brings a variety of events that can affect ORD–YYZ travel: Chicago often hosts international conferences, spring music festivals, and baseball games which raise outbound demand from Chicago O'Hare International Airport (ORD), while Toronto stages cultural festivals, theater premieres, and outdoor markets that can increase inbound demand at Toronto Pearson International Airport (YYZ). Examples include regional business conferences, food and film festivals in Toronto, and college graduations in both cities. Check event calendars before booking May travel and search 'ORD to YYZ May events' to align travel dates with availability and pricing. Book early when major festivals are scheduled to avoid inflated fares.
For May travel, the best time to fly from Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ) is midweek (Tuesday–Thursday) and during early-morning windows (departures before 8:00 AM). These slots often have lower fares and fewer delays compared with peak weekend travel. If you’re traveling for business, midweek late-morning flights balance convenience and reliability. Use fare comparison tools with the keyword 'ORD to YYZ May best time to fly' to find optimal options. Book early to secure preferred times, especially during May events in either city.
For the ORD→YYZ route in May, nonstop flights offer the clearest advantage in saving time and lowering the risk of missed connections or weather-related cascading delays. However, connecting itineraries may be cheaper if you can accept longer travel time and potential layovers. May is a good month to target nonstop 'ORD to YYZ' flights for convenience—especially for short business trips—while budget travelers should compare one-stop options during midweek. If choosing a connection, allow extra layover time to accommodate spring weather variability.
Major carriers operating between Chicago O'Hare International Airport (ORD) and Toronto Pearson International Airport (YYZ) in May typically include Air Canada, United Airlines, Delta, and American Airlines. Air Canada often offers multiple daily nonstops and seamless connections to Canadian cities; United and American provide competitive pricing with frequent flyer benefits for domestic U.S. travelers; Delta operates convenient daytime frequencies. Compare ticket totals including baggage fees and seat selection, and use primary search phrases like 'ORD to YYZ flights May' to surface the best deals. Choose nonstop flights for speed and reliability, and compare loyalty program benefits if you travel frequently between Chicago and Toronto.
Packing for May travel between Chicago O'Hare International Airport (ORD) and Toronto Pearson International Airport (YYZ) should prioritize light layers and a compact umbrella—spring can bring warm days and sudden showers. Allow at least 2–3 hours for international departures from ORD and factor in CBSA processing on arrival at YYZ. Choose flexible fares if your travel involves event timing, and sign up for airline notifications to stay updated on gate changes or weather delays. Consider travel insurance for weather-sensitive itineraries and use keywords like 'May ORD YYZ travel tips' when searching for the latest advisories.
Typical nonstop flights between Chicago O'Hare International Airport (ORD) and Toronto Pearson International Airport (YYZ) take approximately 1 hour 45 minutes to 2 hours airborne. In May, carriers usually schedule multiple daily frequencies—early morning, mid-day, and evening—to serve both business travelers and weekend leisure traffic. To plan your trip, check real-time schedules on airline sites and monitor for any temporary May schedule adjustments. For tighter connections, prefer early flights from ORD to buffer potential weather or delay-related disruptions.
To secure cheap flights from Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ) in May, use a multi-pronged strategy: set fare alerts and track price drops, search flexible dates (±3 days) with primary keywords like 'cheap flights Chicago to Toronto May' and 'ORD to YYZ deals', and compare nonstop versus one-stop itineraries. Midweek departures, early-morning flights, and last-minute seat releases on less-busy days often yield savings. Also check alternative nearby airports (Chicago Midway, Toronto Hamilton) and bundled hotel+flight packages. Consider basic economy fares for short-haul savings but confirm baggage rules. Call-to-action: Sign up for fare alerts now and search 'ORD YYZ May cheap flights' to compare carriers and uncover limited-time sales.
As of May, typical health and safety guidance at Toronto Pearson International Airport (YYZ) includes recommendations to follow local public health rules, which may vary with changing conditions. Always check official government and airport advisories for the latest updates prior to travel. For May travel, plan for routine screening and follow airline-specific rules for masks or documentation if applicable.
To save on ground transportation after landing at Toronto Pearson International Airport (YYZ) in May, use the UP Express (discounts for advance purchase), GO Transit regional buses, or shared airport shuttles to Mississauga and Brampton. Pre-book rideshares or compare taxi flat rates to suburban destinations; consider transit day passes if you plan to explore Toronto and nearby cities. Booking transfers in advance and using contactless payments often reduces wait times and fares.
Toronto Pearson International Airport (YYZ) offers easy access to nearby destinations such as downtown Toronto, Mississauga, Brampton, Hamilton, and Niagara Falls, plus connections to Ottawa and Montreal via regional flights. In May, favorable weather makes day trips to Niagara Falls or exploring the Toronto waterfront simple and convenient using train or shuttle services. Check local transit schedules and seasonal attractions before planning.
