Submit feedbackSubmit feedbackComplete travel information for your November journey
November at O'Hare International Airport (ORD) signals the start of winter travel planning. For ORD to Logan International Airport (BOS) routes, early November often offers the best fares before Thanksgiving surge pricing sets in. Travelers should monitor airline sales—United and American sometimes launch mid-November discounts—and set price alerts for last-minute drops. Expect 1–3 daily nonstop frequencies on weekdays, with peak departures early morning and late afternoon for business travelers. Packing for Boston in November means layers, a warm coat, and an umbrella for coastal showers; keep an eye on nor'easter forecasts that can impact both departure and arrival airports. CTA Blue Line is a dependable option from ORD to downtown Chicago, and ride-hailing availability increases during holiday periods. Book direct flights where possible to reduce disruption risk, and use flexible or refundable fares if traveling over Thanksgiving. CTA and regional connections provide access to nearby major cities such as Milwaukee, Indianapolis, and Detroit—use those as alternative travel hubs if ORD connectivity is affected. Ready to book cheap ORD to BOS flights for November? Compare nonstop options and set fare alerts now to secure your preferred itinerary.
In November, the best strategies for cheap flights from O'Hare International Airport (ORD) to Logan International Airport (BOS) include booking 3–8 weeks in advance, being flexible with midweek travel (Tuesdays and Wednesdays), and setting fare alerts for airlines that serve the route. Watch for early-November off-peak windows outside Thanksgiving week when prices typically drop, and compare carriers like United, American, Delta, and JetBlue for sales and last-minute deals. Use price-tracking tools and sign up for airline newsletters for targeted flight deals.
A nonstop flight between O'Hare International Airport (ORD) and Logan International Airport (BOS) typically takes about 2 hours 10 minutes to 2 hours 30 minutes, depending on winds and routing. Frequent schedule variations can shift block time slightly; expect shorter west-to-east flights when tailwinds are favorable. Check real-time schedules on airline sites for precise departure and arrival times.
Yes—multiple carriers operate nonstop flights between O'Hare International Airport (ORD) and Logan International Airport (BOS) in November, including United, American, Delta, and JetBlue on select days. Flight frequency may be reduced outside peak travel periods, so check schedules early and book direct flights if you want to avoid connections during holiday crowds. Nonstop options are ideal for short business trips or weekend getaways.
Thanksgiving (fourth Thursday in November) is one of the busiest travel weeks of the year; fares between O'Hare International Airport (ORD) and Logan International Airport (BOS) often spike and airports get crowded. If traveling during Thanksgiving week, book early, arrive at least 2–3 hours before departure for domestic flights, and expect heavier security lines and possible delays. Consider flying midweek or early morning/late evening to avoid peak surge travel times.
November brings a transition to colder weather: Chicago can see early snow and Boston can experience nor'easters, both of which can cause delays. Expect occasional de-icing procedures, gate hold times, and air-traffic management impacts; monitor NOAA forecasts and airline advisories the day before travel. Purchase flexible tickets or travel protection if you have strict connections during this variable weather month.
From O'Hare International Airport (ORD), travelers can use the CTA Blue Line to downtown Chicago, ride-share services, taxi cabs, airport shuttles, or rental cars to reach nearby major destinations like Milwaukee, Indianapolis, and Detroit. In November, allow extra time for winter road conditions, and consider pre-booking rides or choosing the Blue Line for reliable transit during peak holiday travel. Check hotel shuttles and off-site parking availability when planning door-to-door travel.
Arriving at Logan International Airport (BOS) in November means cooler temperatures and a bustling pre-holiday atmosphere. For fast access to Boston neighborhoods, use the MBTA Blue Line and Silver Line for cost-effective transport; rideshares remain convenient for door-to-door trips but anticipate longer wait times during weekend events. November is a shoulder season with good hotel deals outside Thanksgiving weekend and major sporting events; consider visiting Cape Cod, Providence, or Salem for short fall getaways. If your arrival coincides with college football or NFL home games, pre-book transfers and give yourself extra time for baggage claim and ground transport. Keep warm clothing handy in your carry-on and check Massport alerts for gate or terminal advisories. Ready to explore Boston this November? Compare arrival transport options and plan activities like off-season coastal walks or city food tours to make the most of your trip.
From Logan International Airport (BOS), the MBTA Blue Line and Silver Line buses provide direct, affordable links to downtown Boston year-round; rideshares and taxis are plentiful but may be subject to surge pricing during holiday events. In November, allow extra transfer time for colder weather and holiday crowds—public transit often remains the fastest option to reach neighborhoods such as Back Bay, Downtown Crossing, and Cambridge. For travelers heading to nearby destinations like Providence, Cape Cod, or New Haven, consider car rentals or scheduled shuttle services.
Pack warm layers, a water-resistant coat, comfortable walking shoes, and a travel umbrella for Boston in November, when temperatures typically range from the low 30s to mid 50s°F (0–12°C). Include a hat and gloves for chilly evenings and an extra outfit if traveling during Thanksgiving when weather can be unpredictable. Also pack portable chargers, a copy of your itinerary, and any medications since pharmacies may have reduced hours during holiday weekends.
Yes—several airlines operate direct flights from O'Hare International Airport (ORD) to Logan International Airport (BOS) during November, with nonstop options available throughout the month. Flight frequency can be higher on weekdays and lower on holiday travel dates; check airline schedules for specific dates. Nonstop arrivals are the quickest way to reach Boston and minimize connection risk during November weather variability.
November brings college football, NFL games (nearby in Foxborough), and early holiday events that can spike arrivals at Logan International Airport (BOS). Expect increased taxi and rideshare wait times and busier baggage claim areas during game weekends and long holiday weekends. Book transportation ahead of time, consider off-peak arrival times, and monitor event schedules for Fenway Park and local universities to avoid congested periods.
From Logan International Airport (BOS), travelers can quickly reach nearby destinations ideal for November: Cape Cod for late-fall coastal views, Salem for historical attractions and off-season charm, Providence and Newport, Rhode Island for food and architecture, and the White Mountains or Green Mountains for early winter foliage and skiing. Plan with flexible dates to take advantage of lower off-peak hotel rates and weekend flight deals.
Logan International Airport (BOS) offers year-round amenities including TSA PreCheck lanes, multiple lounges, rental car centers, and seasonal pop-ups for holiday shopping in November. Expect additional seasonal staffing at customer service desks and information booths during busy holiday travel periods. Check airport and airline apps for real-time gate changes and use TSA PreCheck to speed security during Thanksgiving travel spikes.
November features travel-impacting events on both ends of the ORD–BOS route. Thanksgiving week drives the largest passenger volumes—book early and allow extra airport time. Boston-area college football games and New England Patriots home games in Foxborough can cause spikes in arrivals to Logan International Airport (BOS), while Chicago's Magnificent Mile Lights Festival (early November) and holiday market openings increase inbound traffic to O'Hare International Airport (ORD). Seasonal holiday shopping (Black Friday) and early winter festivals can also affect hotel availability and ground transportation. Check event calendars before booking and plan transfers in advance for game or festival weekends.
For November travel on the ORD to BOS route, the best time to fly for lower fares and fewer crowds is early November (the first two weeks) and midweek (Tuesday–Thursday). Avoid the Wednesday before Thanksgiving and the holiday weekend itself when prices and airport congestion spike. Early-morning flights reduce the likelihood of cascading weather delays, while late-night options can be cheaper but less convenient. If your dates are flexible, search for flights departing on Tuesdays or Wednesdays and returning on Tuesdays or Wednesdays to capture lower seasonal fares.
Nonstop flights between O'Hare International Airport (ORD) and Logan International Airport (BOS) save time—typically about 2 hours 15 minutes airborne—and reduce the risk of missed connections or baggage delays, making them preferable for short November trips or tight schedules. Connecting flights may offer lower fares but add travel time and exposure to weather disruptions; common connection hubs include Newark, Philadelphia, or regional airports depending on the carrier. During November, when early-season snow or nor'easters can affect either airport, nonstop itineraries minimize the number of legs vulnerable to delays. Choose nonstop flights for reliability; choose connecting flights when cost savings outweigh potential time costs.
United typically offers several daily nonstop departures from O'Hare International Airport (ORD) to Logan International Airport (BOS), leveraging ORD as a hub with solid reliability and MileagePlus benefits. American Airlines provides competitive schedules and connection options from its network; check AAdvantage and seasonal sales. Delta often competes on timing and onboard amenities, with SkyMiles perks and reliable operations. JetBlue focuses on customer comfort, offering more legroom in economy and often competitive fares on the Boston market. For November, compare base fares, checked baggage policies, and change fee flexibility—United and JetBlue may have more nonstop frequency on certain days, while American and Delta sometimes undercut prices with targeted sales. Book based on priorities: nonstop frequency and loyalty benefits for business travelers, and seat comfort and low fare for leisure travelers.
Prepare for November travel between O'Hare International Airport (ORD) and Logan International Airport (BOS) by packing layers, waterproof outerwear, and slip-resistant shoes for icy sidewalks. For Thanksgiving travel, arrive 2–3 hours before departure and enroll in TSA PreCheck to speed screening. Keep electronic chargers and essential medications in carry-on luggage, and download airline apps for real-time flight updates and rebooking options. Consider travel insurance if you have tight connections or events that cannot be missed, and monitor NOAA forecasts 48–72 hours before departure to anticipate weather-related delays. For family travel, book seats together early and pack snacks and entertainment for shorter nonstop flights to keep kids comfortable. CTA: Check weather and airline alerts the night before travel and sign up for mobile updates to avoid surprises.
Nonstop flights from O'Hare International Airport (ORD) to Logan International Airport (BOS) generally have block times between 2 hours 10 minutes and 2 hours 30 minutes. Peak departures in November are usually early morning (6:00–9:00) and late afternoon (15:00–19:00) to serve business travelers. Frequency varies by carrier and day—expect multiple nonstop options on weekdays and fewer late-night services. If you need the earliest arrival in Boston, target red-eye and early-morning departures; if you prioritize lower fares, midweek midday flights often offer savings. Check real-time airline schedules before booking and set notifications for gate or time changes the day of travel.
To secure cheap flights from O'Hare International Airport (ORD) to Logan International Airport (BOS) in November, aim to book 3–8 weeks ahead for non-peak dates and earlier for Thanksgiving week. Use flexible-date searches and set fare alerts on meta-search engines (Google Flights, Kayak, Skyscanner) for price drops. Midweek departures (Tuesday–Thursday) frequently offer the best fares, while Friday–Sunday and the Wednesday before Thanksgiving are the most expensive. Compare nonstop carriers (United, American, Delta, JetBlue) with one-stop options if savings justify the longer travel time. Check airline flash sales around Veterans Day and Black Friday for promotional discounts, and consider nearby alternative airports if flexibility is possible. CTA: Sign up for fare alerts and compare nonstop ORD to BOS flights today to lock in lower November fares.