Other Options for This Route
Other Destinations
Boston (BOS) to Oranjestad (AUA) in August from $317
From $317
Boston (BOS) to Santo Domingo (SDQ) in August from $341
From $341
Boston (BOS) to Dublin (DUB) in August from $440
From $440
Boston (BOS) to Frankfurt (Any) in August from $440
From $440
Boston (BOS) to Barcelona (BCN) in August from $453
From $453
Boston (BOS) to Mumbai (BOM) in August from $467
From $467
Flights from Other Cities
Pittsburgh (PIT) to Chicago (ORD) in August from $233
From $233
San Francisco (SFO) to Chicago (ORD) in August from $237
From $237
San Francisco (SFO) to Chicago (ORD) in August from $442
From $442
Tampa (TPA) to Chicago (ORD) in September from $139
From $139
Dallas (DFW) to Chicago (ORD) in September from $154
From $154
Miami (MIA) to Chicago (ORD) in September from $160
From $160
✈️ Flight Guide: Boston (BOS) → Chicago (ORD)
Complete travel information for your August journey
August is a high-demand month for departures from Logan International Airport (BOS) to O'Hare International Airport (ORD). Expect multiple daily nonstop options, heavier airport traffic, and slightly higher average fares compared with off-peak months. For savings, target midweek departures (Tuesdays/Wednesdays) and early morning or late-evening flights. Logan serves Boston, Cambridge, Providence, Cape Cod and Portland-area travelers connecting to Chicago; consider MBTA + Logan Shuttle or rideshare for reliable access. Monitor fare alerts, use flexible date searches, and check airline change/cancellation policies—especially important for summer travel. CTA: Check live fares and book your BOS to ORD August flight now to lock in savings.
Departing from Boston (BOS) FAQs
August is peak summer travel between Logan International Airport (BOS) and O'Hare International Airport (ORD). Expect higher passenger volumes, possible heat-related delays, and fuller flights; booking 3–6 weeks in advance can secure better fares. Check airline policies for baggage and flexible rebooking, and arrive at the airport earlier than usual during August weekends and holiday periods.
For domestic flights from Logan International Airport (BOS) to O'Hare International Airport (ORD) in August, arrive at least 2 hours before departure to allow time for check-in, TSA security, and summer crowds. If you have checked baggage, traveling with family, or require special assistance, add an extra 30–45 minutes. Use TSA PreCheck or CLEAR if available to speed up security screening during busy August travel days.
The cheapest days to fly from Logan International Airport (BOS) to O'Hare International Airport (ORD) in August are typically midweek — Tuesday and Wednesday — and late evening flights. Booking 3–6 weeks out, monitoring fare alerts, or using flexible date searches often yields the best savings. Consider red-eye departures or flights with a single connection to reduce costs further.
Yes, there are multiple nonstop flights from Logan International Airport (BOS) to O'Hare International Airport (ORD) throughout August operated by major carriers. Flight frequency increases on peak summer travel days, so you can usually find several nonstop options daily. Check carriers like United Airlines, American Airlines, and JetBlue for nonstop schedules and compare times and fares.
The best ways to reach Logan International Airport (BOS) before an August flight are the MBTA Blue Line + free Logan Shuttle, rideshare services, or airport shuttle and private car services. Allow extra transit time for summer traffic, special events in downtown Boston, and construction-related detours. Consider off-peak drop-offs or park-and-fly options if you’re leaving a car at the airport.
Baggage and carry-on policies vary by airline but are especially important on busy August flights from Logan International Airport (BOS) to O'Hare International Airport (ORD) when overhead space fills quickly. Check your carrier’s size, weight limits, and fees before packing and consider carry-on-only travel to avoid checked baggage lines. Purchased priority boarding or premium fares often guarantee overhead bin space.
Arriving at O'Hare International Airport (ORD) in August requires planning for summer weather and busy arrival halls. Expect thunderstorms sometimes to impact schedules; give yourself extra time for baggage and ground transport. Use the CTA Blue Line for a fast connection to downtown Chicago, or pre-book express shuttles and rideshares for suburbs like Evanston, Naperville, and Schaumburg. If connecting onward, allow 90–120 minutes for domestic transfers during August peak days. CTA, Metra, and airport shuttle options provide access to surrounding regional destinations including Milwaukee and Indianapolis for business or leisure travelers. CTA schedules and airline apps are the best sources for real-time updates—check them before you land. CTA: Review arrivals and reserve ground transport ahead for a stress-free August arrival at ORD.
Arriving at Chicago (ORD) FAQs
Arrivals at O'Hare International Airport (ORD) from Logan International Airport (BOS) in August are typically smooth but can be affected by Midwest summer storms that occasionally delay incoming flights. Allow additional time for ground transportation, as traffic into downtown Chicago and suburbs like Evanston and Naperville can be heavy. Use airport monitors and airline apps for gate and baggage updates and plan onward travel to destinations such as Chicago, Evanston, Naperville, Schaumburg, and Milwaukee accordingly.
From O'Hare International Airport (ORD), you can use the CTA Blue Line to downtown Chicago, airport shuttles, rideshare services, taxi stands, or rental cars. During August festivals and peak travel times, rideshare wait times may increase and shuttle services may run at capacity, so consider pre-booking or using the CTA for a reliable rail connection to the Loop and nearby neighborhoods. For suburban connections to Naperville, Schaumburg, or Evanston, check Metra or shuttle services ahead of arrival.
O'Hare International Airport (ORD) is a major connecting hub, so if you have a connection after arriving from Logan International Airport (BOS) in August, leave at least 90–120 minutes for domestic-to-domestic transfers during peak times. Follow signage to connections security checkpoints that can be busy in summer, and use airline transfer desks or apps for gate changes. If you booked independent tickets, give yourself extra buffer for baggage re-check and potential weather delays.
Baggage wait times at O'Hare International Airport (ORD) in August can range from 15 minutes to over 45 minutes depending on arrival gate, flight volume, and staffing. For faster retrieval, check if your airline tags bags for expedited handling or use carry-on only for short trips. If your baggage is delayed, report it immediately to the airline baggage service office at ORD for faster resolution.
Flights from Logan International Airport (BOS) to O'Hare International Airport (ORD) typically arrive at Terminals 1, 2 or 3 depending on the carrier and schedule. United often uses Terminal 1 and Terminal 1 gates, American commonly uses Terminal 3, while other carriers may use Terminal 5 on occasion for international connections. Check your airline confirmation and ORD arrival monitors for the exact terminal and gate before travel.
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August Events & Festivals Affecting BOS → ORD Travel — Boston & Chicago Highlights
August events in the Boston and Chicago regions can raise demand and fares on the BOS→ORD route. In Chicago, the Chicago Air & Water Show (typically mid/late August) and large summer concerts or festivals (including late-summer music events) attract regional and national visitors, increasing arrivals into O'Hare International Airport (ORD). Boston-area summer tourism brings travelers to Logan International Airport (BOS) for nearby Cape Cod and coastal destinations; local cultural events and university orientation periods in August also add to demand. If traveling for or around major events, book flights and ground transport early, and consider arriving a day early or departing a day late to avoid peak congestion. CTA: Check event calendars for Boston and Chicago and book your August BOS→ORD travel early to secure the best options.
Best Time to Fly BOS to ORD in August — Save Money & Avoid Delays
The best time to fly from Logan International Airport (BOS) to O'Hare International Airport (ORD) in August is midweek (Tuesday–Wednesday) and during early morning departures (before 8:30 AM) or late evening red-eyes. These windows often provide lower fares and fewer crowds at TSA checkpoints and boarding areas. Avoid Fridays, Sundays, and holiday-adjacent dates when fares and passenger volumes spike. If possible, be flexible by a few days to capture substantial savings; set fare alerts and use flexible-date calendars when booking. CTA: Search flexible dates for August and lock in a midweek morning flight for the best experience.
Direct vs Connecting Flights BOS to ORD in August — Which Should You Choose?
Nonstop flights from Logan International Airport (BOS) to O'Hare International Airport (ORD) are the fastest and most convenient option in August, with typical durations near 2 hours 15 minutes. Connecting flights can be cheaper, especially if you book early or accept longer total travel time, but they carry higher risk of missed connections when Midwest weather impacts schedules. For business travelers or those on tight schedules, a nonstop is usually worth the premium; budget-conscious travelers may prefer a single-connection itinerary to save on fares. CTA: Compare nonstop and 1-stop options now to weigh time versus cost for your August trip.
Airline Comparison for BOS to ORD — United, American, JetBlue & Delta in August
United typically offers the most frequent nonstop options between Logan International Airport (BOS) and O'Hare International Airport (ORD), often with multiple services per day and strong connections at ORD. American Airlines provides competitive schedules and loyalty benefits for AAdvantage members and often has similar nonstop frequencies. JetBlue sometimes offers competitively priced flights with more legroom in economy, while Delta may offer one-stop options via its hubs. For August travel, compare ticket prices, baggage fees, and change policies; consider loyalty status benefits (priority boarding, baggage allowances) that can make a higher base fare more valuable. CTA: Compare fares and perks across carriers to choose the best August itinerary for your needs.
August Seasonal Travel Tips for BOS → ORD — Beat the Heat & Avoid Delays
August weather can affect the Logan International Airport (BOS) to O'Hare International Airport (ORD) corridor—expect hot temperatures and the possibility of afternoon thunderstorms in the Midwest. Pack a refillable water bottle, lightweight clothing, and an extra layer for cool airplane cabins. Arrive early at BOS to account for summer crowds, and if your itinerary is tight, favor earlier departures to reduce risk from afternoon storm delays at ORD. Consider travel protections: refundable fares, flexible change options, or travel insurance for weather-prone August periods. CTA: Prepare for summer travel now—check weather forecasts and confirm flexible booking options before your August trip.
BOS to ORD Flight Time & Schedules in August — Nonstop and Connecting Options
Average nonstop flight time from Logan International Airport (BOS) to O'Hare International Airport (ORD) in August is approximately 2 hours 10 minutes to 2 hours 25 minutes depending on winds and routing. Multiple carriers operate daily nonstops—United and American commonly offer several flights a day, with JetBlue and Delta also offering service or connections. Peak departure windows are early morning (6:00–9:00) and late afternoon/early evening (16:00–20:00) to match business schedules; mid-afternoon slots may have fewer flights. Connecting itineraries via hubs may add 1–4 hours total travel time depending on layover length. CTA: Check carrier schedules and book a nonstop for the fastest travel; compare times to find the most convenient August option.
Cheap Flights BOS to ORD in August — Deals, Tips & Best Booking Windows
To find cheap flights from Logan International Airport (BOS) to O'Hare International Airport (ORD) in August, book roughly 3–6 weeks before departure and target midweek travel (Tuesdays/Wednesdays). Use flexible date searches and set fare alerts to capture temporary sales; consider red-eye or early-morning departures for lower prices. Comparing low-cost options and checking bundled fares (seat + baggage) often reveals better value than strictly low base fares. If you can accept a single connection, that may shave costs further, but weigh time vs savings. CTA: Sign up for fare alerts and compare nonstop vs connecting options now to grab the best August deals.