Best Flights starting from $204
from$204economy
Washington, D.C. (Any)
Wed, Aug 26
Roundtrip
Chicago (ORD)
Sat, Sep 5
from$204economy
Washington, D.C. (Any)
Sat, Aug 29
Roundtrip
Chicago (ORD)
Tue, Sep 8
from$210economy
Washington, D.C. (Any)
Sun, Aug 30
Roundtrip
Chicago (ORD)
Wed, Sep 9
from$224economy
Washington, D.C. (Any)
Thu, Aug 27
Roundtrip
Chicago (ORD)
Sun, Sep 6
from$260economy
Washington, D.C. (Any)
Mon, Aug 31
Roundtrip
Chicago (ORD)
Thu, Sep 10
from$266economy
Washington, D.C. (Any)
Fri, Aug 28
Roundtrip
Chicago (ORD)
Mon, Sep 7
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Other Destinations
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Flights from Other Cities
Miami (Any) to Chicago (ORD) in August from $56
From $56
Dallas (DFW) to Chicago (ORD) in August from $85
From $85
Dallas (Any) to Chicago (ORD) in August from $85
From $85
Atlanta (ATL) to Chicago (ORD) in August from $92
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Denver (DEN) to Chicago (ORD) in August from $94
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Newark (EWR) to Chicago (ORD) in August from $99
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✈️ Flight Guide: Washington, D.C. (Any) → Chicago (ORD)
Complete travel information for your August journey
August travel from Washington (All Airports) (WASA) to Chicago O'Hare (ORD) typically involves summer heat and heightened passenger volumes. Expect average daytime temperatures in the Washington region of 75–90°F and the possibility of afternoon thunderstorms, so pack light, breathable clothing and allow extra time for transit to airports. Book 3–6 weeks in advance for the best August deals, prioritize midweek departures, and consider early-morning flights to avoid traffic and maximize your day in Chicago. For last-minute travelers, check low-cost carriers and set fare alerts; CTA and Metra connections from ORD make it easy to reach downtown Chicago, Naperville and Evanston after arrival.
Departing from Washington, D.C. (Any) FAQs
In August, round-trip fares from Washington (All Airports) (WASA) to Chicago O'Hare (ORD) typically range from budget-friendly $120–$300 depending on booking lead time and carrier. Booking 3–6 weeks in advance and flying midweek often yields the lowest airfare; use fare alerts and flexible-date search to find deals.
Yes — nonstop flights operate regularly between Washington area airports (DCA, IAD, BWI) and Chicago O'Hare (ORD) throughout August. Major carriers like United, American, Southwest and Delta often schedule direct flights; check specific airport (DCA/IAD/BWI) timetables for exact departure times.
Tuesdays and Wednesdays are generally the cheapest days to fly in August, while weekends and holiday-adjacent dates are pricier. Early-morning and late-night departures also tend to have lower fares and fewer crowds.
For domestic August departures to ORD, arrive 90 minutes before departure for Reagan National (DCA) and at least 2 hours for Dulles (IAD) and Baltimore-Washington (BWI) to allow time for security and summer crowds. Allow extra time for parking, security lines, and traffic — August can bring higher passenger volumes due to summer travel.
Washington (All Airports) (WASA) serves travelers from nearby major cities like Baltimore, Arlington, Alexandria, Annapolis and Richmond when heading to Chicago O'Hare (ORD). Ground transport options like Amtrak, regional buses, and shuttle services make these cities convenient for departures from DCA, IAD or BWI.
Airlines often run August promotions, especially early in the month as summer travel winds down; look for student and military discounts and credit card offers for additional savings. Sign up for airline newsletters, enable fare alerts, and compare low-cost carriers for the best August deals.
Arriving at Chicago O'Hare International Airport (ORD) in August from Washington (All Airports) (WASA) usually means warm weather and lively city activity. For the fastest route downtown, take the CTA Blue Line; if you're heading to Naperville or Evanston, consider Metra or pre-booked shuttle services. Expect possible afternoon thunderstorms that can delay ground transport; always check live flight and baggage status via your airline app. If your trip coincides with the Chicago Air and Water Show in mid-late August, reserve lodging and onward transportation well in advance to avoid surge pricing.
Arriving at Chicago (ORD) FAQs
Direct flights from Washington (All Airports) (WASA) to Chicago O'Hare (ORD) typically take about 1 hour 45 minutes to 2 hours, depending on wind and routing. Allow additional time for taxiing, potential delays, and immigration/baggage claim if connecting internationally.
From ORD you can take the CTA Blue Line train, which runs 24/7 to downtown Chicago in about 45 minutes, taxis, rideshares, and airport shuttles. During August, allow extra travel time for road traffic at peak hours and for events like the Chicago Air and Water Show if scheduled near the lakefront.
August in Chicago is warm and humid with average highs around 80–85°F and frequent afternoon thunderstorms possible. Pack lightweight clothing and a compact umbrella; be prepared for sudden weather changes that can affect ground transport times.
From ORD you can easily access downtown Chicago, Evanston (north), Naperville (west), Schaumburg and the greater Chicagoland area; Milwaukee is also reachable by car or regional bus. Metra and Amtrak services plus interstate highways connect ORD to a broad set of nearby destinations.
In August, aim for flights that arrive outside peak commute windows to avoid ground-transport congestion, and check real-time baggage updates in airline apps because summer operations can increase wait times. If attending summer festivals like the Chicago Air and Water Show, book onward transit or hotel transfers in advance.
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August Events & Festivals Impacting WASA → ORD Travel
Major Chicago events in August, such as the Chicago Air and Water Show (typically mid-late August), can increase demand for ORD flights and local lodging. Washington-area summer events — outdoor concerts, cultural festivals, and increased tourism around the National Mall — also affect airport traffic early in the month. If your trip coincides with major festivals, book flights and hotels well in advance, choose off-peak travel days, and allow extra transit time between terminals and ground transport to avoid congestion. Monitor event calendars for updated dates that may shift annual schedules.
Best Time to Fly From Washington (All Airports) (WASA) to Chicago O'Hare (ORD) in August
For August travel, the best time to fly from Washington (All Airports) (WASA) to Chicago O'Hare (ORD) is midweek (Tuesday–Wednesday) and in the early morning to avoid summer congestion and higher fares. Late August can see slightly reduced demand after peak-summer vacations, often producing better deals than early August; monitor fare trends and set alerts. Avoid Friday and Sunday evenings to minimize delays and elevated prices, and consider flying very early to maximize day-time activities in Chicago while saving on airport transit time.
Nonstop vs Connecting Flights — WASA to ORD in August
Nonstop flights between WASA and ORD save time — typically cutting travel time to under two hours — and reduce the risk of missed connections during busy August travel. Connecting itineraries can offer significant savings, especially on flexible dates or when booking late; common layover hubs include Charlotte (CLT), Atlanta (ATL), Philadelphia (PHL) and Dallas-Fort Worth (DFW) depending on the carrier and specific WASA departure airport. If you prioritize speed and convenience, choose nonstop. If budget is paramount and you can tolerate longer travel time, consider a one-stop itinerary but leave at least a 90-minute minimum connection buffer in summer months.
Airline Comparison for WASA → ORD — August Choices & Recommendations
United and American typically offer the most nonstop frequency from Washington area airports to Chicago O'Hare (ORD) and provide robust business and premium economy options, while Southwest often offers competitive low fares and free checked bags from BWI. Delta may route many passengers via its hubs (ATL) depending on the WASA departure airport. Compare base fare, change fees, baggage allowances and schedule convenience when booking for August; use airline websites and booking tools to view bundled fare discounts or loyalty program benefits that can make a higher base fare more valuable.
Seasonal Travel Tips — August Travel From Washington (All Airports) (WASA) to Chicago O'Hare (ORD)
Pack breathable layers, sun protection and a compact umbrella for August travel between Washington (All Airports) (WASA) and Chicago O'Hare (ORD) due to warm, humid conditions and possible afternoon storms. Check airline apps for live flight status the morning of departure and enroll in TSA PreCheck if you travel frequently to speed security screening at DCA/IAD/BWI. Arrive earlier than usual if you have checked baggage or are traveling during a festival weekend; consider travel insurance for flexible rebooking in the event of weather-related disruptions. Finally, use rewards programs and bundled hotel/flight offers to lower overall trip costs.
Flight Time & Schedules — Washington (All Airports) (WASA) to Chicago O'Hare (ORD)
Direct flights from Washington (All Airports) (WASA) to Chicago O'Hare (ORD) usually take approximately 1 hour 45 minutes to 2 hours. Morning and late-evening flights are common across carriers, with peak midday frequency during August due to summer demand. If traveling from Dulles (IAD), expect slightly different departure windows than Reagan National (DCA) due to carrier concentration; Baltimore-Washington (BWI) often provides budget carrier options and flexible times. Check airline schedules for real-time frequency, especially around major August events that can cause schedule upticks or adjustments.
Cheap Flights From Washington (All Airports) (WASA) to Chicago O'Hare (ORD) in August
To find cheap flights from Washington (All Airports) (WASA) to Chicago O'Hare (ORD) in August, start by searching flexible dates +/- 3 days and comparing departures from Reagan National (DCA), Dulles (IAD) and Baltimore-Washington (BWI). Midweek departures (Tuesday–Thursday) and early-morning flights usually have lower fares; aim to book 3–6 weeks ahead for optimal savings. Use fare alerts, clear cookies or use incognito browsing for preliminary searches, and check low-cost carriers like Southwest and Spirit alongside legacy carriers for competitive pricing. Consider one-stop itineraries via major hubs if nonstop prices are high, but weigh potential layover time against savings. CTA, Metra and airport shuttle discounts can further reduce trip costs once you land at ORD — bundle transport and flight deals when possible.