Best Flights starting from $204
from$204economy
Washington, D.C. (Any)
Wed, Sep 16
Roundtrip
Chicago (ORD)
Sun, Sep 20
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Other Destinations
Washington, D.C. (Any) to Orlando (MCO) in September from $40
From $40
Washington, D.C. (Any) to Fort Lauderdale (Any) in September from $64
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Washington, D.C. (Any) to Las Vegas (LAS) in September from $90
From $90
Washington, D.C. (Any) to Orlando (MCO) in September from $110
From $110
Washington, D.C. (Any) to Los Angeles (LAX) in September from $119
From $119
Washington, D.C. (Any) to Cartagena (CTG) in September from $121
From $121
Flights from Other Cities
Fort Lauderdale (Any) to Chicago (ORD) in September from $56
From $56
Dallas (DFW) to Chicago (ORD) in September from $57
From $57
Minneapolis (Any) to Chicago (ORD) in September from $59
From $59
Philadelphia (PHL) to Chicago (ORD) in September from $59
From $59
Dallas (DFW) to Chicago (ORD) in September from $68
From $68
Dallas (Any) to Chicago (ORD) in September from $68
From $68
✈️ Flight Guide: Washington, D.C. (Any) → Chicago (ORD)
Complete travel information for your September journey
September is a transitional travel month for departures from Washington (All Airports) (WASA) to Chicago O'Hare International Airport (ORD). After the summer peak and the Labor Day spike, fares often soften mid-month as business travel stabilizes. Travelers leaving from Ronald Reagan Washington National Airport (DCA), Washington Dulles International Airport (IAD), or Baltimore/Washington Thurgood Marshall Airport (BWI) should compare nonstop flights offered by major carriers like United, American, Southwest, and Delta. Expect morning and late-afternoon peaks; if you want lower fares and fewer crowds, target midweek flights in the second and third weeks of September. Nearby major cities commonly accessed from WASA departures include Baltimore, Annapolis, Alexandria, and Arlington — all within easy transit reach of the listed airports. CTA, Amtrak, and local shuttle links can reduce stress on travel days. Book early and use fare alerts to lock in the best WASA → ORD September deals, and consider refundable or flexible fare options given possible holiday-related schedule changes.
Departing from Washington, D.C. (Any) FAQs
Washington (All Airports) (WASA) refers to service from Ronald Reagan Washington National Airport (DCA), Washington Dulles International Airport (IAD), and Baltimore/Washington Thurgood Marshall Airport (BWI). In September, travelers should compare schedules and fares across these three airports because peak travel days around Labor Day can change availability and price. Check each airport's schedule to find the best connection or nonstop option to Chicago O'Hare International Airport (ORD).
Yes — nonstop service between the Washington area and Chicago O'Hare International Airport (ORD) is common in September, operated by carriers such as American Airlines, United Airlines, and Southwest Airlines depending on the departure airport. Nonstop frequency increases on weekdays and ahead of major business travel days, so book early if you need a specific nonstop time. Use filters on booking sites to prioritize nonstop WASA → ORD flights for the best travel time.
Labor Day weekend typically increases demand for flights out of Washington (All Airports) (WASA), raising fares and filling peak departure times the Friday before and Monday after the holiday. Expect higher airport traffic, longer security lines at Ronald Reagan Washington National Airport (DCA) and Washington Dulles International Airport (IAD), and potential rebooking changes. If you can travel during midweek in September, you'll usually find lower fares and fewer delays.
Baggage rules vary by carrier; major airlines on WASA → ORD routes (United, American, Southwest, Delta) often allow one carry-on and a personal item, but fees for checked bags depend on fare class. In September, pack layers for Chicago's variable weather and confirm your airline's checked bag policy before booking to avoid surprise fees at the gate. Enrolling in a carrier loyalty program or purchasing bundled fares can save on checked baggage costs.
For Ronald Reagan Washington National Airport (DCA), the Metro Yellow/Blue lines and Metrorail connections are convenient; for Washington Dulles International Airport (IAD), the Silver Line Express Bus and rideshares are common; for Baltimore/Washington Thurgood Marshall Airport (BWI), Amtrak, MARC trains, and the BWI Airport Shuttle are efficient. In September, allow extra buffer time for traffic near DCA and IAD, especially during morning and evening commutes, and consider public transit for reliable travel during peak days.
Yes — book midweek (Tuesdays–Wednesdays) for lower fares, set fare alerts, and compare flights across Ronald Reagan Washington National Airport (DCA), Washington Dulles International Airport (IAD), and Baltimore/Washington Thurgood Marshall Airport (BWI). September's shoulder-season mid-month often offers lower business travel demand after Labor Day, so consider flexible dates and alternate airports to find the best deals. Also check bundled fares or credit card offers for added savings.
September arrivals at Chicago O'Hare International Airport (ORD) benefit from cooler weather and generally reliable ground transportation. The CTA Blue Line is the fastest economical option to downtown Chicago, while taxis, rideshares, and airport shuttles connect to suburbs such as Evanston, Naperville, Aurora, and Schaumburg. Travelers should be mindful of weekends around Labor Day and large local events which can increase demand for rides and hotel rooms; booking shuttles or reserving airport parking in advance can reduce stress. For a smooth arrival, confirm your terminal, download your airline's app for baggage updates, and have a transit plan to save time after landing.
Arriving at Chicago (ORD) FAQs
Arrivals at Chicago O'Hare International Airport (ORD) in September typically encounter mild fall weather and moderate passenger volumes, especially after Labor Day. Expect efficient immigration and baggage processing for domestic flights, and plan transit time if heading to downtown Chicago via the CTA Blue Line or taxis/rideshares. Check terminal and gate details ahead of arrival to minimize transfer times, particularly if connecting to other Midwest destinations like Naperville or Evanston.
Peak congestion at Chicago O'Hare International Airport (ORD) typically occurs during weekday morning and evening business rush hours and the holiday weekends such as the Labor Day weekend in early September. Mid-morning to mid-afternoon can be quieter for arrivals, and late-night flights often see fewer crowds at baggage claim. Use airline apps for gate updates and real-time baggage tracking to speed up your arrival process.
The CTA Blue Line provides a direct and budget-friendly connection from Chicago O'Hare International Airport (ORD) to downtown Chicago (The Loop) with frequent service. For nearby suburbs such as Evanston, Naperville, Aurora, and Schaumburg, consider Metra commuter rail (from downtown), regional shuttle services, rental cars, or rideshares depending on your destination. In September, traffic is usually improving compared to summer, but always allow extra time during special events or weekend festivals.
September in Chicago is often mild with daytime highs in the mid-60s to low 70s°F (18–23°C) and cooler mornings/evenings, so pack light layers, a compact umbrella, and a light jacket. Early September can still feel summer-like, but late September typically brings crisp fall air—ideal for layered clothing. Check a 10-day forecast before travel to adjust for any unusual cold snaps or rain.
September often features Chicago-area festivals, college football weekends and Labor Day gatherings that can increase ground transportation demand and local hotel occupancy. While the exact festival calendar varies year to year, expect spikes around major sporting events and popular neighborhood street festivals; plan extra transit time and book hotels in advance if attending an event. Monitoring local event calendars can help you avoid arrival-day congestion at Chicago O'Hare International Airport (ORD).
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Events and Festivals in September Affecting WASA to ORD Travel
September brings a range of events that can impact WASA → ORD travel demand, including Labor Day holiday travel, college football weekends, neighborhood street festivals, food and beer festivals, and arts openings. While specific festival names and dates vary year to year, travelers should expect increased hotel and ground-transport demand during long weekends and big sporting events. If your trip coincides with a major Chicago event or Washington-area festival, book early, secure ground transportation ahead of time, and consider arriving a day earlier or later to avoid peak congestion. Nearby major cities or destinations commonly accessed by travelers include downtown Chicago, Naperville, Evanston, Aurora, Baltimore, Alexandria, and Annapolis.
Best Time to Fly WASA to ORD in September — When to Book and Depart
For September travel from Washington (All Airports) (WASA) to Chicago O'Hare International Airport (ORD), the sweet spot to book is often 3–6 weeks ahead of departure, with mid-September midweek travel offering the best balance of price and availability. Best days to fly: Tuesday and Wednesday for lowest fares; best departure times to avoid delays: early morning flights leave before peak air-traffic and weather buildup. Avoid flying the Friday before Labor Day and the Monday after the holiday if possible, as these are high-demand travel days with elevated fares and fuller airports.
Direct vs Connecting Flights from WASA to ORD in September — Pros and Cons
Direct flights from Washington (All Airports) (WASA) to Chicago O'Hare International Airport (ORD) save time and simplify travel logistics, typically taking about 2 hours door-to-door flight time. Connecting flights can be cheaper, especially when routed through hubs like Charlotte (CLT), Atlanta (ATL), or Philadelphia (PHL), but add risk of missed connections and longer travel times. In September, if price is the top factor, consider single-connection itineraries mid-month; if minimizing travel time and transfer stress is your priority, choose nonstop WASA → ORD flights. Balance cost versus convenience depending on your schedule and whether the trip is for business or leisure.
Airline Comparison for WASA to ORD in September — United, American, Southwest, Delta
Quick comparison for September travel on WASA → ORD routes: - United Airlines: Strong presence from Washington Dulles International Airport (IAD) with frequent nonstop service to Chicago O'Hare International Airport (ORD), solid loyalty program, and premium cabin options. - American Airlines: Reliable nonstop schedules from Ronald Reagan Washington National Airport (DCA) and competitive business traveler times; mainline service and partner connections. - Southwest Airlines: Often offers the best checked-bag policy (two free checked bags) from Baltimore/Washington Thurgood Marshall Airport (BWI) and frequent promotional fares; seats are open (Wanna Get Away) fares with flexible change policies depending on fare class. - Delta Air Lines: Competitive connections via Atlanta (ATL) and good customer service, though fewer direct WASA → ORD nonstops depending on the year. Choose based on priority: nonstop scheduling (United/American), baggage value (Southwest), or loyalty benefits (United/American/Delta). Check current September schedules as carriers adjust frequency seasonally.
Seasonal Travel Tips for WASA to ORD in September
Packing & Clothing: September weather in Chicago can vary—pack light layers, a compact waterproof jacket, and comfortable walking shoes for city exploration. Airport Timing: Allow extra time during the Labor Day period and peak commute hours; aim to arrive at Ronald Reagan Washington National Airport (DCA) 90 minutes before domestic departures, and 2 hours if parking or using busy shuttles at Washington Dulles International Airport (IAD) or Baltimore/Washington Thurgood Marshall Airport (BWI). Transit & Transfers: From Chicago O'Hare International Airport (ORD), the CTA Blue Line is usually the fastest and most predictable way into downtown, while rideshares and shuttles serve suburbs. Book rideshares outside terminal queuing zones where required and verify pickup locations in the app. Booking Tips: For September, prioritize midweek travel for lower fares, sign up for fare alerts, and consider refundable fares if your trip is near event-heavy dates. CTA, Amtrak, and regional transit schedules can change with seasonal adjustments, so confirm times before travel. CTA and airport websites provide up-to-date transit info — use them to plan efficient arrivals and departures.
Flight Time and Schedules for Washington (All Airports) (WASA) to Chicago O'Hare (ORD) in September
Typical nonstop flight time from Washington (All Airports) (WASA) to Chicago O'Hare International Airport (ORD) ranges from about 1 hour 50 minutes to 2 hours 15 minutes depending on routing and winds. Time zone difference: both Washington and Chicago are in the Eastern and Central Time Zones respectively, so expect to set your clocks back 1 hour on arrival. In September, carriers often deploy multiple daily nonstop flights between WASA airports and ORD, with higher frequency on weekdays for business travelers and slightly reduced schedules on Sundays. Check airline schedules (United, American, Southwest, Delta) for exact departure times and seasonal frequency changes, and use the airline app for real-time flight status on travel day.
Find Cheap Flights from Washington (All Airports) (WASA) to Chicago O'Hare (ORD) in September
Best tactics to find cheap September flights from Washington (All Airports) (WASA) to Chicago O'Hare International Airport (ORD): - Book 3–7 weeks ahead for the best September mid-month prices and monitor fares around Labor Day for spikes. - Fly midweek (Tuesdays/Wednesdays) and consider early-morning departures to access the lowest fares and fewer delays. - Compare Ronald Reagan Washington National Airport (DCA), Washington Dulles International Airport (IAD), and Baltimore/Washington Thurgood Marshall Airport (BWI) for price and schedule differences; sometimes a short drive to BWI yields substantial savings. - Use fare alerts, flexible date calendars, and rewards program redemptions to reduce out-of-pocket costs. CTA: Set a fare alert now for WASA → ORD September trips and lock in the best price.