IAD → ORD

Find and Compare the Cheapest Ways to Fly from Washington to Chicago

Compare one-way, round-trip and flight + hotel packages from Washington to Chicago, a nonstop flight of about 1h 40m, with fares from around 125. Nonstop fares seen from United.

Washington to Chicago flight facts

Washington to Chicago is a domestic route covering about 587 miles, arriving at O'Hare International Airport (ORD) in United States. Peak travel season in Chicago runs June–August (warm, lakefront festivals), while November–April is usually the quietest and best-value time to visit. Nonstop fares we've tracked on this route come from United.

Key facts for flights from Washington to Chicago
Departing fromWashington Dulles International Airport (IAD)
Arriving atO'Hare International Airport (ORD)
Distance587 miles (944 km)
Nonstop flight timeAbout 1h 40m
Nonstop airlines seenUnited
Round-trip fares from$125 (estimate)
Cheapest monthsJanuary, September, April
Peak season in ChicagoJune–August
Cheapest hotel months in ChicagoNovember–April
Best time to book1 to 3 months ahead
Route info updatedOctober 16, 2026

When to visit Chicago

  • Peak season

    June–August

    Warm, lakefront festivals

  • Shoulder season

    May & September–October

    Mild and comfortable

  • Off-peak season

    November–April

    Cold, windy and snowy

Estimated round-trip fares by month, Washington to Chicago

Estimated lowest round-trip fare per month
MonthFares from
January$125
February$145
March$150
April$140
May$160
June$195
July$190
August$160
September$130
October$155
November$160
December$205

Flying from Washington to Chicago

Airlines Flying this Route

Nonstop fares we've tracked on this route come from United. Ducoffs.com compares full-service and low-cost airlines flying between Washington and Chicago in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.

Best Time to Book Flights from Washington to Chicago

Fares on this route tend to be lowest in January, September, and April. For the best selection, book about 1 to 3 months before departure and stay flexible by a day or two.

Average Travel Duration

Washington and Chicago are about 587 miles apart. A nonstop flight takes roughly 1h 40m; connecting itineraries usually add 2 to 5 hours.

Washington to Chicago flight questions

How can I find the absolute cheapest flight from Washington to Chicago?

The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.

What is the cheapest month to fly from Washington to Chicago?

Based on typical seasonal demand, January, September, and April tend to offer the lowest fares on this route, with estimated round-trip prices starting around $125. Live prices change daily, so run a search for your exact dates.

How long is the flight from Washington to Chicago?

Washington and Chicago are about 587 miles apart. A nonstop flight takes roughly 1h 40m, while connecting itineraries usually add 2 to 5 hours depending on the layover.

Which airlines fly nonstop from Washington to Chicago?

Recent nonstop fares we've tracked on this route come from United. Schedules change by season, so your live search shows every airline flying your dates.

When are hotels cheapest in Chicago?

Hotel rates in Chicago are usually lowest in November–April, when demand is quieter, and highest during peak season (June–August). Booking your flight and hotel together can save up to 30%.

Which airport do I fly into for Chicago?

This route arrives at O'Hare International Airport (ORD). Your search results also show nearby airports when they offer a cheaper or faster option.

How far in advance should I book a flight to Chicago?

For this route, booking about 1 to 3 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.

Is it cheaper to bundle flights and hotels together?

Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.