Washington to Chicago flights
Round trip · Economy · Prices per person in USD
Prices updated
Prices are low right now
$266 is $64 (19%) below the usual $330 for Washington → Chicago.
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when Washington → Chicago drops below your price.Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $336 |
| November 2026 | $266 (cheapest month) |
| December 2026 | No fares found yet |
| January 2027 | No fares found yet |
| February 2027 | No fares found yet |
| March 2027 | No fares found yet |
| April 2027 | No fares found yet |
| May 2027 | No fares found yet |
| June 2027 | $403 |
| July 2027 | $428 |
Cheapest dates in the next 4 months
Round trip, per person-
Nov 1 – 4 3 nights · leave Sun$266 −19% vs usual$266 −19% vs usual Book
Frontier Airlines 1 stop · 4h 19m -
Nov 26 – 29 3 nights · leave Thu$304 −8% vs usual$304 −8% vs usual Book
Frontier Airlines 1 stop · 2h 28m
-
Oct 2 – 5 3 nights · leave Fri$336$336 Book
United Airlines 1 stop · 2h 14m -
Oct 3 – 7 4 nights · leave Sat$351 +6% vs usual$351 +6% vs usual Book
Frontier Airlines 1 stop · 2h 24m
-
Oct 2 – 4 2 nights · leave Fri$353 +7% vs usual$353 +7% vs usual Book
United Airlines 1 stop · 2h 14m
-
Oct 2 – 7 5 nights · leave Fri$380 +15% vs usual$380 +15% vs usual Book
Frontier Airlines 1 stop · 6h 14m
-
Oct 9 – 12 3 nights · leave Fri$404 +22% vs usual$404 +22% vs usual Book
Frontier Airlines Nonstop · 2h 23m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
Tickets and tours on KlookTo see tours and tickets here, turn on partner content in .
Partner widget: we may earn a commission if you book, at no extra cost to you.
Airport transfer to Chicago
Fixed prices from ORD on KiwitaxiTo see transfer prices here, turn on partner content in .
Partner widget: we may earn a commission if you book, at no extra cost to you.
Plan the rest of your trip
Chicago · Nov 1 – 4Travel insurance · EKTA Airport transfer · Kiwitaxi
Partner links: we may earn a commission if you book, at no extra cost to you.
Good to know
More from Washington
-
-
-
-
-
-
-
-
Flights to Chicago from other cities
-
-
-
-
-
-
Washington to Chicago: questions
How much is a flight from Washington to Chicago?
The cheapest round trip we have found right now is $266, leaving November 1 and returning November 4. The usual price on this route is about $330, so this fare is 19% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Washington to Chicago?
November 2026, with round trips from $266. The most expensive month in our data is July (from $428). Based on the 4 months ahead we have prices for.
About this route
We track round-trip economy fares from Washington (United States) to Chicago (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $266, departing November 1 and returning November 4, about 19% below the usual $330. Right now we're following 7 upcoming date combinations on this route. The cheapest month to fly in our data is November, from $266. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.