
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $199 (Trip.com) |
One-way from | $94 (Super.com) |
Popular in | January |
Cheapest in | August |
Average price | $423 |
Good round-trip deal | $548 or less |
Good one-way deal | $211 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Tue 4/21
6:38 pm-11:03 pm
1 stop3h 25m
Washington, D.C. Dulles Intl
Wed 4/22
6:00 am-9:56 am
1 stop4h 56m
ChicagoWashington, D.C.
ORD - IAD
ORDIAD
Chicago O'Hare Intl
Tue 5/5
6:04 am-12:05 pm
1 stop5h 01m
Washington, D.C. Dulles Intl
Tue 5/5
5:27 pm-10:21 pm
1 stop5h 54m
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Tue 4/28
10:41 am-4:31 pm
1 stop4h 50m
Washington, D.C. Dulles Intl
Sat 5/2
6:00 am-10:14 am
1 stop5h 14m
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Sat 4/11
9:35 am-4:49 pm
1 stop6h 14m
Washington, D.C. Dulles Intl
Thu 4/16
6:00 am-8:47 am
1 stop3h 47m
ChicagoWashington, D.C.
ORD - IAD
ORDIAD
Chicago O'Hare Intl
Tue 5/12
2:27 pm-5:30 pm
Nonstop2h 03m
Washington, D.C. Dulles Intl
Fri 5/15
10:30 pm-11:44 pm
Nonstop2h 14m
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Tue 5/26
6:36 pm-10:56 pm
1 stop3h 20m
Washington, D.C. Dulles Intl
Mon 6/1
5:33 pm-9:09 pm
1 stop4h 36m
ChicagoWashington, D.C.
MDW - IAD
MDWIAD
Chicago Midway
Wed 4/15
6:00 am-11:46 am
1 stop4h 46m
Washington, D.C. Dulles Intl
Wed 4/22
6:00 am-9:56 am
1 stop4h 56m
ChicagoWashington, D.C.
ORD - IAD
ORDIAD
Chicago O'Hare Intl
Wed 4/22
8:15 am-2:04 pm
1 stop4h 49m
Washington, D.C. Dulles Intl
Sat 4/25
6:00 am-10:19 am
1 stop5h 19m
ChicagoWashington, D.C.
ORD - IAD
ORDIAD
Chicago O'Hare Intl
Mon 5/11
5:19 pm-10:56 pm
1 stop4h 37m
Washington, D.C. Dulles Intl
Tue 5/12
3:08 pm-8:26 pm
1 stop6h 18m
ChicagoWashington, D.C.
ORD - IAD
ORDIAD
Chicago O'Hare Intl
Fri 5/15
3:47 pm-11:38 pm
1 stop6h 51m
Washington, D.C. Dulles Intl
Mon 5/18
3:23 pm-8:26 pm
1 stop6h 03m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
The best time to book flights from Chicago to Washington, D.C. Dulles Intl Airport is 65 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, October is the cheapest month in which you can book a flight from Chicago to Washington, D.C. Dulles Intl Airport (average of $142). Flying from Chicago to Washington, D.C. Dulles Intl Airport in November is currently the most expensive (average of $253). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
A simple way to save on the total cost of your ticket is to fly from Chicago to Washington, D.C. Dulles Intl Airport in the morning. If you’re flexible enough to do this you can expect to save up to 46% on your trip compared to booking a flight at noon.
Travelers seeking maximum savings on their Chicago to Washington, D.C. Dulles Intl Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to IAD are scheduled on a Thursday (26 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).
About 18% of weekly flights between Chicago and Washington, D.C. have experienced delays in the past year, with the average delay time being 127 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 18% of flights being delayed.
Overall
Boarding
Food
Comfort
Entertainment
Crew
Reviews
Dane,Jan 2026
TYS - IAD
Overall
Boarding
Food
Comfort
Entertainment
Crew
Reviews
Dane,Jan 2026
TYS - IAD
Overall
Boarding
Food
Comfort
Entertainment
Crew
Reviews
Dane,Jan 2026
TYS - IAD
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$262 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$212 | Average$334 | FlexibilityNo cancel fee | On-time69% |