Find Cheap Flights from Washington Dulles Intl to Chicago (IAD - CHI)

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Washington Dulles Intl to Chicago Flight Information

Avg. Flight Duration 1h 54m
Flights Arrive in Chicago
Flights Depart from Washington Dulles Intl
Flight Price $251
Distance 572 miles
Airlines American Airlines, United Airlines, Major Airline, JetBlue, Delta

Good to Know

Low Season:
September
Best time to beat the crowds
2%
expected price decrease
High Season:
November
Most popular time to fly
4%
expected price increase
Average Price:
$322
(avg. price over the last 2 weeks)
Good Deal:
$262
or less (round trip)

When to Book Flights from Washington Dulles Intl to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top Tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $262 or less.
The cheapest flight from Washington Dulles Intl to Chicago was found 90 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be October, November and December. The cheapest month to fly is September.
Morning departure is around 13% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Washington Dulles Intl to Chicago Flights

How long does a flight from Washington Dulles Intl to Chicago take?
An average nonstop flight takes 2h 01m, covering a distance of 572 miles.
How many flights are there between Washington Dulles Intl and Chicago?
There are 627 (nonstop) flights between Washington Dulles Intl and Chicago per week, averaging 86 per day.
Which airlines provide the cheapest flights from Washington Dulles Intl to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on American Airlines ($251), United Airlines ($263) and JetBlue ($272).
Do I need a passport to fly between Washington Dulles Intl and Chicago?
No.
Which airlines fly most frequently between Washington Dulles Intl and Chicago?
Air Canada (18 times daily), United Airlines (15 times daily), Air New Zealand (12 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Washington Dulles Intl to Chicago?
For Washington Dulles Intl to Chicago, Saturday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to Washington Dulles Intl, the best deals are generally found on Monday, with Wednesday being the most expensive.

Book cheap flights from Washington Dulles Intl to Chicago (round-trip)

Airports
Origin
Washington
$251
only
$251
Destination
Chicago
$251
only
$251
$280
only
$280
Sat, Dec 15
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
6h 10m
Mon, Dec 17
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
6h 53m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 35,239 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.8
Food
6.7
PHL
ATL
Okay 5.0

Pros: I think crew tried to make the best of the bad situation. Got to Atlanta faster than scheduled flight time and they were sympathetic. Don't really know about much else, as I slept the whole flight.

Cons: The 3 hour delay really cost us. Left Rome at 2:30 pm instead of 11:30 am, so missed 6:40 pm flight to Atlanta (so much for the 3 1/2 hour layover we were supposed to have). When we landed in Philadelphia, sat on runway for 45 minutes, waiting for gate. Next flight was supposed to leave at 8:40, took off at midnight.

MIA
SJU
Mediocre 2.0

Pros: None

Cons: Long delay

MAD
DFW
Excellent 10.0

Cons: Delayed 2 hours

FCO
PHL
Good 6.3

Pros: Food was surprisingly pretty good. Good entertainment options.

Cons: The 3 1/2 hour delay was the worst - missed our connecting flight because of it, which is pretty bad when you're supposed to have a 3 1/2 hour layover. Then the flight they put us on was 3 1/2 hours late. We got home at 7 am instead of midnight. Spent 45 minutes sitting on the runway in Philadelphia because another plane was at our gate so we had to wait for them to take off, not just leave the gate. Flight attendants were efficient but not at all friendly - not a smile among them.

DCA
IND
Good 7.6

Pros: Crew had great personalities

Cons: Late to leave and arrive

Wed, Dec 5
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
2h 01m
Mon, Dec 10
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
1h 45m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 72 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAD
ORD
Mediocre 2.6

Cons: We have to pay for entertainment The flight wasn't smooth honestly one of the worst ever Even counting the combat flights that I took to Iraq seriously I almost vomited and that never ever happened to me on a flight

IAD
ORD
Excellent 10.0

Pros: Great fly very attenty personal

IAD
ORD
Good 7.0

Pros: Everything was fine but not having the option of personal device entertainment was annoying, really annoying, I don't appreciate that kind of cheapness annoying.

Cons: No personal device entertainment and I'm 5'2 and my legs felt cramped, I felt sorry for the two guys sitting next to me

IAD
ORD
Excellent 9.0

Cons: No food

IAD
ORD
Excellent 10.0

Pros: Omg the movie selection was amazing!!!!

Thu, Jan 3
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
2h 04m
Mon, Jan 7
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
1h 44m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Nov 27
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
8h 22m
Wed, Nov 28
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
6h 49m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 14,523 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
PHX
BOS
Excellent 8.0

Pros: we got where we were going.

Cons: 45 minute delay of takeoff.

DEN
JFK
Excellent 8.0

Pros: JetBlue provided ear plugs and a sleep mask. I honestly slept most of the trip. Red eyes are awful, but JetBlue made it bearable.

Cons: Couldn't turn brightness down on headrest monitor. Both of the other screens were able to crank brightness down to off

ORH
MCO
Excellent 9.0

Cons: I paid for extra space and there was none available on my flight.

JFK
SLC
Okay 4.3

Pros: Comfortable, nice staff, nice free snacks during delays, solid customer service

Cons: Frustrating to deboard, reboard, be delayed a bunch - maintenance issues

ORD
BOS
Excellent 9.3

Cons: The cabin crew was a little lacking and the captain did not mentioned that we had landed almost a full hour later than scheduled.

Mon, Dec 3
IAD
Washington Dulles Intl
MDW
Chicago Midway
6h 01m
Wed, Dec 5
MDW
Chicago Midway
IAD
Washington Dulles Intl
4h 09m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,502 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MSP
SFO
Excellent 10.0

Pros: Having three seats.

Cons: I had three seats to myself! After getting elbowed all the way from Amsterdam to Minneapolis, I was tired and I slept three good hours.

LIT
ATL
Excellent 10.0

Pros: First time flying into Daytona and it was super easy.

Cons: Nothing

ICT
ATL
Excellent 10.0

Pros: I liked that military boarded first.

Cons: I think disabled US Veterans should board with active duty and retired military

LGA
STL
Mediocre 3.3

Pros: I did get home eventually

Cons: Flight was delayed. Seats are cramped.

DTW
ATL
Mediocre 2.0

Cons: Flight delayed from Detroit. Closed door to Birmingham flight 20 minutes before schedule time. Rebooked me for Friday!

Fri, Jan 18
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
2h 05m
Sun, Jan 20
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
1h 49m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 28
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
2h 04m
Wed, Mar 6
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
1h 44m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 72 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAD
ORD
Mediocre 2.0

Cons: Worst shittiest experience! Delayed by 3 hours

IAD
ORD
Good 7.3

Pros: Everything for this flight was as expected for my ticket purchase.

Cons: I had no problems with this flight.

IAD
ORD
Excellent 10.0

Pros: Great fly very attenty personal

IAD
ORD
Good 7.0

Pros: Everything was fine but not having the option of personal device entertainment was annoying, really annoying, I don't appreciate that kind of cheapness annoying.

Cons: No personal device entertainment and I'm 5'2 and my legs felt cramped, I felt sorry for the two guys sitting next to me

IAD
ORD
Good 6.6

Pros: Nice crew and entertainment

Cons: 3 hrs delay

Thu, Dec 13
IAD
Washington Dulles Intl
MDW
Chicago Midway
6h 15m
Sat, Dec 15
MDW
Chicago Midway
IAD
Washington Dulles Intl
5h 34m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,502 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MSP
BOS
Good 6.3

Cons: They upgraded only my husband and split him up with the rest of our family. We were delayed and once we landed we got stuck in an active taxi way just because of poor arrangements from airport staff

ATL
ORF
Excellent 10.0

Pros: Quick flight

Cons: Not much space for Carry ons. Much smaller than most aircrafts

DTW
ATL
Mediocre 2.0

Cons: Flight delayed from Detroit. Closed door to Birmingham flight 20 minutes before schedule time. Rebooked me for Friday!

LGA
STL
Mediocre 3.3

Pros: I did get home eventually

Cons: Flight was delayed. Seats are cramped.

FLL
ATL
Good 7.6

Pros: Loved being in first class

Cons: Hated gate change and late plane at the last minute.

Sat, Mar 2
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
2h 04m
Mon, Mar 4
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
1h 45m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 72 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAD
ORD
Excellent 9.0

Cons: No food

IAD
ORD
Mediocre 3.6

Pros: It was fine.

Cons: Everything was fine.................................

IAD
ORD
Excellent 10.0

Pros: Great fly very attenty personal

IAD
ORD
Mediocre 2.6

Cons: We have to pay for entertainment The flight wasn't smooth honestly one of the worst ever Even counting the combat flights that I took to Iraq seriously I almost vomited and that never ever happened to me on a flight

IAD
ORD
Okay 5.6

Cons: No leg room

Sat, Dec 15
IAD
Washington Dulles Intl
MDW
Chicago Midway
4h 00m
Mon, Dec 17
MDW
Chicago Midway
IAD
Washington Dulles Intl
4h 25m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,502 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
DTW
ATL
Mediocre 2.0

Cons: Flight delayed from Detroit. Closed door to Birmingham flight 20 minutes before schedule time. Rebooked me for Friday!

IMT
DTW
Excellent 9.6

Pros: How friendly all the staff were and how quickly we boarded the plane.

Cons: How the toilet didn't work, but it's okay because I think we could all hold it for an hour ;)

LAX
SAN
Good 6.0

Cons: seats were broken, armrest broken

MSP
SFO
Excellent 10.0

Pros: Having three seats.

Cons: I had three seats to myself! After getting elbowed all the way from Amsterdam to Minneapolis, I was tired and I slept three good hours.

ATL
AMS
Excellent 10.0

Pros: Military boarded first

Cons: Disabled US Veterans should be allowed to board with active and retired military

Wed, Apr 10
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
2h 03m
Sat, Apr 20
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
1h 49m
Trip: 11 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 72 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAD
ORD
Okay 4.0

Cons: Extended layover by over an hour

IAD
ORD
Excellent 9.0

Cons: No food

IAD
ORD
Okay 4.0

Pros: Nothing

Cons: Having to depart from another airport

IAD
ORD
Excellent 10.0

Pros: Omg the movie selection was amazing!!!!

IAD
ORD
Excellent 10.0

Pros: Great fly very attenty personal

Tue, Jan 8
IAD
Washington Dulles Intl
MDW
Chicago Midway
3h 58m
Mon, Jan 14
MDW
Chicago Midway
IAD
Washington Dulles Intl
3h 37m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,502 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
JFK
TPA
Okay 4.3

Cons: Very late and boarded too long before leaving the gate.

ICT
ATL
Excellent 10.0

Pros: I liked that military boarded first.

Cons: I think disabled US Veterans should board with active duty and retired military

MSP
SFO
Excellent 10.0

Pros: Having three seats.

Cons: I had three seats to myself! After getting elbowed all the way from Amsterdam to Minneapolis, I was tired and I slept three good hours.

LGA
STL
Mediocre 3.3

Pros: I did get home eventually

Cons: Flight was delayed. Seats are cramped.

IMT
DTW
Excellent 9.6

Pros: How friendly all the staff were and how quickly we boarded the plane.

Cons: How the toilet didn't work, but it's okay because I think we could all hold it for an hour ;)

Sat, May 11
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
2h 02m
Mon, May 13
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
1h 46m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 72 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAD
ORD
Okay 4.0

Pros: Nothing

Cons: Having to depart from another airport

IAD
ORD
Excellent 10.0

Pros: Omg the movie selection was amazing!!!!

IAD
ORD
Excellent 10.0

Pros: Great fly very attenty personal

IAD
ORD
Mediocre 3.6

Pros: It was fine.

Cons: Everything was fine.................................

IAD
ORD
Good 7.0

Pros: Everything was fine but not having the option of personal device entertainment was annoying, really annoying, I don't appreciate that kind of cheapness annoying.

Cons: No personal device entertainment and I'm 5'2 and my legs felt cramped, I felt sorry for the two guys sitting next to me

Mon, Nov 26
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
4h 50m
Wed, Nov 28
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
7h 59m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 14,523 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
LAX
Excellent 8.0

Cons: The beginning was a bit confusing when I needed to use JetBlue because I had to go to the help desk to figure out why they wouldn’t issue all of my boarding passes at JFK and the line took an hour just for them to tell me to get my boarding pass at LAX. Other than that it was a great flight!

DCA
JAX
Good 7.0

Pros: The crew was nice and the entertainment was great!

Cons: Paying for bags!

PHX
BOS
Excellent 8.0

Pros: we got where we were going.

Cons: 45 minute delay of takeoff.

LGB
PDX
Excellent 10.0

Pros: Got randomly given a seat with extra leg room. First time on jetblue but the setup was nice!

ORH
MCO
Excellent 9.0

Cons: I paid for extra space and there was none available on my flight.

Sat, Jan 26
IAD
Washington Dulles Intl
MDW
Chicago Midway
4h 01m
Mon, Jan 28
MDW
Chicago Midway
IAD
Washington Dulles Intl
3h 37m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,502 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MSP
SFO
Excellent 10.0

Pros: Having three seats.

Cons: I had three seats to myself! After getting elbowed all the way from Amsterdam to Minneapolis, I was tired and I slept three good hours.

LIT
ATL
Excellent 10.0

Pros: First time flying into Daytona and it was super easy.

Cons: Nothing

ATL
ORF
Excellent 10.0

Pros: Quick flight

Cons: Not much space for Carry ons. Much smaller than most aircrafts

JFK
TPA
Okay 4.3

Cons: Very late and boarded too long before leaving the gate.

ICT
ATL
Excellent 10.0

Pros: I liked that military boarded first.

Cons: I think disabled US Veterans should board with active duty and retired military

Sat, Jan 26
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
4h 16m
Mon, Jan 28
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
3h 53m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,502 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
FLL
ATL
Good 7.6

Pros: Loved being in first class

Cons: Hated gate change and late plane at the last minute.

ATL
ORF
Excellent 10.0

Pros: Quick flight

Cons: Not much space for Carry ons. Much smaller than most aircrafts

MSP
SFO
Excellent 10.0

Pros: Having three seats.

Cons: I had three seats to myself! After getting elbowed all the way from Amsterdam to Minneapolis, I was tired and I slept three good hours.

JFK
TPA
Okay 4.3

Cons: Very late and boarded too long before leaving the gate.

IMT
DTW
Excellent 9.6

Pros: How friendly all the staff were and how quickly we boarded the plane.

Cons: How the toilet didn't work, but it's okay because I think we could all hold it for an hour ;)

Fri, Dec 21
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
2h 04m
Tue, Dec 25
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
1h 44m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 72 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAD
ORD
Mediocre 2.0

Cons: Worst shittiest experience! Delayed by 3 hours

IAD
ORD
Okay 4.0

Pros: Nothing

Cons: Having to depart from another airport

IAD
ORD
Mediocre 3.6

Pros: It was fine.

Cons: Everything was fine.................................

IAD
ORD
Good 6.6

Pros: Nice crew and entertainment

Cons: 3 hrs delay

IAD
ORD
Okay 5.6

Cons: No leg room

Mon, Feb 4
IAD
Washington Dulles Intl
MDW
Chicago Midway
3h 58m
Wed, Feb 6
MDW
Chicago Midway
IAD
Washington Dulles Intl
3h 37m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,502 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
IMT
DTW
Excellent 9.6

Pros: How friendly all the staff were and how quickly we boarded the plane.

Cons: How the toilet didn't work, but it's okay because I think we could all hold it for an hour ;)

DTW
ATL
Mediocre 2.0

Cons: Flight delayed from Detroit. Closed door to Birmingham flight 20 minutes before schedule time. Rebooked me for Friday!

ATL
AMS
Excellent 10.0

Pros: Military boarded first

Cons: Disabled US Veterans should be allowed to board with active and retired military

FLL
ATL
Good 7.6

Pros: Loved being in first class

Cons: Hated gate change and late plane at the last minute.

MSP
BOS
Good 6.3

Cons: They upgraded only my husband and split him up with the rest of our family. We were delayed and once we landed we got stuck in an active taxi way just because of poor arrangements from airport staff

Sat, Mar 2
IAD
Washington Dulles Intl
MDW
Chicago Midway
3h 48m
Wed, Mar 6
MDW
Chicago Midway
IAD
Washington Dulles Intl
3h 30m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 21,502 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
JFK
TPA
Okay 4.3

Cons: Very late and boarded too long before leaving the gate.

FLL
ATL
Good 7.6

Pros: Loved being in first class

Cons: Hated gate change and late plane at the last minute.

LGA
STL
Mediocre 3.3

Pros: I did get home eventually

Cons: Flight was delayed. Seats are cramped.

DTW
ATL
Mediocre 2.0

Cons: Flight delayed from Detroit. Closed door to Birmingham flight 20 minutes before schedule time. Rebooked me for Friday!

MSP
SFO
Excellent 10.0

Pros: Having three seats.

Cons: I had three seats to myself! After getting elbowed all the way from Amsterdam to Minneapolis, I was tired and I slept three good hours.

Fri, Feb 8
IAD
Washington Dulles Intl
ORD
Chicago O'Hare International
2h 05m
Sun, Feb 10
ORD
Chicago O'Hare International
IAD
Washington Dulles Intl
1h 49m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 72 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAD
ORD
Good 6.6

Pros: Nice crew and entertainment

Cons: 3 hrs delay

IAD
ORD
Excellent 10.0

Pros: Omg the movie selection was amazing!!!!

IAD
ORD
Mediocre 2.0

Cons: Worst shittiest experience! Delayed by 3 hours

IAD
ORD
Okay 5.6

Cons: No leg room

IAD
ORD
Okay 4.0

Pros: Nothing

Cons: Having to depart from another airport

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.