Find Cheap Flights from Washington to Chicago (WAS - CHI)

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Good to Know

Low Season:
January
Best time to beat the crowds
3%
expected price decrease
High Season:
April
Most popular time to fly
16%
expected price increase
Average Price:
$232
(avg. price over the last 2 weeks)
Good Deal:
$164
or less (round trip)

When to Book Flights from Washington to Chicago

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 $163 or less.
The cheapest flight from Washington to Chicago was found 53 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 March, April and May. The cheapest month to fly is January.
Morning departure is around 34% more expensive 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 to Chicago Flights

How long does a flight from Washington to Chicago take?
An average nonstop flight takes 1h 57m, covering a distance of 594 miles.
How many flights are there between Washington and Chicago?
There are 1,550 (nonstop) flights between Washington and Chicago per week, averaging 227 per day.
Which airlines provide the cheapest flights from Washington to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on United ($160), JetBlue ($195) and Multiple Airlines ($201).
Do I need a passport to fly between Washington and Chicago?
No.
Which airlines fly most frequently between Washington and Chicago?
United (51 times daily), Southwest (31 times daily), American Airlines (21 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Washington to Chicago?
For Washington to Chicago, Monday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago back to Washington, the best deals are generally found on Wednesday, with Tuesday being the most expensive.

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

Airports
Origin
Washington
$160
only
$160
$195
only
$195
Destination
Chicago
$160
only
$160
$280
only
$280
Mon, Jul 2
IAD
ORD
9h 21m
Tue, Jul 3
ORD
IAD
1h 49m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 66 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
ORD
Okay 5.6

No leg room

IAD
ORD
Mediocre 2.0

Nothing

My connecting flight from Chicago to Madison was cancelled with no explanation and no other alternatives provided, other than to get a hotel in Chicago and try to catch a flight to Madison the next day. United said they would not cover the cost of transportation to a hotel or the cost of the hotel. In addition, my luggage was misplaced and sent to Madison and could not be located. The number United provided to me to check on the whereabouts of my bag no one ever answered, even though I called multiple, multiple times.

IAD
ORD
Excellent 9.0

No food

IAD
ORD
Good 7.0

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.

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 7.3

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

I had no problems with this flight.

Tue, May 1
DCA
ORD
8h 46m
Wed, May 2
ORD
DCA
8h 34m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 8576 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
LGB
SJC
Excellent 10.0

The flight was cancelled but staff was really nice. I received credit for future flight so that was great. And they let me sleep in the terminal and a very nice employee handed me water and snacks at midnight.

FLL
DCA
Okay 5.3

On time take off, nice flight attendants, on time arrival.

The entertainment system stopped working about 10 minutes before take off and never came back up.

JFK
SFO
Excellent 8.0

No food and delayed

LAS
LGB
Excellent 8.0

Everything about the flight was fine, and I was especially pleased that we boarded and disembarked through TWO doors in Long Beach: one in front and one aft.

Both flights were quite delayed. It’s good that I wasn’t on a tight schedule.

BOS
JFK
Mediocre 2.0

Delayed over 4 hours..missed connecting flight..

Tue, Apr 10
DCA
ORD
2h 17m
Wed, May 9
ORD
DCA
5h 38m
Trip: 30 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jun 9
DCA
ORD
2h 01m
Mon, Jun 11
ORD
DCA
1h 52m
Trip: 3 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 37 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
DCA
ORD
Good 7.3

Seating is a bit cramped.

DCA
ORD
Excellent 10.0

On time, good service.

DCA
ORD
Excellent 10.0

I love the fact I've flown with American Airlines 4 times over the last month and have not had any issues, delays or even an unfriendly face no matter the time or airport!

DCA
ORD
Good 7.2

I liked that the flight was basically on time, boarding was a breeze, and the staff was professional, friendly, and helpful.

The seats! They were very uncomfortable. They were more comfortable than United, but less comfortable than JetBlue.

DCA
ORD
Excellent 8.6

The Resolution team assisted me initially when I arrived to correct an issue from my online attempt. The agent printed bag checks for me to my final destination and told me how to get needed boarding pass for the final stage. How wonderful to have pleasant and professional personal attention.

Tue, Mar 13
DCA
ORD
2h 28m
Tue, Mar 20
ORD
DCA
1h 59m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Mar 14
DCA
MDW
5h 57m
Sat, Mar 17
MDW
DCA
7h 22m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

Tue, May 1
DCA
ORD
8h 46m
Tue, May 22
ORD
DCA
8h 28m
Trip: 22 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 8576 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
BOS
CLE
Good 7.6

Crew was excellent!! Pilot and flight attendants really helped to keep things going despite the many problems.

We had to switch planes because of a fuel leak. Then the second plane had computer problems. We left 4 hours after we were supposed to.

JFK
SJU
Excellent 10.0

Very nice crew

LIM
FLL
Mediocre 3.3

Nothing but a little leg room

No entertainment except Spanish movies that you had to watch on their time... No internet like advertised... Unlimited snacks, what the one time they bring them you have to grab them all... One offer in a while 5 hour flight... No meal... Horrible in my opinion...I got a meal on an hour train ride for Christ sake... Won't choose jet blue for any long flight ever again

JFK
SFO
Excellent 8.0

No food and delayed

FLL
BOG
Mediocre 2.0

I missed my flight i spend longer than an hour in the line to get to the gate they never call for passengers or call names they were selling the tickets to other people didn't wait for people who got their tickets in advance, they say is not our fault that all those people missed the flight we not giving any compensation or hotel, I had to come back to New York paid for hotel and without my luggage worse experience in my life.

Tue, Apr 3
IAD
ORD
2h 02m
Sat, Apr 7
ORD
IAD
1h 50m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 66 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
ORD
Good 7.3

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

I had no problems with this flight.

IAD
ORD
Excellent 10.0

Great fly very attenty personal

IAD
ORD
Mediocre 2.0

Nothing

My connecting flight from Chicago to Madison was cancelled with no explanation and no other alternatives provided, other than to get a hotel in Chicago and try to catch a flight to Madison the next day. United said they would not cover the cost of transportation to a hotel or the cost of the hotel. In addition, my luggage was misplaced and sent to Madison and could not be located. The number United provided to me to check on the whereabouts of my bag no one ever answered, even though I called multiple, multiple times.

IAD
ORD
Okay 4.0

Nothing

Having to depart from another airport

IAD
ORD
Good 7.0

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.

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

Tue, Apr 10
IAD
ORD
4h 27m
Wed, May 9
ORD
IAD
6h 24m
Trip: 30 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 10
IAD
ORD
1h 57m
Sat, Apr 14
ORD
IAD
1h 50m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 66 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
ORD
Good 7.0

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.

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
Mediocre 2.0

Nothing

My connecting flight from Chicago to Madison was cancelled with no explanation and no other alternatives provided, other than to get a hotel in Chicago and try to catch a flight to Madison the next day. United said they would not cover the cost of transportation to a hotel or the cost of the hotel. In addition, my luggage was misplaced and sent to Madison and could not be located. The number United provided to me to check on the whereabouts of my bag no one ever answered, even though I called multiple, multiple times.

IAD
ORD
Excellent 9.0

No food

IAD
ORD
Mediocre 2.6

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

No leg room

Tue, May 15
IAD
ORD
9h 31m
Wed, May 16
ORD
IAD
6h 24m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 8606 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
STI
Mediocre 2.3

The fact that I finally reached my destination

The flight was delayed. The gate changed. The flight did not leave until an hour later a AFTER the delay. My seat was switched and the new seat DID NOT recline. I paid more for this flight because I didn’t want to reach me destination late at night. I still reached my destination at 10:00pm. I could have save $50.00 with the later flight, but I ended up paying more for less.

BOS
LGA
Excellent 8.8

Everything was on-time and we arrived early with no problems. Wasn't expecting even snacks/drinks on a 45 minute flight, but they served them. Crew was even more friendly and helpful than usual.

E-mailed me advertising a free drink on BOS-->LGA flights, but I didn't see that.

ATL
BOS
Excellent 8.0

It's a budget carrier - I don't expect great food and brand new upholstery. I expect safe, on-time travel, and JetBlue meets and exceeds my expectations every time. Very happy. A great, community-involved company too.

Free Wi-Fi, but it seems you have to sign up for an account or/and do something with Amazon. Needlessly complicated. If the Wi-Fi is free, just let passengers join.

SFO
JFK
Excellent 10.0

The crew made it very easy to be stress free so I was able to get some sleep on the flight back.

The face mask on the overnight flight was great!

SLC
BOS
Excellent 10.0

My flight was excellent! We took of on time and were 20 minutes early landing. Very smooth flight. Great service, great leg room. I will fly Jet Blue again!

Sat, Aug 11
DCA
ORD
9h 04m
Sun, Aug 12
ORD
DCA
1h 52m
Trip: 2 days
7.5GoodShow reviews
Overall 7.5 Good
Based on 37 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
DCA
ORD
Good 7.0

Overall the flight was good, on time

Nothing at this stage

DCA
ORD
Excellent 8.6

The Resolution team assisted me initially when I arrived to correct an issue from my online attempt. The agent printed bag checks for me to my final destination and told me how to get needed boarding pass for the final stage. How wonderful to have pleasant and professional personal attention.

DCA
ORD
Good 6.3

Boarding was quick (once started)

I flew from DC to Austin, through Chicago. Flight was late leaving DC, was late leaving Chicago (mad had a gate change that wasn't announced), and when we go to Austin had to sit in the runway for 20 minutes due to someone else at the gate. I don't know if this was all AA's fault, or just bad luck.

DCA
ORD
Excellent 10.0

I love the fact I've flown with American Airlines 4 times over the last month and have not had any issues, delays or even an unfriendly face no matter the time or airport!

DCA
ORD
Mediocre 3.0

Delayed flight caused us to become grounded on the Tarmac for an hour. We deplaned and waited another hour. Waited on the Tarmac once again for a half hour until we finally took off. Got in to ohare and had to wait on the Tarmac another half hour before they got us a gate. All in all, 4 hours of waiting and delays.

Tue, May 1
IAD
ORD
1h 57m
Tue, May 22
ORD
IAD
1h 44m
Trip: 22 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 66 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
ORD
Good 7.0

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.

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
Mediocre 2.0

Worst shittiest experience! Delayed by 3 hours

IAD
ORD
Excellent 9.0

No food

IAD
ORD
Good 6.6

Nice crew and entertainment

3 hrs delay

IAD
ORD
Okay 4.0

Extended layover by over an hour

Tue, May 15
IAD
ORD
9h 31m
Wed, May 16
ORD
IAD
6h 24m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 8606 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
LAX
JFK
Excellent 8.0

Lots of snacks offering in the main cabin. Great movie selections free of charge

I didn’t like the seat fees.

SJU
STT
Okay 5.0

Paid more for a flight we would not have to get off of in SJU. They made us get off for no reason. 5h with two kids. All they had was chips.

LAS
LGB
Excellent 10.0

Nice flew. Easy n convenient.

ATL
BOS
Excellent 8.0

It's a budget carrier - I don't expect great food and brand new upholstery. I expect safe, on-time travel, and JetBlue meets and exceeds my expectations every time. Very happy. A great, community-involved company too.

Free Wi-Fi, but it seems you have to sign up for an account or/and do something with Amazon. Needlessly complicated. If the Wi-Fi is free, just let passengers join.

ORD
JFK
Mediocre 3.2

When I scanned my boarding pass the Jetblue staff member told me my carry on was too big and had to be checked. This was puzzling to me because I travel often and do not have a problem with that bag. As I was sitting on the plane I saw everyone's bag's were bigger especially the man next to me. His was significantly larger and he had a large duffle bag between his legs causing him to manspread into my area. and yet i was told "make sure your purse is under the seat" seriously?! What about his giant duffle bag and huge carry on roller?!

Sat, Mar 24
IAD
ORD
2h 03m
Wed, Mar 28
ORD
IAD
1h 50m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sat, May 26
IAD
ORD
14h 26m
Sun, May 27
ORD
IAD
1h 45m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 66 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
ORD
Okay 4.0

Extended layover by over an hour

IAD
ORD
Okay 5.6

No leg room

IAD
ORD
Good 6.6

Nice crew and entertainment

3 hrs delay

IAD
ORD
Mediocre 2.6

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
Mediocre 2.0

Nothing

My connecting flight from Chicago to Madison was cancelled with no explanation and no other alternatives provided, other than to get a hotel in Chicago and try to catch a flight to Madison the next day. United said they would not cover the cost of transportation to a hotel or the cost of the hotel. In addition, my luggage was misplaced and sent to Madison and could not be located. The number United provided to me to check on the whereabouts of my bag no one ever answered, even though I called multiple, multiple times.

Sat, Mar 17
IAD
MDW
3h 47m
Tue, Mar 20
MDW
IAD
3h 35m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

Sat, Jun 9
DCA
ORD
2h 09m
Wed, Jun 13
ORD
DCA
1h 49m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jun 6
DCA
ORD
2h 06m
Tue, Jun 12
ORD
DCA
2h 06m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 113 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
DCA
ORD
Excellent 10.0

Great crew, smooth flight

DCA
ORD
Mediocre 2.0

Flight was cancelled which I accept, but couldn't get me on another flight for 24 hours???? (When at least 15 flights, some with empty seats, went to Chicago in that time!!!). That's bull United.

DCA
ORD
Mediocre 2.3

We didn't have seats assigned and the gate attendent didn't take the time to tell any of the 20 of us waiting for 15-20 mins to speak to a gate agent what was going on until AFTER she boarded the rest of the plane. When asked what was going on she responded "excuse me, I'll get to you when I get to you and thanks for your 'non attitude'" to the woman who asked her if she had any plans to greet us or even ackwnowledge us. Then the flight attendants became flustered as they realized they separated a 5 year old child and his father and sat the child in the emergency seat. When several of us attempted to help they were rude so when I put my headphones in to pass the time and didn't hear the woman ask if I was willing to sit in the emergency isle she snidely said "there's always one millenial not paying attention." Ummm.... I had my eyes closed and was listening to my music since they clearly wanted us to mind our own business and NOT try to help the father (meanwhile all of us strangers were trying to figure out how to rearrange in order to help). The only reason entertainment gets a 2 is bc I had good conversation with the passenger next to me, not because of anything United did. Really unbelievable that they continue to operate this way and treat PAYING customers like this. It's sad actually.

DCA
ORD
Excellent 10.0

Everyone was very helpful and very friendly. I had recently visited my,daughter and her family in March and flew with another airlines. I didn't have a good experience, they seemed rather bothered when I asked for some help. So this time my daughter booked my flight with United. Like I said everyone was helpful and very pleasant, it didn't seem to be an act. I enjoyed my flights. Thank you

Nothing

DCA
ORD
Good 6.0

Captain came out and talked with us

Delay seemed very avoidable.

Tue, Apr 3
DCA
MDW
5h 11m
Sat, Apr 7
MDW
DCA
5h 23m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

JFK
CDG
Excellent 10.0

The food and the service

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

GDL
ATL
Excellent 9.6

Expensive food

FLL
DTW
Excellent 10.0

I like service

Show more results

Washington to Chicago Flight Information

Avg. Flight Duration 1h 58m
Flights Arrive in Chicago
Flights Depart from Washington
Flight Price $160
Distance 594 miles
Airlines United, JetBlue, American Airlines, Major Airline, Delta
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

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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.