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IAD - CHI

$85 Find cheap flights from Washington Dulles Airport to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Dulles Intl to Chicago departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 6/5
Wed 6/12

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,830,901 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Dulles Intl to Chicago (IAD-CHI)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Dulles Intl to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:24 am - 9:35 amIAD-ORD
2h 11mnonstop
8:47 am - 11:46 amORD-IAD
1h 59mnonstop
$169United Airlines
Find Deal
Tue, May 28 - Fri, May 31
12:33 pm - 7:10 pmIAD-ORD
7h 37m1 stop
6:55 pm - 10:30 amORD-IAD
14h 35m1 stop
$183Sun Country Air
Find Deal
Mon, Jul 8 - Tue, Jul 9
6:00 am - 9:20 amIAD-ORD
4h 20m1 stop
12:29 pm - 7:04 pmORD-IAD
5h 35m1 stop
$188Delta
Find Deal
Tue, May 28 - Thu, May 30
6:10 am - 8:49 amIAD-MDW
3h 39m1 stop
6:00 am - 11:40 amMDW-IAD
4h 40m1 stop
$188Delta
Find Deal
Tue, Jul 2 - Wed, Jul 10
8:30 am - 8:03 pmIAD-ORD
12h 33m1 stop
10:58 am - 4:10 pmORD-IAD
28h 12m3 stops
Thu, May 30 - Sun, Jun 2
8:25 am - 10:01 amIAD-ORD
26h 36m3 stops
8:05 pm - 10:37 amORD-IAD
13h 32m1 stop
Sat, Jun 8 - Mon, Jun 10
12:45 pm - 9:46 pmIAD-ORD
10h 01m1 stop
7:00 am - 9:55 amORD-IAD
1h 55mnonstop
$295Spirit Airlines
Find Deal
Sat, May 25 - Sun, May 26
2:14 pm - 5:26 pmIAD-ORD
4h 12m1 stop
5:15 am - 11:15 amORD-IAD
5h 00m1 stop
$304American Airlines
Find Deal
Fri, May 31 - Sun, Jun 2
11:48 am - 3:46 pmIAD-ORD
4h 58m1 stop
6:30 am - 2:57 pmORD-IAD
7h 27m1 stop
$310American Airlines
Find Deal
Thu, May 23 - Sun, May 26
10:20 pm - 6:26 amIAD-ORD
9h 06m1 stop
12:34 pm - 7:26 amORD-IAD
17h 52m2 stops
$330Spirit Airlines
Find Deal
Sat, May 25 - Sun, May 26

Flights from Dulles Intl to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Dulles Intl to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Washington, D.C. Dulles Intl Airport to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Washington, D.C. Dulles Intl Airport to Chicago.
Our data shows that the cheapest route for a one-way flight from Washington, D.C. Dulles Intl Airport to Chicago cost $104 and was between Washington, D.C. Dulles Intl Airport and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport. The average price for a return flight for this route is $198.

What’s the cheapest day of the week to fly from Washington Dulles Airport to Chicago?

The average price of all flights from Washington, D.C. Dulles Intl Airport to Chicago clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago on a Wednesday and more expensive on a Friday. On your return trip to Washington Dulles Airport, you should consider flying back on a Thursday, and avoid Sundays for better deals.

What is the cheapest month to fly from Washington, D.C. Dulles Intl Airport to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Washington, D.C. Dulles Intl Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Washington, D.C. Dulles Intl Airport to Chicago is April, where tickets cost $233 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $329 and $301 respectively.

Can I save money by flying with a layover from Washington, D.C. Dulles Intl Airport to Chicago?

The average price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $199 on average

How far in advance should I book a flight from Washington, D.C. Dulles Intl Airport to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Washington, D.C. Dulles Intl Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Washington, D.C. Dulles Intl Airport to Chicago, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 60 days before departure.

Which airlines provide the cheapest flights from Washington Dulles Airport to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, United Airlines offered the best one-way deal for that route, at $85. KAYAK users also found Washington Dulles Airport to Chicago round-trip flights on United Airlines from $169 and on Sun Country Air from $183.

Which airlines fly non-stop between Washington, D.C. Dulles Intl Airport and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Washington, D.C. Dulles Intl Airport to Chicago.
There is just one airline that flies from Washington, D.C. Dulles Intl Airport to Chicago direct and that is United Airlines. The best one-way deal found from United Airlines for the route is $178.

How many flights are there between Washington, D.C. Dulles Intl Airport and Chicago per day?

Each day, there are between 9 and 10 nonstop flights that take off from Washington, D.C. Dulles Intl Airport and land in Chicago, with an average flight time of 2h 11m. The most common departure time is 5:00 pm and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 64 flights. The most frequent day of departure is Wednesday, when 16% of all weekly flights depart. The fewest flights depart on a Thursday.

Which cabin class options are there for flights between Washington, D.C. Dulles Intl Airport and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Washington Dulles Airport to Chicago take?

Nonstop flights from Washington Dulles Airport generally make it to Chicago in 2h 04m. The flying distance between the two cities is 572 miles.

What’s the earliest departure time from Washington Dulles Airport to Chicago?

Early birds can take the earliest flight from Washington, D.C. Dulles Intl Airport at 6:30 am and will be landing in Chicago at 7:40 am.

What’s the latest departure time from Washington Dulles Airport to Chicago?

If you prefer to fly at night, the latest flight from Washington, D.C. Dulles Intl Airport to Chicago jets off at 10:23 pm and lands at 11:30 pm.

Good to know

Low season

January

High season

May

Cheapest flight

$85
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Washington Dulles Airport to Chicago O'Hare Airport

When to book flights from Dulles Intl to Chicago

Are your dates flexible? Find out the best times to travel from Dulles Intl to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Washington Dulles Airport to Chicago flights

  • What is the cheapest flight from Washington, D.C. Dulles Intl Airport to Chicago?

    In the last 3 days, the lowest price for a flight from Washington, D.C. Dulles Intl Airport to Chicago was $85 for a one-way ticket and $169 for a round-trip.

  • Do I need a passport to fly between Washington Dulles Airport and Chicago?

    No

  • Which airports will I be using when flying from Washington Dulles Airport to Chicago?

    On your way to Chicago, you’ll fly out from Washington, D.C. Dulles Intl. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Washington Dulles Airport to Chicago?

    American Airlines, Alaska Airlines, Delta, and Lufthansa offer inflight Wi-Fi service on the Washington Dulles Airport to Chicago flight route.

  • Which aircraft models fly most regularly from Washington Dulles Airport to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Washington Dulles Airport to Chicago flight route.

  • Which airline alliances offer flights from Washington Dulles Airport to Chicago?

    Star Alliance is the only airline alliance operating flights between Washington Dulles Airport and Chicago.

  • On which days can I fly direct from Washington Dulles Airport to Chicago?

    There are nonstop flights from Washington Dulles Airport to Chicago on a daily basis.

  • Which is the best airline for flights from Washington, D.C. to Chicago, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Delta and United Airlines. With an average price for the route of $227 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $324 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Washington Dulles Airport to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Washington Dulles Airport to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington Dulles Airport to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Washington Dulles Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Washington Dulles Airport to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Washington Dulles Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Washington Dulles Airport to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Washington Dulles Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Washington, D.C. to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $166 or less one-way and $307 or less round-trip.

Prefer to fly non-stop from Washington Dulles Airport to Chicago?

Find which airlines fly direct from Dulles Intl to Chicago, which days they fly and book direct flights.

Nonstop departures

Washington, D.C. Dulles Intl to Chicago

Monday

ANA, Air Canada, Air New Zealand, +5 more

ANA, Air Canada, +6 more

Tuesday

ANA, Air Canada, Air China, +7 more

ANA, Air Canada, +8 more

Wednesday

ANA, Air Canada, Air New Zealand, +5 more

ANA, Air Canada, +6 more

Thursday

ANA, Air Canada, Air New Zealand, +6 more

ANA, Air Canada, +7 more

Friday

ANA, Air Canada, Air New Zealand, +5 more

ANA, Air Canada, +6 more

Saturday

ANA, Air Canada, Air China, +7 more

ANA, Air Canada, +8 more

Sunday

ANA, Air Canada, Air New Zealand, +6 more

ANA, Air Canada, +7 more

See more direct flights

Nonstop returns

Chicago to Washington, D.C. Dulles Intl

Monday

ANA, Air Canada, Air New Zealand, +5 more

ANA, Air Canada, +6 more

Tuesday

ANA, Air Canada, Air China, +6 more

ANA, Air Canada, +7 more

Wednesday

ANA, Air Canada, Air New Zealand, +5 more

ANA, Air Canada, +6 more

Thursday

ANA, Air Canada, Air New Zealand, +5 more

ANA, Air Canada, +6 more

Friday

ANA, Air Canada, Air New Zealand, +5 more

ANA, Air Canada, +6 more

Saturday

ANA, Air Canada, Air China, +7 more

ANA, Air Canada, +8 more

Sunday

ANA, Air Canada, Air New Zealand, +5 more

ANA, Air Canada, +6 more

See more direct flights
See more direct flights

Top 3 airlines serving from Dulles Intl to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Dulles Intl to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10826 reviews
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

10.0 ExcellentBranton, May 2024AVL - ATL
Read more about Delta reviews

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

they made me check my carryon. There was space in the overhead bins.

The plane was delayed 2 hours. The wifi did not work. The seat in first class was not comfortable because the bottom felt like it lost all of its padding. And I did not like when the flight attendant made me wait at my seat to use the bathroom and didn't tell me why. If there were too many people using the 1st Class bathroom, she should have told me to go in the back, coach bathrooms. I guess I have to feel fortunate that they found 2 local pilots to still fly the plane tonight after the original pilots ended up at an airport 60 miles away due to high winds.

The crew were really great, but the 4 hour delay in small chunks was the worst.

Just a crappy airline. The same every time. You feel you are a cow on a farm. You are being being whipped and pulled.

Wasn’t very crowded. Seamless processes. No issues traveling with two little kids.

My interaction with the flight attendent Eve was horrible. I was seated in 3F and was blown away watching her repeatedly skip me as she took other customer orders for lunch...she took the customer next to me but skipped me, then took everyone's order around me (in front of and behind me) . After she had taken every customer's orders to include those behind me, she came to me and said we are out of everything except one last item. I was mortified, in that, I am a 1k flyer, had pre-ordered AND as an African American could only assume why she repeatedly skipped me...mortified. no words

The Flight was good, pilot seemed very skillful. My wheel chair sister who could barely walk was allotted the second last seat in the aircraft, with great difficulty she managed to reach on her seat, as she required attendance we were given separate seat, even on request no one cared, so much so there were single passengers who were given twin seats. May not be taken as complaint but a reminder to the checkin staff to keep in mind in future the allottment of wheel chair passengers seats.

Almost 2 hour delay in boarding with all standing ready to board at original time. No explanation given.

787-9 Transcon from IAD-LAX FYI no meals in premium plus, not considered Premium - seats are wonderful https://www.united.com/ual/en/us/fly/travel/inflight/premium-services.html Horrible handling of delayed flight

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Washington, D.C. to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Washington, D.C. to Chicago found on KAYAK in the last 72 hours.
5/28Tue
nonstopUnited Airlines
2h 10mIAD-ORD
$85
6/5Wed
1 stopSun Country Air
8h 43mIAD-ORD
$86
7/5Fri
1 stopDelta
4h 11mIAD-ORD
$94
5/28Tue
1 stopDelta
4h 06mIAD-MDW
$94
5/21Tue
3 stops
25h 20mIAD-ORD
$117
5/31Fri
1 stopAmerican Airlines
4h 12mIAD-ORD
$128
6/11Tue
3 stops
23h 53mIAD-ORD
$129
5/21Tue
1 stopAmerican Airlines
6h 24mIAD-ORD
$183
7/18Thu
2 stopsAllegiant Air
27h 43mIAD-MDW
$183
5/16Thu
2 stopsAllegiant Air
22h 59mIAD-MDW
$191

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Last minute flights from Dulles Intl to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Washington, D.C. to Chicago that are departing in the next 10 days.
5/10Fri
nonstopUnited Airlines
2h 11mIAD-ORD
5/10Fri
multi-stopUnited Airlines
20h 45mORD-IAD
$363
5/6Mon
multi-stop
28h 46mIAD-ORD
8/15Thu
multi-stop
15h 22mORD-IAD
$391
5/7Tue
multi-stopUnited Airlines
22h 56mIAD-ORD
5/8Wed
nonstopUnited Airlines
1h 58mORD-IAD
$419
5/9Thu
multi-stopSun Country Air
6h 38mIAD-ORD
5/16Thu
multi-stopSun Country Air
16h 02mORD-IAD
$452
5/6Mon
multi-stopDelta
4h 57mIAD-ORD
8/15Thu
multi-stopDelta
5h 40mORD-IAD
$459
5/8Wed
multi-stopAmerican Airlines
4h 12mIAD-ORD
5/11Sat
multi-stopAmerican Airlines
6h 28mORD-IAD
$485
5/7Tue
multi-stopDelta
5h 18mIAD-ORD
5/8Wed
multi-stopDelta
3h 17mORD-IAD
$488
5/7Tue
multi-stopAmerican Airlines
6h 26mIAD-ORD
5/13Mon
multi-stopAmerican Airlines
4h 34mORD-IAD
$490
5/6Mon
multi-stopSouthwest
11h 05mIAD-ORD
5/10Fri
multi-stopSouthwest
10h 20mORD-IAD
$502
5/6Mon
multi-stopSouthwest
9h 40mIAD-MDW
5/9Thu
multi-stopSouthwest
10h 25mMDW-IAD
$599

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Washington Dulles Airport - Chicago Flights

Departure:

Washington Dulles Airport (IAD)United States

Return flight deals:

Chicago - Washington Dulles Airport

Cabin classes:

$959
$614
$936
$198