IAD - CHI

$78 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 8/13. 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
1 adult, Economy

KAYAK searches 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
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Flights Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Dulles Intl to Chicago

Wed, Sep 3 - Sat, Sep 6
Frontier Logo
9:30 am - 2:01 pmIAD-MDW
5h 31m1 stop
Frontier Logo
10:51 am - 6:24 pmMDW-IAD
6h 33m1 stop
$166Frontier
Find Deal
Mon, Aug 18 - Fri, Aug 22
Allegiant Air Logo
1:22 pm - 6:17 pmIAD-MDW
5h 55m1 stop
Allegiant Air Logo
9:32 am - 3:23 pmMDW-IAD
4h 51m1 stop
$174Allegiant Air
Find Deal
Sat, Aug 9 - Sat, Aug 23
Frontier Logo
4:07 pm - 10:33 pmIAD-MDW
7h 26m1 stop
Frontier Logo
6:10 am - 4:30 pmMDW-IAD
9h 20m1 stop
$178Frontier
Find Deal
Sat, Sep 13 - Mon, Sep 15
United Airlines Logo
3:45 pm - 5:00 pmIAD-ORD
2h 15mnonstop
United Airlines Logo
11:40 am - 2:37 pmORD-IAD
1h 57mnonstop
$223United Airlines
Find Deal
Wed, Aug 27 - Sun, Aug 31
United Airlines Logo
6:40 pm - 7:48 pmIAD-ORD
2h 08mnonstop
United Airlines Logo
11:40 am - 2:37 pmORD-IAD
1h 57mnonstop
$227United Airlines
Find Deal
Sat, Aug 30 - Tue, Sep 2
Delta Logo
5:25 pm - 9:12 pmIAD-MDW
4h 47m1 stop
Delta Logo
9:30 am - 11:26 pmMDW-IAD
12h 56m1 stop
$227Delta
Find Deal
Tue, Aug 26 - Wed, Sep 3
Delta Logo
7:22 am - 12:16 pmIAD-ORD
5h 54m1 stop
Delta Logo
3:30 pm - 11:21 pmORD-IAD
6h 51m1 stop
$237Delta
Find Deal
Thu, Aug 21 - Sun, Aug 24
 Logo
4:56 pm - 9:21 amIAD-ORD
17h 25m2 stops
 Logo
5:16 pm - 3:23 pmORD-IAD
21h 07m2 stops
Thu, Aug 28 - Sat, Aug 30
 Logo
4:56 pm - 9:21 amIAD-ORD
17h 25m2 stops
 Logo
5:16 pm - 10:44 amORD-IAD
16h 28m2 stops
Sat, Aug 30 - Sun, Aug 31
American Airlines Logo
1:18 pm - 7:08 pmIAD-ORD
6h 50m1 stop
American Airlines Logo
7:13 am - 12:48 pmORD-IAD
4h 35m1 stop
$258American Airlines
Find Deal
Expert advice

Expert advice for your flight from Dulles Intl to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
IAD

Dulles offers the AeroTrain and mobile lounges for quick terminal transfers. Plan your route with an airport map to save time.

Read more about IADby Stefanie Waldek
ORD

Take the CTA Blue Line from ORD to downtown Chicago in about 45 minutes, avoiding traffic and saving money.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD and IAD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Booking Insights

KAYAK's insights & trends for Dulles Intl to Chicago flights

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 round-trip flights from Washington, D.C. Dulles Intl Airport to Chicago.

Our data shows that the cheapest route for a return flight from Washington, D.C. Dulles Intl Airport to Chicago cost $227 and was between Washington, D.C. Dulles Intl Airport (IAD) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $227.

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

The average price of all round-trip flights from Washington, D.C. Dulles Intl Airport to Chicago clicked on KAYAK for each day over the last 12 months.

When flying from Washington Dulles Airport to Chicago, you should consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to Washington Dulles Airport, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

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 round-trip 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 January, where tickets cost $299 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $381 and $324 respectively.

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

The average round-trip 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.

No, with an average price for the route of $589, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Washington, D.C. Dulles Intl Airport to Chicago, you should book around 4 weeks before departure, which saves you about 51% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$78
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 4% lower on average.
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 $78 for a one-way ticket and $166 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, Hawaiian Airlines, Alaska Airlines, and Delta 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 737-900 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 $236 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 $314 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.

KAYAK’s top tips for finding a cheap flight from Washington, D.C. Dulles Intl Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $222 or less one-way and $335 or less round-trip.

Prefer to fly direct from Washington Dulles Airport to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Washington, D.C. Dulles Intl to Chicago.
Find which airlines fly direct from Washington, D.C. Dulles Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Washington, D.C. Dulles Intl to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Washington, D.C. Dulles Intl

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the 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 7980 reviews
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
7.9Comfort
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

We were given vouchers we couldn’t use with a 5.5 hour delay

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

I fly UAL 7-8 times per year. This flight was not up to snuff because it boarded very late "due to unexpected delays in restocking the plane" and yet Flight Aware showed the plane had landed some 10 hours earlier--so I think they could have planned accordingly. The FA's were nice but harried. The video system had to be rebooted 3-4 times. The food service was rather abrupt; they forgot my row and when I asked for my meal, they brought it with some impatience. Overall, the flight was fine, but the little details made it feel somewhat mundane and hurried.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Everything you need to know for your flight from Dulles Intl to Chicago

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