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 10/24. 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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Flight 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

Sun, Oct 5 - Tue, Oct 7
Frontier Logo
10:17 am - 1:11 pmIAD-MDW
27h 54m1 stop
Frontier Logo
8:05 am - 7:46 pmMDW-IAD
10h 41m1 stop
$136Frontier
Find Deal
Sat, Oct 11 - Mon, Oct 13
Frontier Logo
4:22 pm - 10:47 pmIAD-MDW
7h 25m1 stop
Frontier Logo
9:00 am - 6:45 pmMDW-IAD
8h 45m1 stop
$137Frontier
Find Deal
Tue, Oct 14 - Fri, Oct 17
Frontier Logo
9:00 am - 1:38 pmIAD-MDW
5h 38m1 stop
Frontier Logo
9:45 am - 7:19 pmMDW-IAD
8h 34m1 stop
$139Frontier
Find Deal
Thu, Oct 2 - Mon, Oct 6
Frontier Logo
1:55 pm - 11:41 pmIAD-MDW
10h 46m1 stop
Frontier Logo
6:20 am - 12:55 pmMDW-IAD
5h 35m1 stop
$142Frontier
Find Deal
Fri, Oct 3 - Mon, Oct 6
United Airlines Logo
6:50 pm - 7:58 pmIAD-ORD
2h 08mnonstop
United Airlines Logo
9:20 pm - 12:21 amORD-IAD
2h 01mnonstop
$149United Airlines
Find Deal
Wed, Oct 1 - Fri, Oct 3
 Logo
9:15 am - 12:46 pmIAD-MDW
28h 31m2 stops
 Logo
5:15 pm - 11:39 pmMDW-IAD
5h 24m1 stop
Wed, Oct 8 - Wed, Oct 15
 Logo
9:00 am - 1:47 pmIAD-ORD
5h 47m1 stop
 Logo
6:18 pm - 12:22 pmORD-IAD
17h 04m1 stop
Wed, Oct 8 - Sun, Oct 12
United Airlines Logo
6:50 pm - 7:58 pmIAD-ORD
2h 08mnonstop
United Airlines Logo
8:50 am - 11:55 amORD-IAD
2h 05mnonstop
$164United Airlines
Find Deal
Wed, Dec 10 - Fri, Dec 12
Delta Logo
6:00 am - 9:55 amIAD-ORD
4h 55m1 stop
Delta Logo
5:03 pm - 11:08 pmORD-IAD
5h 05m1 stop
$197Delta
Find Deal
Wed, Oct 1 - Sat, Oct 4
Delta Logo
6:00 am - 8:40 amIAD-MDW
3h 40m1 stop
Delta Logo
6:15 pm - 11:26 pmMDW-IAD
4h 11m1 stop
$197Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Dulles offers the AeroTrain for quick terminal transfers.
Take the CTA Blue Line from ORD to downtown Chicago.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Frontier
Cheapest • from $136 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
IAD-ORD
Cheapest
IAD-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 51% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 12% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$136
Frontier
Sun 10/5Tue 10/7
IAD - MDW • 1 stop
Cheapest non-stop
$149
Typical prices: $232-465
United Airlines
Fri 10/3Mon 10/6
IAD - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Washington, D.C. Dulles Intl Airport to Chicago costs $226 on the route between Washington, D.C. Dulles Intl Airport (IAD) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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 September, where tickets cost $270 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $367 and $326 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.

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 $244 on average.

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 3% drop in price.
Most popular time to fly and prices are also 3% 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 $136 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, Delta, and Alaska Airlines 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 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $312 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 $211 or less one-way and $307 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.
7.9
DeltaOverall score based on 7960 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.2Boarding
8.5Crew
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Very small cramped plane for an international flight. Everything else was good, but it was maybe the smallest comfort-wise I've ever been on for longer than 3-4 hours and the trip was 7.5

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Flight was delayed 3 hours. No food and drink vouchers was provided. They offered a mini pretzel bag and water .

Staff was rude. Didn’t give water for 2 hours. Worst service

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

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.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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