IAD - CHI

$99 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 7/8. 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, 0 bags

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

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

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

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

Everything you should know

Cheapest round-trip
$247
Typical prices: $419-$244
Frontier
Thu 8/27Sun 8/30
IAD - ORD • 1 stop
Cheapest non-stop
$247
Typical prices: $516-$289
United Airlines
Sat 7/11Mon 7/13
IAD - ORD • Non-stop
Top airlines
Cheapest • from $247 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 2h 17m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $198 (round-trip)
Shortest trip • 3h 39m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 54% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 62% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
Flight Deals
Booking Insights
Expert advice
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

Thu, Aug 27 - Sun, Aug 30
Frontier Logo
8:47 pm - 8:03 am
IAD
-
ORD
12h 16m
1 stop
Frontier Logo
6:55 am - 4:20 pm
ORD
-
IAD
8h 25m
1 stop
$247Frontier
Thu, Aug 27 - Sun, Aug 30
Frontier Logo
11:11 am - 10:11 pm
IAD
-
MDW
12h 00m
1 stop
Frontier Logo
6:00 am - 4:20 pm
MDW
-
IAD
9h 20m
1 stop
$247Frontier
Fri, Aug 21 - Sun, Aug 23
Frontier Logo
8:47 pm - 8:03 am
IAD
-
ORD
12h 16m
1 stop
Frontier Logo
6:55 am - 4:20 pm
ORD
-
IAD
8h 25m
1 stop
$248Frontier
Fri, Aug 21 - Sun, Aug 23
Frontier Logo
11:12 am - 10:11 pm
IAD
-
MDW
11h 59m
1 stop
Frontier Logo
6:00 am - 4:20 pm
MDW
-
IAD
9h 20m
1 stop
$248Frontier
Mon, Jul 13 - Tue, Jul 21
Frontier Logo
8:33 pm - 7:53 am
IAD
-
ORD
12h 20m
1 stop
Frontier Logo
1:50 pm - 10:55 pm
ORD
-
IAD
8h 05m
1 stop
$249Frontier
Sun, Jul 12 - Tue, Jul 21
Frontier Logo
8:33 pm - 7:53 am
IAD
-
ORD
12h 20m
1 stop
Frontier Logo
7:05 am - 4:40 pm
ORD
-
IAD
8h 35m
1 stop
$250Frontier
Tue, Jul 21 - Fri, Jul 24
United Airlines Logo
3:39 pm - 5:02 pm
IAD
-
ORD
2h 23mnonstop
United Airlines Logo
1:30 pm - 4:30 pm
ORD
-
IAD
2h 00mnonstop
$253United Airlines
Tue, Jul 14 - Wed, Jul 15
Delta Logo
10:21 am - 4:15 pm
IAD
-
MDW
6h 54m
1 stop
Delta Logo
6:00 am - 11:37 am
MDW
-
IAD
4h 37m
1 stop
$253Delta
Wed, Jul 15 - Sat, Jul 18
Delta Logo
5:26 pm - 8:31 pm
IAD
-
ORD
4h 05m
1 stop
Delta Logo
7:05 am - 11:47 am
ORD
-
IAD
3h 42m
1 stop
$257Delta
Mon, Jul 13 - Wed, Jul 15
Delta Logo
5:46 pm - 10:15 pm
IAD
-
MDW
5h 29m
1 stop
Delta Logo
6:00 am - 11:37 am
MDW
-
IAD
4h 37m
1 stop
$257Delta
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.

How much is a round-trip flight from Washington, D.C. Dulles Intl Airport to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Washington, D.C. Dulles Intl Airport to Chicago departing in August.

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 $258 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 Thursday 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 $38 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $197 and $138 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 $269 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 54% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Expert advice

Expert advice for your flight from Dulles Intl to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD and IAD

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.

Good to know

Low seasonFebruary
Cheapest flight$99
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 7% 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 5 days, the lowest price for a flight from Washington, D.C. Dulles Intl Airport to Chicago was $99 for a one-way ticket and $247 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, 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?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Washington Dulles Airport and Chicago, with SkyTeam being the most commonly used for this route.

  • 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, United Airlines or Frontier?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are United Airlines and Frontier. With an average price for the route of $334 and an overall rating of 7.4, United Airlines is the most popular choice. Frontier is also a great choice for the route, with an average price of $197 and an overall rating of 5.6.

  • 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 $242 or less one-way and $353 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 airlines flying 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.
7.4
United AirlinesOverall score based on 9831 reviews
6.6Food
7.1Entertainment
8.1Crew
7.7Boarding
7.3Comfort
Airline reviews

Like: departed and arrived on time. Unlike: Food options for purchase allways bad, 1 of 2 of the crew members not very friendly at all. Seats and leg room aweful. At this point I am thinking on switching to AA.

6.0 GoodEnrique, Jun 2026
IAD - LAX
Read more United Airlines reviews

Like: departed and arrived on time. Unlike: Food options for purchase allways bad, 1 of 2 of the crew members not very friendly at all. Seats and leg room aweful. At this point I am thinking on switching to AA.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

Our flight was canceled same day and we were never informed. Had to pay more and worse seating on another airline.

Did not like that we couldn't complete check in on-line without providing pictures of our passports. Worry about identity theft. We had no delays and boarding was handled In an efficient manner.

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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

Information on your arrival and departure airports