IAD - CHI

$67 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 2/21. 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

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Everything you should know

Cheapest round-trip
$147
Overall average: $369
Frontier
Mon 2/23Fri 2/27
IAD - ORD • 1 stop
Cheapest non-stop
$231
Typical prices: $284-$558
United Airlines
Tue 2/24Tue 3/3
IAD - ORD • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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 $147 (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 55% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 15% price drop
July
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

Mon, Feb 23 - Fri, Feb 27
Frontier Logo
11:41 am - 10:39 pm
IAD
-
ORD
11h 58m
1 stop
Frontier Logo
5:05 am - 4:24 pm
ORD
-
IAD
10h 19m
1 stop
$147Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
5:37 pm - 10:37 pm
IAD
-
MDW
6h 00m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$148Frontier
Thu, Feb 19 - Mon, Mar 2
Frontier Logo
11:22 am - 10:39 pm
IAD
-
ORD
12h 17m
1 stop
Frontier Logo
5:05 am - 4:08 pm
ORD
-
IAD
10h 03m
1 stop
$154Frontier
Mon, Feb 23 - Mon, Mar 2
Frontier Logo
5:22 pm - 10:29 pm
IAD
-
MDW
6h 07m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$154Frontier
Sat, Feb 28 - Mon, Mar 2
Frontier Logo
10:29 am - 10:39 pm
IAD
-
ORD
13h 10m
1 stop
Frontier Logo
5:05 am - 4:08 pm
ORD
-
IAD
10h 03m
1 stop
$155Frontier
Mon, Feb 23 - Mon, Mar 2
Frontier Logo
11:41 am - 10:39 pm
IAD
-
ORD
11h 58m
1 stop
Frontier Logo
5:05 am - 4:08 pm
ORD
-
IAD
10h 03m
1 stop
$156Frontier
Mon, Feb 23 - Mon, Mar 2
Frontier Logo
5:22 pm - 10:29 pm
IAD
-
MDW
6h 07m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$156Frontier
Mon, Feb 23 - Sat, Feb 28
Frontier Logo
5:22 pm - 10:39 pm
IAD
-
ORD
6h 17m
1 stop
Frontier Logo
4:42 pm - 10:30 am
ORD
-
IAD
16h 48m
1 stop
$158Frontier
Mon, Feb 23 - Tue, Mar 3
Multiple Airlines Logo
5:22 pm - 10:39 pm
IAD
-
ORD
6h 17m
1 stop
Multiple Airlines Logo
6:51 pm - 10:33 am
ORD
-
IAD
38h 42m
2 stops
$159Multiple Airlines
Mon, Feb 23 - Wed, Feb 25
Multiple Airlines Logo
5:22 pm - 10:39 pm
IAD
-
ORD
6h 17m
1 stop
Multiple Airlines Logo
6:51 pm - 4:43 pm
ORD
-
IAD
20h 52m
2 stops
$164Multiple Airlines
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 $267 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 October, where tickets cost $261 (return) on average. On the other hand, the most expensive months are January and March, where the average cost of round-trip tickets is $405 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 $263 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 55% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 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$67
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 $67 for a one-way ticket and $147 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, 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?

    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, 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 $313 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 $246 or less one-way and $342 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 8121 reviews
7.8Entertainment
7.2Food
7.9Comfort
8.5Crew
8.1Boarding
Airline reviews

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

10.0 ExcellentSenthil Kumar, Jan 2026
PDX - ATL
Read more Delta reviews

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Ineffective communication with United resulted in lost baggage. Their Baggage Tracing counter at MUC was shut down from 11:00-14:15 on my arrival. Undertrained, underinformed staff had me Running all over MUC to find someone to help me to no avail. Staff was rude, unhelpful, and unable to effectively use the systems they did have operational. They refused to contact United in any way or provide any accommodation or other resources while I waited for my luggage. This has destroyed my downstream itinerary. If they had even the slightest visibility I may have been able to reschedule/plan, but again, their staff provided nothing, and did nothing more than their website, which doesn’t even work on a standard phone browser. Miserable failure at all levels that weren’t associated with the operation of the aircraft.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Sat next to a one year old. She crawled all over the place and made me laugh.

They did the one thing that really matters - got to Chicago early.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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

Information on your arrival and departure airports