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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $50

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. Dulles Intl Airport to Chicago departing on 5/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Washington, D.C. Dulles Intl Airport to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Washington, D.C. Dulles Intl Airport to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.
10:09 am - 4:38 pmIAD-ORD
7h 29m1 stop
8:43 am - 8:16 pmORD-IAD
10h 33m1 stop
$100Frontier
Find Deal
Tue, Mar 11 - Wed, Mar 12
8:44 pm - 7:45 amIAD-ORD
12h 01m1 stop
9:20 am - 4:56 pmORD-IAD
6h 36m1 stop
$103Frontier
Find Deal
Tue, Apr 1 - Thu, Apr 3
10:25 pm - 10:57 amIAD-ORD
13h 32m1 stop
8:43 am - 8:16 pmORD-IAD
10h 33m1 stop
$105Frontier
Find Deal
Mon, Mar 10 - Wed, Mar 12
6:30 am - 7:41 amIAD-ORD
2h 11mnonstop
1:28 pm - 4:30 pmORD-IAD
2h 02mnonstop
$178United Airlines
Find Deal
Tue, Apr 1 - Thu, Apr 3
6:00 am - 9:43 amIAD-ORD
4h 43m1 stop
8:50 am - 11:46 amORD-IAD
1h 56mnonstop
$188United Airlines
Find Deal
Tue, Mar 11 - Thu, Mar 13
3:05 pm - 9:47 pmIAD-ORD
7h 42m1 stop
6:15 pm - 11:00 pmORD-IAD
3h 45m1 stop
$194Delta
Find Deal
Tue, Mar 25 - Thu, Mar 27
12:45 pm - 7:09 pmIAD-ORD
7h 24m1 stop
6:20 am - 2:23 pmORD-IAD
7h 03m1 stop
Thu, May 1 - Mon, May 5
6:00 am - 9:31 amIAD-ORD
4h 31m1 stop
10:35 am - 7:19 pmORD-IAD
7h 44m1 stop
$197Delta
Find Deal
Thu, Mar 6 - Thu, Mar 13
12:37 pm - 6:19 pmIAD-ORD
6h 42m1 stop
7:12 pm - 8:18 amORD-IAD
12h 06m1 stop
Thu, Apr 24 - Sun, Apr 27
6:27 am - 10:39 amIAD-ORD
5h 12m1 stop
6:30 pm - 11:58 pmORD-IAD
4h 28m1 stop
$292American Airlines
Find Deal
Thu, Mar 13 - Sun, Mar 16

Frontier flights from Washington, D.C. Dulles Intl Airport to Chicago

Our best Frontier deals on Washington, D.C. Dulles Intl Airport to Chicago flight tickets
Frontier
Mar 11
IAD10:09 amWashington, D.C. Dulles Intl
7h 29m
1 stop
ORD4:38 pmChicago O'Hare Intl
Mar 12
ORD8:43 amChicago O'Hare Intl
10h 33m
1 stop
IAD8:16 pmWashington, D.C. Dulles Intl
Frontier
Apr 1
IAD8:44 pmWashington, D.C. Dulles Intl
12h 01m
1 stop
ORD7:45 amChicago O'Hare Intl
Apr 3
ORD9:20 amChicago O'Hare Intl
6h 36m
1 stop
IAD4:56 pmWashington, D.C. Dulles Intl
Frontier
Mar 10
IAD10:25 pmWashington, D.C. Dulles Intl
13h 32m
1 stop
ORD10:57 amChicago O'Hare Intl
Mar 12
ORD8:43 amChicago O'Hare Intl
10h 33m
1 stop
IAD8:16 pmWashington, D.C. Dulles Intl

United Airlines flights from Washington, D.C. Dulles Intl Airport to Chicago

Our best United Airlines deals on Washington, D.C. Dulles Intl Airport to Chicago flight tickets
United Airlines
Apr 1
IAD6:30 amWashington, D.C. Dulles Intl
2h 11m
ORD7:41 amChicago O'Hare Intl
Apr 3
ORD1:28 pmChicago O'Hare Intl
2h 02m
IAD4:30 pmWashington, D.C. Dulles Intl
United Airlines
Mar 11
IAD6:00 amWashington, D.C. Dulles Intl
4h 43m
1 stop
ORD9:43 amChicago O'Hare Intl
Mar 13
ORD8:50 amChicago O'Hare Intl
1h 56m
IAD11:46 amWashington, D.C. Dulles Intl
United Airlines
May 2
IAD6:22 amWashington, D.C. Dulles Intl
2h 12m
ORD7:34 amChicago O'Hare Intl
May 5
ORD9:05 pmChicago O'Hare Intl
1h 54m
IAD11:59 pmWashington, D.C. Dulles Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Washington, D.C. Dulles Intl Airport to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Washington, D.C. Dulles Intl Airport and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Washington, D.C. Dulles Intl Airport, with most prices found around $299. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from Washington, D.C. Dulles Intl Airport to Chicago during October average around $301.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $404. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. Dulles Intl Airport to Chicago for around $497.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. Dulles Intl Airport to Chicago during this time can be as low as $334. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $458.

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

Fly from Washington, D.C. Dulles Intl to Chicago O'Hare Intl for the best Washington, D.C. Dulles Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Washington, D.C. Dulles Intl Airport when booking 21 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $340 when searching 21 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. Dulles Intl Airport for as low as $231 on momondo.

What cabin class options are available on Washington, D.C. Dulles Intl to Chicago flights?

There are 4 cabin classes available to choose from on Washington, D.C. Dulles Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Washington, D.C. Dulles Intl Airport to Chicago flight prices changed over time?

As of February 2025, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 8% more expensive when compared to flights at the same time last year.

When to book flights from Washington, D.C. Dulles Intl Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. Dulles Intl Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Washington, D.C. Dulles Intl Airport to Chicago (IAD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. Dulles Intl Airport to Chicago

Best Price Found

$50

Fastest flight time

2h 08m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Washington, D.C. Dulles Intl Airport in the past 72 hours is $50. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $100.
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago takes 2h 08m
Direct flights go from Washington, D.C. Dulles Intl Airport to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Washington, D.C. Dulles Intl to Chicago by plane?

    The distance between Washington, D.C. Dulles Intl and Chicago is about 571.5 mi. Flights usually cover this in 2h 09m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Washington, D.C. Dulles Intl Airport to Chicago?

    Prices for flights from Washington, D.C. Dulles Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Washington, D.C. Dulles Intl Airport to Chicago?

  • How old do you have to be to fly from Washington, D.C. Dulles Intl Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Washington, D.C. Dulles Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Washington, D.C. Dulles Intl Airport to Chicago?

  • What is the most popular airline from Washington, D.C. Dulles Intl Airport to Chicago?


Best airlines flying from Washington, D.C. Dulles Intl Airport to Chicago

Compare and see reviews for airlines that fly from Washington, D.C. Dulles Intl Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $63Free CancellationRating
6.0
3,355 reviews
Search Frontier flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,219 reviews
Search Delta flights
United AirlinesPriceFrom $187Free CancellationRating
7.4
8,765 reviews
Search United Airlines flights
American AirlinesPriceFrom $364Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
  • United Airlines Flights From Washington, D.C. Dulles Intl Airport to Chicago

    United Airlines flies from Washington, D.C. Dulles Intl Airport to Chicago around 20 times per week, with 8,766 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Washington, D.C. Dulles Intl Airport to Chicago in the last 72 hours was $187 (round-trip), much lower than the average airfare cost of $342 for United Airlines flights on this route.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Washington, D.C..

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Washington, D.C. which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Washington, D.C. to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Washington, D.C..

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Washington, D.C. are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago