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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $74

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 6/5. 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

Frontier Logo
6:00 am - 10:26 amIAD-ORD
5h 26m1 stop
Frontier Logo
10:25 am - 4:13 pmORD-IAD
4h 48m1 stop
$158Frontier
Find Deal
Thu, Sep 4 - Mon, Sep 8
Frontier Logo
5:15 am - 1:45 pmIAD-ORD
9h 30m1 stop
Frontier Logo
5:01 am - 3:29 pmORD-IAD
9h 28m1 stop
$160Frontier
Find Deal
Wed, Jun 4 - Sat, Jun 7
United Airlines Logo
6:48 am - 8:02 amIAD-ORD
2h 14mnonstop
United Airlines Logo
8:52 am - 11:55 amORD-IAD
2h 03mnonstop
$179United Airlines
Find Deal
Wed, May 28 - Fri, May 30
United Airlines Logo
8:30 am - 9:43 amIAD-ORD
2h 13mnonstop
United Airlines Logo
2:24 pm - 5:30 pmORD-IAD
2h 06mnonstop
$195United Airlines
Find Deal
Mon, Jun 30 - Wed, Jul 2
Delta Logo
5:29 pm - 9:24 pmIAD-ORD
4h 55m1 stop
Delta Logo
5:35 am - 12:48 pmORD-IAD
6h 13m1 stop
$197Delta
Find Deal
Tue, Jul 1 - Sat, Jul 5
Delta Logo
1:00 pm - 6:41 pmIAD-MDW
6h 41m1 stop
Delta Logo
6:20 pm - 10:55 pmMDW-IAD
3h 35m1 stop
$197Delta
Find Deal
Tue, Jul 1 - Fri, Jul 4
Allegiant Air Logo
1:42 pm - 5:02 pmIAD-MDW
4h 20m1 stop
Allegiant Air Logo
4:46 pm - 11:19 amMDW-IAD
17h 33m1 stop
$207Allegiant Air
Find Deal
Fri, Oct 31 - Sun, Nov 2
Allegiant Air Logo
3:53 pm - 7:13 amIAD-MDW
16h 20m1 stop
Allegiant Air Logo
11:07 am - 2:23 pmMDW-IAD
26h 16m2 stops
$270Allegiant Air
Find Deal
Thu, Aug 7 - Sun, Aug 10
American Airlines Logo
8:06 pm - 11:57 pmIAD-ORD
4h 51m1 stop
American Airlines Logo
5:15 am - 12:49 pmORD-IAD
6h 34m1 stop
$317American Airlines
Find Deal
Fri, Jul 18 - Sun, Jul 20
American Airlines Logo
5:02 am - 9:01 amIAD-ORD
4h 59m1 stop
American Airlines Logo
1:34 pm - 7:32 pmORD-IAD
4h 58m1 stop
$319American Airlines
Find Deal
Thu, May 29 - Thu, May 29

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
Sep 4
IAD6:00 amWashington, D.C. Dulles Intl
5h 26m
1 stop
ORD10:26 amChicago O'Hare Intl
Sep 8
ORD10:25 amChicago O'Hare Intl
4h 48m
1 stop
IAD4:13 pmWashington, D.C. Dulles Intl
Frontier
Jun 4
IAD5:15 amWashington, D.C. Dulles Intl
9h 30m
1 stop
ORD1:45 pmChicago O'Hare Intl
Jun 7
ORD5:01 amChicago O'Hare Intl
9h 28m
1 stop
IAD3:29 pmWashington, D.C. Dulles Intl
Frontier
Jun 4
IAD5:15 amWashington, D.C. Dulles Intl
9h 30m
1 stop
ORD1:45 pmChicago O'Hare Intl
Jun 7
ORD5:01 amChicago O'Hare Intl
9h 28m
1 stop
IAD3:29 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
May 28
IAD6:48 amWashington, D.C. Dulles Intl
2h 14m
ORD8:02 amChicago O'Hare Intl
May 30
ORD8:52 amChicago O'Hare Intl
2h 03m
IAD11:55 amWashington, D.C. Dulles Intl
United Airlines
Jun 30
IAD8:30 amWashington, D.C. Dulles Intl
2h 13m
ORD9:43 amChicago O'Hare Intl
Jul 2
ORD2:24 pmChicago O'Hare Intl
2h 06m
IAD5:30 pmWashington, D.C. Dulles Intl
United Airlines
May 31
IAD1:20 pmWashington, D.C. Dulles Intl
2h 13m
ORD2:33 pmChicago O'Hare Intl
Jun 21
ORD9:31 pmChicago O'Hare Intl
1h 59m
IAD12:30 amWashington, 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 cheapest month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Washington, D.C. Dulles Intl Airport, with most prices found around $298. If you’re not able to fly to Chicago in July, then January is your next best option. Flight prices from Washington, D.C. Dulles Intl Airport to Chicago during January average around $299.

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 $392. 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 $492.

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 $333. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $444.

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 6 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $332 when searching 6 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 $268 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 May 2025, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 38% cheaper 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

$74

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 $74. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $158.
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 11m, 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 $87Free CancellationRating
5.9
3,284 reviews
Search Frontier flights
United AirlinesPriceFrom $161Free CancellationRating
7.4
8,730 reviews
Search United Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
7,946 reviews
Search Delta 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 50 times per week, with 8,730 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 $161 (round-trip), much lower than the average airfare cost of $340 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
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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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1 adult
Mon 5/19
Mon 5/26

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