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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $54

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 1/16. 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.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Washington, D.C. Dulles Intl Airport to Chicago.

Cheap last minute flights

Planning a quick getaway from Washington, D.C. Dulles Intl Airport to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Washington, D.C. Dulles Intl Airport to Chicago

Find recent round-trip train or bus tickets from Washington, D.C. Dulles Intl Airport to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
8:05 am - 5:54 pmIAD-MDW
10h 49m1 stop
6:50 am - 4:28 pmMDW-IAD
8h 38m1 stop
$108Frontier
Find Deal
Tue, Dec 17 - Wed, Dec 18
12:58 pm - 8:45 pmIAD-ORD
8h 47m1 stop
8:33 am - 2:39 pmORD-IAD
5h 06m1 stop
$118Frontier
Find Deal
Fri, Feb 7 - Wed, Feb 12
10:16 pm - 11:20 pmIAD-ORD
2h 04mnonstop
6:16 pm - 9:16 pmORD-IAD
2h 00mnonstop
$197United Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
1:15 pm - 2:34 pmIAD-ORD
2h 19mnonstop
6:08 pm - 9:01 pmORD-IAD
1h 53mnonstop
$207United Airlines
Find Deal
Wed, Jan 8 - Thu, Jan 9
5:35 pm - 8:28 pmIAD-ORD
3h 53m1 stop
3:40 pm - 9:29 pmORD-IAD
4h 49m1 stop
$216Delta
Find Deal
Tue, Dec 17 - Wed, Dec 18
6:00 am - 8:54 amIAD-MDW
3h 54m1 stop
9:34 am - 3:53 pmMDW-IAD
5h 19m1 stop
$216Delta
Find Deal
Tue, Jan 14 - Wed, Jan 15
5:00 am - 8:45 amIAD-ORD
4h 45m1 stop
12:25 pm - 7:28 pmORD-IAD
6h 03m1 stop
$256American Airlines
Find Deal
Thu, Dec 12 - Sat, Dec 14
5:00 am - 8:45 amIAD-ORD
4h 45m1 stop
12:25 pm - 7:28 pmORD-IAD
6h 03m1 stop
$271American Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
11:00 am - 5:29 pmIAD-ORD
7h 29m1 stop
8:00 pm - 11:00 amORD-IAD
14h 00m1 stop
$275Sun Country Air
Find Deal
Thu, Apr 3 - Sun, Apr 6
12:31 pm - 6:19 pmIAD-ORD
6h 48m1 stop
7:00 pm - 10:43 amORD-IAD
14h 43m1 stop
$305Sun Country Air
Find Deal
Thu, Apr 17 - Sun, Apr 20
8:15 am - 1:50 pmIAD-ORD
6h 35m1 stop
$54Frontier
Find Deal
Thu, Jan 16
4:42 pm - 11:14 pmIAD-MDW
7h 32m1 stop
$54Frontier
Find Deal
Mon, Jan 6
10:16 pm - 11:22 pmIAD-ORD
2h 06mnonstop
$99United Airlines
Find Deal
Sat, Feb 1
5:57 pm - 11:59 pmIAD-ORD
7h 02m1 stop
$108Delta
Find Deal
Wed, Jan 15
6:00 am - 8:50 amIAD-MDW
3h 50m1 stop
$108Delta
Find Deal
Wed, Dec 25
12:45 pm - 2:03 pmIAD-ORD
2h 18mnonstop
$109United Airlines
Find Deal
Thu, Feb 13
5:00 am - 10:33 amIAD-ORD
6h 33m1 stop
$128American Airlines
Find Deal
Thu, Dec 12
9:15 pm - 8:00 pmIAD-ORD
23h 45m2 stops
Thu, Dec 19
12:55 pm - 12:34 amIAD-ORD
12h 39m3 stops
Wed, Dec 4
5:00 am - 11:01 amIAD-ORD
7h 01m1 stop
$161American Airlines
Find Deal
Fri, Jan 3
8:48 am - 5:12 pmIAD-MDW
9h 24m1 stop
8:50 am - 5:40 pmMDW-IAD
7h 50m1 stop
$272Frontier
Find Deal
Tue, Nov 26 - Thu, Nov 28
8:48 am - 5:58 pmIAD-MDW
10h 10m1 stop
8:50 am - 5:40 pmMDW-IAD
7h 50m1 stop
$328Frontier
Find Deal
Sun, Nov 24 - Tue, Nov 26
6:20 am - 7:34 amIAD-ORD
2h 14mnonstop
10:35 am - 7:25 amORD-IAD
19h 50m1 stop
$369United Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 23
8:48 am - 5:00 pmIAD-ORD
9h 12m1 stop
7:50 pm - 11:25 amORD-IAD
14h 35m1 stop
Sun, Nov 24 - Wed, Nov 27
10:15 pm - 1:27 pmIAD-ORD
16h 12m1 stop
3:56 pm - 6:50 pmORD-IAD
1h 54mnonstop
$409United Airlines
Find Deal
Sat, Nov 23 - Sun, Nov 24
6:00 am - 8:50 amIAD-MDW
3h 50m1 stop
5:42 pm - 11:22 pmMDW-IAD
4h 40m1 stop
$498Delta
Find Deal
Tue, Nov 26 - Tue, Dec 3
1:33 pm - 5:02 pmIAD-MDW
4h 29m1 stop
5:42 pm - 11:22 pmMDW-IAD
4h 40m1 stop
$512Delta
Find Deal
Mon, Nov 25 - Wed, Nov 27
12:55 pm - 9:20 amIAD-ORD
21h 25m3 stops
7:50 pm - 11:25 amORD-IAD
14h 35m1 stop
Mon, Nov 25 - Wed, Nov 27
10:59 am - 2:24 pmIAD-ORD
4h 25m1 stop
11:58 am - 5:18 pmORD-IAD
4h 20m1 stop
$693American Airlines
Find Deal
Tue, Nov 26 - Sat, Nov 30
5:48 pm - 10:29 pmIAD-ORD
5h 41m1 stop
5:00 am - 10:29 amORD-IAD
4h 29m1 stop
$743American Airlines
Find Deal
Sat, Nov 23 - Sun, Dec 1
10:16 pm - 11:20 pmIAD-ORD
2h 04mnonstop
1:19 pm - 4:13 pmORD-IAD
1h 54mnonstop
$197United Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
10:09 pm - 11:15 pmIAD-ORD
2h 06mnonstop
6:08 pm - 9:01 pmORD-IAD
1h 53mnonstop
$207United Airlines
Find Deal
Wed, Jan 8 - Mon, Jan 13
10:16 pm - 11:20 pmIAD-ORD
2h 04mnonstop
1:19 pm - 4:13 pmORD-IAD
1h 54mnonstop
$213United Airlines
Find Deal
Fri, Dec 13 - Sun, Dec 15
8:20 am - 9:34 amIAD-ORD
2h 14mnonstop
3:56 pm - 6:50 pmORD-IAD
1h 54mnonstop
$217United Airlines
Find Deal
Wed, Dec 4 - Wed, Dec 4
10:20 pm - 11:25 pmIAD-ORD
2h 05mnonstop
9:05 pm - 11:59 pmORD-IAD
1h 54mnonstop
$219United Airlines
Find Deal
Sun, Dec 22 - Wed, Jan 1
7:00 am - 8:20 amIAD-ORD
2h 20mnonstop
9:05 pm - 11:59 pmORD-IAD
1h 54mnonstop
$223United Airlines
Find Deal
Thu, Dec 19 - Thu, Jan 2
10:20 pm - 11:25 pmIAD-ORD
2h 05mnonstop
9:05 pm - 11:59 pmORD-IAD
1h 54mnonstop
$227United Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
10:20 pm - 11:25 pmIAD-ORD
2h 05mnonstop
8:50 am - 11:48 amORD-IAD
1h 58mnonstop
$229United Airlines
Find Deal
Mon, Dec 23 - Fri, Jan 3
10:20 pm - 11:29 pmIAD-ORD
2h 09mnonstop
8:45 am - 11:41 amORD-IAD
1h 56mnonstop
$232United Airlines
Find Deal
Sun, Mar 2 - Tue, Mar 4
7:00 am - 8:20 amIAD-ORD
2h 20mnonstop
9:05 pm - 11:59 pmORD-IAD
1h 54mnonstop
$238United Airlines
Find Deal
Thu, Dec 19 - Thu, Dec 26

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
Dec 13
IAD10:16 pmWashington, D.C. Dulles Intl
2h 04m
ORD11:20 pmChicago O'Hare Intl
Dec 17
ORD6:16 pmChicago O'Hare Intl
2h 00m
IAD9:16 pmWashington, D.C. Dulles Intl
United Airlines
Jan 8
IAD1:15 pmWashington, D.C. Dulles Intl
2h 19m
ORD2:34 pmChicago O'Hare Intl
Jan 9
ORD6:08 pmChicago O'Hare Intl
1h 53m
IAD9:01 pmWashington, D.C. Dulles Intl
United Airlines
Jan 8
IAD5:36 pmWashington, D.C. Dulles Intl
2h 19m
ORD6:55 pmChicago O'Hare Intl
Jan 12
ORD6:08 pmChicago O'Hare Intl
1h 53m
IAD9:01 pmWashington, D.C. Dulles Intl

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

Our best Delta deals on Washington, D.C. Dulles Intl Airport to Chicago flight tickets
Delta
Dec 17
IAD5:35 pmWashington, D.C. Dulles Intl
3h 53m
1 stop
ORD8:28 pmChicago O'Hare Intl
Dec 18
ORD3:40 pmChicago O'Hare Intl
4h 49m
1 stop
IAD9:29 pmWashington, D.C. Dulles Intl
Delta
Jan 8
IAD3:05 pmWashington, D.C. Dulles Intl
7h 53m
1 stop
ORD9:58 pmChicago O'Hare Intl
Jan 11
ORD2:55 pmChicago O'Hare Intl
5h 10m
1 stop
IAD9:05 pmWashington, D.C. Dulles Intl
Delta
Mar 4
IAD12:27 pmWashington, D.C. Dulles Intl
6h 58m
1 stop
ORD6:25 pmChicago O'Hare Intl
Mar 11
ORD7:00 amChicago O'Hare Intl
3h 33m
1 stop
IAD11:33 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 September is, on average, the cheapest month to fly to Chicago from Washington, D.C. Dulles Intl Airport, with most prices found around $208. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Washington, D.C. Dulles Intl Airport to Chicago during January average around $229.

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 Monday when prices can be found for as low as $248. 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 $304.

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 afternoon. Flights from Washington, D.C. Dulles Intl Airport to Chicago during this time can be as low as $257. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $302.

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?

The best time to book a flight to Chicago from Washington, D.C. Dulles Intl Airport is 60 days out, which is when prices tend to be around $260. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $203.

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.

Can stopping save me money on Washington, D.C. Dulles Intl Airport to Chicago flights?

You could potentially save up to 45% on your flight if you consider stops on a Washington, D.C. Dulles Intl Airport to Chicago flight.

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

As of November 2024, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 16% 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

$54

Fastest flight time

2h 04m

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 $54. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $108.
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago takes 2h 04m
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 04m, 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
6.1
3,536 reviews
Search Frontier flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,755 reviews
Search Delta flights
United AirlinesPriceFrom $184Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
American AirlinesPriceFrom $223Free 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 21 times per week, with 9,172 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 $184 (round-trip), much lower than the average airfare cost of $345 for United Airlines flights on this route.


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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago