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District of Columbia

$89+ Cheap flights from Chicago (CHI) to District of Columbia

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — IAD
Sep 11 — Sep 181
Fri 9/11
Fri 9/18
1 adult, Economy
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Cheap flight deals from Chicago to District of Columbia

Cheapest flights from Chicago to District of Columbia
Explore the most affordable flight options available from Chicago to District of Columbia. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 12, 2026.

This CheapOair deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:30 am -
1 stop14h 29m
Tue 9/156:00 pm -
1 stop7h 23m
Deal found 8/12$181
This iWofly deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:50 pm -
1 stop17h 27m
Fri 10/211:12 am -
1 stop12h 47m
Deal found 8/11$181
This Super.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:30 am -
1 stop28h 41m
Sat 9/266:00 pm -
1 stop7h 23m
Deal found 8/7$182
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:45 am -
1 stop6h 30m
Sun 9/66:00 am -
1 stop4h 40m
Deal found 8/11$182
This Expedia deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:50 am -
1 stop10h 02m
Mon 9/76:20 am -
1 stop5h 35m
Deal found 8/11$182
This Priceline deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am -
1 stop9h 02m
Thu 9/38:59 am -
1 stop10h 38m
Deal found 8/10$182
This Trip.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:25 am -
1 stop9h 53m
Mon 9/147:50 am -
1 stop11h 01m
Deal found 8/11$183
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:00 am -
Nonstop2h 04m
Mon 9/141:04 pm -
Nonstop2h 16m
Deal found 8/10$184
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:50 pm -
Nonstop1h 55m
Sun 9/62:55 pm -
Nonstop2h 00m
Deal found 8/10$184
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:15 pm -
Nonstop2h 05m
Mon 9/1410:27 pm -
Nonstop2h 13m
Deal found 8/11$184
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:00 pm -
Nonstop2h 06m
Mon 9/146:30 am -
Nonstop2h 28m
Deal found 8/10$185
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:45 am -
Nonstop1h 45m
Mon 9/141:00 pm -
2 stops5h 50m
Deal found 8/10$185

Find flight deals from Chicago to District of Columbia

Keep the following information in mind while searching for Chicago to District of Columbia flight deals. Data was last updated August 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$181
(CheapOair)

One-way from

$89
(United Airlines)

Popular in

June

Cheapest in

September

Average price

$252

Good round-trip deal

$268 or less

Good one-way deal

$128 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
Search Deals
From Chicago (CHI) to District of Columbia
Search Deals
One-way flight from Chicago (CHI) to District of Columbia
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to District of Columbia.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to District of Columbia.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to District of Columbia that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 12, 2026.
Use the filters below to find and compare flights from Chicago to District of Columbia that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWashington, D.C.

ORD Chicago O'Hare Intl - DCA Washington, D.C. Reagan-National

ORDDCA

Chicago O'Hare Intl

Sat 9/5

3:25 pm-11:48 pm

1 stop7h 23m

Washington, D.C. Reagan-National

Sun 9/6

9:00 am-12:40 pm

1 stop4h 40m

$197

ChicagoWashington, D.C.

ORD Chicago O'Hare Intl - DCA Washington, D.C. Reagan-National

ORDDCA

Chicago O'Hare Intl

Fri 10/30

3:40 pm-10:49 pm

1 stop6h 09m

Washington, D.C. Reagan-National

Mon 11/2

2:00 pm-7:11 pm

1 stop6h 11m

$204

ChicagoWashington, D.C.

MDW Chicago Midway - IAD Washington, D.C. Dulles Intl

MDWIAD

Chicago Midway

Fri 10/30

6:44 pm-11:16 pm

1 stop3h 32m

Washington, D.C. Dulles Intl

Mon 11/2

12:20 pm-6:00 pm

1 stop6h 40m

$204

ChicagoWashington, D.C.

MDW Chicago Midway - IAD Washington, D.C. Dulles Intl

MDWIAD

Chicago Midway

Thu 9/3

10:54 am-4:42 pm

1 stop4h 48m

Washington, D.C. Dulles Intl

Sun 9/6

6:10 am-9:17 am

1 stop4h 07m

$206

ChicagoWashington, D.C.

ORD Chicago O'Hare Intl - DCA Washington, D.C. Reagan-National

ORDDCA

Chicago O'Hare Intl

Wed 9/9

7:00 am-12:34 pm

1 stop4h 34m

Washington, D.C. Reagan-National

Wed 9/16

12:32 pm-4:13 pm

1 stop4h 41m

$211

ChicagoWashington, D.C.

MDW Chicago Midway - IAD Washington, D.C. Dulles Intl

MDWIAD

Chicago Midway

Sat 10/3

6:05 am-2:11 pm

1 stop7h 06m

Washington, D.C. Dulles Intl

Wed 10/7

10:14 am-4:19 pm

1 stop7h 05m

$211

ChicagoWashington, D.C.

MDW Chicago Midway - DCA Washington, D.C. Reagan-National

MDWDCA

Chicago Midway

Wed 9/23

8:50 am-3:00 pm

1 stop5h 10m

Washington, D.C. Reagan-National

Sat 9/26

1:20 pm-4:40 pm

1 stop4h 20m

$214

ChicagoWashington, D.C.

MDW Chicago Midway - IAD Washington, D.C. Dulles Intl

MDWIAD

Chicago Midway

Thu 9/3

6:42 pm-11:26 pm

1 stop3h 44m

Washington, D.C. Dulles Intl

Mon 9/7

6:10 am-9:17 am

1 stop4h 07m

$215

ChicagoWashington, D.C.

MDW Chicago Midway - DCA Washington, D.C. Reagan-National

MDWDCA

Chicago Midway

Wed 9/9

4:40 pm-10:10 pm

1 stop4h 30m

Washington, D.C. Reagan-National

Tue 9/15

6:00 am-12:05 pm

2 stops7h 05m

$217

ChicagoWashington, D.C.

MDW Chicago Midway - DCA Washington, D.C. Reagan-National

MDWDCA

Chicago Midway

Tue 9/1

11:10 am-2:00 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Sun 9/6

8:35 am-11:40 am

1 stop4h 05m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Chicago to District of Columbia

Have a flexible travel schedule? Discover the best time to fly to District of Columbia from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to District of Columbia

What is the cheapest month to book a flight from Chicago to District of Columbia?

Currently, September is the cheapest month in which you can book a flight from Chicago to District of Columbia (average of $271). Flying from Chicago to District of Columbia in June is currently the most expensive (average of $402). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to DC?

Find hourly flight availability from Chicago to District of Columbia. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 12, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago to District of Columbia in the morning. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight in the afternoon.

Weekly flight availability from Chicago to District of Columbia

Explore weekly flight availability from Chicago to District of Columbia. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 12, 2026.

The most flights from CHI to USDC are scheduled on a Tuesday (34 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (17 on average).

How much does it cost to fly round-trip from Chicago to District of Columbia?

Airfare is below average for this route at the moment.
Chicago to District of Columbia flights typically cost between $229 and $426 in September.
The cheapest round-trip price found within the last 5 days was $180 on Frontier (Sep 26-Oct 3).

How far ahead should I book a flight from Chicago to District of Columbia?

Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to District of Columbia. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from Chicago to District of Columbia?

Use this chart to determine the cheapest time to fly round-trip from Chicago to District of Columbia. Price data was last updated on August 8, 2026.

Travelers seeking maximum savings on their Chicago to District of Columbia flight should consider departing on Monday at noon when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing District of Columbia

Get insights into the airlines that provide service to District of Columbia. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to District of Columbia. Reviews last updated August 12, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to District of Columbia have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,218 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Southwest
8.0
Very good
4,218 reviews
Southwest
8.0
Very good
4,218 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
United Airlines
7.4
Good
10,111 reviews
Southwest
8.0
Very good
4,218 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
American Airlines
7.1
Good
11,913 reviews
Southwest
8.0
Very good
4,218 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.
Frontier
5.6
Fair
2,701 reviews
Southwest
8.0
Very good
4,218 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chicago to District of Columbia. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to District of Columbia?

    There are many flights that can get you from Chicago to District of Columbia in 1h 54m. Fly via Delta, Southwest, or United Airlines to get the fastest option. Airlines will cover a distance of 587 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to District of Columbia one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $33. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Chicago to District of Columbia for a low price.

  • What are the most popular routes from Chicago to District of Columbia?

    The most popular flight routes from Chicago to District of Columbia are Chicago O'Hare Intl - Washington, D.C. Dulles Intl, Chicago O'Hare Intl - Washington, D.C. Reagan-National and Chicago Midway - Washington, D.C. Dulles Intl.

  • What are the most reliable airlines from Chicago to District of Columbia?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to District of Columbia on time: Egyptair (96%), ITA Airways (94%), Air China (94%).

  • What are the cheapest flights from Chicago to District of Columbia?

    While on average a flight from Chicago to District of Columbia is generally $1,908, our data shows the cheapest flight currently is $128. When looking at the most popular route, (Chicago O'Hare Intl - Washington, D.C. Dulles Intl), you can expect to pay $165 for that flight.

  • Can I find deals for flights from Chicago to District of Columbia that include hotel bookings?

    Yes. In addition to deals on Chicago to District of Columbia flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to District of Columbia?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to District of Columbia.

  • Can I find deals for business class flights from Chicago to District of Columbia?

    Yes. Cheapflights offers flight deals from Chicago to District of Columbia by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to District of Columbia?

    Currently, September is the cheapest month in which you can book a flight from Chicago to District of Columbia (average of $271). Flying from Chicago to District of Columbia in June is currently the most expensive (average of $402). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Chicago to District of Columbia

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to District of Columbia

Discover the top 5 airlines that operate flights from Chicago to District of Columbia. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$196FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$122Average$318FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$141Average$264FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$149Average$366FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$177Average$324FlexibilityNo cancel feeOn-time71%

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