District of Columbia

$80+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — IAD
Jan 16 — Jan 231
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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 December 17, 2025.

This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:12 amMDW - IAD
1 stop11h 04mFrontier
Wed 1/75:42 pmIAD - MDW
1 stop5h 35mFrontier
Deal found 12/16$188
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:14 amMDW - IAD
1 stop9h 23mFrontier
Wed 1/75:42 pmIAD - MDW
1 stop5h 35mFrontier
Deal found 12/16$213
This CheapOair deal was found by Cheapflights users on 12/14. 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.
Tue 12/306:00 amORD - IAD
1 stop9h 37mFrontier
Sat 1/310:15 pmIAD - ORD
1 stop21h 44mFrontier
Deal found 12/14$215
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/246:00 pmORD - DCA
Nonstop1h 59mUnited Airlines
Wed 12/316:00 pmDCA - ORD
Nonstop2h 17mUnited Airlines
Deal found 12/15$223
This Southwest deal was found by Cheapflights users on 12/14. 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 12/247:30 amMDW - DCA
Nonstop1h 45mSouthwest
Wed 12/316:55 pmDCA - MDW
Nonstop2h 05mSouthwest
Deal found 12/14$223
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 12/259:15 pmORD - IAD
Nonstop2h 00mUnited Airlines
Wed 12/3110:33 pmIAD - ORD
Nonstop2h 11mUnited Airlines
Deal found 12/16$223
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/318:58 pmORD - DCA
Nonstop2h 01mUnited Airlines
Tue 1/610:30 amDCA - ORD
Nonstop2h 16mUnited Airlines
Deal found 12/16$227
This Southwest deal was found by Cheapflights users on 12/16. 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 12/317:30 amMDW - DCA
Nonstop1h 45mSouthwest
Tue 1/66:55 pmDCA - MDW
Nonstop2h 10mSouthwest
Deal found 12/16$227
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/316:21 pmORD - IAD
Nonstop2h 00mUnited Airlines
Tue 1/61:05 pmIAD - ORD
Nonstop2h 20mUnited Airlines
Deal found 12/16$227
This Trip.com deal was found by Cheapflights users on 12/15. 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.
Thu 12/186:12 amMDW - IAD
1 stop11h 04mFrontier
Thu 1/86:00 amIAD - MDW
1 stop6h 31mFrontier
Deal found 12/15$229
This Frontier deal was found by Cheapflights users on 12/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 amMDW - IAD
1 stop8h 32mFrontier
Thu 1/86:00 amIAD - MDW
1 stop6h 31mFrontier
Deal found 12/16$232
This Southwest deal was found by Cheapflights users on 12/14. 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 12/245:40 pmMDW - DCA
Nonstop1h 50mSouthwest
Thu 1/111:40 amDCA - MDW
2 stops6h 30mSouthwest
Deal found 12/14$238

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 December 17, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$157
(Kiwi.com)

One-way from

$80
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$237

Good round-trip deal

$309 or less

Good one-way deal

$174 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
From Chicago (CHI) to District of Columbia
One-way flight from Chicago (CHI) to District of Columbia
Highest demand for flights based on searches. 10% potential increase in price ($28 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in December 2025
Price to beat on a round-trip flight from Chicago (CHI) to District of Columbia.
Price to beat on a one-way flight from Chicago (CHI) to District of Columbia.

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 December 17, 2025.
Use the filters below to find and compare flights from Chicago to District of Columbia that are best for you.

Fly from

Chicago

Fly to

District of Columbia

Route

Depart

Return

Price

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 1/22

6:20 am-4:28 pm

1 stop9h 08m

Washington, D.C. Dulles Intl

Mon 1/26

5:33 pm-10:19 pm

1 stop5h 46m

$162

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 1/7

3:01 pm-1:01 pm

1 stop21h 00m

Washington, D.C. Dulles Intl

Tue 1/13

6:00 am-10:34 am

1 stop5h 34m

$163

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 1/23

5:01 pm-10:44 am

1 stop16h 43m

Washington, D.C. Dulles Intl

Mon 1/26

1:31 pm-7:58 pm

1 stop7h 27m

$169

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 1/16

8:28 am-9:13 pm

1 stop11h 45m

Washington, D.C. Dulles Intl

Mon 1/19

10:08 pm-12:05 pm

1 stop14h 57m

$174

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sun 1/25

5:01 pm-4:28 pm

1 stop22h 27m

Washington, D.C. Dulles Intl

Mon 2/2

5:33 pm-12:05 pm

1 stop19h 32m

$174

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Thu 1/8

7:45 am-4:19 pm

1 stop7h 34m

Washington, D.C. Reagan-National

Sun 1/11

1:00 pm-5:43 pm

1 stop5h 43m

$197

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Sat 1/17

7:45 am-5:04 pm

1 stop8h 19m

Washington, D.C. Reagan-National

Wed 1/21

10:05 am-5:43 pm

1 stop8h 38m

$197

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Wed 1/14

7:45 am-5:34 pm

1 stop8h 49m

Washington, D.C. Reagan-National

Wed 1/21

10:05 am-5:43 pm

1 stop8h 38m

$197

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Thu 1/15

7:45 am-5:34 pm

1 stop8h 49m

Washington, D.C. Reagan-National

Wed 1/21

11:55 am-5:43 pm

1 stop6h 48m

$197

ChicagoWashington, D.C.

ORD - DCA

ORDDCA

Chicago O'Hare Intl

Tue 1/6

10:55 am-6:49 pm

1 stop6h 54m

Washington, D.C. Reagan-National

Sun 1/11

10:05 am-5:43 pm

1 stop8h 38m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 60 results
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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, February is the cheapest month in which you can book a flight from Chicago to District of Columbia (average of $58). Flying from Chicago to District of Columbia in April is currently the most expensive (average of $169). 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 December 17, 2025.

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 24% on your trip compared to booking a flight in the afternoon.

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 December 13, 2025.

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

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

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 December 17, 2025.
See what other customers who have flown with Southwest, United Airlines, and American 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.

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 45m. Fly via Frontier, JetBlue, or Southwest to get the fastest option. Airlines will cover a distance of 599 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 Spirit Airlines, with whom users have recently found tickets for as low as $43. However, be on the lookout for offers from Frontier and Southwest, 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?

  • 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: Air China (82%), Avianca (82%), ANA (70%).

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

    While on average a flight from Chicago to District of Columbia is generally $1,068, our data shows the cheapest flight currently is $134. When looking at the most popular route, (Chicago O'Hare Intl - Washington, D.C. Reagan-National), you can expect to pay $185 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, February is the cheapest month in which you can book a flight from Chicago to District of Columbia (average of $58). Flying from Chicago to District of Columbia in April is currently the most expensive (average of $169). 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.

See more FAQs

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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.

Top 7 airlines flying from Chicago to District of Columbia

Discover the top 7 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 December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$147FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$190FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$142Average$311FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$149Average$277FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$152Average$268FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$284FlexibilityNo cancel feeOn-time63%
DeltaCheapest$166Average$196FlexibilityNo cancel feeOn-timeN/A

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