District of Columbia

$78+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — IAD
Oct 16 — Oct 231
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Cheap 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 September 16, 2025.

Round-trip from

$143
(CheapOair)

One-way from

$78
(CheapOair)

Popular in

January

Cheapest in

August

Average price

$212

Good round-trip deal

$240 or less

Good one-way deal

$112 or less
From Chicago (CHI) to District of Columbia
One-way flight from Chicago (CHI) to District of Columbia
Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Average for round-trip flights in September 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.

Find 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 September 16, 2025.

This CheapOair deal was found by Cheapflights users on 9/13. 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.
Fri 10/39:48 amMDW - IAD
1 stop7h 31mFrontier
Mon 10/66:10 amIAD - MDW
1 stop11h 15mFrontier
Deal found 9/13$143
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:00 amORD - IAD
1 stop8h 26mFrontier
Mon 10/204:45 pmIAD - ORD
1 stop7h 54mFrontier
Deal found 9/14$143
This Flightnetwork deal was found by Cheapflights users on 9/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1811:31 amMDW - IAD
1 stop8h 22mFrontier
Mon 10/204:45 pmIAD - MDW
1 stop8h 01mFrontier
Deal found 9/14$144
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:24 amORD - IAD
1 stop8h 43mFrontier
Mon 10/275:00 pmIAD - ORD
1 stop7h 39mFrontier
Deal found 9/14$144
This Flightnetwork deal was found by Cheapflights users on 9/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/249:00 amMDW - IAD
1 stop9h 55mFrontier
Thu 9/251:55 pmIAD - MDW
1 stop10h 25mFrontier
Deal found 9/14$145
This Flightnetwork deal was found by Cheapflights users on 9/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/246:44 pmORD - IAD
1 stop13h 33mFrontier
Thu 9/251:55 pmIAD - ORD
1 stop11h 15mFrontier
Deal found 9/14$145
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:56 pmMDW - IAD
1 stop5h 43mFrontier
Sun 10/57:14 pmIAD - MDW
1 stop13h 09mFrontier
Deal found 9/13$146
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/28:05 amORD - IAD
1 stop11h 04mFrontier
Sun 10/57:14 pmIAD - ORD
1 stop25h 30mFrontier
Deal found 9/13$146
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amMDW - IAD
1 stop5h 49mFrontier
Wed 12/108:00 amIAD - MDW
1 stop14h 32mFrontier
Deal found 9/14$147
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:20 amMDW - IAD
1 stop5h 35mFrontier
Mon 9/296:10 amIAD - MDW
1 stop10h 50mFrontier
Deal found 9/15$149
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Fri 10/248:44 amORD - IAD
1 stop11h 29mFrontier
Sun 10/268:02 pmIAD - ORD
1 stop12h 08mFrontier
Deal found 9/14$149
This Flightnetwork deal was found by Cheapflights users on 9/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:20 amMDW - IAD
1 stop5h 35mFrontier
Thu 9/258:59 pmIAD - MDW
1 stop16h 45mFrontier
Deal found 9/14$150

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 September 16, 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

Fri 10/3

5:15 pm-11:39 pm

1 stop5h 24m

Washington, D.C. Dulles Intl

Wed 10/8

9:00 am-1:38 pm

1 stop5h 38m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 10/4

11:21 am-6:29 pm

1 stop6h 08m

Washington, D.C. Dulles Intl

Mon 10/6

1:55 pm-11:41 pm

1 stop10h 46m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/3

5:15 pm-11:39 pm

1 stop5h 24m

Washington, D.C. Dulles Intl

Sat 10/4

7:14 pm-9:18 am

1 stop15h 04m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/17

5:28 pm-8:53 pm

1 stop26h 25m

Washington, D.C. Dulles Intl

Mon 10/20

4:45 pm-11:46 pm

1 stop8h 01m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/31

1:37 pm-11:29 pm

1 stop8h 52m

Washington, D.C. Dulles Intl

Sun 11/2

8:36 pm-8:32 am

1 stop12h 56m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sun 11/16

1:37 pm-12:11 am

1 stop9h 34m

Washington, D.C. Dulles Intl

Wed 11/19

8:40 am-12:41 pm

1 stop5h 01m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Mon 11/3

6:20 am-5:23 pm

1 stop10h 03m

Washington, D.C. Dulles Intl

Wed 11/5

8:40 am-12:41 pm

1 stop5h 01m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 9/26

6:21 am-8:09 pm

1 stop12h 48m

Washington, D.C. Dulles Intl

Tue 9/30

9:15 am-3:58 pm

1 stop7h 43m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 10/25

6:15 am-3:17 pm

1 stop8h 02m

Washington, D.C. Dulles Intl

Mon 10/27

5:00 pm-11:46 pm

1 stop7h 46m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 10/23

10:49 am-7:07 pm

1 stop7h 18m

Washington, D.C. Dulles Intl

Mon 10/27

5:00 pm-11:46 pm

1 stop7h 46m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, August is the cheapest month in which you can book a flight from Chicago to District of Columbia (average of $292). Flying from Chicago to District of Columbia in April is currently the most expensive (average of $337). 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 September 16, 2025.

When flying from Chicago to District of Columbia, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 16, 2025.

The most flights from CHI to USDC are scheduled on a Monday (33 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).

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 September 16, 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.

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 55m. Fly via Frontier, JetBlue, 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 $78. However, be on the lookout for offers from JetBlue 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: Egyptair (100%), Air China (82%), Avianca (80%).

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

    While on average a flight from Chicago to District of Columbia is generally $1,832, our data shows the cheapest flight currently is $142. When looking at the most popular route, (Chicago O'Hare Intl - Washington, D.C. Reagan-National), you can expect to pay $173 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, August is the cheapest month in which you can book a flight from Chicago to District of Columbia (average of $292). Flying from Chicago to District of Columbia in April is currently the most expensive (average of $337). 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 6 airlines flying from Chicago to District of Columbia

Discover the top 6 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$142FlexibilityNo cancel feeOn-time65%
FrontierCheapest$75Average$186FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$124Average$271FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$153Average$285FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$154Average$301FlexibilityNo cancel feeOn-time69%
DeltaCheapest$166Average$310FlexibilityNo cancel feeOn-timeN/A

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