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District of Columbia

$120+ Cheap flights from Chicago (CHI) to District of Columbia

CHI — IAD
Dec 9 — Dec 161
Wed 12/9
Wed 12/16
1 adult, Economy
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Cheap flight deals from Chicago to District of Columbia

Cheapest flights from Chicago to District of Columbia

Sat 12/1210:40 am -
1 stop8h 30m
Tue 12/158:55 pm -
1 stop13h 50m
Deal found 11/6$210
Wed 12/28:15 am -
1 stop5h 34m
Tue 12/812:06 pm -
1 stop10h 54m
Deal found 11/8$210
Thu 12/310:29 pm -
1 stop15h 20m
Mon 12/710:35 pm -
1 stop16h 55m
Deal found 11/6$211
Wed 12/212:28 pm -
1 stop25h 20m
Wed 12/910:35 pm -
1 stop18h 31m
Deal found 11/4$220
Wed 12/27:00 am -
2 stops26h 05m
Wed 12/912:06 pm -
1 stop10h 54m
Deal found 11/4$220
Wed 12/168:30 am -
1 stop5h 19m
Sun 1/176:18 am -
1 stop6h 47m
Deal found 11/7$221
Thu 12/37:00 am -
1 stop8h 52m
Sat 12/51:40 pm -
1 stop12h 14m
Deal found 11/5$222
Thu 11/269:09 am -
1 stop4h 54m
Tue 12/158:55 pm -
1 stop13h 50m
Deal found 11/5$222
Fri 12/1110:29 pm -
1 stop15h 20m
Mon 12/148:26 pm -
2 stops19h 04m
Deal found 11/5$222
Mon 12/77:25 am -
1 stop8h 30m
Tue 12/86:00 pm -
1 stop7h 54m
Deal found 11/5$223
Mon 12/75:02 pm -
1 stop17h 09m
Wed 12/910:35 pm -
1 stop18h 31m
Deal found 11/9$223
Tue 12/158:30 am -
1 stop5h 19m
Tue 12/1510:35 pm -
2 stops27h 33m
Deal found 11/6$223

Find flight deals from Chicago to District of Columbia

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$210
(Frontier)

One-way from

$120
(CheapOair)

Popular in

June

Cheapest in

January

Average price

$339

Good round-trip deal

$350 or less

Good one-way deal

$185 or less
Provider with most accurate pricing for Chicago (CHI)-Washington, D.C. (WAS) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Washington, D.C. (WAS) flights.
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From Chicago (CHI) to District of Columbia
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One-way flight from Chicago (CHI) to District of Columbia
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Highest demand for flights based on searches. 12% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in November 2026
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Price to beat on a round-trip flight from Chicago (CHI) to District of Columbia.
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Price to beat on a one-way flight from Chicago (CHI) to District of Columbia.
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Cheapflights Fare Finder

 
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.

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

MDWIAD

Chicago Midway

Wed 12/30

1:11 pm-12:51 am

1 stop10h 40m

Washington, D.C. Dulles Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$133

ChicagoWashington, D.C.

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

MDWDCA

Chicago Midway

Wed 12/23

5:35 am-8:25 am

Nonstop1h 50m

Washington, D.C. Reagan-National

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$139

ChicagoWashington, D.C.

ORD Chicago O'Hare Intl - IAD Washington, D.C. Dulles Intl

ORDIAD

Chicago O'Hare Intl

Mon 12/7

9:35 pm-12:24 am

Nonstop1h 49m

Washington, D.C. Dulles Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$139

ChicagoWashington, D.C.

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

MDWDCA

Chicago Midway

Sat 12/19

6:45 pm-9:35 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$139

ChicagoWashington, D.C.

ORD Chicago O'Hare Intl - IAD Washington, D.C. Dulles Intl

ORDIAD

Chicago O'Hare Intl

Wed 12/23

9:35 pm-12:38 am

Nonstop2h 03m

Washington, D.C. Dulles Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$139

ChicagoWashington, D.C.

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

MDWIAD

Chicago Midway

Sat 11/14

7:15 am-5:12 pm

1 stop8h 57m

Washington, D.C. Dulles Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$143

ChicagoWashington, D.C.

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

ORDDCA

Chicago O'Hare Intl

Sat 12/19

5:55 pm-10:59 pm

1 stop4h 04m

Washington, D.C. Reagan-National

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$149

ChicagoWashington, D.C.

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

MDWDCA

Chicago Midway

Thu 11/26

11:27 am-7:30 pm

1 stop7h 03m

Washington, D.C. Reagan-National

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$149

ChicagoWashington, D.C.

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

MDWIAD

Chicago Midway

Mon 12/21

9:29 am-3:38 pm

1 stop5h 09m

Washington, D.C. Dulles Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$149

ChicagoWashington, D.C.

ORD Chicago O'Hare Intl - IAD Washington, D.C. Dulles Intl

ORDIAD

Chicago O'Hare Intl

Tue 1/5

1:55 pm-4:58 pm

Nonstop2h 03m

Washington, D.C. Dulles Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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

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, December is the cheapest month in which you can book a flight from Chicago to District of Columbia (average of $327). Flying from Chicago to District of Columbia in October is currently the most expensive (average of $408). 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?

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 20% on your trip compared to booking a flight at noon.

Weekly flight availability from Chicago to District of Columbia

The most flights from CHI to USDC are scheduled on a Sunday (34 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 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 $329 and $567 in December.
The cheapest round-trip price found within the last 5 days was $210 on Frontier (Dec 12-Dec 15).

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

Booking 39 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?

Travelers seeking maximum savings on their Chicago to District of Columbia flight should consider departing on Thursday 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

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
4,219 reviews

Food

7.0

Boarding

8.1

Entertainment

7.4

Comfort

8.0

Crew

8.6

Overall

8.0

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
4,219 reviews
Southwest
8.0
Very good
4,219 reviews

Food

7.0

Boarding

8.1

Entertainment

7.4

Comfort

8.0

Crew

8.6

Overall

8.0

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
7.3
Good
10,479 reviews
Southwest
8.0
Very good
4,219 reviews

Food

7.0

Boarding

8.1

Entertainment

7.4

Comfort

8.0

Crew

8.6

Overall

8.0

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
7.0
Good
12,227 reviews
Southwest
8.0
Very good
4,219 reviews

Food

7.0

Boarding

8.1

Entertainment

7.4

Comfort

8.0

Crew

8.6

Overall

8.0

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
5.5
Fair
2,506 reviews
Southwest
8.0
Very good
4,219 reviews

Food

7.0

Boarding

8.1

Entertainment

7.4

Comfort

8.0

Crew

8.6

Overall

8.0

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

  • 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 50m. Fly via United Airlines, Southwest, or Delta 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 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. Reagan-National, Chicago O'Hare Intl - Washington, D.C. Dulles Intl 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: Air China (94%), Avianca (93%), Copa Airlines (85%).

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

    While on average a flight from Chicago to District of Columbia is generally $1,014, our data shows the cheapest flight currently is $160. When looking at the most popular route, (Chicago O'Hare Intl - Washington, D.C. Reagan-National), you can expect to pay $218 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, December is the cheapest month in which you can book a flight from Chicago to District of Columbia (average of $327). Flying from Chicago to District of Columbia in October is currently the most expensive (average of $408). 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

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Top 5 airlines flying from Chicago to District of Columbia

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$219FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$141Average$248FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$177Average$401FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$186Average$341FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%

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