Chicago

$84+ Cheap flights from District of Columbia to Chicago (CHI)

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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Apr 27 — May 41
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Cheap flight deals from District of Columbia to Chicago

Keep the following information in mind while searching for District of Columbia to Chicago flight deals. Data was last updated April 22, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$178
(Frontier)

One-way from

$84
(Flightnetwork)

Popular in

May

Cheapest in

September

Average price

$273

Good round-trip deal

$256 or less

Good one-way deal

$164 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
From District of Columbia to Chicago (CHI)
One-way flight from District of Columbia to Chicago (CHI)
Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Average for round-trip flights in April 2025
Price to beat on a round-trip flight from District of Columbia to Chicago (CHI).
Price to beat on a one-way flight from District of Columbia to Chicago (CHI).

Find flight deals from District of Columbia to Chicago

Cheapest flights from District of Columbia to Chicago
Explore the most affordable flight options available from District of Columbia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

This Frontier deal was found by Cheapflights users on 4/20. 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.
Sat 5/244:49 pmIAD - MDW
1 stop6h 13mFrontier
Wed 5/286:40 amMDW - IAD
1 stop8h 34mFrontier
Deal found 4/20$178
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Thu 5/299:30 amDCA - ORD
Nonstop2h 13mAmerican Airlines
Fri 5/306:00 amORD - DCA
Nonstop1h 54mAmerican Airlines
Deal found 4/22$179
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/2810:18 pmIAD - ORD
Nonstop2h 12mUnited Airlines
Sat 5/3111:23 amORD - IAD
Nonstop2h 05mUnited Airlines
Deal found 4/22$179
This Southwest deal was found by Cheapflights users on 4/22. 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.
Thu 5/2911:55 amDCA - MDW
Nonstop2h 00mSouthwest
Fri 5/308:10 pmMDW - DCA
Nonstop1h 50mSouthwest
Deal found 4/22$179
This CheapOair deal was found by Cheapflights users on 4/22. 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.
Thu 5/83:32 pmIAD - ORD
1 stop8h 39mFrontier
Sat 5/109:19 amORD - IAD
1 stop22h 25mFrontier
Deal found 4/22$180
This CheapOair deal was found by Cheapflights users on 4/22. 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.
Wed 5/287:00 amDCA - ORD
1 stop17h 52mFrontier
Sat 5/316:00 amORD - DCA
1 stop29h 00mFrontier
Deal found 4/22$181
This CheapOair deal was found by Cheapflights users on 4/21. 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 5/51:00 pmDCA - MDW
1 stop7h 08mFrontier
Thu 5/88:03 pmMDW - DCA
1 stop24h 56mFrontier
Deal found 4/21$181
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/217:25 amDCA - ORD
Nonstop2h 16mUnited Airlines
Sun 5/258:00 amORD - DCA
Nonstop1h 56mUnited Airlines
Deal found 4/21$193
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:10 pmDCA - ORD
1 stop4h 50mDelta
Sun 5/257:10 amORD - DCA
1 stop3h 21mDelta
Deal found 4/22$197
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/15:24 pmIAD - ORD
1 stop4h 03mDelta
Sat 7/55:35 amORD - IAD
1 stop6h 13mDelta
Deal found 4/22$197
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/243:37 pmIAD - MDW
1 stop6h 36mDelta
Sun 5/256:25 pmMDW - IAD
1 stop3h 29mDelta
Deal found 4/22$197
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/286:00 amDCA - MDW
1 stop3h 40mDelta
Fri 5/309:20 amMDW - DCA
1 stop7h 39mDelta
Deal found 4/22$199

Cheapflights Fare Finder

Customize your flight search to find flights from District of Columbia to Chicago 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 April 22, 2025.
Use the filters below to find and compare flights from District of Columbia to Chicago that are best for you.

Fly from

District of Columbia

Fly to

Chicago

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/24

4:49 pm-12:17 am

1 stop8h 28m

Chicago O'Hare Intl

Wed 5/28

3:22 pm-10:30 pm

1 stop6h 08m

$178

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/24

4:49 pm-10:02 pm

1 stop6h 13m

Chicago Midway

Wed 5/28

6:40 am-4:14 pm

1 stop8h 34m

$178

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 5/29

9:30 am-10:43 am

Nonstop2h 13m

Chicago O'Hare Intl

Fri 5/30

6:00 am-8:54 am

Nonstop1h 54m

$179

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 5/28

10:18 pm-11:30 pm

Nonstop2h 12m

Chicago O'Hare Intl

Sat 5/31

11:23 am-2:28 pm

Nonstop2h 05m

$179

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/29

11:55 am-12:55 pm

Nonstop2h 00m

Chicago Midway

Fri 5/30

8:10 pm-11:00 pm

Nonstop1h 50m

$179

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 5/28

7:00 am-11:52 pm

1 stop17h 52m

Chicago O'Hare Intl

Sat 5/31

6:00 am-12:00 pm

1 stop29h 00m

$181

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 5/5

7:00 am-7:08 pm

1 stop13h 08m

Chicago Midway

Thu 5/8

8:03 pm-9:59 pm

1 stop24h 56m

$181

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 5/21

7:25 am-8:41 am

Nonstop2h 16m

Chicago O'Hare Intl

Sun 5/25

8:00 am-10:56 am

Nonstop1h 56m

$193

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/24

5:10 pm-9:00 pm

1 stop4h 50m

Chicago O'Hare Intl

Sun 5/25

7:10 am-11:31 am

1 stop3h 21m

$197

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/24

1:20 pm-6:48 pm

1 stop6h 28m

Chicago O'Hare Intl

Sun 5/25

11:23 am-4:45 pm

1 stop4h 22m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 42 results
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Best time to book a flight from District of Columbia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from District of Columbia 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 District of Columbia to Chicago

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

Currently, August is the cheapest month in which you can book a flight from District of Columbia to Chicago (average of $245). Flying from District of Columbia to Chicago in March is currently the most expensive (average of $321). 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 DC to CHI?

Find hourly flight availability from District of Columbia to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 22, 2025.

When flying from District of Columbia to Chicago, 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 District of Columbia to Chicago

Explore weekly flight availability from District of Columbia to Chicago. 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 April 22, 2025.

The most flights from USDC to CHI are scheduled on a Tuesday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 22, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from District of Columbia to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
8.0
Very good

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from District of Columbia to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What are the cheapest airlines to fly from District of Columbia to Chicago one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $84. Southwest flights start at $86 while deals on American Airlines start at $90 one-way.

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

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

    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 District of Columbia to Chicago on time: Sun Country Air (100%), Ethiopian Air (85%), Avianca (82%).

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

    Looking for the cheapest flight from District of Columbia to Chicago? While on average our users pay $700, our data indicates the cheapest price to be $114. The most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), is priced around $176.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from District of Columbia to Chicago 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 District of Columbia to Chicago?

    Currently, August is the cheapest month in which you can book a flight from District of Columbia to Chicago (average of $245). Flying from District of Columbia to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near District of Columbia?

Book flights to District of Columbia if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for District of Columbia to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from District of Columbia to Chicago

Discover the top 6 airlines that operate flights from District of Columbia to Chicago. 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$56Average$171FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$181FlexibilityNo cancel feeOn-time62%
DeltaCheapest$99Average$269FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$144Average$326FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$154Average$330FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$167Average$300FlexibilityNo cancel feeOn-time63%

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