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$79+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — CHI
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
1 adult, Economy
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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 August 7, 2025.

Round-trip from

$135
(United Airlines)

One-way from

$79
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$254

Good round-trip deal

$196 or less

Good one-way deal

$167 or less
From District of Columbia to Chicago (CHI)
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One-way flight from District of Columbia to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from District of Columbia to Chicago (CHI).
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Price to beat on a one-way flight from District of Columbia to Chicago (CHI).
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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 August 7, 2025.

This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/76:50 pmIAD - ORD
Nonstop2h 08mUnited Airlines
Sat 10/112:39 pmORD - IAD
Nonstop1h 58mUnited Airlines
Deal found 8/7$134
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/252:00 pmDCA - ORD
Nonstop2h 13mUnited Airlines
Sat 8/3011:15 amORD - DCA
Nonstop2h 01mUnited Airlines
Deal found 8/7$135
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/256:35 amIAD - ORD
Nonstop2h 11mUnited Airlines
Sat 8/305:55 pmORD - IAD
Nonstop2h 00mUnited Airlines
Deal found 8/7$135
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/138:25 amDCA - MDW
Nonstop2h 00mSouthwest
Mon 9/158:30 pmMDW - DCA
Nonstop1h 55mSouthwest
Deal found 8/7$135
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/135:08 pmDCA - ORD
Nonstop2h 20mAmerican Airlines
Mon 9/156:54 pmORD - DCA
Nonstop2h 06mAmerican Airlines
Deal found 8/7$136
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:05 amDCA - MDW
Nonstop1h 55mSouthwest
Sat 9/135:30 pmMDW - DCA
Nonstop1h 55mSouthwest
Deal found 8/7$139
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/297:00 pmDCA - ORD
Nonstop2h 15mUnited Airlines
Tue 9/28:00 amORD - DCA
Nonstop1h 58mUnited Airlines
Deal found 8/7$140
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2710:10 pmIAD - ORD
Nonstop2h 05mUnited Airlines
Sun 8/3111:40 amORD - IAD
Nonstop1h 57mUnited Airlines
Deal found 8/7$140
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/48:45 pmDCA - MDW
Nonstop2h 10mSouthwest
Fri 11/78:55 pmMDW - DCA
Nonstop1h 45mSouthwest
Deal found 8/7$140
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:05 amDCA - ORD
1 stop7h 10mSouthwest
Sat 12/61:45 pmORD - DCA
1 stop4h 45mSouthwest
Deal found 8/7$142
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/32:45 pmDCA - MDW
1 stop6h 45mSouthwest
Sat 12/66:25 amMDW - DCA
1 stop6h 30mSouthwest
Deal found 8/7$142
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:00 amDCA - ORD
1 stop5h 35mUnited Airlines
Tue 9/163:00 pmORD - DCA
Nonstop2h 03mUnited Airlines
Deal found 8/7$145

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 August 7, 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

Tue 10/7

6:50 pm-7:58 pm

Nonstop2h 08m

Chicago O'Hare Intl

Sat 10/11

2:39 pm-5:37 pm

Nonstop1h 58m

$134

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 9/13

8:25 am-9:25 am

Nonstop2h 00m

Chicago Midway

Mon 9/15

8:30 pm-11:25 pm

Nonstop1h 55m

$135

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 8/25

5:00 pm-6:16 pm

Nonstop2h 16m

Chicago O'Hare Intl

Tue 8/26

3:00 pm-6:03 pm

Nonstop2h 03m

$135

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 8/25

10:10 pm-11:15 pm

Nonstop2h 05m

Chicago O'Hare Intl

Tue 8/26

5:55 pm-8:55 pm

Nonstop2h 00m

$135

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 11/8

7:56 pm-9:16 pm

Nonstop2h 20m

Chicago O'Hare Intl

Mon 11/10

6:04 am-8:59 am

Nonstop1h 55m

$136

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 9/9

6:05 am-7:00 am

Nonstop1h 55m

Chicago Midway

Sat 9/13

5:30 pm-8:25 pm

Nonstop1h 55m

$139

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 11/4

8:45 pm-9:55 pm

Nonstop2h 10m

Chicago Midway

Fri 11/7

8:55 pm-11:40 pm

Nonstop1h 45m

$140

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 9/12

3:30 pm-4:43 pm

Nonstop2h 13m

Chicago O'Hare Intl

Tue 9/16

7:00 am-9:58 am

Nonstop1h 58m

$140

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 8/30

6:40 pm-7:48 pm

Nonstop2h 08m

Chicago O'Hare Intl

Sun 8/31

11:40 am-2:37 pm

Nonstop1h 57m

$140

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 12/3

6:05 am-12:15 pm

1 stop7h 10m

Chicago O'Hare Intl

Sat 12/6

1:45 pm-7:30 pm

1 stop4h 45m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/6

Showing 1-10 of 60 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 August 7, 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 August 7, 2025.

The most flights from USDC to CHI are scheduled on a Thursday (35 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

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 August 7, 2025.
Read through reviews of airlines operating flights from District of Columbia to Chicago, such as Southwest, Delta, and Avelo Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,987 reviews
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,247 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 United Airlines, which is currently one of the cheapest options available, starting at $79. Southwest flights start at $79 while deals on Frontier start at $80 one-way.

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

    While some choose either Washington, D.C. Dulles Intl - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago Midway, Washington, D.C. Reagan-National - Chicago O'Hare Intl is the most popular route 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: ANA (95%), Royal Jordanian (91%), Japan Airlines (85%).

  • 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 $796, our data indicates the cheapest price to be $75. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $123.

  • 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 Chicago?

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

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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.
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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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$46Average$147FlexibilityNo cancel feeOn-time65%
FrontierCheapest$62Average$189FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$292FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$157Average$329FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$291FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$293FlexibilityNo cancel feeOn-time69%

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