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$81+ 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 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$156
(Frontier)

One-way from

$81
(Frontier)

Popular in

March

Cheapest in

September

Average price

$244

Good round-trip deal

$229 or less

Good one-way deal

$176 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
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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. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/20. 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.
Fri 5/94:00 pmIAD - ORD
1 stop8h 11mFrontier
Mon 5/126:20 amORD - IAD
1 stop7h 03mFrontier
Deal found 2/20$156
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/610:25 pmIAD - MDW
1 stop24h 00mFrontier
Mon 3/104:20 pmMDW - IAD
1 stop19h 56mFrontier
Deal found 2/20$159
This Frontier deal was found by Cheapflights users on 2/19. 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.
Sun 3/91:03 pmDCA - ORD
1 stop12h 20mFrontier
Tue 3/116:45 amORD - DCA
1 stop9h 14mFrontier
Deal found 2/19$160
This Frontier deal was found by Cheapflights users on 2/19. 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.
Sun 3/91:03 pmDCA - MDW
1 stop12h 16mFrontier
Tue 3/116:40 amMDW - DCA
1 stop9h 19mFrontier
Deal found 2/19$160
This United Airlines deal was found by Cheapflights users on 2/19. 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 4/18:30 amDCA - ORD
Nonstop2h 15mUnited Airlines
Thu 4/36:00 amORD - DCA
Nonstop1h 58mUnited Airlines
Deal found 2/19$177
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/158:55 pmDCA - MDW
Nonstop2h 00mSouthwest
Mon 4/217:20 amMDW - DCA
Nonstop1h 50mSouthwest
Deal found 2/20$177
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1910:20 pmIAD - ORD
Nonstop2h 09mUnited Airlines
Tue 3/254:05 pmORD - IAD
Nonstop1h 52mUnited Airlines
Deal found 2/20$178
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 4/211:59 amDCA - ORD
Nonstop2h 19mAmerican Airlines
Tue 4/811:29 amORD - DCA
Nonstop1h 51mAmerican Airlines
Deal found 2/19$181
This JetBlue deal was found by Cheapflights users on 2/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/267:11 amDCA - ORD
1 stop6h 16mJetBlue
Tue 4/291:22 pmORD - DCA
1 stop6h 37mJetBlue
Deal found 2/20$183
This KAYAK deal was found by Cheapflights users on 2/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/253:05 pmIAD - ORD
1 stop7h 42mDelta
Thu 3/276:15 pmORD - IAD
1 stop3h 45mDelta
Deal found 2/20$194
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/112:45 pmIAD - ORD
1 stop7h 24mMultiple Airlines
Mon 5/56:20 amORD - IAD
1 stop7h 03mMultiple Airlines
Deal found 2/20$196
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2311:00 amDCA - ORD
1 stop7h 55mDelta
Mon 4/286:15 pmORD - DCA
1 stop3h 55mDelta
Deal found 2/20$197

Find flights from District of Columbia to Chicago within your budget

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 February 20, 2025.

Fly from

District of Columbia

Fly to

Chicago

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 5/9

4:00 pm-11:11 pm

1 stop8h 11m

Chicago O'Hare Intl

Mon 5/12

6:20 am-2:23 pm

1 stop7h 03m

$156

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 3/6

10:25 pm-9:25 pm

1 stop24h 00m

Chicago Midway

Mon 3/10

4:20 pm-1:16 pm

1 stop19h 56m

$159

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sun 3/9

1:03 pm-12:23 am

1 stop12h 20m

Chicago O'Hare Intl

Thu 3/13

6:45 am-4:59 pm

1 stop9h 14m

$160

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 3/9

1:03 pm-12:19 am

1 stop12h 16m

Chicago Midway

Tue 3/11

6:40 am-4:59 pm

1 stop9h 19m

$160

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 4/1

8:30 am-9:45 am

Nonstop2h 15m

Chicago O'Hare Intl

Thu 4/3

6:00 am-8:58 am

Nonstop1h 58m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/15

8:55 pm-9:55 pm

Nonstop2h 00m

Chicago Midway

Mon 4/21

7:20 am-10:10 am

Nonstop1h 50m

$177

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 3/19

10:20 pm-11:29 pm

Nonstop2h 09m

Chicago O'Hare Intl

Tue 3/25

4:05 pm-6:57 pm

Nonstop1h 52m

$178

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 4/2

11:59 am-1:18 pm

Nonstop2h 19m

Chicago O'Hare Intl

Tue 4/8

11:29 am-2:20 pm

Nonstop1h 51m

$181

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 4/26

7:11 am-12:27 pm

1 stop6h 16m

Chicago O'Hare Intl

Tue 4/29

1:22 pm-8:59 pm

1 stop6h 37m

$183

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 3/25

3:05 pm-9:47 pm

1 stop7h 42m

Chicago O'Hare Intl

Thu 3/27

6:15 pm-11:00 pm

1 stop3h 45m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 39 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.

Travel insights for flights from District of Columbia to Chicago

Get recent, data-driven insights about flights from District of Columbia to Chicago including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.

The most flights from USDC to CHI are scheduled on a Thursday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 February 20, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $81. United Airlines flights start at $89 while deals on Southwest start at $89 one-way.

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

    While some choose either Washington, D.C. Reagan-National - Chicago O'Hare Intl or Washington, D.C. Reagan-National - Chicago Midway, Washington, D.C. Dulles Intl - 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: Ethiopian Air (85%), Copa Airlines (83%), ANA (83%).

  • 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 $1,024, our data indicates the cheapest price to be $108. The most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), is priced around $122.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$173FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$197FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$133Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$149Average$329FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$158Average$292FlexibilityNo cancel feeOn-time63%
DeltaCheapest$175Average$294FlexibilityNo cancel feeOn-timeN/A
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