What are the cheapest airlines flying from Washington, D.C. to Chicago round-trip?

Cheapflights users have booked flights from Washington, D.C. to Chicago round-trip from $116. Other airlines that can offer you cheap pricing are Spirit Airlines, from $124, and United Airlines, from $157. Frontier is 54% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest airlines to fly from Washington, D.C. to Chicago one-way?

One-way options have recently been found by users for as low as $63 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $76 and Southwest from $79 one-way.

What are the most popular routes from Washington, D.C. to Chicago?

The most popular route from Washington, D.C. to Chicago is Washington, D.C. Dulles Intl - Chicago O'Hare Intl. You may also consider Baltimore/Washington - Chicago O'Hare Intl or Washington, D.C. Reagan-National - Chicago O'Hare Intl.

What are the cheapest flights from Washington, D.C. to Chicago?

Looking at all options, your cheapest flight can be booked for $114. While the most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) can be booked for $177 on average our data indicates $1,800 when flying from Washington, D.C. to Chicago.

What are the most reliable airlines from Washington, D.C. to Chicago?

The top 3 most reliable airlines when flying from Washington, D.C. to Chicago are Sun Country Air (100%), Emirates (100%) and Austrian Airlines (88%).

What are the most popular airlines that fly from Washington, D.C. to Chicago?

Consider American Airlines, Delta or Frontier when booking your flight. These represent the most popular airlines when flying from Washington, D.C. to Chicago.

What is the cheapest day to fly round-trip from Washington, D.C. to Chicago?

Saturday flights are generally found to be more expensive for flights from Washington, D.C. to Chicago. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

How far in advance should I book a flight from Washington, D.C. to Chicago?

To save on the cost of your flight from Washington, D.C. to Chicago, book at least 51 days before your planned departure. Booking around this time can save you about 90% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $274 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $485.

What is the cheapest month to fly from Washington, D.C. to Chicago?

September can be a great time to fly to Chicago from Washington, D.C. with a flight ticket averaging about $253. Cheapflights users have found deals in the month of September for as cheap as $63. The most expensive prices can be found in the month of March.

Most accurate provider : When it comes to deals on Washington, D.C.-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C.-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C.-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Washington, D.C.-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C.-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Can I find deals for flights from Washington, D.C. to Chicago that include hotel bookings?

Yes. In addition to deals on Washington, D.C. to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Washington, D.C. to Chicago?

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

Can I find deals for business class flights from Washington, D.C. to Chicago?

Yes. Cheapflights offers flight deals from Washington, D.C. 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.

$63+ Flights from Washington, D.C. to Chicago

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 88 days in advance, depart on a Friday or Wednesday and return on a Friday

Cheap flight deals from Washington, D.C. to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$116 (Frontier)
One-way from	$63 (Mytrip)
Popular in	March
Cheapest in	September
Average price	$289
Good round-trip deal	$163 or less
Good one-way deal	$64 or less

Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.

Search Deals

From Washington, D.C. (WAS) to Chicago (CHI)

Search Deals

One-way flight from Washington, D.C. (WAS) to Chicago (CHI)

Search Deals

High demand for flights, 0% potential price rise

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in March 2025

Search Deals

Price to beat on a round-trip flight from Washington, D.C. (WAS) to Chicago (CHI).

Search Deals

Price to beat on a one-way flight from Washington, D.C. (WAS) to Chicago (CHI).

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Find flight deals from Washington, D.C. to Chicago

Cheapest flights from Washington, D.C. to Chicago
Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2025.

Wed 4/94:45 pmBWI - MDW

Nonstop2h 06mFrontier

Wed 4/161:05 pmMDW - BWI

Nonstop1h 50mFrontier

Deal found 3/24

$116

Thu 5/86:20 amBWI - ORD

1 stop27h 35mSpirit Airlines

Mon 5/1211:00 amORD - BWI

1 stop23h 04mSpirit Airlines

Deal found 3/23

$124

Tue 4/226:15 amBWI - ORD

Nonstop2h 17mUnited Airlines

Tue 4/2911:20 amORD - BWI

Nonstop1h 58mUnited Airlines

Deal found 3/23

$157

Tue 5/66:40 amBWI - MDW

Nonstop2h 05mSouthwest

Tue 5/67:35 pmMDW - BWI

Nonstop1h 50mSouthwest

Deal found 3/24

$159

Tue 5/610:35 amBWI - ORD

Nonstop2h 15mSouthwest

Thu 5/81:50 pmORD - BWI

Nonstop1h 55mSouthwest

Deal found 3/24

$168

Mon 4/148:00 pmDCA - ORD

Nonstop2h 17mUnited Airlines

Thu 4/1712:45 pmORD - DCA

Nonstop1h 56mUnited Airlines

Deal found 3/24

$177

Mon 4/1410:20 pmIAD - ORD

Nonstop2h 09mUnited Airlines

Thu 4/171:28 pmORD - IAD

Nonstop2h 02mUnited Airlines

Deal found 3/24

$177

Tue 4/227:30 amDCA - MDW

Nonstop2h 00mSouthwest

Tue 4/293:20 pmMDW - DCA

Nonstop1h 50mSouthwest

Deal found 3/23

$177

Fri 5/306:00 amDCA - ORD

Nonstop2h 20mAmerican Airlines

Wed 6/47:11 pmORD - DCA

Nonstop2h 04mAmerican Airlines

Deal found 3/23

$178

Wed 4/3010:15 amDCA - ORD

1 stop9h 20mJetBlue

Tue 5/68:45 amORD - DCA

1 stop7h 10mJetBlue

Deal found 3/24

$183

Wed 4/235:47 pmDCA - ORD

1 stop3h 58mDelta

Wed 4/306:15 pmORD - DCA

1 stop3h 55mDelta

Deal found 3/24

$197

Thu 4/246:00 amIAD - MDW

1 stop3h 40mDelta

Wed 4/306:04 amMDW - IAD

1 stop4h 19mDelta

Deal found 3/24

$197

Best flights from Washington, D.C. to Chicago
Discover carefully curated flight deals from Washington, D.C. to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 25, 2025.

Wed 4/94:45 pmBWI - MDW

Nonstop2h 06mFrontier

Wed 4/161:05 pmMDW - BWI

Nonstop1h 50mFrontier

Deal found 3/24

$116

Thu 5/86:20 amBWI - ORD

1 stop27h 35mSpirit Airlines

Mon 5/1211:00 amORD - BWI

1 stop23h 04mSpirit Airlines

Deal found 3/23

$124

Tue 4/226:15 amBWI - ORD

Nonstop2h 17mUnited Airlines

Tue 4/2911:20 amORD - BWI

Nonstop1h 58mUnited Airlines

Deal found 3/23

$157

Tue 5/66:40 amBWI - MDW

Nonstop2h 05mSouthwest

Tue 5/67:35 pmMDW - BWI

Nonstop1h 50mSouthwest

Deal found 3/24

$159

Fri 5/306:00 amDCA - ORD

Nonstop2h 20mAmerican Airlines

Wed 6/47:11 pmORD - DCA

Nonstop2h 04mAmerican Airlines

Deal found 3/23

$178

Wed 4/3010:15 amDCA - ORD

1 stop9h 20mJetBlue

Wed 5/74:03 pmORD - DCA

1 stop5h 55mJetBlue

Deal found 3/24

$183

Wed 4/236:00 amDCA - ORD

1 stop4h 21mDelta

Wed 4/235:05 pmORD - DCA

1 stop5h 05mDelta

Deal found 3/23

$197

Mon 4/149:32 pmBWI - ORD

1 stop12h 52mMultiple Airlines

Thu 4/177:10 pmORD - BWI

1 stop13h 53mMultiple Airlines

Deal found 3/24

$199

Sun 5/412:49 pmIAD - ORD

1 stop7h 20mSun Country Air

Thu 5/88:05 pmORD - IAD

1 stop15h 18mSun Country Air

Deal found 3/24

$255

Tue 5/610:35 amBWI - ORD

Nonstop2h 15mSouthwest

Thu 5/81:50 pmORD - BWI

Nonstop1h 55mSouthwest

Deal found 3/24

$168

Sun 6/83:58 pmIAD - MDW

1 stop16h 17mAllegiant Air

Fri 6/132:53 pmMDW - IAD

2 stops29h 00mAllegiant Air

Deal found 3/23

$349

Thu 5/16:25 amDCA - ORD

Nonstop2h 15mUnited Airlines

Thu 5/13:22 pmORD - DCA

Nonstop2h 01mUnited Airlines

Deal found 3/24

$177

Last-minute flights from Washington, D.C. to Chicago
Discover last-minute flight deals from Washington, D.C. to Chicago. Data last updated March 25, 2025 and is based on user searches.

Tue 4/14:50 pmBWI - MDW

Nonstop2h 10mSouthwest

Tue 4/87:35 pmMDW - BWI

Nonstop1h 50mSouthwest

Deal found 3/23

$263

Tue 4/16:25 amBWI - ORD

1 stop8h 35mSouthwest

Tue 4/81:50 pmORD - BWI

Nonstop1h 55mSouthwest

Deal found 3/23

$273

Tue 4/17:30 amBWI - ORD

Nonstop2h 21mAmerican Airlines

Wed 4/22:59 pmORD - BWI

Nonstop1h 47mAmerican Airlines

Deal found 3/23

$296

Wed 4/24:45 pmBWI - MDW

Nonstop2h 06mFrontier

Wed 4/91:05 pmMDW - BWI

Nonstop1h 50mFrontier

Deal found 3/23

$116

Wed 4/26:05 amBWI - ORD

1 stop27h 39mSpirit Airlines

Mon 4/78:33 pmORD - BWI

1 stop26h 39mSpirit Airlines

Deal found 3/23

$184

Wed 4/24:35 pmIAD - MDW

1 stop5h 58mFrontier

Thu 4/310:19 amMDW - IAD

1 stop5h 45mFrontier

Deal found 3/24

$218

Wed 4/21:03 pmDCA - MDW

1 stop12h 18mFrontier

Wed 4/96:45 amMDW - DCA

1 stop9h 14mFrontier

Deal found 3/24

$218

Wed 4/25:18 pmBWI - ORD

1 stop8h 24mMultiple Airlines

Thu 4/36:25 pmORD - BWI

1 stop4h 47mMultiple Airlines

Deal found 3/23

$234

Wed 4/21:03 pmDCA - ORD

1 stop12h 39mFrontier

Wed 4/96:40 amORD - DCA

1 stop14h 19mFrontier

Deal found 3/24

$240

Wed 4/25:18 pmBWI - ORD

1 stop8h 24mFrontier

Sat 4/57:20 amORD - BWI

1 stop7h 48mFrontier

Deal found 3/24

$240

Wed 4/25:07 pmBWI - ORD

Nonstop2h 18mUnited Airlines

Wed 4/97:00 amORD - BWI

Nonstop1h 54mUnited Airlines

Deal found 3/24

$263

Thu 4/311:45 amIAD - ORD

1 stop9h 10mFrontier

Fri 4/49:54 amORD - IAD

1 stop6h 11mFrontier

Deal found 3/24

$218

One-way flights from Washington, D.C. to Chicago
Search for one-way flight options from Washington, D.C. to Chicago. Find affordable one-way fares based on user searches. Data last updated March 25, 2025.

Wed 5/1412:20 pmBWI - ORD

1 stop21h 35mSpirit Airlines

Deal found 3/24

$63

Wed 6/116:27 pmBWI - MDW

Nonstop2h 04mFrontier

Deal found 3/23

$76

Wed 4/236:40 amBWI - MDW

Nonstop2h 05mSouthwest

Deal found 3/24

$79

Wed 4/236:15 amBWI - ORD

Nonstop2h 17mUnited Airlines

Deal found 3/24

$79

Mon 4/217:30 amBWI - ORD

Nonstop2h 10mAmerican Airlines

Deal found 3/23

$88

Thu 4/1710:30 amDCA - ORD

Nonstop2h 14mUnited Airlines

Deal found 3/24

$89

Tue 4/2910:20 pmIAD - ORD

Nonstop2h 09mUnited Airlines

Deal found 3/24

$89

Wed 6/119:00 amDCA - MDW

Nonstop2h 15mSouthwest

Deal found 3/24

$89

Sun 4/206:45 amDCA - ORD

Nonstop2h 09mAmerican Airlines

Deal found 3/24

$90

Mon 4/286:00 amDCA - ORD

1 stop5h 03mDelta

Deal found 3/24

$99

Mon 4/285:32 pmIAD - ORD

1 stop7h 27mDelta

Deal found 3/24

$99

Mon 4/216:00 amIAD - MDW

1 stop3h 40mDelta

Deal found 3/24

$99

Cheapflights Fare Finder

Use the filters below to find and compare flights from Washington, D.C. to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 4/9

4:45 pm-5:51 pm

Nonstop2h 06m

Chicago Midway

Wed 4/16

1:05 pm-3:55 pm

Nonstop1h 50m

$116

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 5/8

6:20 am-8:55 am

1 stop27h 35m

Chicago O'Hare Intl

Mon 5/12

11:00 am-11:04 am

1 stop23h 04m

$124

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 4/22

6:15 am-7:32 am

Nonstop2h 17m

Chicago O'Hare Intl

Tue 4/29

11:20 am-2:18 pm

Nonstop1h 58m

$157

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Tue 5/6

6:40 am-7:45 am

Nonstop2h 05m

Chicago Midway

Tue 5/6

7:35 pm-10:25 pm

Nonstop1h 50m

$159

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 5/6

10:35 am-11:50 am

Nonstop2h 15m

Chicago O'Hare Intl

Thu 5/8

1:50 pm-4:45 pm

Nonstop1h 55m

$168

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 4/14

8:00 pm-9:17 pm

Nonstop2h 17m

Chicago O'Hare Intl

Thu 4/17

12:45 pm-3:41 pm

Nonstop1h 56m

$177

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 4/14

10:20 pm-11:29 pm

Nonstop2h 09m

Chicago O'Hare Intl

Thu 4/17

1:28 pm-4:30 pm

Nonstop2h 02m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/22

7:30 am-8:30 am

Nonstop2h 00m

Chicago Midway

Tue 4/29

3:20 pm-6:10 pm

Nonstop1h 50m

$177

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 5/30

6:00 am-7:20 am

Nonstop2h 20m

Chicago O'Hare Intl

Wed 6/4

7:11 pm-10:15 pm

Nonstop2h 04m

$178

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 4/30

10:15 am-6:35 pm

1 stop9h 20m

Chicago O'Hare Intl

Tue 5/6

8:45 am-4:55 pm

1 stop7h 10m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 60 results

...

Compare providers for flights from Washington, D.C. to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Washington, D.C. to Chicago in March.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Mytrip	Price Accuracy3 stars	Trust Score*3 stars
Cheapflightsfares	Price Accuracy3 stars	Trust Score*2 stars
Cheapfaremart	Price Accuracy-	Trust Score*3 stars
CheapOair	Price Accuracy1 star	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Washington, D.C.-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C.-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C.-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Washington, D.C.-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C.-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Washington, D.C. to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. to Chicago trip

Airlines

United Airlines

United's Economy Plus offers extra legroom and priority boarding, ideal for frequent business travelers.

United's Polaris Lounges in Chicago offer showers, napping areas, and dining for premium passengers.

Read more about United Airlinesby Harriet Baskas

Southwest

Southwest's Wanna Get Away fare includes two free checked bags, perfect for budget-conscious travelers.

Southwest offers free in-flight entertainment streamed to your device, enhancing the travel experience.

Read more about Southwestby Marisa Garcia

Airports

DCA

DCA offers easy Metro access with its own stop on the Yellow and Blue lines, making it a convenient choice for travelers from D.C. and nearby areas.

IAD

At IAD, the Aerotrain connects terminals, but be prepared for long walks, especially to United Express gates. Plan extra time for navigation.

ORD

ORD's 'L' train offers a reliable route to downtown Chicago, avoiding traffic and providing a cost-effective travel option from the airport.

MDW

MDW is well-connected to Chicago via the Orange Line, offering a quick, 30-minute ride to the city center, making it a convenient arrival option.

Our travel experts

Harriet Baskas

Expert on United Airlines

Marisa Garcia

Expert on Southwest

Ramsey Qubein

Expert on ORD, MDW and IAD

Emily Zemler

Expert on DCA

Best time to book a flight from Washington, D.C. to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Washington, D.C. 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 Washington, D.C. to Chicago

How far ahead should I book a flight from Washington, D.C. to Chicago?

To ensure you get the cheapest price possible for a flight from Washington, D.C. to Chicago, you should look to book at least 88 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Washington, D.C. to Chicago?

Currently, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $245). Flying from Washington, D.C. to Chicago in March is currently the most expensive (average of $323). 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 WAS to CHI?

Unlike at noon, when flights are generally more expensive, you can save up to 27% on flights from Washington, D.C. to Chicago by exploring options for tickets in the evening.

What is the cheapest day to fly from Washington, D.C. to Chicago?

Travelers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Washington, D.C. to Chicago

The most flights from WAS to CHI are scheduled on a Monday (76 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (57 on average).

Rainfall in Chicago 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

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

Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

9,785 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines

8.0

Very good

9,785 reviews

Alaska Airlines

8.0

Very good

9,785 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Southwest

8.0

Very good

4,272 reviews

Alaska Airlines

8.0

Very good

9,785 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta

8.0

Very good

7,890 reviews

Alaska Airlines

8.0

Very good

9,785 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines

7.4

Good

8,605 reviews

Alaska Airlines

8.0

Very good

9,785 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

JetBlue

7.3

Good

2,924 reviews

Alaska Airlines

8.0

Very good

9,785 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

What are the cheapest airlines flying from Washington, D.C. to Chicago round-trip?
Cheapflights users have booked flights from Washington, D.C. to Chicago round-trip from $116. Other airlines that can offer you cheap pricing are Spirit Airlines, from $124, and United Airlines, from $157. Frontier is 54% cheaper than the average price of flights available within the next 90 days to this destination.
What are the cheapest airlines to fly from Washington, D.C. to Chicago one-way?
One-way options have recently been found by users for as low as $63 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $76 and Southwest from $79 one-way.
What are the most popular routes from Washington, D.C. to Chicago?
The most popular route from Washington, D.C. to Chicago is Washington, D.C. Dulles Intl - Chicago O'Hare Intl. You may also consider Baltimore/Washington - Chicago O'Hare Intl or Washington, D.C. Reagan-National - Chicago O'Hare Intl.
What are the most reliable airlines from Washington, D.C. to Chicago?
The top 3 most reliable airlines when flying from Washington, D.C. to Chicago are Sun Country Air (100%), Emirates (100%) and Austrian Airlines (88%).
What are the cheapest flights from Washington, D.C. to Chicago?
Looking at all options, your cheapest flight can be booked for $114. While the most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) can be booked for $177 on average our data indicates $1,800 when flying from Washington, D.C. to Chicago.
Can I find deals for flights from Washington, D.C. to Chicago that include hotel bookings?
Yes. In addition to deals on Washington, D.C. to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Washington, D.C. to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Washington, D.C. to Chicago.
Can I find deals for business class flights from Washington, D.C. to Chicago?
Yes. Cheapflights offers flight deals from Washington, D.C. 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 Washington, D.C. to Chicago?
Currently, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $245). Flying from Washington, D.C. to Chicago in March is currently the most expensive (average of $323). 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.

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Top 6 airlines flying from Washington, D.C. to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$58	Average$176	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$101	Average$193	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$137	Average$326	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$151	Average$347	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$160	Average$300	FlexibilityNo cancel fee	On-time63%
Delta	Cheapest$176	Average$319	FlexibilityNo cancel fee	On-timeN/A

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$63+ Cheap flights from Washington, D.C. (WAS) 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.

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Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 88 days in advance, depart on a Friday or Wednesday and return on a Friday

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Cheapest flights from Washington, D.C. to ChicagoExplore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2025.

Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2025.

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Compare providers for flights from Washington, D.C. to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Washington, D.C. to Chicago in March.

The best insider tips for Washington, D.C. to Chicago flights

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Best time to book a flight from Washington, D.C. to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Washington, D.C. with our price prediction graph.

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Everything you need to know about your flight from Washington, D.C. to Chicago

How far ahead should I book a flight from Washington, D.C. to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Washington, D.C. to Chicago. Price data was last updated on March 21, 2025.

What is the cheapest month to book a flight from Washington, D.C. to Chicago?

What is the cheapest time of day to fly from WAS to CHI?

Find hourly flight availability from Washington, D.C. 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 March 25, 2025.

What is the cheapest day to fly from Washington, D.C. to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Washington, D.C. to Chicago. Price data was last updated on March 16, 2025.

Weekly flight availability from Washington, D.C. to Chicago

Rainfall in Chicago by month

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

Temperature in Chicago by month

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Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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What are the cheapest airlines flying from Washington, D.C. to Chicago round-trip?

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Can I find deals for business class flights from Washington, D.C. to Chicago?

What is the cheapest month to book a flight from Washington, D.C. to Chicago?

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Cheapest flights from Washington, D.C. to Chicago
Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2025.