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 $124. Other airlines that can offer you cheap pricing are Frontier, from $125, and Southwest, from $169. Spirit Airlines is 51% 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 $69 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $72 and Southwest from $80 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 $97. While the most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) can be booked for $160 on average our data indicates $723 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 ANA (97%), Japan Airlines (89%) and Air New Zealand (85%).

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 87% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $262 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $466.

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 May.

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.

$68+ 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”

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Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 87 days in advance, depart on a Wednesday or Friday and return on a Thursday

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

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$124 (Flightnetwork)
One-way from	$69 (CheapOair)
Popular in	May
Cheapest in	September
Average price	$268
Good round-trip deal	$167 or less
Good one-way deal	$86 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

Highest demand for flights based on searches. 6% potential increase in price ($19 potential increase over avg. RT price).

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 April 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).

Search Deals

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 abril 11, 2025.

jue. 5/88:10 amBWI - ORD

Nonstop2h 14mSpirit Airlines

lun. 5/129:55 amORD - BWI

1 stop12h 38mSpirit Airlines

Deal found 4/10

$124

mié. 5/286:36 pmBWI - MDW

Nonstop2h 07mFrontier

vie. 5/302:53 pmMDW - BWI

Nonstop1h 53mFrontier

Deal found 4/10

$125

sáb. 5/106:45 amBWI - ORD

1 stop7h 56mMultiple Airlines

dom. 5/1110:33 amORD - BWI

Nonstop1h 46mMultiple Airlines

Deal found 4/10

$134

sáb. 7/510:35 amBWI - ORD

Nonstop2h 15mSouthwest

mié. 7/91:50 pmORD - BWI

Nonstop2h 00mSouthwest

Deal found 4/10

$169

dom. 5/116:45 amBWI - ORD

Nonstop2h 17mUnited Airlines

mar. 5/136:30 pmORD - BWI

Nonstop2h 07mUnited Airlines

Deal found 4/9

$170

mié. 7/210:35 amBWI - MDW

1 stop3h 45mSouthwest

mar. 7/87:15 amMDW - BWI

Nonstop1h 45mSouthwest

Deal found 4/10

$175

mar. 4/151:03 pmDCA - MDW

1 stop12h 18mFrontier

mié. 4/166:45 amMDW - DCA

1 stop9h 14mFrontier

Deal found 4/10

$178

mié. 5/288:30 amDCA - ORD

Nonstop2h 25mUnited Airlines

vie. 5/304:00 pmORD - DCA

Nonstop2h 02mUnited Airlines

Deal found 4/10

$179

mié. 5/283:35 pmIAD - ORD

Nonstop2h 13mUnited Airlines

sáb. 5/319:31 pmORD - IAD

Nonstop1h 59mUnited Airlines

Deal found 4/10

$179

mié. 5/289:35 amDCA - MDW

Nonstop1h 55mSouthwest

sáb. 5/315:35 pmMDW - DCA

Nonstop1h 55mSouthwest

Deal found 4/10

$179

vie. 4/255:25 pmIAD - ORD

1 stop7h 11mFrontier

lun. 4/286:30 amORD - IAD

1 stop6h 52mFrontier

Deal found 4/10

$180

jue. 4/249:08 amIAD - MDW

1 stop14h 18mFrontier

dom. 4/274:00 pmMDW - IAD

1 stop15h 18mFrontier

Deal found 4/10

$180

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 abril 11, 2025.

jue. 5/88:10 amBWI - ORD

Nonstop2h 14mSpirit Airlines

lun. 5/129:55 amORD - BWI

1 stop12h 38mSpirit Airlines

Deal found 4/10

$124

mié. 5/286:36 pmBWI - MDW

Nonstop2h 07mFrontier

vie. 5/302:53 pmMDW - BWI

Nonstop1h 53mFrontier

Deal found 4/10

$125

sáb. 5/106:45 amBWI - ORD

1 stop7h 56mMultiple Airlines

dom. 5/1110:33 amORD - BWI

Nonstop1h 46mMultiple Airlines

Deal found 4/10

$134

sáb. 7/510:35 amBWI - ORD

Nonstop2h 15mSouthwest

mié. 7/91:50 pmORD - BWI

Nonstop2h 00mSouthwest

Deal found 4/10

$169

dom. 5/116:45 amBWI - ORD

Nonstop2h 17mUnited Airlines

mar. 5/136:30 pmORD - BWI

Nonstop2h 07mUnited Airlines

Deal found 4/9

$170

sáb. 5/246:00 amDCA - ORD

1 stop4h 18mDelta

dom. 5/255:30 amORD - DCA

1 stop4h 30mDelta

Deal found 4/10

$197

mié. 5/72:54 pmDCA - ORD

Nonstop2h 19mAmerican Airlines

dom. 5/116:00 amORD - DCA

Nonstop1h 54mAmerican Airlines

Deal found 4/10

$198

sáb. 5/36:15 amDCA - ORD

1 stop6h 58mJetBlue

mar. 5/64:03 pmORD - DCA

1 stop5h 55mJetBlue

Deal found 4/10

$203

jue. 7/33:53 pmIAD - MDW

1 stop16h 20mAllegiant Air

dom. 7/611:37 amMDW - IAD

2 stops25h 46mAllegiant Air

Deal found 4/9

$317

jue. 8/2812:45 pmIAD - ORD

1 stop7h 27mSun Country Air

dom. 8/316:16 pmORD - IAD

1 stop16h 34mSun Country Air

Deal found 4/9

$325

mié. 7/210:35 amBWI - MDW

1 stop3h 45mSouthwest

mar. 7/87:15 amMDW - BWI

Nonstop1h 45mSouthwest

Deal found 4/10

$175

mar. 4/151:03 pmDCA - MDW

1 stop12h 18mFrontier

mié. 4/166:45 amMDW - DCA

1 stop9h 14mFrontier

Deal found 4/10

$178

Last-minute flights from Washington, D.C. to Chicago
Discover last-minute flight deals from Washington, D.C. to Chicago. Data last updated abril 11, 2025 and is based on user searches.

mar. 4/151:03 pmDCA - MDW

1 stop12h 18mFrontier

mié. 4/166:45 amMDW - DCA

1 stop9h 14mFrontier

Deal found 4/10

$178

mié. 4/1611:58 amBWI - ORD

1 stop5h 34mFrontier

mar. 4/2211:57 amORD - BWI

1 stop10h 04mFrontier

Deal found 4/10

$178

mié. 4/161:03 pmDCA - MDW

1 stop12h 18mFrontier

mar. 4/226:45 amMDW - DCA

1 stop28h 24mFrontier

Deal found 4/10

$180

mié. 4/161:03 pmDCA - ORD

1 stop12h 34mFrontier

jue. 4/176:45 amORD - DCA

1 stop28h 19mFrontier

Deal found 4/10

$190

vie. 4/189:32 pmBWI - ORD

1 stop12h 52mMultiple Airlines

mié. 4/239:28 amORD - BWI

1 stop10h 17mMultiple Airlines

Deal found 4/10

$247

sáb. 4/1912:48 pmIAD - ORD

1 stop7h 16mFrontier

lun. 4/286:30 amORD - IAD

1 stop6h 52mFrontier

Deal found 4/10

$190

sáb. 4/1910:25 pmIAD - MDW

1 stop14h 18mFrontier

jue. 4/241:26 pmMDW - IAD

1 stop26h 09mFrontier

Deal found 4/10

$190

sáb. 4/197:00 amDCA - ORD

1 stop7h 42mDelta

dom. 4/205:30 amORD - DCA

1 stop6h 16mDelta

Deal found 4/10

$217

sáb. 4/197:35 amIAD - ORD

1 stop7h 07mDelta

dom. 4/207:05 amORD - IAD

1 stop4h 49mDelta

Deal found 4/10

$217

sáb. 4/195:09 pmIAD - MDW

1 stop6h 13mDelta

dom. 4/206:04 amMDW - IAD

1 stop5h 50mDelta

Deal found 4/10

$217

sáb. 4/1912:30 pmDCA - MDW

1 stop6h 50mDelta

dom. 4/206:04 amMDW - DCA

1 stop4h 21mDelta

Deal found 4/10

$217

sáb. 4/192:55 pmDCA - ORD

Nonstop2h 17mAmerican Airlines

dom. 4/206:04 amORD - DCA

Nonstop1h 54mAmerican Airlines

Deal found 4/10

$249

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 abril 11, 2025.

vie. 5/306:36 pmBWI - MDW

Nonstop2h 07mFrontier

Deal found 4/10

$69

vie. 5/1612:51 pmBWI - ORD

1 stop11h 38mSpirit Airlines

Deal found 4/10

$72

sáb. 5/247:25 pmBWI - MDW

Nonstop2h 00mSouthwest

Deal found 4/9

$80

mar. 5/275:30 pmBWI - ORD

Nonstop2h 15mUnited Airlines

Deal found 4/9

$80

sáb. 5/247:00 amDCA - ORD

Nonstop2h 26mAmerican Airlines

Deal found 4/10

$82

lun. 5/53:32 pmIAD - ORD

1 stop8h 39mFrontier

Deal found 4/9

$84

lun. 5/53:32 pmIAD - MDW

1 stop9h 15mFrontier

Deal found 4/10

$86

jue. 5/17:00 amDCA - MDW

1 stop13h 08mFrontier

Deal found 4/10

$86

mié. 4/1611:58 amBWI - ORD

1 stop5h 34mFrontier

Deal found 4/10

$89

dom. 4/206:20 amDCA - ORD

Nonstop2h 15mUnited Airlines

Deal found 4/10

$90

dom. 4/209:35 pmDCA - MDW

Nonstop1h 55mSouthwest

Deal found 4/10

$90

mar. 7/16:05 amDCA - ORD

1 stop7h 40mSouthwest

Deal found 4/10

$91

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 - ORD

BWIORD

Baltimore/Washington

jue. 5/8

8:10 am-9:24 am

Nonstop2h 14m

Chicago O'Hare Intl

lun. 5/12

9:55 am-11:33 pm

1 stop12h 38m

$124

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

mié. 5/28

6:36 pm-7:43 pm

Nonstop2h 07m

Chicago Midway

vie. 5/30

2:53 pm-5:46 pm

Nonstop1h 53m

$125

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

sáb. 5/10

6:45 am-1:41 pm

1 stop7h 56m

Chicago O'Hare Intl

dom. 5/11

10:33 am-1:19 pm

Nonstop1h 46m

$134

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

sáb. 7/5

10:35 am-11:50 am

Nonstop2h 15m

Chicago O'Hare Intl

mié. 7/9

1:50 pm-4:50 pm

Nonstop2h 00m

$169

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

dom. 5/11

6:45 am-8:02 am

Nonstop2h 17m

Chicago O'Hare Intl

mar. 5/13

6:30 pm-9:37 pm

Nonstop2h 07m

$170

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

mié. 7/2

10:35 am-1:20 pm

1 stop3h 45m

Chicago Midway

mar. 7/8

7:15 am-10:00 am

Nonstop1h 45m

$175

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mar. 4/15

1:03 pm-12:21 am

1 stop12h 18m

Chicago Midway

mié. 4/16

6:45 am-4:59 pm

1 stop9h 14m

$178

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

mié. 5/28

8:30 am-9:55 am

Nonstop2h 25m

Chicago O'Hare Intl

vie. 5/30

4:00 pm-7:02 pm

Nonstop2h 02m

$179

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

mié. 5/28

3:35 pm-4:48 pm

Nonstop2h 13m

Chicago O'Hare Intl

sáb. 5/31

9:31 pm-12:30 am

Nonstop1h 59m

$179

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

mié. 5/28

9:35 am-10:30 am

Nonstop1h 55m

Chicago Midway

sáb. 5/31

5:35 pm-8:30 pm

Nonstop1h 55m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/11

Showing 1-10 of 59 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 April.

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 87 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 $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 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 Friday 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 Wednesday (81 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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

9,851 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

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

Alaska Airlines

8.0

Very good

9,851 reviews

Alaska Airlines

8.0

Very good

9,851 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

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

Southwest

8.0

Very good

4,279 reviews

Alaska Airlines

8.0

Very good

9,851 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

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

Delta

8.0

Very good

7,911 reviews

Alaska Airlines

8.0

Very good

9,851 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

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

United Airlines

7.4

Good

8,636 reviews

Alaska Airlines

8.0

Very good

9,851 reviews

Reviews

1 / 20

4.0

Okay

Anonymous,Apr 2025

LAS - STS

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

JetBlue

7.3

Good

2,924 reviews

Alaska Airlines

8.0

Very good

9,851 reviews

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

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 $124. Other airlines that can offer you cheap pricing are Frontier, from $125, and Southwest, from $169. Spirit Airlines is 51% 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 $69 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $72 and Southwest from $80 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 ANA (97%), Japan Airlines (89%) and Air New Zealand (85%).
What are the cheapest flights from Washington, D.C. to Chicago?
Looking at all options, your cheapest flight can be booked for $97. While the most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) can be booked for $160 on average our data indicates $723 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 $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.

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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$59	Average$181	FlexibilityNo cancel fee	On-time65%
American Airlines	Cheapest$142	Average$326	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$151	Average$345	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$164	Average$301	FlexibilityNo cancel fee	On-time63%
Delta	Cheapest$176	Average$322	FlexibilityNo cancel fee	On-timeN/A

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$68+ 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 5/30. 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 87 days in advance, depart on a Wednesday or Friday and return on a Thursday

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

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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 abril 11, 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 abril 11, 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 April.

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

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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.

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?

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 April 4, 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 abril 11, 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 30, 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

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

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

Find useful and relevant information for your journey from Washington, D.C. 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 flying from Washington, D.C. to Chicago round-trip?

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

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

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

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

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

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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Top 6 airlines flying 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 abril 11, 2025.