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$90+ Cheap flights from Washington 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
SEA — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Washington to Chicago

Keep the following information in mind while searching for Washington to Chicago flight deals. Data was last updated July 30, 2025.

Round-trip from

$175
(Kiwi.com)

One-way from

$90
(KAYAK)

Popular in

December

Cheapest in

January

Average price

$333

Good round-trip deal

$241 or less

Good one-way deal

$165 or less
From Washington to Chicago (CHI)
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One-way flight from Washington to Chicago (CHI)
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Highest demand for flights based on searches. 4% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Washington to Chicago (CHI).
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Price to beat on a one-way flight from Washington to Chicago (CHI).
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Find flight deals from Washington to Chicago

Cheapest flights from Washington to Chicago
Explore the most affordable flight options available from Washington to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/95:55 pmSEA - ORD
Nonstop4h 08mHawaiian Airlines
Tue 9/165:45 pmORD - SEA
Nonstop4h 32mHawaiian Airlines
Deal found 7/28$175
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/305:50 pmSEA - ORD
Nonstop4h 01mDelta
Sun 8/317:15 amORD - SEA
Nonstop4h 30mDelta
Deal found 7/27$179
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2512:59 amSEA - ORD
Nonstop4h 04mAlaska Airlines
Tue 8/2610:00 amORD - SEA
Nonstop4h 34mAlaska Airlines
Deal found 7/28$183
This Southwest deal was found by Cheapflights users on 7/30. 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 8/3011:10 pmSEA - MDW
Nonstop4h 05mSouthwest
Sat 9/65:25 pmMDW - SEA
Nonstop4h 30mSouthwest
Deal found 7/30$184
This CheapOair deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/75:30 pmSEA - ORD
1 stop10h 33mSpirit Airlines
Tue 8/127:08 amORD - SEA
1 stop11h 17mSpirit Airlines
Deal found 7/29$188
This Hawaiian Airlines deal was found by Cheapflights users on 7/30. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/61:40 pmGEG - ORD
1 stop8h 23mHawaiian Airlines
Sat 9/135:45 pmORD - GEG
1 stop8h 34mHawaiian Airlines
Deal found 7/30$194
This United Airlines deal was found by Cheapflights users on 7/29. 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 9/168:00 amSEA - ORD
1 stop8h 25mUnited Airlines
Sat 9/207:10 amORD - SEA
Nonstop4h 33mUnited Airlines
Deal found 7/29$195
This Delta deal was found by Cheapflights users on 7/28. 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 8/271:00 pmGEG - ORD
1 stop7h 04mDelta
Wed 9/36:05 pmORD - GEG
1 stop7h 57mDelta
Deal found 7/28$195
This American Airlines deal was found by Cheapflights users on 7/30. 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 11/51:14 pmGEG - ORD
Nonstop3h 58mAmerican Airlines
Sat 11/1510:30 amORD - GEG
Nonstop4h 02mAmerican Airlines
Deal found 7/30$197
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:50 amGEG - MDW
2 stops12h 22mDelta
Sat 9/139:20 amMDW - GEG
1 stop5h 57mDelta
Deal found 7/29$200
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:04 pmPDX - ORD
1 stop6h 45mSpirit Airlines
Wed 10/16:00 amORD - PDX
1 stop7h 12mSpirit Airlines
Deal found 7/28$201
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/2710:38 amPDX - ORD
Nonstop4h 09mAmerican Airlines
Sun 8/317:00 amORD - PDX
Nonstop4h 24mAmerican Airlines
Deal found 7/28$203

Cheapflights Fare Finder

 
Customize your flight search to find flights from Washington 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 July 30, 2025.
Use the filters below to find and compare flights from Washington to Chicago that are best for you.

Fly from

Washington

Fly to

Chicago

Route

Depart

Return

Price

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Tue 9/9

5:55 pm-12:03 am

Nonstop4h 08m

Chicago O'Hare Intl

Tue 9/16

5:45 pm-8:17 pm

Nonstop4h 32m

$175

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Sat 8/30

5:50 pm-11:51 pm

Nonstop4h 01m

Chicago O'Hare Intl

Sun 8/31

7:15 am-9:45 am

Nonstop4h 30m

$179

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Mon 8/25

12:59 am-7:03 am

Nonstop4h 04m

Chicago O'Hare Intl

Tue 8/26

10:00 am-12:34 pm

Nonstop4h 34m

$183

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 8/30

11:10 pm-5:15 am

Nonstop4h 05m

Chicago Midway

Sat 9/6

5:25 pm-7:55 pm

Nonstop4h 30m

$184

SpokaneChicago

GEG - ORD

GEGORD

Spokane

Sat 9/6

1:40 pm-12:03 am

1 stop8h 23m

Chicago O'Hare Intl

Sat 9/13

5:45 pm-12:19 am

1 stop8h 34m

$194

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Tue 9/16

8:00 am-6:25 pm

1 stop8h 25m

Chicago O'Hare Intl

Sat 9/20

7:10 am-9:43 am

Nonstop4h 33m

$195

SpokaneChicago

GEG - ORD

GEGORD

Spokane

Wed 8/27

1:00 pm-10:04 pm

1 stop7h 04m

Chicago O'Hare Intl

Wed 9/3

6:05 pm-12:02 am

1 stop7h 57m

$195

SpokaneChicago

GEG - MDW

GEGMDW

Spokane

Sat 9/6

6:50 am-9:12 pm

2 stops12h 22m

Chicago Midway

Sat 9/13

9:20 am-1:17 pm

1 stop5h 57m

$200

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 9/19

8:04 pm-4:49 am

1 stop6h 45m

Chicago O'Hare Intl

Wed 10/1

6:00 am-11:12 am

1 stop7h 12m

$201

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 8/27

10:38 am-4:47 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sun 8/31

7:00 am-9:24 am

Nonstop4h 24m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 60 results
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Best time to book a flight from Washington to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Washington 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 to Chicago

What is the cheapest month to book a flight from State of Washington to Chicago?

Currently, August is the cheapest month in which you can book a flight from State of Washington to Chicago (average of $245). Flying from State of Washington 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 WA to CHI?

Find hourly flight availability from Washington 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 July 30, 2025.

When flying from State of Washington 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 State of Washington to Chicago

Explore weekly flight availability from Washington 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 July 30, 2025.

The most flights from USWA to CHI are scheduled on a Monday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (36 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 July 30, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Washington to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

Find useful and relevant information for your journey from Washington 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 State of Washington to Chicago one-way?

    To fly one-way, consider booking your trip with Hawaiian Airlines, which is currently one of the cheapest options available, starting at $90. Delta flights start at $98 while deals on United Airlines start at $98 one-way.

  • What are the most popular routes from State of Washington to Chicago?

    While some choose either Portland - Chicago O'Hare Intl or Seattle/Tacoma Intl - Chicago Midway, Seattle/Tacoma Intl - Chicago O'Hare Intl is the most popular route from State of Washington to Chicago.

  • What are the most reliable airlines from State of Washington to Chicago?

    No one likes to see their flight delayed. When booking a flight from State of Washington to Chicago consider choosing Air France (100%), Austrian Airlines (91%) or Korean Air (85%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from State of Washington to Chicago?

    While on average a flight from State of Washington to Chicago is generally $1,085, our data shows the cheapest flight currently is $119. When looking at the most popular route, (Seattle/Tacoma Intl - Chicago O'Hare Intl), you can expect to pay $155 for that flight.

  • Can I find deals for flights from Washington to Chicago that include hotel bookings?

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

  • How can I find direct flights from Washington to Chicago?

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

  • Can I find deals for business class flights from Washington to Chicago?

    Yes. Cheapflights offers flight deals from Washington 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 State of Washington to Chicago?

    Currently, August is the cheapest month in which you can book a flight from State of Washington to Chicago (average of $245). Flying from State of Washington 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 Washington to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Washington to Chicago

Discover the top 8 airlines that operate flights from Washington 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$161FlexibilityNo cancel feeOn-time65%
DeltaCheapest$117Average$368FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$121Average$289FlexibilityNo cancel feeOn-time85%
FrontierCheapest$137Average$276FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$160Average$380FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$168Average$438FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$169Average$306FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$179Average$386FlexibilityNo cancel feeOn-time63%

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