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$74+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SEA — CHI
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
1 adult, Economy
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Cheap 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 January 31, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/261:16 pm
SEA
-
ORD
1 stop22h 09m
Frontier
Thu 3/54:16 pm
ORD
-
SEA
1 stop21h 03m
Frontier
Deal found 1/29$160
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Fri 2/2012:07 am
SEA
-
ORD
Nonstop4h 16m
American Airlines
Sat 2/289:40 pm
ORD
-
SEA
Nonstop4h 44m
American Airlines
Deal found 1/30$163
This Southwest deal was found by Cheapflights users on 1/30. 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 2/217:10 am
SEA
-
MDW
Nonstop4h 05m
Southwest
Sat 2/2811:10 am
MDW
-
SEA
Nonstop4h 40m
Southwest
Deal found 1/30$164
This WAYA deal was found by Cheapflights users on 1/30. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/191:16 pm
SEA
-
ORD
1 stop7h 58m
Multiple Airlines
Tue 2/245:29 pm
ORD
-
SEA
Nonstop4h 47m
Multiple Airlines
Deal found 1/30$174
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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.
Fri 2/275:55 pm
SEA
-
ORD
Nonstop4h 01m
Alaska Airlines
Sat 3/75:29 pm
ORD
-
SEA
Nonstop4h 47m
Alaska Airlines
Deal found 1/28$177
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:35 am
SEA
-
MDW
Nonstop4h 00m
Southwest
Sun 3/111:00 am
MDW
-
SEA
Nonstop4h 35m
Southwest
Deal found 1/28$177
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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.
Fri 2/276:00 am
SEA
-
ORD
Nonstop4h 01m
Alaska Airlines
Mon 3/25:29 pm
ORD
-
SEA
Nonstop4h 47m
Alaska Airlines
Deal found 1/28$179
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:30 pm
SEA
-
MDW
1 stop9h 11m
Frontier
Mon 3/23:29 pm
MDW
-
SEA
2 stops28h 49m
Frontier
Deal found 1/30$180
This Southwest deal was found by Cheapflights users on 1/31. 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 3/145:00 am
SEA
-
MDW
Nonstop3h 55m
Southwest
Wed 3/189:20 pm
MDW
-
SEA
Nonstop4h 35m
Southwest
Deal found 1/31$181
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/2012:30 pm
SEA
-
ORD
1 stop26h 23m
Frontier
Mon 2/237:19 pm
ORD
-
SEA
1 stop17h 35m
Frontier
Deal found 1/31$182
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2112:32 pm
SEA
-
ORD
1 stop8h 54m
United Airlines
Fri 2/274:20 pm
ORD
-
SEA
Nonstop4h 43m
United Airlines
Deal found 1/28$183
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:00 am
SEA
-
ORD
Nonstop4h 11m
Alaska Airlines
Fri 3/62:07 pm
ORD
-
SEA
1 stop8h 54m
Alaska Airlines
Deal found 1/30$186

Find flight deals from Washington to Chicago

Keep the following information in mind while searching for Washington to Chicago flight deals. Data was last updated January 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$160
(Kiwi.com)

One-way from

$74
(Frontier)

Popular in

December

Cheapest in

February

Average price

$277

Good round-trip deal

$292 or less

Good one-way deal

$158 or less
Provider with most accurate pricing for Seattle/Tacoma Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Seattle/Tacoma Intl-Chicago (CHI) flights.
Search Deals
From Washington to Chicago (CHI)
Search Deals
One-way flight from Washington to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Washington to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Washington to Chicago (CHI).
Search Deals

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 January 31, 2026.
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 - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 2/21

7:10 am-1:15 pm

Nonstop4h 05m

Chicago Midway

Sat 2/28

11:10 am-1:50 pm

Nonstop4h 40m

$164

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Wed 2/25

5:55 pm-11:52 pm

Nonstop3h 57m

Chicago O'Hare Intl

Thu 3/5

7:40 am-10:25 am

Nonstop4h 45m

$177

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Sat 3/14

5:55 pm-11:51 pm

Nonstop3h 56m

Chicago O'Hare Intl

Wed 3/18

7:25 am-10:05 am

Nonstop4h 40m

$177

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Mon 2/23

6:35 am-12:35 pm

Nonstop4h 00m

Chicago Midway

Sun 3/1

11:00 am-1:35 pm

Nonstop4h 35m

$177

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 3/14

5:00 am-10:55 am

Nonstop3h 55m

Chicago Midway

Wed 3/18

9:20 pm-11:55 pm

Nonstop4h 35m

$181

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Thu 3/5

5:15 am-11:10 am

Nonstop3h 55m

Chicago Midway

Mon 3/9

6:25 pm-1:40 am

1 stop9h 15m

$187

SeattleChicago

SEA - MDW

SEAMDW

Seattle/Tacoma Intl

Sat 3/14

7:55 pm-5:35 am

1 stop7h 40m

Chicago Midway

Tue 3/17

12:25 pm-6:20 pm

1 stop7h 55m

$197

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Sat 3/14

11:59 pm-5:56 am

Nonstop3h 57m

Chicago O'Hare Intl

Tue 3/17

12:54 pm-7:28 pm

1 stop8h 34m

$207

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Fri 2/20

6:00 am-12:01 pm

Nonstop4h 01m

Chicago O'Hare Intl

Sat 2/28

7:00 am-9:51 am

Nonstop4h 51m

$207

SeattleChicago

SEA - ORD

SEAORD

Seattle/Tacoma Intl

Thu 2/26

11:59 pm-5:56 am

Nonstop3h 57m

Chicago O'Hare Intl

Sat 2/28

6:17 pm-12:59 am

1 stop8h 42m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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, February is the cheapest month in which you can book a flight from State of Washington to Chicago (average of $114). Flying from State of Washington to Chicago in July is currently the most expensive (average of $169). 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 January 31, 2026.

When flying from State of Washington to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 15% versus a flight in the evening.

What is the cheapest day to fly from State of Washington to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Washington to Chicago. Price data was last updated on January 24, 2026.

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

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 January 31, 2026.

The most flights from USWA to CHI are scheduled on a Friday (36 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (22 on average).

How much does it cost to fly round-trip from State of Washington to Chicago?

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.

  • How long is the flight from State of Washington to Chicago?

    For as low as $177, Southwest can have you in Chicago from State of Washington in 3h 57m. Airlines will cover a distance of 1715 mi. Generally, flights for this route are nonstop.

  • 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 Austrian Airlines (88%), Gulf Air (85%) or Alaska Airlines (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 $826, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Seattle/Tacoma Intl - Chicago O'Hare Intl), you can expect to pay $175 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, February is the cheapest month in which you can book a flight from State of Washington to Chicago (average of $114). Flying from State of Washington to Chicago in July is currently the most expensive (average of $169). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 7 airlines flying from Washington to Chicago

Discover the top 7 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 January 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$97Average$327FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$114Average$258FlexibilityNo cancel feeOn-time85%
FrontierCheapest$137Average$271FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$154Average$339FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$169Average$436FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$178Average$324FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$184Average$349FlexibilityNo cancel feeOn-time63%

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