How does KAYAK find such low prices on flights from Washington to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Washington to Chicago. Visit our flight page for the latest deals!>/a>

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Washington is likely to change within 7 days, so travelers know whether to wait or book now. Visit our flight page for the latest deals!>/a>

What is the Hacker Fare option on flights from Washington to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Washington with another airline. Visit our flight page for the latest deals!>/a>

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Washington to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Washington up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!>/a>

$48 CHEAP FLIGHTS from Washington to Chicago

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Cheap Flight Deals from Washington to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Washington to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Washington to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Washington to Chicago.

Discover the best prices and deals for you by selecting your travel dates.

Choose your dates

1:36 pm - 12:17 amSEA-MDW

8h 41m1 stop

6:40 am - 12:02 pmMDW-SEA

7h 22m1 stop

$108Frontier

Find Deal

Wed, Mar 5 - Mon, Mar 10

2:02 pm - 12:23 amSEA-ORD

8h 21m1 stop

6:30 am - 12:02 pmORD-SEA

7h 32m1 stop

$110Frontier

Find Deal

Thu, Mar 6 - Mon, Mar 10

5:38 pm - 4:45 amSEA-ORD

9h 07m1 stop

6:30 am - 12:02 pmORD-SEA

7h 32m1 stop

$112

Find Deal

Tue, Mar 4 - Mon, Mar 10

7:47 pm - 6:07 amSEA-ORD

8h 20m1 stop

6:30 am - 12:02 pmORD-SEA

7h 32m1 stop

$115

Find Deal

Mon, Mar 3 - Mon, Mar 10

5:38 pm - 5:28 amSEA-ORD

9h 50m1 stop

10:48 am - 7:02 pmORD-SEA

10h 14m1 stop

$118Spirit Airlines

Find Deal

Wed, Feb 26 - Wed, Mar 5

10:16 am - 4:45 amPDX-ORD

16h 29m2 stops

7:47 am - 6:37 pmORD-PDX

12h 50m1 stop

$118Spirit Airlines

Find Deal

Tue, Mar 4 - Wed, Mar 5

11:59 pm - 5:59 amSEA-ORD

4h 00mnonstop

8:25 pm - 11:05 pmORD-SEA

4h 40mnonstop

$169American Airlines

Find Deal

Tue, Apr 1 - Wed, Apr 30

6:10 pm - 12:11 amSEA-ORD

4h 01mnonstop

7:00 am - 9:58 amORD-SEA

4h 58mnonstop

$179Delta

Find Deal

Wed, Feb 12 - Wed, Feb 19

5:55 pm - 11:56 pmSEA-ORD

4h 01mnonstop

7:00 am - 9:55 amORD-SEA

4h 55mnonstop

$184Delta

Find Deal

Sat, Feb 22 - Sat, Mar 1

1:33 pm - 7:43 pmSEA-ORD

4h 10mnonstop

8:25 pm - 11:06 pmORD-SEA

4h 41mnonstop

$198American Airlines

Find Deal

Sat, Mar 1 - Mon, Mar 3

Low season	January
High season	August
Cheapest flight	$48

Best time to beat the crowds with an average 5% drop in price.

Most popular time to fly and prices are also 4% lower on average.

Flight from Seattle to Chicago Midway Airport

Verified travelerFlew with Alaska AirlinesSEA-ORDOct 2024

Alaska airline has best boarding and baggage policy.

ShirleyFlew with Alaska AirlinesSEA-ORDJun 2024

I generally fly United or Delta out of South Bend, IN into Seattle or wherever I'm going. I have no issues with Alaska. I only use Alaska when flying with my family from the Seattle area back to Chicago O'Hare and then we drive to SW Michigan where I live. Alaska Airlines has a beautiful new terminal at SeaTac as well. A good airline. I do like planes that have screens on the back of the seats.

Verified travelerFlew with United AirlinesSEA-ORDJul 2024

Budget if you’re planning on shopping for meals or souvenirs at Sea-Tac, it’s not cheap.

Verified travelerFlew with Alaska AirlinesSEA-ORDJun 2024

Bring books and earplugs for the four hour flight and enjoy Chicago!

How does KAYAK find such low prices on flights from Washington to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Washington to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Washington is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Washington to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Washington with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Washington to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Washington up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.