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.

$145 CHEAP FLIGHTS from Washington to Chicago

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Flight Deals

Cheap Flights from Washington to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Washington to Chicago

Wed, Oct 7 - Wed, Oct 14

7:25 pm - 6:34 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

9h 09m1 stop Los Angeles Los Angeles

6:30 am - 3:12 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

10h 42m1 stop Denver Intl

$279Frontier

Sat, Oct 10 - Tue, Oct 13

8:00 pm - 6:34 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

8h 34m1 stop Los Angeles Los Angeles

6:30 am - 3:12 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

10h 42m1 stop Denver Intl

$279Frontier

Sat, Sep 12 - Sat, Sep 19

7:15 am - 1:29 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 14mnonstop

5:44 pm - 8:20 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 36mnonstop

$279Delta

Sat, Sep 26 - Tue, Sep 29

6:00 am - 12:07 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 07mnonstop

1:03 pm - 3:41 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 38mnonstop

$279Alaska Airlines

Fri, Sep 11 - Sat, Sep 19

12:16 am - 6:20 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 04mnonstop

7:00 pm - 9:38 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 38mnonstop

$279Alaska Airlines

Fri, Sep 11 - Tue, Sep 15

9:45 pm - 5:38 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

29h 53m1 stop Las Vegas Harry Reid Intl

6:00 am - 8:30 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 30mnonstop

$279Multiple Airlines

Thu, Oct 1 - Mon, Oct 26

6:00 am - 12:07 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 07mnonstop

8:01 pm - 6:54 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

24h 53m1 stop Los Angeles Los Angeles

$279Multiple Airlines

Sat, Sep 26 - Tue, Sep 29

5:50 pm - 11:57 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 07mnonstop

7:00 am - 9:35 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 35mnonstop

$280Delta

Mon, Sep 14 - Tue, Sep 15

5:13 pm - 11:17 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 04mnonstop

8:01 pm - 10:45 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 44mnonstop

$287United Airlines

Tue, Oct 20 - Sat, Oct 24

1:20 pm - 11:00 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

7h 40m1 stop San Francisco

8:12 pm - 10:56 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 44mnonstop

$287United Airlines

Recent last minute flight deals from Washington to Chicago

Thu, Aug 27 - Mon, Sep 28

9:29 pm - 7:02 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

19h 33m1 stop Las Vegas Harry Reid Intl

8:55 pm - 9:42 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

14h 47m1 stop Las Vegas Harry Reid Intl

$313Frontier

Thu, Aug 27 - Mon, Sep 28

9:29 pm - 7:02 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

19h 33m1 stop Las Vegas Harry Reid Intl

6:00 am - 8:30 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 30mnonstop

$326Multiple Airlines

Wed, Aug 26 - Wed, Sep 2

8:53 pm - 7:02 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

20h 09m1 stop Las Vegas Harry Reid Intl

2:41 pm - 9:19 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

20h 38m1 stop Denver Intl

$328Frontier

Sat, Aug 29 - Sat, Sep 5

5:56 pm - 5:59 amPDX Portland-ORD Chicago O'Hare Intl

10h 03m1 stop Los Angeles Los Angeles

2:22 pm - 4:50 pmORD Chicago O'Hare Intl-PDX Portland

4h 28mnonstop

$364Multiple Airlines

Thu, Aug 27 - Mon, Sep 28

5:50 am - 12:07 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 17mnonstop

7:17 am - 10:09 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 52mnonstop

$372American Airlines

Sat, Aug 29 - Sat, Sep 5

1:37 pm - 9:30 pmGEG Spokane-ORD Chicago O'Hare Intl

5h 53m1 stop Denver Intl

9:15 am - 11:38 amORD Chicago O'Hare Intl-GEG Spokane

4h 23mnonstop

$390United Airlines

Sat, Aug 29 - Sat, Sep 5

1:00 pm - 11:29 pmGEG Spokane-ORD Chicago O'Hare Intl

8h 29m1 stop Seattle/Tacoma Intl

7:00 am - 12:08 pmORD Chicago O'Hare Intl-GEG Spokane

7h 08m1 stop Seattle/Tacoma Intl

$400Delta

Sat, Aug 29 - Sat, Sep 5

9:52 am - 9:47 pmGEG Spokane-ORD Chicago O'Hare Intl

9h 55m2 stops Salt Lake City Minneapolis St Paul

12:54 pm - 7:32 pmORD Chicago O'Hare Intl-GEG Spokane

8h 38m1 stop Seattle/Tacoma Intl

$405Delta

Sat, Aug 29 - Sat, Sep 5

2:37 pm - 8:28 pmGEG Spokane-ORD Chicago O'Hare Intl

3h 51mnonstop

11:30 am - 1:37 pmORD Chicago O'Hare Intl-GEG Spokane

4h 07mnonstop

$415American Airlines

Sat, Aug 29 - Sat, Sep 5

2:27 pm - 8:40 pmPDX Portland-ORD Chicago O'Hare Intl

4h 13mnonstop

7:00 am - 9:29 amORD Chicago O'Hare Intl-PDX Portland

4h 29mnonstop

$423United Airlines

Recent direct flight deals from Washington to Chicago

Sat, Sep 12 - Sat, Sep 19

7:15 am - 1:29 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 14mnonstop

5:44 pm - 8:20 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 36mnonstop

$279Delta

Sat, Sep 26 - Tue, Sep 29

6:00 am - 12:07 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 07mnonstop

1:03 pm - 3:41 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 38mnonstop

$279Alaska Airlines

Fri, Sep 11 - Sat, Sep 19

12:16 am - 6:20 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 04mnonstop

7:00 pm - 9:38 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 38mnonstop

$279Alaska Airlines

Sat, Sep 26 - Tue, Sep 29

5:50 pm - 11:57 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 07mnonstop

7:00 am - 9:35 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 35mnonstop

$280Delta

Mon, Sep 14 - Tue, Sep 15

5:13 pm - 11:17 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 04mnonstop

8:01 pm - 10:45 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 44mnonstop

$287United Airlines

Thu, Sep 10 - Tue, Sep 15

5:13 pm - 11:17 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 04mnonstop

8:01 pm - 10:45 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 44mnonstop

$287United Airlines

Thu, Sep 17 - Sat, Sep 19

1:40 pm - 8:15 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 35mnonstop

6:40 pm - 9:36 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 56mnonstop

$287American Airlines

Wed, Nov 11 - Mon, Nov 16

3:10 pm - 9:35 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 25mnonstop

12:54 pm - 3:44 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 50mnonstop

$287American Airlines

Wed, Oct 28 - Tue, Nov 3

12:10 am - 6:05 amSEA Seattle/Tacoma Intl-MDW Chicago Midway

3h 55mnonstop

8:45 pm - 11:30 pmMDW Chicago Midway-SEA Seattle/Tacoma Intl

4h 45mnonstop

$287Southwest

Thu, Sep 17 - Tue, Sep 22

5:15 am - 11:15 amSEA Seattle/Tacoma Intl-MDW Chicago Midway

4h 00mnonstop

9:00 pm - 11:40 pmMDW Chicago Midway-SEA Seattle/Tacoma Intl

4h 40mnonstop

$287Southwest

Useful Info

Low season	February
High season	July
Cheapest flight	$145

Best time to beat the crowds with an average 28% drop in price.

Most popular time to fly and prices are also 10% lower on average.

Flight from Seattle to Chicago O'Hare Airport

Verified travelerFlew with Alaska Airlines-Aug 2026

Be prepared to have a very difficult time checking in if you are not technology savvy. I could not figure out how to check in. It made me scan with my phone to check in, but I couldn’t figure out how to do it and then an employer was there pushed buttons on the kiosk and printed up a boarding pass. Where did customer service go?! and then, we had to wait in a huge long long long line just to drop off the bag. Be certain you give yourself extra time for all of this chaos. Flying is getting worse and worse every time I fly.

Verified travelerFlew with United Airlines-Jul 2024

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

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.

Merrillville

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Origins

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Return flight deals

Cabin class types available on flights to Washington

First Class flights to Chicagofrom $768

Business Class flights to Chicagofrom $768

Premium Economy Class flights to Chicagofrom $707

Economy Class flights to Chicagofrom $266

$145 Find Cheap Flights from Washington to Chicago - Compare and Save

Cheap Flights from Washington to Chicago

Recent round-trip flight deals from Washington to Chicago

Recent one-way flight deals from Washington to Chicago

Recent last minute flight deals from Washington to Chicago

Recent direct flight deals from Washington to Chicago

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High season

Cheapest flight

Flights from Washington to Chicago: the best tips from KAYAK users

FAQs for booking flights from Washington to Chicago

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Washington

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

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Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight