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.

$159 CHEAP FLIGHTS from Washington to Chicago

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Cheap Flights from Washington to Chicago

Cheap flights from Washington to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Wed, Dec 2 - Wed, Dec 9

4:58 pm - 12:53 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

5h 55m1 stop Denver Intl

7:25 am - 3:43 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

10h 18m1 stop Denver Intl

$281Frontier

Fri, Nov 6 - Thu, Nov 12

4:27 pm - 12:21 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

5h 54m1 stop Denver Intl

5:15 pm - 9:45 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

18h 30m1 stop Las Vegas Harry Reid Intl

$283Frontier

Mon, Nov 23 - Fri, Nov 27

9:53 pm - 5:10 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

29h 17m1 stop Las Vegas Harry Reid Intl

6:00 am - 8:41 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 41mnonstop

$283Multiple Airlines

Wed, Nov 11 - Wed, Nov 18

8:44 am - 3:00 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 16mnonstop

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

10h 42m1 stop Denver Intl

$283Multiple Airlines

Tue, Dec 1 - Tue, Dec 8

5:51 pm - 11:59 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 08mnonstop

3:19 pm - 6:11 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 52mnonstop

$285Alaska Airlines

Mon, Nov 23 - Tue, Dec 1

3:15 pm - 9:35 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 20mnonstop

6:49 am - 9:43 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 54mnonstop

$293American Airlines

Mon, Nov 9 - Mon, Nov 16

11:34 pm - 5:35 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 01mnonstop

9:53 pm - 12:35 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 42mnonstop

$293American Airlines

Wed, Nov 18 - Wed, Nov 25

7:27 am - 1:37 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 10mnonstop

12:58 pm - 3:36 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 38mnonstop

$293Delta

Sat, Nov 7 - Fri, Nov 13

8:44 am - 3:00 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 16mnonstop

9:30 am - 12:14 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 44mnonstop

$296Alaska Airlines

Thu, Nov 26 - Fri, Nov 27

5:55 pm - 11:59 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 04mnonstop

12:58 pm - 3:36 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 38mnonstop

$307Delta

Tue, Oct 20 - Tue, Nov 10

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

8h 34m1 stop Los Angeles

9:30 am - 12:14 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 44mnonstop

$348Multiple Airlines

Sun, Oct 25 - Mon, Nov 16

9:16 pm - 5:16 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

30h 00m1 stop Las Vegas Harry Reid Intl

7:00 am - 9:50 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 50mnonstop

$353Multiple Airlines

Sun, Oct 25 - Mon, Nov 16

9:16 pm - 5:16 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

30h 00m1 stop Las Vegas Harry Reid Intl

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

10h 42m1 stop Denver Intl

$356Frontier

Wed, Oct 21 - Wed, Oct 28

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

8h 34m1 stop Los Angeles

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

10h 42m1 stop Denver Intl

$374Frontier

Tue, Oct 20 - Sat, Nov 7

7:19 am - 6:53 pmGEG Spokane-ORD Chicago O'Hare Intl

9h 34m1 stop San Diego

2:15 pm - 9:47 pmORD Chicago O'Hare Intl-GEG Spokane

9h 32m1 stop San Diego

$410Alaska Airlines

Sat, Oct 24 - Sat, Oct 31

5:43 pm - 5:40 amGEG Spokane-ORD Chicago O'Hare Intl

9h 57m1 stop Seattle/Tacoma Intl

2:21 pm - 9:40 pmORD Chicago O'Hare Intl-GEG Spokane

9h 19m1 stop San Diego

$412Alaska Airlines

Sun, Oct 25 - Mon, Nov 16

10:31 am - 4:55 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 24mnonstop

11:30 am - 2:20 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 50mnonstop

$417American Airlines

Tue, Oct 20 - Tue, Nov 10

5:30 pm - 11:34 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 04mnonstop

5:55 pm - 8:38 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 43mnonstop

$417Delta

Tue, Oct 20 - Sat, Nov 7

12:49 pm - 10:10 pmGEG Spokane-ORD Chicago O'Hare Intl

7h 21m1 stop Dallas/Fort Worth

11:11 am - 1:23 pmORD Chicago O'Hare Intl-GEG Spokane

4h 12mnonstop

$438American Airlines

Tue, Oct 20 - Sat, Nov 7

1:00 pm - 11:57 pmGEG Spokane-ORD Chicago O'Hare Intl

8h 57m1 stop Atlanta Hartsfield-Jackson

11:19 am - 9:22 pmORD Chicago O'Hare Intl-GEG Spokane

12h 03m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

$462Delta

Tue, Dec 1 - Tue, Dec 8

5:51 pm - 11:59 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 08mnonstop

3:19 pm - 6:11 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 52mnonstop

$285Alaska Airlines

Sat, Dec 12 - Mon, Dec 21

11:39 pm - 5:35 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

3h 56mnonstop

6:54 am - 9:52 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 58mnonstop

$293American Airlines

Sat, Dec 12 - Tue, Dec 22

7:45 am - 1:56 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 11mnonstop

6:00 am - 8:54 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 54mnonstop

$293Delta

Wed, Nov 18 - Wed, Nov 25

7:27 am - 1:37 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 10mnonstop

12:58 pm - 3:36 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 38mnonstop

$293Delta

Mon, Nov 23 - Tue, Dec 1

3:15 pm - 9:35 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 20mnonstop

6:49 am - 9:43 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 54mnonstop

$293American Airlines

Sat, Dec 5 - Mon, Dec 14

8:20 am - 2:20 pmSEA Seattle/Tacoma Intl-MDW Chicago Midway

4h 00mnonstop

8:45 pm - 11:35 pmMDW Chicago Midway-SEA Seattle/Tacoma Intl

4h 50mnonstop

$294Southwest

Thu, Dec 3 - Thu, Dec 10

6:30 am - 12:25 pmSEA Seattle/Tacoma Intl-MDW Chicago Midway

3h 55mnonstop

8:45 pm - 11:35 pmMDW Chicago Midway-SEA Seattle/Tacoma Intl

4h 50mnonstop

$294Southwest

Sat, Nov 7 - Fri, Nov 13

8:44 am - 3:00 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 16mnonstop

9:30 am - 12:14 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 44mnonstop

$296Alaska Airlines

Sat, Nov 14 - Mon, Nov 16

10:56 pm - 5:06 amSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 10mnonstop

4:15 pm - 7:03 pmORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 48mnonstop

$307United Airlines

Thu, Jan 14 - Thu, Jan 21

10:52 am - 5:00 pmSEA Seattle/Tacoma Intl-ORD Chicago O'Hare Intl

4h 08mnonstop

9:00 am - 11:47 amORD Chicago O'Hare Intl-SEA Seattle/Tacoma Intl

4h 47mnonstop

$307United Airlines

Low season	February
High season	July
Cheapest flight	$159

Best time to beat the crowds with an average 33% drop in price.

Most popular time to fly and prices are also 15% 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.