$152 Find Cheap Flights from Washington to Chicago - Compare and Save

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1 adult, Economy, 0 bags

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Cheap Flights from Washington to Chicago

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

Recent round-trip flight deals from Washington to Chicago

Thu, Oct 8 - Wed, Oct 14
Frontier Logo
9:16 pm - 5:16 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
30h 00m1 stop Las Vegas Harry Reid Intl
Frontier Logo
8:01 pm - 6:45 pmORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
24h 44m1 stop Los Angeles Los Angeles
$279Frontier
Fri, Nov 6 - Mon, Nov 9
Multiple Airlines Logo
4:27 pm - 12:21 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
5h 54m1 stop Denver Intl
Multiple Airlines Logo
7:00 am - 9:50 amORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
4h 50mnonstop
$280Multiple Airlines
Fri, Sep 25 - Sat, Oct 10
Delta Logo
5:50 pm - 11:57 pmSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
4h 07mnonstop
Delta Logo
5:48 pm - 8:34 pmORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
4h 46mnonstop
$283Delta
Mon, Nov 2 - Thu, Nov 5
Delta Logo
11:10 pm - 10:11 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
9h 01m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:50 pm - 3:25 pmORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
4h 35mnonstop
$283Delta
Sat, Oct 24 - Mon, Oct 26
Frontier Logo
8:00 pm - 6:34 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
8h 34m1 stop Los Angeles Los Angeles
Frontier Logo
6:30 am - 3:12 pmORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
10h 42m1 stop Denver Intl
$283Frontier
Sat, Oct 3 - Tue, Oct 6
Multiple Airlines Logo
11:41 pm - 5:40 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
3h 59mnonstop
Multiple Airlines Logo
6:30 am - 3:08 pmORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
10h 38m1 stop Denver Intl
$283Multiple Airlines
Tue, Sep 29 - Wed, Oct 7
Alaska Airlines Logo
8:41 am - 7:21 pmSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
8h 40m1 stop San Diego
Alaska Airlines Logo
7:00 am - 9:42 amORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
4h 42mnonstop
$286Alaska Airlines
Wed, Sep 30 - Sat, Oct 3
Alaska Airlines Logo
8:41 am - 7:21 pmSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
8h 40m1 stop San Diego
Alaska Airlines Logo
7:00 am - 9:42 amORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
4h 42mnonstop
$286Alaska Airlines
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
2:10 pm - 12:15 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
8h 05m1 stop Denver Intl
Southwest Logo
10:05 pm - 12:40 amMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 35mnonstop
$287Southwest
Tue, Oct 20 - Fri, Nov 20
Southwest Logo
12:10 am - 6:05 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
3h 55mnonstop
Southwest Logo
9:45 pm - 12:30 amMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 45mnonstop
$287Southwest
Useful Info

Good to know

Low season

February

Cheapest flight

$152
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Seattle to Chicago O'Hare Airport

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

Insights shared by verified travelers who flew the route from Washington to Chicago 
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.

FAQs for booking flights from Washington to 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Saint Joseph
Portage
Lansing
Valparaiso
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

More options for your flight to Chicago