$142 Find Cheap Flights from Washington to Chicago - Compare and Save

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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

Sun, Sep 13 - Sat, Oct 17
Frontier Logo
9:45 pm - 5:38 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
29h 53m1 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
$278Frontier
Wed, Sep 9 - Sun, Sep 13
Frontier Logo
9:45 pm - 5:38 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
29h 53m1 stop Las Vegas Harry Reid Intl
Frontier Logo
8:55 pm - 6:28 pmORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
23h 33m1 stop Las Vegas Harry Reid Intl
$278Frontier
Mon, Sep 14 - Mon, Sep 21
Multiple Airlines Logo
7:45 pm - 5:38 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
7h 53m1 stop Las Vegas Harry Reid Intl
Multiple Airlines Logo
6:00 am - 8:30 amORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
4h 30mnonstop
$278Multiple Airlines
Sat, Oct 24 - Wed, Oct 28
Multiple Airlines Logo
8:00 pm - 6:34 amSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
8h 34m1 stop Los Angeles
Multiple Airlines Logo
3:49 pm - 6:28 pmORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
4h 39mnonstop
$278Multiple Airlines
Mon, Sep 28 - Wed, Sep 30
Alaska Airlines Logo
5:51 pm - 11:59 pmSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
4h 08mnonstop
Alaska Airlines Logo
6:00 am - 8:30 amORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
4h 30mnonstop
$280Alaska Airlines
Sat, Sep 12 - Sat, Sep 19
Alaska Airlines Logo
7:40 am - 7:21 pmSEA  Seattle/Tacoma Intl-ORD Chicago O'Hare Intl
9h 41m1 stop San Diego
Alaska Airlines Logo
4:08 pm - 6:47 pmORD  Chicago O'Hare Intl-SEA Seattle/Tacoma Intl
4h 39mnonstop
$283Alaska Airlines
Wed, Sep 23 - Sat, Sep 26
Southwest Logo
11:05 pm - 5:05 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
4h 00mnonstop
Southwest Logo
6:50 am - 1:10 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
8h 20m1 stop Denver Intl
$287Southwest
Tue, Sep 15 - Tue, Sep 22
Southwest Logo
6:40 pm - 5:00 amSEA  Seattle/Tacoma Intl-MDW Chicago Midway
8h 20m1 stop San Jose
Southwest Logo
3:30 pm - 5:55 pmMDW  Chicago Midway-SEA Seattle/Tacoma Intl
4h 25mnonstop
$287Southwest
Thu, Nov 12 - Sat, Nov 14
American Airlines Logo
2:14 pm - 8:07 pmGEG  Spokane-ORD Chicago O'Hare Intl
3h 53mnonstop
American Airlines Logo
11:12 am - 1:24 pmORD  Chicago O'Hare Intl-GEG Spokane
4h 12mnonstop
$297American Airlines
Thu, Sep 24 - Mon, Sep 28
American Airlines Logo
2:19 pm - 8:15 pmGEG  Spokane-ORD Chicago O'Hare Intl
3h 56mnonstop
American Airlines Logo
11:10 am - 1:19 pmORD  Chicago O'Hare Intl-GEG Spokane
4h 09mnonstop
$297American Airlines
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Good to know

Low season

February

Cheapest flight

$142
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Seattle to Chicago Midway 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
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Munster
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Washington

First Class flights to Chicagofrom $768
Business Class flights to Chicagofrom $748
Premium Economy Class flights to Chicagofrom $707
Economy Class flights to Chicagofrom $239