$125 Find Cheap Flights from Washington to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 7/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

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

Recent round-trip flight deals from Washington to Chicago

Fri, Jul 10 - Sat, Jul 18
Frontier Logo
8:12 pm - 5:28 am
SEA
-
ORD
7h 16m
1 stop
Frontier Logo
9:57 pm - 9:49 am
ORD
-
SEA
13h 52m
1 stop
$245Frontier
Fri, Jun 12 - Tue, Jun 16
Frontier Logo
7:41 pm - 8:43 pm
SEA
-
ORD
23h 02m
1 stop
Frontier Logo
9:48 pm - 9:48 am
ORD
-
SEA
14h 00m
1 stop
$246Frontier
Thu, Aug 13 - Mon, Aug 17
Frontier Logo
7:41 pm - 8:52 pm
SEA
-
ORD
23h 11m
1 stop
Frontier Logo
7:15 am - 10:35 am
ORD
-
SEA
29h 20m
1 stop
$248Frontier
Tue, May 26 - Tue, Jun 2
Alaska Airlines Logo
1:59 pm - 10:59 pm
GEG
-
ORD
7h 00m
1 stop
Alaska Airlines Logo
6:00 am - 1:04 pm
ORD
-
GEG
9h 04m
1 stop
$277Alaska Airlines
Wed, Sep 2 - Tue, Sep 8
Multiple Airlines Logo
12:28 pm - 8:53 pm
GEG
-
ORD
6h 25m
1 stop
Multiple Airlines Logo
7:00 am - 11:52 am
ORD
-
GEG
6h 52m
1 stop
$284Multiple Airlines
Mon, May 25 - Tue, Jun 2
Alaska Airlines Logo
5:00 am - 2:32 pm
GEG
-
ORD
7h 32m
1 stop
Alaska Airlines Logo
6:00 am - 11:42 am
ORD
-
GEG
7h 42m
1 stop
$286Alaska Airlines
Mon, Jul 20 - Fri, Jul 31
Multiple Airlines Logo
12:26 pm - 8:52 pm
PDX
-
ORD
6h 26m
1 stop
Multiple Airlines Logo
7:20 am - 9:45 am
ORD
-
PDX
4h 25mnonstop
$289Multiple Airlines
Wed, May 27 - Wed, Jun 3
American Airlines Logo
2:08 pm - 8:07 pm
GEG
-
ORD
3h 59mnonstop
American Airlines Logo
11:30 am - 1:24 pm
ORD
-
GEG
3h 54mnonstop
$297American Airlines
Wed, Jun 3 - Tue, Jun 9
Southwest Logo
11:55 pm - 5:50 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
10:15 am - 12:30 pm
MDW
-
PDX
4h 15mnonstop
$305Southwest
Thu, May 28 - Wed, Jun 3
Southwest Logo
5:10 am - 11:05 am
PDX
-
MDW
3h 55mnonstop
Southwest Logo
5:35 pm - 11:00 pm
MDW
-
PDX
7h 25m
1 stop
$315Southwest
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Good to know

Low seasonFebruary
Cheapest flight$125
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Seattle to Chicago O'Hare Airport

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
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Washington

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.