Find flights
When to book
FAQs & Tips
Direct Flights
Deals

$40 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 6/5. 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
0 bags
Sun 6/30
Sun 7/7

Search hundreds of travel sites at once for deals on flights to Chicago

In the last 7 days travelers have searched 42,787,818 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Good to know

Low season

January

High season

June

Cheapest flight

$40
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Portland 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.

See more FAQs

Prefer to fly non-stop from Washington to Chicago?

Find which airlines fly direct from Washington to Chicago, which days they fly and book direct flights.

Nonstop departures

Washington to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

See more direct flights

Nonstop returns

Chicago to Washington

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

See more direct flights
See more direct flights

Book cheap flights from Washington to Chicago

Recent round-trip flight deals

8/21Wed
nonstopSpirit Airlines
3h 50mPDX-ORD
8/28Wed
nonstopSpirit Airlines
4h 30mORD-PDX
$86
9/7Sat
nonstopSpirit Airlines
3h 50mPDX-ORD
9/11Wed
nonstopSpirit Airlines
4h 30mORD-PDX
$87
8/24Sat
1 stop
10h 17mPDX-ORD
8/28Wed
nonstop
4h 30mORD-PDX
$135
9/18Wed
nonstop
3h 50mPDX-ORD
9/23Mon
1 stop
6h 52mORD-PDX
$147
10/29Tue
nonstopAlaska Airlines
3h 53mSEA-ORD
11/2Sat
nonstopAlaska Airlines
4h 38mORD-SEA
$149
8/20Tue
1 stopUnited Airlines
9h 45mSEA-ORD
8/24Sat
nonstopUnited Airlines
4h 37mORD-SEA
$154
8/14Wed
1 stopAlaska Airlines
8h 24mSEA-ORD
8/31Sat
nonstopAlaska Airlines
4h 34mORD-SEA
$168
6/10Mon
2 stopsFrontier
11h 51mPDX-ORD
6/12Wed
1 stopFrontier
11h 57mORD-PDX
$168
9/7Sat
1 stopFrontier
15h 17mSEA-ORD
9/17Tue
1 stopFrontier
25h 31mORD-SEA
$176
8/20Tue
1 stopUnited Airlines
9h 45mSEA-ORD
8/25Sun
nonstopUnited Airlines
4h 33mORD-SEA
$184

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/5Wed
nonstopSpirit Airlines
4h 07mPDX-ORD
$40
8/21Wed
nonstopSpirit Airlines
3h 50mPDX-ORD
$50
8/31Sat
nonstopDelta
3h 56mSEA-ORD
$75
8/31Sat
nonstopDelta
3h 56mSEA-ORD
$85
7/4Thu
nonstopAlaska Airlines
4h 04mPDX-ORD
$90
6/8Sat
1 stopFrontier
8h 13mPDX-MDW
$90
7/9Tue
1 stopAlaska Airlines
7h 30mSEA-ORD
$94
6/10Mon
2 stopsFrontier
11h 51mPDX-ORD
$95
6/11Tue
2 stops
24h 52mPDX-RFD
$97
7/2Tue
2 stops
27h 01mSEA-RFD
$107

Search by stops

Search by airline

Search by price

Last minute flights from Washington to Chicago

Last minute flight, train and bus deals

6/5Wed
nonstopSpirit Airlines
4h 07mPDX-ORD
6/8Sat
nonstopSpirit Airlines
4h 27mORD-PDX
$99
6/5Wed
nonstopSpirit Airlines
4h 07mPDX-ORD
6/22Sat
nonstopSpirit Airlines
4h 27mORD-PDX
$101
6/5Wed
nonstop
4h 07mPDX-ORD
6/8Sat
multi-stop
12h 34mORD-PDX
$135
6/1Sat
multi-stop
20h 02mPDX-ORD
6/8Sat
nonstop
4h 27mORD-PDX
$153
6/2Sun
multi-stopFrontier
10h 23mPDX-ORD
6/5Wed
multi-stopFrontier
11h 57mORD-PDX
$180
6/1Sat
multi-stopFrontier
8h 36mPDX-MDW
6/9Sun
multi-stopFrontier
13h 27mMDW-PDX
$180
6/1Sat
multi-stopAmerican Airlines
8h 20mGEG-ORD
6/8Sat
multi-stopAmerican Airlines
10h 01mORD-GEG
$299
6/4Tue
nonstopAlaska Airlines
4h 05mPDX-ORD
6/6Thu
nonstopAlaska Airlines
4h 20mORD-PDX
$308
6/4Tue
multi-stopAmerican Airlines
7h 35mSEA-ORD
6/12Wed
nonstopAmerican Airlines
4h 49mORD-SEA
$325
6/4Tue
nonstopAlaska Airlines
4h 05mPDX-ORD
6/5Wed
nonstopAlaska Airlines
4h 20mORD-PDX
$327

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Washington

Cabin classes:

$504
$776
$516
$144