Can I fly direct from Washington, D.C. to Chicago?

Yes, direct flights from Washington, D.C. to Chicago are available. Historically, approximately 40% of flights on this route have been direct. For journeys involving one or more stops, travelers typically experience a median of 2 stopovers. This indicates a significant portion of travelers opt for direct connections on this route.

How often do Washington, D.C. to Chicago flight prices drop?

Historically, flight prices for the Washington, D.C. to Chicago route have shown frequent drops. This suggests that travelers may often find opportunities for lower fares. The route is classified as having frequent price fluctuations, based on observations over the trailing 30 days.

Flights From Washington, D.C.

To Chicago

Cheap Flights from Washington, D.C. to Chicago

Q: How long is the flight from Washington, D.C. to Chicago?

The typical direct flight from Washington, D.C. to Chicago has a median duration of 2 hours and 19 minutes. This route covers an approximate distance of 964 kilometers. For flights with one stop, the median travel time is considerably longer, averaging 10 hours and 58 minutes. Travelers can expect a significantly shorter journey when flying direct.

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Deals from

Washington, D.C.

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

Prices updated 2 days ago

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Washington, D.C. to Chicago

Explore current cheapest deals departing from Washington, D.C. to Chicago

2026-10-05 – 2026-10-29
WAS - Chicago
41% AI deal score
$88
$102
Round trip
2026-10-05 – 2026-10-26
WAS - Chicago
41% AI deal score
$89
$105
Round trip
2026-12-10 – 2026-12-17
WAS - Chicago
45% AI deal score
$123
$109
Round trip
2026-12-03 – 2026-12-10
WAS - Chicago
44% AI deal score
$119
$109
Round trip
2026-12-03 – 2026-12-17
WAS - Chicago
41% AI deal score
$104
$109
Round trip
2026-10-29 – 2026-11-13
WAS - Chicago
41% AI deal score
$91
$113
Round trip
2026-10-08 – 2026-10-29
WAS - Chicago
40% AI deal score
$89
$123
Round trip
2026-10-06 – 2026-10-21
WAS - Chicago
75% AI deal score
$206
$124
Round trip
2026-10-13 – 2026-10-21
WAS - Chicago
77% AI deal score
$231
$124
Round trip
2026-10-06 – 2026-10-20
WAS - Chicago
75% AI deal score
$210
$124
Round trip

Washington, D.C. to Chicago: Overview

Insights for flights from Washington, D.C. to Chicago

For travelers seeking cheap flights from Washington, D.C. to Chicago, the most affordable month to fly is typically October, with a median fare of $132. Following closely, January also offers competitive pricing, with a median fare of $149. February is another economical option, showing a median fare of $185.

Fares for this route typically range from $257–$735, with a median of $458. Right now, fares are below the typical level for this route. Approximately 12% of recent fares were classified as a good price, indicating that finding a favorable deal is possible. New deals appear almost daily, suggesting frequent opportunities to secure a good price.

When considering how long is the flight from Washington, D.C. to Chicago, a typical journey takes about 2h 19m. This median duration includes both direct and connecting itineraries. For non-stop flights, the typical flight time is also 2h 19m, while itineraries with connections average a significantly longer 14h 20m.

A meaningful share of recent fares, specifically 40%, are for direct flights from Washington, D.C. to Chicago. This means you have a good chance of finding a non-stop option. For the remaining itineraries that involve connections, the typical number of stopovers is 2.

How much is a round trip from Washington, D.C. to Chicago

Regular price: $189 - $249

Prices are currently below the regular range.

The regular price range for flights from Washington, D.C. to Chicago is $189-$249. The current lowest deal is $109 with Frontier Airlines for travel from Nov 17-Nov 19.

now $109

Low $189

High $249

The cheapest time to fly from Washington, D.C. to Chicago

The cheapest month to fly from WAS to CHI is January, with a median price of $147. The most expensive month is June, with a median price of $596. Prices are generally lower from January to December.

January

Cheapest

Flights from $147

June

Most Expensive

Flights from $596

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Washington, D.C. to Chicago

Frontier Airlines

Southwest Airlines

Last-minute flights going from Washington, D.C. to Chicago

Fri, Oct 2

⌛ Last-Minute

IAD - Chicago

Washington, D.C. (IAD) - Chicago (MDW)

Frontier Airlines

$271

$188

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$108

$127

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$91

$128

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$117

$134

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$230

$134

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$212

$134

One-way

Biggest price drops on these dates for flights from Washington, D.C. to Chicago

1 night

Sep 15 - Sep 16

$465 → $356

23%

2 nights

Sep 15 - Sep 17

$438 → $331

24%

2 nights

Sep 22 - Sep 24

$340 → $239

30%

3 nights

Sep 15 - Sep 18

$432 → $331

23%

Popular Airports to fly from Washington, D.C. to Chicago

Washington, D.C. - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Washington, D.C. to Chicago are below the typical level at $109.

📅 Best time to fly

October is historically the cheapest month to fly.

Historically, the cheapest month to fly from Washington, D.C. to Chicago is October, at $132.

⏱️ Flight duration

Direct flights take 2h 19m.

Direct flights from Washington, D.C. to Chicago typically take 2h 19m.

✈️ Airlines & availability

40% of recent flights are direct.

40% of recent flights from Washington, D.C. to Chicago are direct, with 2 stopovers when connecting.

🏆 Airline highlight

Frontier Airlines offers direct flights.

Frontier Airlines offers direct flights from Washington, D.C. to Chicago, with 1 direct deal.

🎯 Booking tip

Deals appear frequently on this route.

Deals on flights from Washington, D.C. to Chicago appear frequently, with good prices at $257.

Washington, D.C. main airports to depart from

Baltimore–Washington International (BWI)

Cheapest

Baltimore–Washington International Airport offers flights to Chicago, providing a potentially cheaper departure option.

📍 ~44 km from Washington, D.C. (reachable by car or train)

💸 Flights from ~$170

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering many flight options to Chicago.

📍 ~25 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$68

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~$245

Business & First Class Flight Deals to Chicago

74% AI deal score

$1,123

$649

Save $474

Frequently Asked Questions About Flights to Chicago

Historically, booking flights from Washington, D.C. to Chicago 60 or more days in advance typically yields the lowest prices. Across the trailing quarter, the average price for flights booked in this window was $325. In contrast, booking 0-6 days before departure saw average prices rise to $873. For the best value, consider securing your flight at least two months before your intended travel date.

Based on historical data from the trailing 90 days, a good price for a flight from Washington, D.C. to Chicago is considered to be around $257. This threshold represents the lowest 25% of fares observed. The median price for this route during the same period was $458, indicating that a fare of $257 or less is a notable saving.

Historically, October has been the cheapest month to fly from Washington, D.C. to Chicago, with a median price of $132. January also offers competitive fares, with a median price of $149. While February was identified as the most expensive month in the trailing 270 days, its median price of $185 is still significantly lower than the annual median of $458 for the route.

Related routes

More routes from Washington, D.C.

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Flights to Chicago from other cities

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Washington, D.C. to Chicago: Overview

Insights for flights from Washington, D.C. to Chicago

How much is a round trip from Washington, D.C. to Chicago

Regular price: $189 - $249

Prices are currently below the regular range.

The regular price range for flights from Washington, D.C. to Chicago is $189-$249. The current lowest deal is $109 with Frontier Airlines for travel from Nov 17-Nov 19.

now $109

Low $189

High $249

The cheapest time to fly from Washington, D.C. to Chicago

The cheapest month to fly from WAS to CHI is January, with a median price of $147. The most expensive month is June, with a median price of $596. Prices are generally lower from January to December.

January

Cheapest

Flights from $147

June

Most Expensive

Flights from $596

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Washington, D.C. to Chicago

Frontier Airlines

Southwest Airlines

Last-minute flights going from Washington, D.C. to Chicago

Fri, Oct 2

⌛ Last-Minute

IAD - Chicago

Washington, D.C. (IAD) - Chicago (MDW)

Frontier Airlines

$271

$188

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$108

$127

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$91

$128

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$117

$134

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$230

$134

One-way

Sat, Oct 3

⌛ Last-Minute

BWI - Chicago

Washington, D.C. (BWI) - Chicago (ORD)

Frontier Airlines

$212

$134

One-way

Biggest price drops on these dates for flights from Washington, D.C. to Chicago

1 night

Sep 15 - Sep 16

$465 → $356

23%

2 nights

Sep 15 - Sep 17

$438 → $331

24%

2 nights

Sep 22 - Sep 24

$340 → $239

30%

3 nights

Sep 15 - Sep 18

$432 → $331

23%

Popular Airports to fly from Washington, D.C. to Chicago