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 a stopover, travelers typically experience a median of 2 stopovers. This indicates that while direct options are common, connecting flights also make up a significant portion of the available routes.

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

A direct flight from Washington, D.C. to Chicago typically takes about 2 hours and 19 minutes, covering a 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 significant difference in duration depending on whether their itinerary includes layovers.

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

Historically, flight prices for the Washington, D.C. to Chicago route experience frequent drops. This route is classified as one where price fluctuations occur regularly. Travelers monitoring this route over the trailing 30 days would have observed consistent opportunities for price reductions, indicating it's a dynamic market for deals.

Flights From Washington, D.C.

To Chicago

Cheap Flights from Washington, D.C. to Chicago

Browse current best options from Washington, D.C.. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Washington, D.C.

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

Prices updated 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

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

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

2026-08-24 – 2026-08-27
WAS - Chicago
74% AI deal score
$144
$62
Round trip
2026-11-04 – 2026-11-05
WAS - Chicago
73% AI deal score
$136
$63
Round trip
2026-09-21 – 2026-09-24
WAS - Chicago
75% AI deal score
$109
$64
Round trip
2026-09-14 – 2026-09-19
WAS - Chicago
73% AI deal score
$104
$65
Round trip
2026-10-28 – 2026-10-31
WAS - Chicago
77% AI deal score
$125
$65
Round trip
2026-08-20 – 2026-08-27
WAS - Chicago
78% AI deal score
$135
$66
Round trip
2026-08-27 – 2026-08-31
WAS - Chicago
78% AI deal score
$144
$66
Round trip
2026-09-14 – 2026-09-17
WAS - Chicago
73% AI deal score
$106
$66
Round trip
2026-09-12 – 2026-09-17
WAS - Chicago
73% AI deal score
$104
$66
Round trip
2026-09-12 – 2026-09-19
WAS - Chicago
73% AI deal score
$100
$66
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, October stands out as the most affordable month, with a median fare of $132. Following closely, January offers a median fare of $149, and February presents a median of $185. These months typically provide the best value for this route.

Fares for flights from Washington, D.C. to Chicago typically range from $257 to $735, with a median price of $458. Right now, current fares are below the typical level for this route. Approximately 12% of recent fares have been classified as a good price, indicating that competitive deals do appear regularly.

When flying from Washington, D.C. to Chicago, 40% of recent itineraries are non-stop, meaning a meaningful share are non-stop, the rest connect once. For those itineraries that do include connections, the typical number of stopovers is 2.

A typical journey from Washington, D.C. to Chicago takes about 2h 19m, including connections. For direct flights from Washington, D.C. to Chicago, the non-stop flight time is also 2h 19m. Connecting itineraries, however, have a significantly longer median duration of 14h 20m.

The distance between Washington, D.C. and Chicago is approximately 981 kilometers. This classifies the route as a short-haul flight, typically involving shorter travel times and fewer in-flight services compared to longer routes.

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

Regular price: $103 - $219

Prices for flights from Washington, D.C. to Chicago are currently below the regular range.

The regular price range for flights from Washington, D.C. to Chicago is $103 to $219. The current lowest deal is $63 with Frontier Airlines for travel from Nov 4-Nov 5.

now $63

Low $103

High $219

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

Sat, Aug 8

⌛ Last-Minute

DCA - Chicago

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

Deutsche Luft Hansa

$376

$195

One-way

Sat, Aug 8

⌛ Last-Minute

IAD - Chicago

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

Allegiant Air

$373

$218

One-way

Wed, Aug 12

⌛ Last-Minute

IAD - Chicago

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

Frontier Airlines

$287

$181

One-way

Thu, Aug 13

⌛ Last-Minute

DCA - Chicago

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

$279

$177

One-way

Sat, Aug 15

⌛ Last-Minute

DCA - Chicago

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

$336

$177

One-way

Sat, Aug 15

⌛ Last-Minute

DCA - Chicago

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

$335

$177

One-way

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

5 nights

Aug 19 - Aug 24

$315 → $133

58%

4 nights

Aug 8 - Aug 12

$376 → $195

48%

1 night

Aug 26 - Aug 27

$324 → $149

54%

1 night

Aug 19 - Aug 20

$328 → $168

49%

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 $63.

📅 Best time to fly

Fly in October for the best prices

Historically, October has the lowest median price at $132, making it the cheapest month to fly.

⏱️ Flight duration

Direct flights average 2h 19m

The typical direct flight from Washington, D.C. to Chicago takes 2 hours and 19 minutes.

✈️ Airlines & availability

40% of recent flights are direct

About 40% of flights on this route are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines is one of the carriers providing direct flights from Washington, D.C. to Chicago.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Washington, D.C. to Chicago are frequent, appearing often in 30-day windows.

Washington, D.C. main airports to depart from

Baltimore–Washington International (BWI)

Cheapest

Baltimore–Washington International is a great option for flights from Washington, D.C. to Chicago.

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

💸 Flights from ~$65

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago from Washington, D.C.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$65

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 rail or car)

💸 Flights from ~$196

Business & First Class Flight Deals to Chicago

78% AI deal score

$1,573

$853

Save $720

Frequently Asked Questions About Flights to Chicago

Historically, booking flights from Washington, D.C. to Chicago 60+ days in advance typically yields the lowest prices. Across the trailing quarter, the average price for flights booked within this window was $325. In contrast, booking 0-6 days before departure saw average prices rise to $873. For optimal savings, consider securing your tickets well over two months ahead of your planned 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 or less. The median price for this route was $458 during the same period. Prices can vary, with 75% of fares being $735 or less, indicating that deals below the $257 threshold represent significant savings.

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. These months tend to be significantly more affordable than the annual median price of $458 for this route, based on data from the trailing 270 days.

Related routes

More routes from Washington, D.C.

Flights from Washington, D.C. to Charleston Flights from Washington, D.C. to Cleveland Flights from Washington, D.C. to Copenhagen Flights from Washington, D.C. to Dallas Flights from Washington, D.C. to Darwin Flights from Washington, D.C. to Denver Flights from Washington, D.C. to Dubai Flights from Washington, D.C. to Dublin Flights from Washington, D.C. to Edinburgh Flights from Washington, D.C. to Frankfurt Flights from Washington, D.C. to Kochi Flights from Washington, D.C. to New Delhi

Flights to Chicago from other cities

Flights from Accra to Chicago Flights from Addis Ababa to Chicago Flights from Albuquerque to Chicago Flights from Amman to Chicago Flights from Auckland to Chicago Flights from Calgary to Chicago Flights from Edmonton to Chicago Flights from Halifax to Chicago Flights from Montreal to Chicago Flights from Toronto to Chicago Flights from Warsaw to Chicago Flights from Zürich to Chicago

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: $103 - $219

Prices for flights from Washington, D.C. to Chicago are currently below the regular range.

The regular price range for flights from Washington, D.C. to Chicago is $103 to $219. The current lowest deal is $63 with Frontier Airlines for travel from Nov 4-Nov 5.

now $63

Low $103

High $219

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

Sat, Aug 8

⌛ Last-Minute

DCA - Chicago

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

Deutsche Luft Hansa

$376

$195

One-way

Sat, Aug 8

⌛ Last-Minute

IAD - Chicago

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

Allegiant Air

$373

$218

One-way

Wed, Aug 12

⌛ Last-Minute

IAD - Chicago

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

Frontier Airlines

$287

$181

One-way

Thu, Aug 13

⌛ Last-Minute

DCA - Chicago

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

$279

$177

One-way

Sat, Aug 15

⌛ Last-Minute

DCA - Chicago

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

$336

$177

One-way

Sat, Aug 15

⌛ Last-Minute

DCA - Chicago

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

$335

$177

One-way

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

5 nights

Aug 19 - Aug 24

$315 → $133

58%

4 nights

Aug 8 - Aug 12

$376 → $195

48%

1 night

Aug 26 - Aug 27

$324 → $149

54%

1 night

Aug 19 - Aug 20

$328 → $168

49%

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