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

Yes, direct flights are available from Washington, D.C. to Chicago. Historically, approximately 40% of the available flights on this route have been direct. For journeys involving connecting flights, travelers typically experience a median of 2 stopovers. This indicates that while direct options are common, a significant portion of flights will include at least one stop.

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 that include one stop, the median travel time increases significantly to 10 hours and 58 minutes. Travelers should factor in these duration differences when planning their journey.

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

Historically, flight prices for the Washington, D.C. to Chicago route tend to drop frequently. This route is classified as one with frequent price fluctuations, based on observations over the trailing 30 days. Travelers can often find opportunities for price reductions, suggesting that monitoring fares can be beneficial for securing a better deal.

Flights From Washington, D.C.

To Chicago

Cheap Flights from Washington, D.C. to Chicago

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Deals from

Washington, D.C.

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Prices updated 2 days ago

444 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Aug 9, 2026.)

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

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

2026-09-06 – 2026-09-11
WAS - Chicago
75% AI deal score
$105
$61
Round trip
2026-10-29 – 2026-10-31
WAS - Chicago
73% AI deal score
$120
$75
Round trip
2026-10-28 – 2026-10-31
WAS - Chicago
73% AI deal score
$118
$75
Round trip
2026-10-26 – 2026-10-28
WAS - Chicago
49% AI deal score
$118
$89
Round trip
2026-11-04 – 2026-11-05
WAS - Chicago
47% AI deal score
$125
$102
Round trip
2026-10-13 – 2026-10-20
WAS - Chicago
45% AI deal score
$112
$103
Round trip
2026-09-06 – 2026-09-12
WAS - Chicago
41% AI deal score
$101
$104
Round trip
2026-09-06 – 2026-09-10
WAS - Chicago
42% AI deal score
$107
$106
Round trip
2026-09-06 – 2026-09-17
WAS - Chicago
41% AI deal score
$89
$106
Round trip
2026-09-10 – 2026-09-11
WAS - Chicago
42% AI deal score
$108
$106
Round trip

Washington, D.C. to Chicago: Overview

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

For travelers planning cheap flights from Washington, D.C. to Chicago, the most affordable month to fly is typically October, with a median fare of $132. Other cost-effective options include January, where the median fare is $149, and February, with a median of $185. These months present the best opportunities for finding lower prices.

Fares from Washington, D.C. to Chicago 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 competitive deals are available if you monitor prices. New deals appear almost daily, making it beneficial to set up a price alert.

If you fly from Washington, D.C. to Chicago, a meaningful share of itineraries are non-stop, while the rest connect once. Approximately 40% of recent fares for this route were for direct flights from Washington, D.C. to Chicago. For itineraries that 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 non-stop flights, the median flight time is also 2h 19m. Connecting itineraries, however, have a significantly longer median duration of 14h 20m, reflecting the impact of layovers on overall travel time.

The distance between Washington, D.C. and Chicago is approximately 981 kilometers. This classifies the route as a short-haul journey, meaning it is a relatively short flight suitable for quick trips.

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

Regular price: $82 - $222

Prices are currently below the regular range.

The regular price range for flights from Washington, D.C. to Chicago is $82-$222. The current lowest deal is $61 with Frontier Airlines for travel from Sep 6-Sep 11.

now $61

Low $82

High $222

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

The cheapest month to fly from Washington to Chicago 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

IAD - Chicago

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

Allegiant Air

$609

$323

One-way

Mon, Aug 10

⌛ Last-Minute

DCA - Chicago

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

Frontier Airlines

$539

$305

One-way

Mon, Aug 10

⌛ Last-Minute

IAD - Chicago

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

American Airlines

$521

$310

One-way

Mon, Aug 10

⌛ Last-Minute

BWI - Chicago

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

Frontier Airlines

$544

$312

One-way

Tue, Aug 11

⌛ Last-Minute

BWI - Chicago

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

Frontier Airlines

$519

$252

One-way

Tue, Aug 11

⌛ Last-Minute

BWI - Chicago

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

Frontier Airlines

$522

$297

One-way

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

4 nights

Aug 8 - Aug 12

$609 → $323

47%

1 night

Aug 13 - Aug 14

$538 → $267

50%

4 nights

Aug 11 - Aug 15

$519 → $252

51%

1 night

Aug 12 - Aug 13

$585 → $318

46%

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 $61.

📅 Best time to fly

October is historically the cheapest month to fly

Historically, October is the cheapest month to fly, with a median price of $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 on connecting flights.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines is one of the airlines offering direct flights on this route.

🎯 Booking tip

Deals appear frequently

Deals for flights from Washington, D.C. to Chicago appear frequently.

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

Ronald Reagan Washington National (DCA)

Ronald Reagan Washington National is a convenient choice for flights from Washington, D.C. to Chicago.

📍 ~6 km from Washington, D.C. (reachable by car or train)

💸 Flights from ~$176

Washington Dulles International (IAD)

Washington Dulles International is a good alternative for flights from Washington, D.C. to Chicago.

📍 ~36 km from Washington, D.C. (reachable by car or train)

💸 Flights from ~$159

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago, offering many connections.

📍 ~25 km from Chicago (reachable by car)

💸 Flights from ~$62

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

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

💸 Flights from ~$227

Business & First Class Flight Deals to Chicago

77% AI deal score

$2,047

$1,137

Save $910

Porter Airlines, +1

Business Class

From IAD

Elite

Oct 19

Chicago, United States

77% AI deal score

$2,038

$1,137

Save $901

Porter Airlines, +1

Business Class

From DCA

Elite

Sep 15

Chicago, United States

76% AI deal score

$1,205

$663

Save $542

From DCA

Elite

Nov 08

Chicago, United States

76% AI deal score

$1,185

$672

Save $513

From DCA

Elite

Aug 16

Chicago, United States

76% AI deal score

$1,491

$775

Save $716

From DCA

Elite

Aug 18

Chicago, United States

76% AI deal score

$1,527

$813

Save $714

Frequently Asked Questions About Flights to Chicago

Historically, booking at least 60 days in advance typically yields the lowest prices for flights from Washington, D.C. to Chicago. Across the trailing quarter, the average price for flights booked 60+ days out was $325. In comparison, flights booked 0-6 days before departure averaged $873, indicating a significant increase for last-minute bookings. Planning ahead by more than two months can lead to substantial savings on this route.

A good price for a flight from Washington, D.C. to Chicago is considered to be around $257 or less. This threshold represents the lowest 25% of prices observed across the trailing 90 days. The median price for this route historically stands at $458, with prices reaching up to $735 for the higher end of fares. Travelers aiming for a budget-friendly trip should target fares at or below $257.

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. February is another relatively inexpensive option, showing a median price of $185. These months typically present better value compared to the annual median price of $458 for this route.

Related routes

More routes from Washington, D.C.

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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: $82 - $222

Prices are currently below the regular range.

The regular price range for flights from Washington, D.C. to Chicago is $82-$222. The current lowest deal is $61 with Frontier Airlines for travel from Sep 6-Sep 11.

now $61

Low $82

High $222

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

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

IAD - Chicago

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

Allegiant Air

$609

$323

One-way

Mon, Aug 10

⌛ Last-Minute

DCA - Chicago

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

Frontier Airlines

$539

$305

One-way

Mon, Aug 10

⌛ Last-Minute

IAD - Chicago

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

American Airlines

$521

$310

One-way

Mon, Aug 10

⌛ Last-Minute

BWI - Chicago

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

Frontier Airlines

$544

$312

One-way

Tue, Aug 11

⌛ Last-Minute

BWI - Chicago

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

Frontier Airlines

$519

$252

One-way

Tue, Aug 11

⌛ Last-Minute

BWI - Chicago

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

Frontier Airlines

$522

$297

One-way

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

4 nights

Aug 8 - Aug 12

$609 → $323

47%

1 night

Aug 13 - Aug 14

$538 → $267

50%

4 nights

Aug 11 - Aug 15

$519 → $252

51%

1 night

Aug 12 - Aug 13

$585 → $318

46%

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 $61.

📅 Best time to fly

October is historically the cheapest month to fly

Historically, October is the cheapest month to fly, with a median price of $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 on connecting flights.

🏆 Airline highlight

Frontier Airlines offers direct flights

Frontier Airlines is one of the airlines offering direct flights on this route.

🎯 Booking tip

Deals appear frequently

Deals for flights from Washington, D.C. to Chicago appear frequently.

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

Ronald Reagan Washington National (DCA)

Ronald Reagan Washington National is a convenient choice for flights from Washington, D.C. to Chicago.

📍 ~6 km from Washington, D.C. (reachable by car or train)

💸 Flights from ~$176

Washington Dulles International (IAD)

Washington Dulles International is a good alternative for flights from Washington, D.C. to Chicago.

📍 ~36 km from Washington, D.C. (reachable by car or train)

💸 Flights from ~$159

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago, offering many connections.

📍 ~25 km from Chicago (reachable by car)

💸 Flights from ~$62

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

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

💸 Flights from ~$227

Chicago, United States

77% AI deal score

$2,047

$1,137

Save $910

Porter Airlines, +1

Business Class

From IAD

Elite

Oct 19

Chicago, United States

77% AI deal score

$2,038

$1,137

Save $901

Porter Airlines, +1

Business Class

From DCA

Elite

Sep 15

Chicago, United States

76% AI deal score

$1,205

$663

Save $542

From DCA

Elite

Nov 08

Chicago, United States

76% AI deal score

$1,185

$672

Save $513

From DCA

Elite

Aug 16

Chicago, United States

76% AI deal score

$1,491

$775

Save $716

From DCA

Elite

Aug 18

Chicago, United States

76% AI deal score

$1,527

$813

Save $714

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Washington, D.C. to Chicago

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

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

Direct flights from Washington, D.C. to Chicago

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

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

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

Washington, D.C. - Chicago route insights

Recent fares are below the typical level

October is historically the cheapest month to fly

Direct flights take 2h 19m

40% of recent flights are direct

Frontier Airlines offers direct flights

Deals appear frequently

Washington, D.C. main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Aug 30

Aug 10

Aug 11

Aug 11

Sep 11

Sep 23

Oct 19

Oct 19

Sep 15

Nov 08

Aug 16

Aug 18

Frequently Asked Questions About Flights to Chicago

How early should I book Washington, D.C. to Chicago flights to get the cheapest price?

What's a cheap fare from Washington, D.C. to Chicago?

What's the cheapest month to fly from Washington, D.C. to Chicago?

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

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

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

Related routes

More routes from Washington, D.C.

Flights to Chicago from other cities

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

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

Direct flights from Washington, D.C. to Chicago

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

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

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

Washington, D.C. - Chicago route insights

Recent fares are below the typical level

October is historically the cheapest month to fly

Direct flights take 2h 19m

40% of recent flights are direct

Frontier Airlines offers direct flights

Deals appear frequently

Washington, D.C. main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Aug 30

Aug 10

Aug 11

Aug 11

Sep 11

Sep 23

Oct 19

Oct 19

Sep 15

Nov 08

Aug 16

Aug 18

Frequently Asked Questions About Flights to Chicago

How early should I book Washington, D.C. to Chicago flights to get the cheapest price?

What's a cheap fare from Washington, D.C. to Chicago?

What's the cheapest month to fly from Washington, D.C. to Chicago?