How many flights depart from Washington, D.C. to Chicago on average per week?

As of August 2025, 466 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Tue, with 25% of weekly flights taking off on this day.

How many flights depart from Washington, D.C. to Chicago on average per day?

As of August 2025, there are 66 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 5:00PM, with 44% of flights taking off in the afternoon.

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Washington, D.C. according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Washington, D.C. to Chicago?

Spirit Airlines, United Airlines, and Southwest are the most popular carriers operating from Washington, D.C. to Chicago

How long does it take to fly to Chicago?

Average flight duration from Washington, D.C. to Chicago depends on which airport you fly into and out of. Flying from Washington, D.C. to Chicago O'Hare Intl Airport is 2h on average, while flying from Baltimore to Chicago O'Hare Intl Airport is 2h 06m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

Which layover airport has the shortest connection time from Washington, D.C. to Chicago?

Detroit (DTW) has the shortest average layover time for this route: 0h 53m.

Which layover airport offers the lowest fares from Washington, D.C. to Chicago?

Flights via Denver (DEN) offer the lowest average round-trip price of $178.

Which airport is the most popular layover for flights between Washington, D.C. and Chicago?

Detroit (DTW) was the most common stop: 43% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest travel time from Washington, D.C. to Chicago?

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 3h 40m.

Is flying the fastest way to get from Washington, D.C. to Chicago?

The quickest way is to book a flight from Washington, D.C. to Chicago, which can be as quick as 1h 55m onboard Southwest. You can also get a train from Washington, D.C. to Chicago, or a bus from Washington, D.C. to Chicago which can take you longer to arrive at your destination.

Is flying the cheapest way to get from Washington, D.C. to Chicago?

The cheapest way is to get a flight from Washington, D.C. to Chicago, which can be as cheap as $88. A train from Washington, D.C. to Chicago is more expensive than a flight, with prices starting at $202. A bus from Washington, D.C. to Chicago is also an option, with an average price of $144.

When did momondo last update prices for flights from Washington, D.C. to Chicago?

Prices for flights from Washington, D.C. to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Washington, D.C. to Chicago?

There are 6 operators available for flights from Washington, D.C. to Chicago as of August 2025.

How old do you have to be to fly from Washington, D.C. to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Washington, D.C. to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$43 Cheap Flights from Washington, D.C. to Chicago (WAS-CHI) in 2025

Q: What is the typical price of a round-trip flight between Washington, D.C. and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $170 to $359. The lowest price recently found on this route was $88.

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Find the cheapest flights from Washington, D.C. to Chicago (WAS-CHI)

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

9:57 am - 11:10 amBWI-ORD

2h 13mnonstop

6:10 am - 9:02 amORD-BWI

1h 52mnonstop

$88Spirit Airlines

Find Deal

Thu, Sep 11 - Sun, Sep 14

10:17 am - 11:30 amBWI-ORD

2h 13mnonstop

6:30 am - 9:22 amORD-BWI

1h 52mnonstop

$89Spirit Airlines

Find Deal

Fri, Oct 17 - Sun, Oct 19

9:59 pm - 11:20 pmBWI-ORD

2h 21mnonstop

6:11 pm - 9:14 pmORD-BWI

2h 03mnonstop

$99Frontier

Find Deal

Fri, Oct 3 - Sun, Oct 5

5:40 pm - 6:43 pmBWI-MDW

2h 03mnonstop

1:49 pm - 4:50 pmMDW-BWI

2h 01mnonstop

$119Frontier

Find Deal

Sun, Sep 21 - Thu, Sep 25

6:04 pm - 7:20 pmDCA-ORD

2h 16mnonstop

6:00 am - 8:58 amORD-DCA

1h 58mnonstop

$123United Airlines

Find Deal

Sat, Oct 4 - Wed, Oct 8

1:15 pm - 2:29 pmIAD-ORD

2h 14mnonstop

9:31 pm - 12:32 amORD-IAD

2h 01mnonstop

$123United Airlines

Find Deal

Tue, Sep 2 - Tue, Sep 9

10:45 am - 11:45 amBWI-MDW

2h 00mnonstop

2:55 pm - 5:45 pmMDW-BWI

1h 50mnonstop

$123Southwest

Find Deal

Wed, Sep 3 - Wed, Sep 10

10:35 am - 11:50 amBWI-ORD

2h 15mnonstop

1:30 pm - 4:25 pmORD-BWI

1h 55mnonstop

$123Southwest

Find Deal

Sat, Oct 4 - Sat, Oct 18

6:00 am - 7:16 amDCA-ORD

2h 16mnonstop

6:04 am - 8:59 amORD-DCA

1h 55mnonstop

$136American Airlines

Find Deal

Sat, Nov 8 - Mon, Nov 10

5:08 pm - 6:28 pmDCA-ORD

2h 20mnonstop

6:10 am - 9:00 amORD-DCA

1h 50mnonstop

$140American Airlines

Find Deal

Wed, Sep 10 - Fri, Sep 12

Spirit Airlines flights from Washington, D.C. to Chicago

Our best Spirit Airlines deals on Washington, D.C. to Chicago flight tickets

Spirit Airlines

Sep 11

BWI9:57 amBaltimore/Washington

2h 13m

ORD11:10 amChicago O'Hare Intl

Sep 14

ORD6:10 amChicago O'Hare Intl

1h 52m

BWI9:02 amBaltimore/Washington

$88

Find similar

Spirit Airlines

Oct 17

BWI10:17 amBaltimore/Washington

2h 13m

ORD11:30 amChicago O'Hare Intl

Oct 19

ORD6:30 amChicago O'Hare Intl

1h 52m

BWI9:22 amBaltimore/Washington

$89

Find similar

Spirit Airlines

Sep 11

BWI9:57 amBaltimore/Washington

2h 13m

ORD11:10 amChicago O'Hare Intl

Sep 14

ORD6:10 amChicago O'Hare Intl

1h 52m

BWI9:02 amBaltimore/Washington

$90

Find similar

United Airlines flights from Washington, D.C. to Chicago

Our best United Airlines deals on Washington, D.C. to Chicago flight tickets

United Airlines

Oct 4

DCA6:04 pmWashington, D.C. Reagan-National

2h 16m

ORD7:20 pmChicago O'Hare Intl

Oct 8

ORD6:00 amChicago O'Hare Intl

1h 58m

DCA8:58 amWashington, D.C. Reagan-National

$123

Find similar

United Airlines

Aug 27

DCA3:30 pmWashington, D.C. Reagan-National

2h 13m

ORD4:43 pmChicago O'Hare Intl

Aug 28

ORD4:00 pmChicago O'Hare Intl

2h 03m

DCA7:03 pmWashington, D.C. Reagan-National

$135

Find similar

United Airlines

Sep 10

IAD10:10 pmWashington, D.C. Dulles Intl

2h 05m

ORD11:15 pmChicago O'Hare Intl

Sep 12

ORD10:43 amChicago O'Hare Intl

2h 06m

IAD1:49 pmWashington, D.C. Dulles Intl

$140

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 9/11

9:57 am-11:10 am

Nonstop2h 13m

Chicago O'Hare Intl

Sun 9/14

6:10 am-9:02 am

Nonstop1h 52m

$88

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 10/17

10:17 am-11:30 am

Nonstop2h 13m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:22 am

Nonstop1h 52m

$89

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 10/3

9:59 pm-11:20 pm

Nonstop2h 21m

Chicago O'Hare Intl

Sun 10/5

6:11 pm-9:14 pm

Nonstop2h 03m

$99

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sun 9/21

5:40 pm-6:43 pm

Nonstop2h 03m

Chicago Midway

Thu 9/25

1:49 pm-4:50 pm

Nonstop2h 01m

$119

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 10/4

6:04 pm-7:20 pm

Nonstop2h 16m

Chicago O'Hare Intl

Wed 10/8

6:00 am-8:58 am

Nonstop1h 58m

$123

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 9/2

1:15 pm-2:29 pm

Nonstop2h 14m

Chicago O'Hare Intl

Tue 9/9

9:31 pm-12:32 am

Nonstop2h 01m

$123

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 9/3

10:45 am-11:45 am

Nonstop2h 00m

Chicago Midway

Wed 9/10

2:55 pm-5:45 pm

Nonstop1h 50m

$123

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 10/4

10:35 am-11:50 am

Nonstop2h 15m

Chicago O'Hare Intl

Sat 10/18

1:30 pm-4:25 pm

Nonstop1h 55m

$123

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 11/8

6:00 am-7:16 am

Nonstop2h 16m

Chicago O'Hare Intl

Mon 11/10

6:04 am-8:59 am

Nonstop1h 55m

$136

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 9/10

5:08 pm-6:28 pm

Nonstop2h 20m

Chicago O'Hare Intl

Fri 9/12

6:10 am-9:00 am

Nonstop1h 50m

$140

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Washington, D.C. to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

Other information

What is the typical price of a round-trip flight between Washington, D.C. and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around $202. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Washington, D.C. to Chicago during January average around $229.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $386. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. to Chicago for around $492.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. to Chicago during this time can be as low as $333. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $436.

What is the cheapest Washington, D.C. to Chicago flight route?

Fly from Baltimore/Washington to Chicago Midway for the best Washington, D.C. - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Washington, D.C. when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $284 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. for as low as $221 on momondo.

What cabin class options are available on Washington, D.C. to Chicago flights?

There are 4 cabin classes available to choose from on Washington, D.C. to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Washington, D.C. to Chicago flights?

No. A direct flight is the cheapest option for a flight between Washington, D.C. to Chicago.

How have Washington, D.C. to Chicago flight prices changed over time?

As of August 2025, prices for Washington, D.C. to Chicago flights are approximately 43% cheaper when compared to flights at the same time last year.

When to book flights from Washington, D.C. to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Washington, D.C. to Chicago (WAS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. to Chicago

Best Price Found	$43
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Washington, D.C. in the past 72 hours is $43. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $88.

The fastest flight from Washington, D.C. to Chicago takes 1h 55m

Direct flights go from Washington, D.C. to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

Is flying the fastest way to get from Washington, D.C. to Chicago?
The quickest way is to book a flight from Washington, D.C. to Chicago, which can be as quick as 1h 55m onboard Southwest. You can also get a train from Washington, D.C. to Chicago, or a bus from Washington, D.C. to Chicago which can take you longer to arrive at your destination.
Is flying the cheapest way to get from Washington, D.C. to Chicago?
The cheapest way is to get a flight from Washington, D.C. to Chicago, which can be as cheap as $88. A train from Washington, D.C. to Chicago is more expensive than a flight, with prices starting at $202. A bus from Washington, D.C. to Chicago is also an option, with an average price of $144.
How far is Washington, D.C. to Chicago by plane?
The straight-line distance from Washington, D.C. to Chicago is 593.1 mi. 1h 55m is a normal flight duration for this route.
When did momondo last update prices for flights from Washington, D.C. to Chicago?
Prices for flights from Washington, D.C. to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Washington, D.C. to Chicago?
There are 6 operators available for flights from Washington, D.C. to Chicago as of August 2025.
How old do you have to be to fly from Washington, D.C. to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Washington, D.C. to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Washington, D.C. to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Washington, D.C. to Chicago is Boeing 737-800, representing 11.16% of all bookings. The subsequent popular models are Airbus A319 at 10.77%, Airbus A320-100/200 at 10.67%, and Boeing 737 MAX 8 at 8.62%.
What is the most popular airline from Washington, D.C. to Chicago?
momondo data reveals that the most frequently booked airline on the route from Washington, D.C. to Chicago is United Airlines, representing 28% of all bookings. The subsequent popular airlines are Southwest at 26%, Frontier at 23%, and American Airlines at 22%.

Best airlines flying from Washington, D.C. to Chicago

Compare and see reviews for airlines that fly from Washington, D.C. to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $46	Free Cancellation	Rating 6.3 8,052 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $62	Free Cancellation	Rating 5.8 3,232 reviews	Search Frontier flights
Delta	PriceFrom $98	Free Cancellation	Rating 8.0 7,990 reviews	Search Delta flights
American Airlines	PriceFrom $157	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,247 reviews	Search Southwest flights
United Airlines	PriceFrom $158	Free Cancellation	Rating 7.4 8,910 reviews	Search United Airlines flights

Southwest Flights From Washington, D.C. to Chicago
Southwest flies from Washington, D.C. to Chicago around 14 times per week, with 4,247 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $157 (round-trip), much lower than the average airfare cost of $291 for Southwest flights on this route.
United Airlines Flights From Washington, D.C. to Chicago
The best United Airlines deal for Washington, D.C. to Chicago flight tickets found on momondo in the last 72 hours was $158, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $293 round-trip. United Airlines operates 79 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 8,910 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

It is quick and easy to find Washington, D.C. to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

Flights from Washington, D.C. to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Washington, D.C. to Chicago?

Once you have performed a search for Washington, D.C. to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Washington, D.C. are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Washington, D.C. to Chicago from $43

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. to Chicago departing on 9/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Find the cheapest flights from Washington, D.C. to Chicago (WAS-CHI)

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Spirit Airlines flights from Washington, D.C. to Chicago

Our best Spirit Airlines deals on Washington, D.C. to Chicago flight tickets

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Our best United Airlines deals on Washington, D.C. to Chicago flight tickets

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How to get the cheapest flight ticket from Washington, D.C. to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Washington, D.C. and Chicago?

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. to Chicago during this time can be as low as $333. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $436.

What is the cheapest Washington, D.C. to Chicago flight route?

Fly from Baltimore/Washington to Chicago Midway for the best Washington, D.C. - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Washington, D.C. to Chicago flights?

There are 4 cabin classes available to choose from on Washington, D.C. to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Washington, D.C. to Chicago flights?

No. A direct flight is the cheapest option for a flight between Washington, D.C. to Chicago.

How have Washington, D.C. to Chicago flight prices changed over time?

As of August 2025, prices for Washington, D.C. to Chicago flights are approximately 43% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Washington, D.C. to Chicago?

Spirit Airlines, United Airlines, and Southwest are the most popular carriers operating from Washington, D.C. to Chicago

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Washington, D.C. and Chicago?

Detroit (DTW) was the most common stop: 43% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Washington, D.C. to Chicago?

Flights via Denver (DEN) offer the lowest average round-trip price of $178.

Which layover airport has the shortest travel time from Washington, D.C. to Chicago?

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 3h 40m.

Which layover airport has the shortest connection time from Washington, D.C. to Chicago?

Detroit (DTW) has the shortest average layover time for this route: 0h 53m.

How many flights depart from Washington, D.C. to Chicago on average per day?

As of August 2025, there are 66 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 5:00PM, with 44% of flights taking off in the afternoon.

How many flights depart from Washington, D.C. to Chicago on average per week?

As of August 2025, 466 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Tue, with 25% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

When to book flights from Washington, D.C. to Chicago

Cheap Washington, D.C. to Chicago (WAS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Is flying the fastest way to get from Washington, D.C. to Chicago?

Is flying the cheapest way to get from Washington, D.C. to Chicago?

How far is Washington, D.C. to Chicago by plane?

When did momondo last update prices for flights from Washington, D.C. to Chicago?

How many operators does momondo search for flights from Washington, D.C. to Chicago?

How old do you have to be to fly from Washington, D.C. to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Washington, D.C. to Chicago?

What is the most popular airline from Washington, D.C. to Chicago?

Best airlines flying from Washington, D.C. to Chicago

Compare and see reviews for airlines that fly from Washington, D.C. to Chicago with momondo

Southwest Flights From Washington, D.C. to Chicago

United Airlines Flights From Washington, D.C. to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Washington, D.C. to Chicago?

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?