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

Flights via New York (JFK) offer the lowest average round-trip price of $152.

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

As of January 2026, there are 65 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 5:00PM, with 49% of flights taking off in the afternoon.

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

Atlanta (ATL) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

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.

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 03m on average, while flying from Baltimore to Chicago O'Hare Intl Airport is 2h 10m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

As of January 2026, 457 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Thu, with 19% of weekly flights taking off on this day.

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.

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

Frontier, Southwest, and United Airlines are the most popular carriers operating from Washington, D.C. to 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 45m.

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 2h 05m 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 $102. 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 $156.

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 January 2026.

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.

$55 Cheap Flights from Washington, D.C. to Chicago in 2026

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 $148 to $308. The lowest price recently found on this route was $102.

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Find the cheapest flights from Washington, D.C. to Chicago

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

10:06 am - 9:13 pm

BWI

ORD

12h 07m

1 stop

10:44 am - 10:53 pm

ORD

BWI

11h 09m

1 stop

$102Spirit Airlines

Tue, Feb 24 - Tue, Mar 3

7:19 pm - 8:46 pm

BWI

ORD

2h 27mnonstop

4:42 pm - 12:31 am

ORD

BWI

6h 49m

1 stop

$103Frontier

Thu, Feb 19 - Sat, Feb 21

9:19 am - 10:46 am

BWI

ORD

2h 27mnonstop

8:16 pm - 9:06 am

ORD

BWI

11h 50m

1 stop

$104Multiple Airlines

Thu, Mar 5 - Mon, Mar 9

12:30 pm - 11:22 am

BWI

ORD

23h 52m

1 stop

3:15 pm - 6:24 pm

ORD

BWI

2h 09mnonstop

$105Multiple Airlines

Tue, Feb 17 - Thu, Feb 19

9:19 am - 10:46 am

BWI

ORD

2h 27mnonstop

3:21 pm - 8:26 am

ORD

BWI

16h 05m

1 stop

$106Frontier

Thu, Feb 26 - Thu, Mar 5

12:30 pm - 7:11 pm

BWI

ORD

7h 41m

1 stop

11:51 am - 12:31 am

ORD

BWI

11h 40m

1 stop

$107Multiple Airlines

Wed, Feb 25 - Wed, Mar 4

1:00 pm - 2:22 pm

DCA

ORD

2h 22mnonstop

7:00 am - 9:54 am

ORD

DCA

1h 54mnonstop

$197United Airlines

Wed, Feb 25 - Wed, Mar 4

6:55 pm - 8:00 pm

DCA

MDW

2h 05mnonstop

4:35 pm - 7:20 pm

MDW

DCA

1h 45mnonstop

$197Southwest

Tue, Mar 10 - Tue, Mar 17

7:59 pm - 9:24 pm

DCA

ORD

2h 25mnonstop

7:48 pm - 11:00 pm

ORD

DCA

2h 12mnonstop

$198American Airlines

Tue, Feb 24 - Tue, Mar 3

9:00 pm - 10:15 pm

DCA

MDW

2h 15mnonstop

2:35 pm - 10:00 pm

MDW

DCA

6h 25m

1 stop

$207Southwest

Tue, Feb 24 - Tue, Mar 3

JetBlue flights from Washington, D.C. to Chicago

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

JetBlue

Feb 24

DCA6:00 amWashington, D.C. Reagan-National

6h 59m

1 stop

ORD11:59 amChicago O'Hare Intl

Mar 3

ORD10:00 amChicago O'Hare Intl

7h 55m

1 stop

DCA6:55 pmWashington, D.C. Reagan-National

$207

JetBlue

Mar 2

DCA6:00 amWashington, D.C. Reagan-National

6h 49m

1 stop

ORD11:49 amChicago O'Hare Intl

Mar 6

ORD12:41 pmChicago O'Hare Intl

9h 18m

1 stop

DCA10:59 pmWashington, D.C. Reagan-National

$226

JetBlue

Feb 11

DCA10:05 amWashington, D.C. Reagan-National

7h 50m

1 stop

ORD4:55 pmChicago O'Hare Intl

Feb 12

ORD10:00 amChicago O'Hare Intl

5h 04m

1 stop

DCA4:04 pmWashington, D.C. Reagan-National

$233

Frontier flights from Washington, D.C. to Chicago

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

Frontier

Feb 6

BWI10:00 amBaltimore/Washington

2h 27m

ORD11:27 amChicago O'Hare Intl

Feb 9

ORD8:45 amChicago O'Hare Intl

2h 00m

BWI11:45 amBaltimore/Washington

$102

Frontier

Feb 19

BWI7:19 pmBaltimore/Washington

2h 27m

ORD8:46 pmChicago O'Hare Intl

Feb 21

ORD4:42 pmChicago O'Hare Intl

6h 49m

1 stop

BWI12:31 amBaltimore/Washington

$103

Frontier

Feb 26

BWI9:19 amBaltimore/Washington

2h 27m

ORD10:46 amChicago O'Hare Intl

Mar 5

ORD3:21 pmChicago O'Hare Intl

16h 05m

1 stop

BWI8:26 amBaltimore/Washington

$106

Fly from

Fly to

Route

Depart

Return

Price

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 2/24

10:06 am-9:13 pm

1 stop12h 07m

Chicago O'Hare Intl

Tue 3/3

10:44 am-10:53 pm

1 stop11h 09m

$102

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 2/19

7:19 pm-8:46 pm

Nonstop2h 27m

Chicago O'Hare Intl

Sat 2/21

4:42 pm-12:31 am

1 stop6h 49m

$103

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 3/5

9:19 am-10:46 am

Nonstop2h 27m

Chicago O'Hare Intl

Mon 3/9

8:16 pm-9:06 am

1 stop11h 50m

$104

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Tue 2/17

12:30 pm-11:22 am

1 stop23h 52m

Chicago O'Hare Intl

Thu 2/19

3:15 pm-6:24 pm

Nonstop2h 09m

$105

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 2/26

9:19 am-10:46 am

Nonstop2h 27m

Chicago O'Hare Intl

Thu 3/5

3:21 pm-8:26 am

1 stop16h 05m

$106

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 2/25

12:30 pm-7:11 pm

1 stop7h 41m

Chicago O'Hare Intl

Wed 3/4

11:51 am-12:31 am

1 stop11h 40m

$107

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 2/25

1:00 pm-2:22 pm

Nonstop2h 22m

Chicago O'Hare Intl

Wed 3/4

7:00 am-9:54 am

Nonstop1h 54m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 3/10

6:55 pm-8:00 pm

Nonstop2h 05m

Chicago Midway

Tue 3/17

4:35 pm-7:20 pm

Nonstop1h 45m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 2/24

7:59 pm-9:24 pm

Nonstop2h 25m

Chicago O'Hare Intl

Tue 3/3

7:48 pm-11:00 pm

Nonstop2h 12m

$198

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 2/24

9:00 pm-10:15 pm

Nonstop2h 15m

Chicago Midway

Tue 3/3

2:35 pm-10:00 pm

1 stop6h 25m

$207

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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

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 $203. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Washington, D.C. to Chicago during February average around $218.

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 $378. 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 $500.

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 $353. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $418.

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

Fly from Baltimore/Washington to Chicago O'Hare Intl 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 $334 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 $216 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 January 2026, 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	$121
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Washington, D.C. in the past 72 hours is $121. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $219.

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 3 airports in Chicago. From Washington, D.C. there are direct flights to 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 2h 05m 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 $102. 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 $156.
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 January 2026.
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 10.58% of all bookings. The subsequent popular models are Airbus A319 at 10.55%, Boeing 737 MAX 8 at 9.36%, and Boeing 737-900 at 9.03%.
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 Frontier, representing 28% of all bookings. The subsequent popular airlines are United Airlines at 28%, Southwest at 26%, and American Airlines at 17%.

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 $41	Free Cancellation	Rating 6.3 8,394 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $57	Free Cancellation	Rating 5.7 3,056 reviews	Search Frontier flights
Southwest	PriceFrom $148	Free Cancellation	Rating 8.0 4,267 reviews	Search Southwest flights
United Airlines	PriceFrom $153	Free Cancellation	Rating 7.4 9,215 reviews	Search United Airlines flights
American Airlines	PriceFrom $159	Free Cancellation	Rating 7.2 11,206 reviews	Search American Airlines flights
Delta	PriceFrom $194	Free Cancellation	Rating 7.9 8,127 reviews	Search Delta flights

Southwest Flights From Washington, D.C. to Chicago
Southwest flies from Washington, D.C. to Chicago around 30 times per week, with 4,267 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $148 (round-trip), much lower than the average airfare cost of $299 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 $153, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $322 round-trip. United Airlines operates 76 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 9,215 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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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Find better results for your trip to the United States

Cheap flights from Washington, D.C. to Chicago from $55

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 2/28. 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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JetBlue flights from Washington, D.C. to Chicago

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

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

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See travel insights to Chicago from

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

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 $353. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $418.

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

Fly from Baltimore/Washington to Chicago O'Hare Intl 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 January 2026, 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?

Frontier, Southwest, and United Airlines 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?

Atlanta (ATL) was the most common stop: 60% 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 New York (JFK) offer the lowest average round-trip price of $152.

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 45m.

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

As of January 2026, there are 65 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 5:00PM, with 49% of flights taking off in the afternoon.

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

As of January 2026, 457 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Thu, with 19% 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?

An easier way to manage your Chicago trip