Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from District of Columbia to Chicago from $74

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from District of Columbia to Chicago departing on 3/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from District of Columbia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
10:29 am - 9:33 pm
IAD
-
MDW
12h 04m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$143Frontier
Sat, Feb 21 - Mon, Feb 23
Frontier Logo
11:39 am - 10:44 pm
IAD
-
ORD
12h 05m
1 stop
Frontier Logo
5:40 am - 4:28 pm
ORD
-
IAD
9h 48m
1 stop
$144Frontier
Sat, Feb 7 - Mon, Feb 9
Multiple Airlines Logo
3:58 pm - 8:18 am
IAD
-
ORD
17h 20m
1 stop
Multiple Airlines Logo
6:57 pm - 7:58 pm
ORD
-
IAD
24h 01m
1 stop
$145Multiple Airlines
Mon, Feb 2 - Thu, Feb 5
Frontier Logo
6:00 am - 5:12 pm
IAD
-
ORD
12h 12m
1 stop
Frontier Logo
10:12 am - 9:13 pm
ORD
-
IAD
10h 01m
1 stop
$150Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
5:37 pm - 10:37 pm
IAD
-
MDW
6h 00m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$150Frontier
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
5:33 pm - 11:22 am
IAD
-
ORD
18h 49m
2 stops
Multiple Airlines Logo
6:57 pm - 7:58 pm
ORD
-
IAD
24h 01m
1 stop
$154Multiple Airlines
Mon, Feb 2 - Thu, Feb 5
JetBlue Logo
11:55 am - 5:43 pm
DCA
-
ORD
6h 48m
1 stop
JetBlue Logo
7:45 am - 4:19 pm
ORD
-
DCA
7h 34m
1 stop
$178JetBlue
Thu, Feb 5 - Mon, Feb 9
JetBlue Logo
6:00 am - 11:54 am
DCA
-
ORD
6h 54m
1 stop
JetBlue Logo
10:00 am - 4:03 pm
ORD
-
DCA
5h 03m
1 stop
$183JetBlue
Fri, Feb 27 - Fri, Mar 6
Southwest Logo
6:05 am - 7:20 am
DCA
-
MDW
2h 15mnonstop
Southwest Logo
5:25 pm - 8:15 pm
MDW
-
DCA
1h 50mnonstop
$211Southwest
Sat, Feb 7 - Tue, Feb 10
Southwest Logo
11:10 am - 12:20 pm
DCA
-
MDW
2h 10mnonstop
Southwest Logo
6:00 am - 12:15 pm
MDW
-
DCA
5h 15m
1 stop
$221Southwest
Sat, Feb 7 - Tue, Feb 10

JetBlue flights from District of Columbia to Chicago

Our best JetBlue deals on District of Columbia to Chicago flight tickets
JetBlue
Feb 5
DCA11:55 amWashington, D.C. Reagan-National
6h 48m
1 stop
ORD5:43 pmChicago O'Hare Intl
Feb 9
ORD7:45 amChicago O'Hare Intl
7h 34m
1 stop
DCA4:19 pmWashington, D.C. Reagan-National
$178
JetBlue
Feb 27
DCA6:00 amWashington, D.C. Reagan-National
6h 54m
1 stop
ORD11:54 amChicago O'Hare Intl
Mar 6
ORD10:00 amChicago O'Hare Intl
5h 03m
1 stop
DCA4:03 pmWashington, D.C. Reagan-National
$183
JetBlue
Feb 3
DCA11:55 amWashington, D.C. Reagan-National
6h 48m
1 stop
ORD5:43 pmChicago O'Hare Intl
Feb 5
ORD7:45 amChicago O'Hare Intl
5h 44m
1 stop
DCA2:29 pmWashington, D.C. Reagan-National
$189

Frontier flights from District of Columbia to Chicago

Our best Frontier deals on District of Columbia to Chicago flight tickets
Frontier
Feb 21
IAD10:29 amWashington, D.C. Dulles Intl
12h 04m
1 stop
MDW9:33 pmChicago Midway
Feb 23
MDW6:00 amChicago Midway
9h 08m
1 stop
IAD4:08 pmWashington, D.C. Dulles Intl
$143
Frontier
Feb 7
IAD11:39 amWashington, D.C. Dulles Intl
12h 05m
1 stop
ORD10:44 pmChicago O'Hare Intl
Feb 9
ORD5:40 amChicago O'Hare Intl
9h 48m
1 stop
IAD4:28 pmWashington, D.C. Dulles Intl
$144
Frontier
Apr 9
IAD6:00 amWashington, D.C. Dulles Intl
12h 12m
1 stop
ORD5:12 pmChicago O'Hare Intl
Apr 11
ORD11:39 amChicago O'Hare Intl
6h 04m
1 stop
IAD6:43 pmWashington, D.C. Dulles Intl
$150

momondo Fare Finder

 
Customize your flight search to find flights from District of Columbia to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 13, 2026.
Use the filters below to find and compare flights from District of Columbia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 2/21

10:29 am-9:33 pm

1 stop12h 04m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$143

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 2/7

11:39 am-10:44 pm

1 stop12h 05m

Chicago O'Hare Intl

Mon 2/9

5:40 am-4:28 pm

1 stop9h 48m

$144

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 2/2

3:58 pm-8:18 am

1 stop17h 20m

Chicago O'Hare Intl

Thu 2/5

6:57 pm-7:58 pm

1 stop24h 01m

$145

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 4/9

6:00 am-5:12 pm

1 stop12h 12m

Chicago O'Hare Intl

Mon 4/13

10:12 am-9:13 pm

1 stop10h 01m

$150

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/19

5:37 pm-10:37 pm

1 stop6h 00m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$150

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 2/2

5:33 pm-11:22 am

2 stops18h 49m

Chicago O'Hare Intl

Thu 2/5

6:57 pm-7:58 pm

1 stop24h 01m

$154

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 2/5

11:55 am-5:43 pm

1 stop6h 48m

Chicago O'Hare Intl

Mon 2/9

7:45 am-4:19 pm

1 stop7h 34m

$178

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 2/27

6:00 am-11:54 am

1 stop6h 54m

Chicago O'Hare Intl

Fri 3/6

10:00 am-4:03 pm

1 stop5h 03m

$183

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 2/7

6:05 am-7:20 am

Nonstop2h 15m

Chicago Midway

Tue 2/10

5:25 pm-8:15 pm

Nonstop1h 50m

$211

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 2/7

11:10 am-12:20 pm

Nonstop2h 10m

Chicago Midway

Tue 2/10

6:00 am-12:15 pm

1 stop5h 15m

$221

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from District of Columbia 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 cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from District of Columbia, with most prices found around $203. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from District of Columbia to Chicago during August average around $227.

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 $379. 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 District of Columbia to Chicago for around $502.

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 District of Columbia to Chicago during this time can be as low as $350. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $419.

What is the cheapest District of Columbia to Chicago flight route?

Fly from Baltimore/Washington to Chicago O'Hare Intl for the best District of Columbia - 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 District of Columbia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $327 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from District of Columbia for as low as $216 on momondo.

What cabin class options are available on District of Columbia to Chicago flights?

There are 4 cabin classes available to choose from on District of Columbia 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 District of Columbia to Chicago flights?

No. A direct flight is the cheapest option for a flight between District of Columbia to Chicago.

Cheap District of Columbia to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from District of Columbia to Chicago

Best Price Found

$164

Fastest flight time

1h 55m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from District of Columbia in the past 72 hours is $164. The best round-trip flight deal from District of Columbia to Chicago found on momondo in the last 72 hours is $309.
The fastest flight from District of Columbia to Chicago takes 1h 55m
Direct flights go from District of Columbia to Chicago every day.
There are 3 airports in Chicago. From District of Columbia there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • When did momondo last update prices for flights from District of Columbia to Chicago?

    Prices for flights from District of Columbia to Chicago are updated daily.

  • How many operators does momondo search for flights from District of Columbia to Chicago?

  • How old do you have to be to fly from District of Columbia to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from District of Columbia to Chicago.

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

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from District of Columbia to Chicago?

Best airlines flying from District of Columbia to Chicago

Compare and see reviews for airlines that fly from District of Columbia to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $52Free CancellationRating
6.3
8,305 reviews
Search Spirit Airlines flights
FrontierPriceFrom $58Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,257 reviews
Search Southwest flights
United AirlinesPriceFrom $158Free CancellationRating
7.4
9,152 reviews
Search United Airlines flights
American AirlinesPriceFrom $160Free CancellationRating
7.2
11,116 reviews
Search American Airlines flights
DeltaPriceFrom $234Free CancellationRating
7.9
8,039 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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 District of Columbia to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from District of Columbia to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from District of Columbia to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from District of Columbia with this policy.

How can momondo help me find flights from District of Columbia to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from District of Columbia to Chicago.

I’m not ready to book a flight from District of Columbia to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for District of Columbia to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 2/12
Thu 2/19
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport