What are the cheapest airlines to fly from District of Columbia to Chicago one-way?

To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $83. Avelo Airlines flights start at $93 while deals on JetBlue start at $102 one-way.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from District of Columbia to Chicago?

While some choose either Washington, D.C. Dulles Intl - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago Midway, Washington, D.C. Reagan-National - Chicago O'Hare Intl is the most popular route from District of Columbia to Chicago.

What are the cheapest flights from District of Columbia to Chicago?

Looking for the cheapest flight from District of Columbia to Chicago? While on average our users pay $1,494, our data indicates the cheapest price to be $76. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $203.

What are the most reliable airlines from District of Columbia to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from District of Columbia to Chicago on time: ANA (95%), Spirit Airlines (93%), Royal Jordanian (88%).

What are the most popular airlines that fly from District of Columbia to Chicago?

Before booking your flight from District of Columbia to Chicago check out the most popular airlines for this route: American Airlines, Delta or Frontier.

How far in advance should I book a flight from District of Columbia to Chicago?

Users have found that booking a flight from District of Columbia to Chicago at least 51 days early can save you up to 76% on average compared to booking a flight this week. If booking 51 days before your flight isn’t an option for you, users have found flights from District of Columbia to Chicago for as little as $265 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $497 for flights departing within the next 3 days.

What is the cheapest month to fly from District of Columbia to Chicago?

The best pricing can be found in the month of September. Prices to Chicago from District of Columbia average $250. You can even find prices in September for less than $250, as users have found deals to Chicago from as low as $70. The month of April appears to be one of the more expensive times to travel to Chicago from District of Columbia. Flying in the targeted month can save you up to 9%.

Can I find deals for flights from District of Columbia to Chicago that include hotel bookings?

Yes. In addition to deals on District of Columbia to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from District of Columbia to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from District of Columbia to Chicago.

Can I find deals for business class flights from District of Columbia to Chicago?

Yes. Cheapflights offers flight deals from District of Columbia to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$83+ Flights from District of Columbia to Chicago

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Cheap flight deals from District of Columbia to Chicago

Round-trip from	$174 (Mytrip)
One-way from	$83 (Cheapflightsfares)
Popular in	April
Cheapest in	September
Average price	$266
Good round-trip deal	$220 or less
Good one-way deal	$155 or less

From District of Columbia to Chicago (CHI)

Search Deals

One-way flight from District of Columbia to Chicago (CHI)

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Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).

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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Price to beat on a round-trip flight from District of Columbia to Chicago (CHI).

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Price to beat on a one-way flight from District of Columbia to Chicago (CHI).

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Find flight deals from District of Columbia to Chicago

Cheapest flights from District of Columbia to Chicago
Explore the most affordable flight options available from District of Columbia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

Mon 8/181:22 pmIAD - MDW

1 stop5h 55mAllegiant Air

Fri 8/229:32 amMDW - IAD

1 stop4h 51mAllegiant Air

Deal found 7/29

$174

Sat 9/137:14 pmIAD - MDW

1 stop15h 04mFrontier

Sat 9/2010:51 amMDW - IAD

1 stop6h 33mFrontier

Deal found 7/30

$177

Sun 9/216:10 amIAD - ORD

1 stop5h 21mFrontier

Sat 9/275:40 pmORD - IAD

1 stop5h 15mFrontier

Deal found 7/29

$195

Tue 8/266:30 amDCA - ORD

1 stop5h 48mJetBlue

Wed 9/39:42 amORD - DCA

1 stop7h 18mJetBlue

Deal found 7/31

$203

Sat 8/237:00 amDCA - ORD

Nonstop2h 22mAmerican Airlines

Sat 8/2310:15 amORD - DCA

1 stop4h 44mAmerican Airlines

Deal found 7/30

$209

Tue 8/2612:00 pmDCA - ORD

Nonstop2h 13mUnited Airlines

Tue 9/27:00 amORD - DCA

Nonstop1h 58mUnited Airlines

Deal found 7/29

$217

Sat 8/308:25 amDCA - MDW

Nonstop2h 00mSouthwest

Sat 9/612:45 pmMDW - DCA

Nonstop1h 55mSouthwest

Deal found 7/31

$217

Sat 9/61:00 pmDCA - ORD

1 stop9h 28mFrontier

Wed 9/107:20 amORD - DCA

1 stop13h 39mFrontier

Deal found 7/30

$218

Tue 9/210:10 pmIAD - ORD

Nonstop2h 05mUnited Airlines

Thu 9/42:32 pmORD - IAD

Nonstop1h 58mUnited Airlines

Deal found 7/31

$223

Sat 8/3012:29 pmDCA - ORD

1 stop8h 54mDelta

Tue 9/912:59 pmORD - DCA

1 stop5h 00mDelta

Deal found 7/28

$227

Sat 8/305:25 pmIAD - MDW

1 stop4h 47mDelta

Tue 9/29:30 amMDW - IAD

1 stop12h 56mDelta

Deal found 7/29

$227

Sat 8/161:00 pmDCA - MDW

1 stop8h 54mFrontier

Mon 8/1812:35 pmMDW - DCA

1 stop27h 24mFrontier

Deal found 7/29

$228

Best flights from District of Columbia to Chicago
Discover carefully curated flight deals from District of Columbia to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 31, 2025.

Mon 8/181:22 pmIAD - MDW

1 stop5h 55mAllegiant Air

Fri 8/229:32 amMDW - IAD

1 stop4h 51mAllegiant Air

Deal found 7/29

$174

Sat 9/137:14 pmIAD - MDW

1 stop15h 04mFrontier

Sat 9/2010:51 amMDW - IAD

1 stop6h 33mFrontier

Deal found 7/30

$177

Tue 8/266:30 amDCA - ORD

1 stop5h 48mJetBlue

Wed 9/39:42 amORD - DCA

1 stop7h 18mJetBlue

Deal found 7/31

$203

Sat 8/237:00 amDCA - ORD

Nonstop2h 22mAmerican Airlines

Sat 8/2310:15 amORD - DCA

1 stop4h 44mAmerican Airlines

Deal found 7/30

$209

Tue 8/2612:00 pmDCA - ORD

Nonstop2h 13mUnited Airlines

Tue 9/27:00 amORD - DCA

Nonstop1h 58mUnited Airlines

Deal found 7/29

$217

Sat 8/308:25 amDCA - MDW

Nonstop2h 00mSouthwest

Sat 9/612:45 pmMDW - DCA

Nonstop1h 55mSouthwest

Deal found 7/31

$217

Sat 8/3012:29 pmDCA - ORD

1 stop8h 54mDelta

Tue 9/912:59 pmORD - DCA

1 stop5h 00mDelta

Deal found 7/28

$227

Thu 8/214:56 pmIAD - ORD

2 stops17h 25mMultiple Airlines

Sun 8/245:16 pmORD - IAD

2 stops21h 07mMultiple Airlines

Deal found 7/29

$241

Sun 9/216:10 amIAD - ORD

1 stop5h 21mFrontier

Sat 9/275:40 pmORD - IAD

1 stop5h 15mFrontier

Deal found 7/29

$195

Tue 9/210:10 pmIAD - ORD

Nonstop2h 05mUnited Airlines

Thu 9/42:32 pmORD - IAD

Nonstop1h 58mUnited Airlines

Deal found 7/31

$223

Sat 8/305:25 pmIAD - MDW

1 stop4h 47mDelta

Tue 9/29:30 amMDW - IAD

1 stop12h 56mDelta

Deal found 7/29

$227

Sat 9/61:00 pmDCA - ORD

1 stop9h 28mFrontier

Sat 9/138:25 amORD - DCA

1 stop12h 34mFrontier

Deal found 7/28

$218

Last-minute flights from District of Columbia to Chicago
Discover last-minute flight deals from District of Columbia to Chicago. Data last updated July 31, 2025 and is based on user searches.

Tue 8/56:10 amIAD - MDW

1 stop5h 30mFrontier

Wed 9/33:03 pmMDW - IAD

1 stop5h 36mFrontier

Deal found 7/30

$178

Tue 8/56:10 amIAD - ORD

1 stop11h 28mFrontier

Tue 8/125:38 pmORD - IAD

1 stop5h 41mFrontier

Deal found 7/30

$198

Tue 8/56:27 amIAD - ORD

1 stop9h 38mAmerican Airlines

Tue 8/56:25 pmORD - IAD

1 stop4h 33mAmerican Airlines

Deal found 7/29

$362

Tue 8/57:00 amDCA - ORD

Nonstop2h 27mAmerican Airlines

Wed 9/31:37 pmORD - DCA

Nonstop1h 52mAmerican Airlines

Deal found 7/30

$374

Tue 8/59:39 amDCA - MDW

1 stop3h 50mDelta

Wed 9/36:17 pmMDW - DCA

1 stop3h 42mDelta

Deal found 7/30

$429

Tue 8/56:05 amDCA - MDW

Nonstop1h 55mSouthwest

Fri 9/52:45 pmMDW - DCA

Nonstop1h 50mSouthwest

Deal found 7/30

$435

Tue 8/51:40 pmDCA - ORD

1 stop5h 19mDelta

Fri 9/511:15 amORD - DCA

1 stop5h 05mDelta

Deal found 7/31

$455

Fri 8/83:39 pmIAD - ORD

Nonstop2h 13mUnited Airlines

Fri 8/87:35 pmORD - IAD

1 stop10h 53mUnited Airlines

Deal found 7/31

$309

Fri 8/811:45 amDCA - ORD

2 stops10h 45mSouthwest

Tue 8/193:10 pmORD - DCA

1 stop6h 50mSouthwest

Deal found 7/29

$451

Sat 8/99:20 pmIAD - ORD

3 stops35h 30mMultiple Airlines

Wed 8/1312:10 pmORD - IAD

2 stops21h 04mMultiple Airlines

Deal found 7/30

$365

Sun 8/107:00 amDCA - ORD

1 stop18h 32mFrontier

Sun 8/175:40 amORD - DCA

1 stop29h 24mFrontier

Deal found 7/29

$238

Sun 8/107:00 amDCA - MDW

1 stop29h 41mFrontier

Thu 8/142:44 pmMDW - DCA

1 stop30h 13mFrontier

Deal found 7/29

$238

One-way flights from District of Columbia to Chicago
Search for one-way flight options from District of Columbia to Chicago. Find affordable one-way fares based on user searches. Data last updated July 31, 2025.

Tue 8/56:10 amIAD - MDW

1 stop5h 30mFrontier

Deal found 7/29

$83

Sun 9/79:03 amIAD - ORD

1 stop9h 08mAvelo Airlines

Deal found 7/29

$93

Tue 8/199:30 amIAD - ORD

1 stop6h 40mFrontier

Deal found 7/30

$99

Thu 8/214:56 pmIAD - ORD

2 stops17h 25mMultiple Airlines

Deal found 7/30

$101

Tue 8/266:30 amDCA - ORD

1 stop5h 48mJetBlue

Deal found 7/30

$102

Wed 8/272:00 pmDCA - ORD

Nonstop2h 13mUnited Airlines

Deal found 7/30

$109

Tue 8/2611:55 amDCA - MDW

Nonstop1h 55mSouthwest

Deal found 7/29

$109

Wed 9/31:00 pmDCA - ORD

1 stop9h 42mFrontier

Deal found 7/30

$110

Tue 8/263:50 pmDCA - ORD

Nonstop2h 21mAmerican Airlines

Deal found 7/29

$111

Thu 8/286:35 amIAD - ORD

Nonstop2h 11mUnited Airlines

Deal found 7/29

$115

Sat 10/116:00 pmDCA - MDW

1 stop29h 38mFrontier

Deal found 7/30

$116

Tue 8/266:00 amIAD - ORD

1 stop5h 04mDelta

Deal found 7/29

$119

Cheapflights Fare Finder

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

Mon 8/18

1:22 pm-6:17 pm

1 stop5h 55m

Chicago Midway

Fri 8/22

9:32 am-3:23 pm

1 stop4h 51m

$174

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/13

7:14 pm-9:18 am

1 stop15h 04m

Chicago Midway

Sat 9/20

10:51 am-6:24 pm

1 stop6h 33m

$177

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 9/21

6:10 am-10:31 am

1 stop5h 21m

Chicago O'Hare Intl

Sat 9/27

5:40 pm-11:55 pm

1 stop5h 15m

$195

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 8/26

6:30 am-11:18 am

1 stop5h 48m

Chicago O'Hare Intl

Wed 9/3

9:42 am-6:00 pm

1 stop7h 18m

$203

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 8/23

7:00 am-8:22 am

Nonstop2h 22m

Chicago O'Hare Intl

Sat 8/23

10:15 am-3:59 pm

1 stop4h 44m

$209

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 8/26

12:00 pm-1:13 pm

Nonstop2h 13m

Chicago O'Hare Intl

Tue 9/2

7:00 am-9:58 am

Nonstop1h 58m

$217

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/30

8:25 am-9:25 am

Nonstop2h 00m

Chicago Midway

Sat 9/6

12:45 pm-3:40 pm

Nonstop1h 55m

$217

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 9/6

1:00 pm-9:28 pm

1 stop9h 28m

Chicago O'Hare Intl

Sat 9/13

8:25 am-9:59 pm

1 stop12h 34m

$218

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 9/2

10:10 pm-11:15 pm

Nonstop2h 05m

Chicago O'Hare Intl

Thu 9/4

2:32 pm-5:30 pm

Nonstop1h 58m

$223

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 8/30

12:29 pm-8:23 pm

1 stop8h 54m

Chicago O'Hare Intl

Tue 9/9

12:59 pm-6:59 pm

1 stop5h 00m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 36 results

Best time to book a flight from District of Columbia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from District of Columbia with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from District of Columbia to Chicago

What is the cheapest month to book a flight from District of Columbia to Chicago?

Currently, August is the cheapest month in which you can book a flight from District of Columbia to Chicago (average of $245). Flying from District of Columbia to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DC to CHI?

When flying from District of Columbia to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from District of Columbia to Chicago

The most flights from USDC to CHI are scheduled on a Thursday (34 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (12 on average).

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from District of Columbia to Chicago, such as Southwest, Delta, and Avelo Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Southwest

8.0

Very good

4,246 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

Delta

8.0

Very good

7,981 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

Avelo Airlines

7.5

Good

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

United Airlines

7.4

Good

8,900 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

American Airlines

7.2

Good

10,000 reviews

Southwest

8.0

Very good

4,246 reviews

Reviews

1 / 20

8.0

Excellent

Gina,Jul 2025

LAS - DEN

Related info for your journey

What are the cheapest airlines to fly from District of Columbia to Chicago one-way?
To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $83. Avelo Airlines flights start at $93 while deals on JetBlue start at $102 one-way.
What are the most popular routes from District of Columbia to Chicago?
While some choose either Washington, D.C. Dulles Intl - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago Midway, Washington, D.C. Reagan-National - Chicago O'Hare Intl is the most popular route from District of Columbia to Chicago.
What are the most reliable airlines from District of Columbia to Chicago?
Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from District of Columbia to Chicago on time: ANA (95%), Spirit Airlines (93%), Royal Jordanian (88%).
What are the cheapest flights from District of Columbia to Chicago?
Looking for the cheapest flight from District of Columbia to Chicago? While on average our users pay $1,494, our data indicates the cheapest price to be $76. The most popular route (Washington, D.C. Reagan-National - Chicago O'Hare Intl), is priced around $203.
Can I find deals for flights from District of Columbia to Chicago that include hotel bookings?
Yes. In addition to deals on District of Columbia to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from District of Columbia to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from District of Columbia to Chicago.
Can I find deals for business class flights from District of Columbia to Chicago?
Yes. Cheapflights offers flight deals from District of Columbia to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from District of Columbia to Chicago?
Currently, August is the cheapest month in which you can book a flight from District of Columbia to Chicago (average of $245). Flying from District of Columbia to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Porter

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Top 6 airlines flying from District of Columbia to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$52	Average$152	FlexibilityNo cancel fee	On-time65%
Frontier	Cheapest$61	Average$188	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$98	Average$296	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$152	Average$329	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$157	Average$292	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$157	Average$328	FlexibilityNo cancel fee	On-time69%

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$83+ Cheap flights from District of Columbia to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from District of Columbia to Chicago with Cheapflights

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Cheap flight deals from District of Columbia to Chicago

Keep the following information in mind while searching for District of Columbia to Chicago flight deals. Data was last updated July 31, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from District of Columbia to Chicago

Cheapest flights from District of Columbia to ChicagoExplore the most affordable flight options available from District of Columbia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

Explore the most affordable flight options available from District of Columbia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from District of Columbia to Chicago that are best for you.

Best time to book a flight from District of Columbia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from District of Columbia with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from District of Columbia to Chicago

What is the cheapest month to book a flight from District of Columbia to Chicago?

What is the cheapest time of day to fly from DC to CHI?

Find hourly flight availability from District of Columbia to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

Weekly flight availability from District of Columbia to Chicago

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from District of Columbia to Chicago, such as Southwest, Delta, and Avelo Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from District of Columbia to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What are the cheapest airlines to fly from District of Columbia to Chicago one-way?

What are the most popular routes from District of Columbia to Chicago?

What are the most reliable airlines from District of Columbia to Chicago?

What are the cheapest flights from District of Columbia to Chicago?

Can I find deals for flights from District of Columbia to Chicago that include hotel bookings?

How can I find direct flights from District of Columbia to Chicago?

Can I find deals for business class flights from District of Columbia to Chicago?

What is the cheapest month to book a flight from District of Columbia to Chicago?

Traveling to a place near Chicago?

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Alternative routes for District of Columbia to Chicago

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Top 6 airlines flying from District of Columbia to Chicago

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Cheapest flights from District of Columbia to Chicago
Explore the most affordable flight options available from District of Columbia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.