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Cheap flights from District of Columbia to Chicago from $37

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 1/22. 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 District of Columbia to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from District of Columbia to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from District of Columbia to Chicago.

Cheap last minute flights

Planning a quick getaway from District of Columbia to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from District of Columbia to Chicago

Find recent round-trip train or bus tickets from District of Columbia to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
1:17 pm - 7:06 pmIAD-MDW
6h 49m1 stop
8:12 am - 2:39 pmMDW-IAD
5h 27m1 stop
$100Frontier
Find Deal
Wed, Feb 5 - Wed, Feb 12
3:04 pm - 10:51 pmIAD-MDW
8h 47m1 stop
8:30 am - 4:55 pmMDW-IAD
7h 25m1 stop
$101Frontier
Find Deal
Sat, Mar 1 - Tue, Mar 4
7:00 am - 12:00 pmDCA-ORD
6h 00m1 stop
1:00 pm - 8:59 pmORD-DCA
6h 59m1 stop
$183JetBlue
Find Deal
Sat, Feb 22 - Sat, Mar 1
9:31 pm - 10:21 pmIAD-ORD
25h 50m1 stop
6:01 pm - 8:31 pmORD-IAD
25h 30m1 stop
Thu, May 1 - Sun, May 4
7:02 am - 8:20 amDCA-ORD
2h 18mnonstop
7:30 am - 10:43 amORD-DCA
2h 13mnonstop
$191United Airlines
Find Deal
Wed, Jan 29 - Sun, Feb 2
6:55 am - 8:10 amDCA-MDW
2h 15mnonstop
6:35 am - 9:25 amMDW-DCA
1h 50mnonstop
$191Southwest
Find Deal
Wed, Jan 29 - Fri, Jan 31
7:44 am - 9:05 amDCA-ORD
2h 21mnonstop
4:00 pm - 7:02 pmORD-DCA
2h 02mnonstop
$197United Airlines
Find Deal
Sat, Mar 1 - Tue, Mar 4
8:00 am - 11:30 amDCA-MDW
4h 30m1 stop
9:00 pm - 11:50 pmMDW-DCA
1h 50mnonstop
$201Southwest
Find Deal
Wed, Jan 29 - Sun, Feb 2
11:57 am - 6:06 pmIAD-ORD
7h 09m1 stop
9:25 am - 4:56 pmORD-IAD
6h 31m1 stop
Thu, Apr 10 - Sun, Apr 13
7:59 am - 12:27 pmDCA-ORD
5h 28m1 stop
9:43 am - 3:43 pmORD-DCA
5h 00m1 stop
$220JetBlue
Find Deal
Mon, Apr 7 - Wed, Apr 16
1:17 pm - 7:06 pmIAD-MDW
6h 49m1 stop
$37Frontier
Find Deal
Wed, Jan 22
10:11 am - 7:45 pmIAD-MDW
10h 34m1 stop
$49Frontier
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Tue, Apr 8
1:00 pm - 5:55 pmDCA-ORD
5h 55m1 stop
$92JetBlue
Find Deal
Wed, Feb 5
8:45 pm - 10:04 pmDCA-ORD
2h 19mnonstop
$96American Airlines
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Wed, Feb 5
2:54 pm - 4:14 pmDCA-ORD
2h 20mnonstop
$99American Airlines
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Tue, Feb 4
12:38 pm - 1:56 pmIAD-ORD
2h 18mnonstop
$99United Airlines
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Sat, Feb 15
6:00 am - 9:16 amIAD-ORD
4h 16m1 stop
$106Delta
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Wed, Feb 5
1:59 pm - 6:47 pmDCA-ORD
5h 48m1 stop
$109Delta
Find Deal
Sat, Feb 8
7:45 am - 9:06 amDCA-ORD
2h 21mnonstop
$115United Airlines
Find Deal
Thu, Mar 6
11:22 am - 3:40 pmDCA-ORD
5h 18m1 stop
$129JetBlue
Find Deal
Thu, Mar 13
1:00 pm - 5:53 pmDCA-ORD
5h 53m1 stop
11:00 am - 6:59 pmORD-DCA
6h 59m1 stop
$223JetBlue
Find Deal
Sat, Jan 11 - Thu, Jan 30
11:45 am - 5:59 pmDCA-ORD
7h 14m1 stop
9:05 am - 6:01 pmORD-DCA
7h 56m1 stop
$262JetBlue
Find Deal
Mon, Jan 13 - Wed, Jan 15
1:01 pm - 12:13 amDCA-MDW
12h 12m1 stop
8:15 am - 9:56 pmMDW-DCA
12h 41m1 stop
$268Frontier
Find Deal
Mon, Jan 13 - Wed, Jan 15
1:01 pm - 12:13 amDCA-MDW
12h 12m1 stop
8:15 am - 9:56 pmMDW-DCA
12h 41m1 stop
$278Frontier
Find Deal
Fri, Jan 10 - Tue, Jan 14
8:20 am - 8:25 pmIAD-ORD
13h 05m1 stop
9:20 am - 9:14 pmORD-IAD
10h 54m1 stop
$393United Airlines
Find Deal
Mon, Jan 13 - Wed, Jan 15
8:20 am - 6:55 pmIAD-ORD
11h 35m1 stop
10:51 am - 9:14 pmORD-IAD
9h 23m1 stop
$403United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 18
8:00 am - 4:45 pmDCA-ORD
9h 45m2 stops
3:10 pm - 10:30 pmORD-DCA
6h 20m1 stop
$459Southwest
Find Deal
Thu, Jan 9 - Thu, Jan 30
9:29 am - 10:47 amDCA-ORD
2h 18mnonstop
7:17 pm - 10:15 pmORD-DCA
1h 58mnonstop
$469American Airlines
Find Deal
Thu, Jan 9 - Thu, Jan 30
6:45 am - 10:51 amDCA-ORD
5h 06m1 stop
6:00 am - 8:55 amORD-DCA
1h 55mnonstop
$479American Airlines
Find Deal
Thu, Jan 9 - Thu, Jan 30
8:00 am - 4:45 pmDCA-ORD
9h 45m2 stops
11:25 am - 10:05 pmORD-DCA
9h 40m2 stops
$498Southwest
Find Deal
Thu, Jan 9 - Thu, Jan 30
6:55 am - 8:10 amDCA-MDW
2h 15mnonstop
6:35 am - 9:25 amMDW-DCA
1h 50mnonstop
$191Southwest
Find Deal
Wed, Jan 29 - Fri, Jan 31
10:09 pm - 11:15 pmIAD-ORD
2h 06mnonstop
6:14 pm - 9:09 pmORD-IAD
1h 55mnonstop
$197United Airlines
Find Deal
Tue, Feb 11 - Sat, Feb 15
10:09 pm - 11:15 pmIAD-ORD
2h 06mnonstop
1:15 pm - 4:13 pmORD-IAD
1h 58mnonstop
$210United Airlines
Find Deal
Tue, Feb 4 - Tue, Feb 11
6:05 am - 7:15 amDCA-MDW
2h 10mnonstop
6:10 am - 9:00 amMDW-DCA
1h 50mnonstop
$210Southwest
Find Deal
Sat, Feb 15 - Mon, Feb 17
10:20 pm - 11:29 pmIAD-ORD
2h 09mnonstop
8:45 am - 11:41 amORD-IAD
1h 56mnonstop
$213United Airlines
Find Deal
Tue, Feb 18 - Sun, Feb 23
10:00 am - 11:05 amDCA-MDW
2h 05mnonstop
9:00 pm - 11:50 pmMDW-DCA
1h 50mnonstop
$213Southwest
Find Deal
Tue, Feb 4 - Thu, Feb 6
6:55 am - 8:10 amDCA-MDW
2h 15mnonstop
12:10 pm - 2:55 pmMDW-DCA
1h 45mnonstop
$224Southwest
Find Deal
Thu, Feb 13 - Thu, Feb 13
11:59 am - 1:15 pmDCA-ORD
2h 16mnonstop
8:14 am - 11:00 amORD-DCA
1h 46mnonstop
$230American Airlines
Find Deal
Sat, Feb 22 - Sat, Mar 1
9:05 am - 10:35 amDCA-ORD
2h 30mnonstop
8:26 pm - 11:20 pmORD-DCA
1h 54mnonstop
$231American Airlines
Find Deal
Sat, Mar 1 - Mon, Mar 3
9:05 am - 10:35 amDCA-ORD
2h 30mnonstop
4:09 pm - 6:57 pmORD-DCA
1h 48mnonstop
$232American Airlines
Find Deal
Sat, Feb 22 - Sat, Mar 1

Frontier flights from District of Columbia to Chicago

Our best Frontier deals on District of Columbia to Chicago flight tickets
Frontier
Feb 5
IAD1:17 pmWashington, D.C. Dulles Intl
6h 49m
1 stop
MDW7:06 pmChicago Midway
Feb 12
MDW8:12 amChicago Midway
5h 27m
1 stop
IAD2:39 pmWashington, D.C. Dulles Intl
Frontier
Mar 1
IAD3:04 pmWashington, D.C. Dulles Intl
8h 47m
1 stop
MDW10:51 pmChicago Midway
Mar 4
MDW8:30 amChicago Midway
7h 25m
1 stop
IAD4:55 pmWashington, D.C. Dulles Intl
Frontier
Mar 1
DCA6:00 pmWashington, D.C. Reagan-National
7h 17m
1 stop
MDW12:17 amChicago Midway
Mar 3
MDW6:40 amChicago Midway
9h 19m
1 stop
DCA4:59 pmWashington, D.C. Reagan-National

United Airlines flights from District of Columbia to Chicago

Our best United Airlines deals on District of Columbia to Chicago flight tickets
United Airlines
Jan 29
DCA7:02 amWashington, D.C. Reagan-National
2h 18m
ORD8:20 amChicago O'Hare Intl
Feb 2
ORD7:30 amChicago O'Hare Intl
2h 13m
DCA10:43 amWashington, D.C. Reagan-National
United Airlines
Feb 11
IAD10:09 pmWashington, D.C. Dulles Intl
2h 06m
ORD11:15 pmChicago O'Hare Intl
Feb 15
ORD6:14 pmChicago O'Hare Intl
1h 55m
IAD9:09 pmWashington, D.C. Dulles Intl
United Airlines
Jan 28
IAD5:45 pmWashington, D.C. Dulles Intl
4h 58m
1 stop
ORD9:43 pmChicago O'Hare Intl
Jan 29
ORD8:50 amChicago O'Hare Intl
1h 58m
IAD11:48 amWashington, D.C. Dulles Intl

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 $208. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from District of Columbia 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 Monday when prices can be found for as low as $249. 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 $303.

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 afternoon. Flights from District of Columbia to Chicago during this time can be as low as $254. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $299.

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

Fly from Baltimore/Washington to Chicago Midway for the best District of Columbia - Chicago flight prices

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

The best time to book a flight to Chicago from District of Columbia is 53 days out, which is when prices tend to be around $280. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $193.

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.

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

$37

Fastest flight time

1h 55m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from District of Columbia in the past 72 hours is $37. The best round-trip flight deal from District of Columbia to Chicago found on momondo in the last 72 hours is $100.
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 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • 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
FrontierPriceFrom $58Free CancellationRating
6.0
3,428 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $101Free CancellationRating
6.3
8,074 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $136Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $151Free CancellationRating
7.4
8,939 reviews
Search United Airlines flights
SouthwestPriceFrom $159Free CancellationRating
8.1
4,648 reviews
Search Southwest flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,499 reviews
Search Delta flights

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.


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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