IAD - MDW

$118 Find Cheap Flights from Washington Dulles Airport to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$220
Typical prices: $181-$331
Frontier
Wed 11/21Sat 11/24
IAD - MDW • 1 stop
Cheapest one-way
$118
Typical prices: $98-$170
Frontier
Sat 11/24
IAD - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Washington, D.C. Dulles Intl Airport and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
December
Cheapest • 50% price drop
January
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $202 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 3h 53m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
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Flight Deals

Cheap Flights from Dulles Intl to Midway (IAD-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Dulles Intl to Midway

Sat, Nov 21 - Tue, Nov 24
Frontier Logo
10:47 pm - 8:14 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
10h 27m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
9:09 am - 3:03 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
4h 54m1 stop Atlanta Hartsfield-Jackson
$220Frontier
Sat, Dec 12 - Tue, Dec 15
Frontier Logo
10:35 pm - 4:06 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
18h 31m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:28 pm - 11:11 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
21h 43m1 stop Atlanta Hartsfield-Jackson
$223Frontier
Wed, Dec 2 - Tue, Dec 8
Frontier Logo
10:33 pm - 2:41 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
17h 08m2 stops Atlanta Hartsfield-Jackson Orlando
Frontier Logo
12:28 pm - 2:49 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
25h 21m1 stop Atlanta Hartsfield-Jackson
$223Frontier
Tue, Dec 1 - Mon, Dec 7
Frontier Logo
12:06 pm - 11:33 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
24h 27m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:02 pm - 2:49 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
20h 47m1 stop Atlanta Hartsfield-Jackson
$223Frontier
Wed, Nov 18 - Thu, Nov 19
Frontier Logo
7:48 am - 5:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
10h 59m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:08 am - 11:43 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
16h 35m1 stop Atlanta Hartsfield-Jackson
$227Frontier
Mon, Jan 11 - Thu, Jan 14
Frontier Logo
5:30 am - 4:26 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
11h 56m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
1:18 pm - 12:19 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
10h 01m1 stop Atlanta Hartsfield-Jackson
$227Frontier
Thu, Dec 10 - Sat, Dec 12
Frontier Logo
9:23 pm - 5:16 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
20h 53m1 stop Orlando
Frontier Logo
10:40 am - 8:10 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
8h 30m1 stop Dallas/Fort Worth
$227Frontier
Sat, Feb 13 - Tue, Feb 16
Frontier Logo
6:37 am - 11:46 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
18h 09m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:47 pm - 12:19 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
26h 32m2 stops Orlando Atlanta Hartsfield-Jackson
$227Frontier
Sat, Jan 16 - Fri, Jan 22
Delta Logo
7:10 am - 4:53 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
10h 43m1 stop Minneapolis St Paul
Delta Logo
12:44 pm - 11:51 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
10h 07m1 stop Minneapolis St Paul
$263Delta
Tue, Nov 24 - Tue, Dec 1
Multiple Airlines Logo
8:34 pm - 2:37 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
19h 03m1 stop Knoxville McGhee Tyson
Multiple Airlines Logo
12:33 pm - 11:11 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
21h 38m1 stop Atlanta Hartsfield-Jackson
$277Multiple Airlines
Booking Insights

Price, demand and travel trends for Washington, D.C. Dulles Intl Airport to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

Round-trip flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport typically range from $181 to $331. The lowest price found in the past 5 days was $220, on Frontier.

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Key details for Washington, D.C. Dulles Intl Airport to Chicago Midway Airport flights

Low season

September

Cheapest flight

$118
Beat the crowds with an average 48% drop in travelers.
The most popular month to fly with an average 18% increase in travelers.
One-way flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport

When to book flights from Dulles Intl to Midway

Are your dates flexible? Find out the best times to travel from Dulles Intl to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Washington, D.C. Dulles Intl Airport to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

    Only Economy Class is available on flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport.

  • How long is a flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

    A nonstop flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport takes 00m, covering 576 miles.

  • Do I need a passport to fly from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Washington, D.C. Dulles Intl Airport to Chicago Midway Airport flight?

    Round-trip flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport range from $181 to $331, with an average of $270 over the past 12 months. Anything below $181 counts as a good deal.

  • Have flight prices from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $220 to $1,260. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport looking right now?

    One-way fares from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport are currently in line with typical prices for this route. Average one-way fares are about $120.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

    Flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport usually depart from Washington, D.C. Dulles Intl (IAD) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport pass through?

    One-stop flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 84% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 14% of one-stop connections
    • Orlando (MCO) - 2% of one-stop connections

  • Can I save money by using flexible dates for flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 77% on flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport. Friday is the cheapest departure day at $151 round-trip on average, while Wednesday is the most expensive at $634, a difference of $483.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 53m, compared with 8h 17m via Atlanta Hartsfield-Jackson (ATL) and 17h 11m via Orlando (MCO).

  • What is the time difference between Washington, D.C. Dulles Intl Airport and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Washington, D.C. Dulles Intl Airport (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking Washington, D.C. Dulles Intl Airport to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Friday departure and avoid flying on Wednesday. On this route, Friday flights average $151, about $483 less than Wednesday fares (76% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Washington, D.C. Dulles Intl Airport to Chicago Midway Airport trip for December. Fares historically average $135 round-trip in that month - typically $602 less than the most expensive month, which is March (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

More options for your flight from Dulles Intl to Midway

Complete your trip to Midway with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago