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Flights from Dulles to Chicago – Airlines & connecting routes

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IAD to MDW flights and routes map IAD to MDW – All flight route options from Washington Dulles International, Virginia, USA to Chicago Midway International, Illinois, USA. These flights are operated by 4 different airlines through 3 different connections. The shortest flight time is 4 hours and 20 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA IAD Washington Dulles Dulles, VA, USA
USA MDW Chicago Midway , IL, USA
IAD
Washington Dulles
USADulles, VA, USA
Chicago Midway
USAChicago, IL, USA
MDW
No direct flights found
6 routes with 1 stop found »
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1 stop route options with the same airline:

Duration

Via Detroit DTW
1 stop with Delta Air Lines. 1-2 flights per day.

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3h 41m

Via Detroit DTW
1 stop with Delta Air Lines.
3h 41m
1-2 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines.
Begins in 27/11

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4h 20m

Begins in 27/11
Via Nashville BNA
1 stop with Southwest Airlines.
4h 20m
Begins in 27/11
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Via Atlanta ATL
1 stop with Delta Air Lines. 4-5 flights per day.

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5h 19m

Via Atlanta ATL
1 stop with Delta Air Lines.
5h 19m
4-5 flights per day.
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Via Atlanta ATL
1 stop with Frontier Airlines. 0-1 flights per day.
Tue & Wed

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5h 31m

Tue & Wed
Via Atlanta ATL
1 stop with Frontier Airlines.
5h 31m
0-1 flights per day.
Tue & Wed
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1 stop route options with codeshare or different airlines:

Duration

Via Detroit DTW With United Airlines & Delta Air Lines 1-2 flights per day.

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4h 59m

Via Detroit DTW
4h 59m
With United Airlines & Delta Air Lines 1-2 flights per day.
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Via Atlanta ATL With United Airlines & Delta Air Lines 0-2 flights per day.

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6h 07m

Via Atlanta ATL
6h 07m
With United Airlines & Delta Air Lines 0-2 flights per day.
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Dulles to Chicago flights

With over 57 flights every week and 3 different airlines you have a wide range of options. While flying to Chicago from Dulles you will be doing a stopover in Detroit, Nashville or any other of the 3 alternatives with flight connections.

Are there any non-stop flights from IAD to MDW?

You could fly non-stop from IAD to MDW before with Southwest Airlines but not anymore.

Tip! You can also fly to Chicago from Ronald Reagan Washington National (DCA).

Dulles to Chicago with Southwest Airlines

If you fly from Dulles with Southwest Airlines you will do a stopover in Nashville, BNA before reaching Chicago. This flight trip will take 4 hours and 20 minutes and you can fly every Thursday with departures at 12:45.

Distance & flight times: Dulles to Midway International Airport

The shortest flight time between IAD and MDW is 3 hours and 41 minutes.

ViaTotal flight timeLayover timeDistance
DTW Detroit3h 41m37m614 miles (988 km)
BNA Nashville4h 20m45m941 miles (1514 km)
ATL Atlanta5h 19m1h 57m1131 miles (1820 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.IAD-MDW flight routesDulles to Chicago flight routes illustrated on a map.
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Dulles - Chicago route map and flight paths
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Show all destinations from IAD Show all destinations from MDW

The fastest way to fly from Dulles (IAD) to Chicago (MDW) is via Detroit and it will take about 3 hours and 41 minutes. The second fastest route is via Nashville and will take 4 hours and 20 minutes.

You can fly with Delta Air Lines or Southwest Airlines from Dulles to Chicago.

The flight time between Washington Dulles (IAD) and Chicago Midway International (MDW) via Detroit Metropolitan Airport, DTW is 3 hours and 41 minutes.

Not anymore. But you could fly direct from IAD to MDW with Southwest Airlines once. However, you can still fly via Detroit or Nashville among other routes.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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