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Cheap flights from Washington Dulles to Chicago Midway

Compare Washington Dulles to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Washington Dulles to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Washington Dulles to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.$76 per passenger.Departing Sat, 2 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Sat, 2 May, arriving in Chicago Midway.Price includes taxes and charges.From $76, select.
Chicago.$105 per passenger.Departing Fri, 24 Apr.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Fri, 24 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $105, select.
Chicago.$112 per passenger.Departing Tue, 24 Mar.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Tue, 24 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $112, select.
Chicago.$140 per passenger.Departing Sun, 7 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Sun, 7 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $140, select.
Chicago.$170 per passenger.Departing Wed, 12 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Wed, 12 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $170, select.
Chicago.$182 per passenger.Departing Wed, 2 Sep.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Wed, 2 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $182, select.
Chicago.$182 per passenger.Departing Sat, 2 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Sat, 2 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $182, select.
Chicago.$182 per passenger.Departing Sat, 24 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Sat, 24 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $182, select.

Find the cheapest month to fly from Washington Dulles to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Washington Dulles to Chicago Midway flights are currently cheapest in May.
Feb
from $202
Mar
from $112
Apr
from $105
May
from $76
Jun
from $140
Jul
from $183
Aug
from $170
Sep
from $182
Oct
from $182
Nov
from $195
Dec
from $182
Jan
from $182

Washington Dulles to Chicago Midway: Alternative routes

Compare routes from Washington Dulles to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
ClosestCheapest
from $76
Search flights

Chicago O'Hare International

25km from central Chicago
from $87
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from $113
Search flights

Washington D.C. to Chicago: Flight information

The things to know before you go.
Cheapest flight found$76
Cheapest month to flyMay

Finding cheap flights from Washington Dulles to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Washington Dulles to Chicago Midway is $202. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Washington Dulles to Chicago Midway. But we found flights with one or more stops from $202.
As of February 2026, there are no flights flying from Washington Dulles to Chicago Midway.
The cheapest month to fly from Washington Dulles to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Washington Dulles Airport to Chicago Midway Airport on Saturday, 25 April 2026.
No airlines currently offer direct flights between Washington Dulles Airport and Chicago Midway Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Frontier Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Washington Dulles International Airport (IAD) to Chicago Midway International Airport (MDW): what you need to know

  • The timezone in Chicago is UTC-5, which is one hour behind Washington DC.

  • Arrive at the airport on time so you don't miss your IAD to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid a last-minute sprint to the gate.

  • Flying during a peak time such as April? School holidays and other popular periods can lead to longer lines at airport checkpoints. Play it safe and get there up to four hours before an international flight and two hours before domestic departures.

  • If you want to add a stop to your trip, just uncheck 'Direct flights only' when searching for your ticket from Washington Dulles International Airport to Chicago Midway International Airport. These are the top stopovers between IAD and MDW:

    • Detroit Metropolitan Wayne County Airport

    • Pittsburgh International Airport

    • John Glenn Columbus International Airport

How to find the cheapest flights from Washington Dulles International Airport (IAD) to Chicago Midway International Airport (MDW)

  • $76 is currently the lowest price for a one-way Washington Dulles International Airport to Chicago Midway International Airport flight. Return flights start from $202. These fares may change based on availability and demand.

  • To pick up cheap tickets from IAD to MDW, book ahead. Airlines tend to offer lower prices when flights are first made available.

  • The 'Whole month' search tool shows you the cheapest flights from Washington Dulles International Airport to Chicago Midway International Airport throughout the entire month. It's a good way to snap up a bargain if your plans are flexible.

  • Getting your hands on cheap flights from IAD to MDW is easy with Price Alerts. All you need to do is create one of these automatic alerts and we'll notify you when fares go down.

  • Lock in the perfect flight for you with the help of the filters. To see the 'Fastest,' 'Best' or 'Cheapest' flights from Washington Dulles International Airport to Chicago Midway International Airport, use the 'Sort by' tool. You can also filter by departure and arrival times, airline, and number of stops.

Handy information about Washington Dulles International Airport (IAD)

  • IAD is located at 1 Saarinen Circle.

  • 74.39% of flights leaving from Washington Dulles International Airport arrive at their destination on time.

  • Washington Dulles International Airport is about 56 kilometres from central Washington DC. If you're driving, ride-sharing or catching a cab from the centre, it'll take you 50 minutes or so to get there, depending on the traffic.

  • You can expect a journey time of about 3 hours 25 minutes on public transport.

  • Get your trip off to a hassle-free start by staying near IAD. Whether you're taking an early flight from Washington Dulles International Airport to Chicago Midway International Airport or just don't like being rushed, these stays are the answer:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you need is a lengthy journey to your hotel if you're landing late on a Washington Dulles International Airport to Chicago Midway International Airport flight. Reserve one of these accommodation options near MDW instead:

  • Say yes to new adventures by picking up a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget and explore beyond Chicago's usual tourist stops.

  • For the lowest price, reserve your ride from Chicago Midway International Airport about four weeks before you travel.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • Chicago Midway International Airport is approximately 19 kilometres from central Chicago. Driving there takes about 20 minutes.

  • Getting to the centre by public transport will take you around 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to choose your travel dates for your flight from Washington Dulles International Airport to Chicago Midway International Airport. July is the most popular month to head to Chicago. If you'd like a more laid-back vibe, go in May.

  • When reserving your flight from Washington Dulles International Airport to Chicago Midway International Airport, think about the kind of weather you like. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • Look for cheap tickets from IAD to MDW in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

Explore more of United States

  • Chicago has loads to offer, but there are so many other parts of United States just waiting to be explored. About 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the move. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Experience this destination's highlights firsthand at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Washington D.C. to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.