WAS - MDW

$116 Find Cheap Flights from Washington, D.C. to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$216
Typical prices: $273-$439
Frontier
Sat 11/24Mon 11/26
IAD - MDW • 1 stop
Cheapest non-stop
$259
Typical prices: $278-$440
Southwest
Sat 12/1Mon 12/3
DCA - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 09m
Direct flights
+1
Direct flights
+1
Top routes
IAD - MDW
Cheapest • 18% average savings
DCA - MDW
Most popular
Insights
Insights
When to book
25 weeks
in advance
Our data shows that travelers who book at least 25 weeks in advance save around 63% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 9% price drop
August
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 51m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Washington, D.C. to Midway (WAS-MDW)

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

Recent round-trip flight deals from Washington, D.C. to Midway

Sat, Nov 14 - Tue, Nov 17
Frontier Logo
11:16 am - 11:47 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
13h 31m2 stops Orlando Atlanta Hartsfield-Jackson
Frontier Logo
6:08 am - 5:12 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
10h 04m1 stop Atlanta Hartsfield-Jackson
$216Frontier
Tue, Nov 24 - Thu, Nov 26
Frontier Logo
6:50 am - 12:21 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
6h 31m1 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
$216Frontier
Sat, Dec 12 - Sat, Jan 9
Frontier Logo
9:23 pm - 7:42 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
23h 19m1 stop Orlando
Frontier Logo
5:21 pm - 12:39 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
6h 18m1 stop Atlanta Hartsfield-Jackson
$220Frontier
Wed, Nov 25 - Wed, Dec 2
Frontier Logo
10:47 pm - 8:14 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
10h 27m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
10:21 am - 8:12 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
8h 51m1 stop Dallas/Fort Worth
$220Frontier
Tue, Nov 17 - Sat, Nov 21
Southwest Logo
8:55 pm - 10:10 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
5:30 am - 8:20 amMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$259Southwest
Sat, Nov 21 - Thu, Nov 26
Southwest Logo
6:00 am - 7:05 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
1:50 pm - 4:35 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 45mnonstop
$259Southwest
Thu, Nov 19 - Mon, Nov 23
Southwest Logo
6:10 am - 7:15 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
9:05 pm - 11:55 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$259Southwest
Thu, Dec 10 - Mon, Dec 14
Delta Logo
6:00 am - 9:37 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:23 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
3h 42m1 stop Detroit Metropolitan Wayne County
$278Delta
Wed, Dec 2 - Sat, Dec 5
Delta Logo
10:11 am - 4:16 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
7h 05m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:41 pm - 11:23 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
3h 42m1 stop Detroit Metropolitan Wayne County
$279Delta
Thu, Nov 19 - Sat, Nov 21
Delta Logo
6:00 am - 11:59 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
6h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:44 pm - 11:01 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
3h 17m1 stop Detroit Metropolitan Wayne County
$279Delta
Booking Insights

Price, demand and travel trends for Washington, D.C. 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. to Chicago Midway Airport?

Round-trip flights from Washington, D.C. to Chicago Midway Airport typically range from $273 to $439. The lowest price found in the past 5 days was $216, on Frontier.

What is the cheapest Washington, D.C. to Chicago Midway Airport flight route?

Washington, D.C. Dulles Intl Airport (IAD) to Chicago Midway Airport (MDW) is the cheapest Washington, D.C. to Chicago Midway Airport route, averaging $230 round-trip. Other Washington, D.C. to Chicago Midway Airport routes average $333, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Washington, D.C. to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Washington, D.C. to Chicago Midway Airport. It’s 10% cheaper than the average day, while Monday is the most expensive, with prices 9% higher.

What’s the cheapest month to fly from Washington, D.C. to Chicago Midway Airport?

•February is the cheapest month to fly from Washington, D.C. to Chicago Midway Airport at $300 round-trip.
•November ($374) and June ($370) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 24% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Washington, D.C. to Chicago Midway Airport the cheapest?

Flights from Washington, D.C. to Chicago Midway Airport are cheapest 25 weeks before departure. Booking in this window typically costs about 63% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals
Expert advice

Expert advice for your flight from Washington, D.C. to Midway

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on DCA

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

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

Low season

January

Cheapest flight

$116
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 47% increase in travelers.
One-way flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport

When to book flights from Washington, D.C. to Midway

Are your dates flexible? Find out the best times to travel from Washington, D.C. 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. to Chicago Midway Airport flight questions, answered

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

  • What are the earliest and latest flights from Washington, D.C. to Chicago Midway Airport?

    These are the earliest and latest flight times available from Washington, D.C. to Chicago Midway Airport:

    • Earliest: departs at 6:00 am and lands at 8:09 am
    • Latest: departs at 9:35 pm and lands at 11:44 pm.

    The flight takes about 2h 09m.

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

    Two cabin classes are available on flights from Washington, D.C. to Chicago Midway Airport:

    • Economy Class
    • First Class

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

    A nonstop flight from Washington, D.C. to Chicago Midway Airport takes 2h 09m, covering 597 miles.

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

    Round-trip flights from Washington, D.C. to Chicago Midway Airport range from $273 to $439, with an average of $331 over the past 12 months. Anything below $273 counts as a good deal.

  • How expensive are last-minute Washington, D.C. to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 78% above the $331 route average. Book 25 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Washington, D.C. to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $202 round-trip via Orlando (MCO), compared to $333 for nonstop.

  • What is the standard checked-bag allowance on flights from Washington, D.C. to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Washington, D.C. to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Washington, D.C. to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 34%, evening flights for 16%, and night flights for 16%.

  • Have flight prices from Washington, D.C. 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 $216 to $1,397. That means the highest observed fare was about 6x higher than the lowest one.

  • Which airlines offer Wi-Fi on Washington, D.C. to Chicago Midway Airport flights?

    JetBlue is the only airline on the Washington, D.C. to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

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

    One-way fares from Washington, D.C. to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $127, which is 40% below the typical average for this route.

  • 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. to Chicago Midway Airport?

    Flights from Washington, D.C. to Chicago Midway Airport may depart from several airports in Washington, D.C. area, including Washington, D.C. Reagan-National (DCA) and Washington, D.C. Dulles Intl (IAD). Flights usually arrive at Chicago Midway (MDW).

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

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

    • Atlanta Hartsfield-Jackson (ATL) - 73% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 20% of one-stop connections
    • Columbus (CMH) - 2% 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. to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 18% on flights from Washington, D.C. to Chicago Midway Airport. Tuesday is the cheapest departure day at $299 round-trip on average, while Monday is the most expensive at $362, a difference of $63.

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

  • What airlines fly from Washington, D.C. to Chicago Midway Airport?

    Only Southwest operates flights between Washington, D.C. and Chicago Midway Airport.

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

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 51m, compared with 4h 10m via Lambert-St Louis (STL) and 6h 02m via Columbus (CMH).

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

    Chicago Midway Airport is 1 hour behind Washington, D.C. (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.

  • Which airlines offer extra legroom and free seat selection on Washington, D.C. to Chicago Midway Airport flights?

    Among airlines operating Washington, D.C. to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Washington, D.C. to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Washington, D.C. 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 Tuesday departure and avoid flying on Monday. On this route, Tuesday flights average $299, about $63 less than Monday fares (17% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 25 weeks before you fly. On this route, that window historically saves about 63% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Washington, D.C. to Chicago Midway Airport trip for February. Fares historically average $300 round-trip in that month - typically $74 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Orlando Airport (MCO) can be cheaper than flying direct. The cheapest layover option averages $202 round-trip on this route - about $131 less than direct flights (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

Prefer to fly direct from Washington, D.C. to Chicago Midway Airport?

 
Find which airlines fly direct from Washington, D.C. to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Washington, D.C. to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Washington, D.C.

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

More options for your flight from Washington, D.C. to Midway

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

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago