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Dulles International Airport to Chicago Midway International Airport flight

Explore the cheapest one-way and round-trip flights from Dulles International Airport to Chicago Midway International Airport over the next 90 days, with one-way fares from S$ 109 and round-trip from S$ 204. Based on Trip.com's latest 7-day flight data.

      • IAD 08:05
        10h 42m
        1 stop
        MDW 17:47
        Washington D.C. - Chicago | Wed, Oct 28 | Frontier Airlines
        ORD 06:30
        9h 17m
        1 stop
        DCA 16:47
        Chicago - Washington D.C. | Sat, Oct 31 | Frontier Airlines
        S$ 204 S$ 679
        70% off
        70% off
        S$ 679 S$ 204
      • IAD 07:00
        4h 58m
        1 stop
        MDW 10:58
        Washington D.C. - Chicago | Thu, Oct 29 | Frontier Airlines
        ORD 11:06
        9h 52m
        1 stop
        DCA 21:58
        Chicago - Washington D.C. | Sat, Oct 31 | Frontier Airlines
        S$ 209 S$ 679
        69% off
        69% off
        S$ 679 S$ 209
      • IAD 07:50
        10h 55m
        1 stop
        MDW 17:45
        Washington D.C. - Chicago | Thu, Oct 15 | Frontier Airlines
        ORD 06:30
        9h 26m
        1 stop
        DCA 16:56
        Chicago - Washington D.C. | Sat, Oct 17 | Frontier Airlines
        S$ 214 S$ 679
        68% off
        68% off
        S$ 679 S$ 214
      • IAD 18:12
        5h 21m
        1 stop
        MDW 22:33
        Washington D.C. - Chicago | Sat, Oct 10 | Delta Air Lines
        ORD 06:30
        9h 26m
        1 stop
        DCA 16:56
        Chicago - Washington D.C. | Sat, Oct 17 | Frontier Airlines
        S$ 215
        68% off
        S$ 679 S$ 215
      • IAD 07:00
        4h 58m
        1 stop
        MDW 10:58
        Washington D.C. - Chicago | Sat, Nov 14 | Frontier Airlines
        ORD 14:03
        9h 25m
        1 stop
        IAD 00:28
        Chicago - Washington D.C. | Mon, Nov 16 | Frontier Airlines
        S$ 216
        68% off
        S$ 679 S$ 216
      • IAD 08:05
        10h 42m
        1 stop
        MDW 17:47
        Washington D.C. - Chicago | Wed, Nov 11 | Frontier Airlines
        ORD 07:15
        8h 57m
        1 stop
        IAD 17:12
        Chicago - Washington D.C. | Sat, Nov 14 | Frontier Airlines
        S$ 217
        68% off
        S$ 679 S$ 217
      • IAD 07:52
        10h 55m
        1 stop
        MDW 17:47
        Washington D.C. - Chicago | Sat, Oct 31 | Frontier Airlines
        ORD 07:15
        8h 57m
        1 stop
        IAD 17:12
        Chicago - Washington D.C. | Tue, Nov 3 | Frontier Airlines
        S$ 218
        68% off
        S$ 679 S$ 218
      • IAD 07:40
        11h 7m
        1 stop
        MDW 17:47
        Washington D.C. - Chicago | Thu, Nov 5 | Frontier Airlines
        ORD 06:30
        9h 17m
        1 stop
        DCA 16:47
        Chicago - Washington D.C. | Tue, Nov 10 | Frontier Airlines
        S$ 220
        68% off
        S$ 679 S$ 220
      • IAD 07:50
        11h 1m
        1 stop
        MDW 17:51
        Washington D.C. - Chicago | Wed, Oct 7 | Frontier Airlines
        MDW 06:21
        9h 52m
        1 stop
        IAD 17:13
        Chicago - Washington D.C. | Tue, Oct 13 | Frontier Airlines
        S$ 220
        68% off
        S$ 679 S$ 220
      • IAD 08:05
        10h 42m
        1 stop
        MDW 17:47
        Washington D.C. - Chicago | Tue, Nov 10 | Frontier Airlines
        MDW 06:16
        9h 56m
        1 stop
        IAD 17:12
        Chicago - Washington D.C. | Fri, Nov 13 | Frontier Airlines
        S$ 222
        67% off
        S$ 679 S$ 222
      • IAD 07:50
        10h 55m
        1 stop
        MDW 17:45
        Washington D.C. - Chicago | Thu, Oct 22 | Frontier Airlines
        ORD 10:26
        5h 52m
        1 stop
        IAD 17:18
        Chicago - Washington D.C. | Mon, Oct 26 | Frontier Airlines
        S$ 226
        67% off
        S$ 679 S$ 226
      • IAD 07:50
        10h 56m
        1 stop
        MDW 17:46
        Washington D.C. - Chicago | Tue, Oct 6 | Frontier Airlines
        MDW 06:15
        10h 3m
        1 stop
        IAD 17:18
        Chicago - Washington D.C. | Thu, Oct 8 | Frontier Airlines
        S$ 516
        24% off
        S$ 679 S$ 516
      • WAS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Washington D.C. - Chicago | Wed, Oct 7 | Normal Airline
        CHI 15:00
        6h
        Direct
        WAS 16:00
        Chicago - Washington D.C. | Fri, Oct 9 | Normal Airline
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      • IAD 08:05
        16h 42m
        1 stop
        MDW 23:47
        Washington D.C. - Chicago | Tue, Nov 10 | Frontier Airlines
        S$ 109 S$ 189
        42% off
        42% off
        S$ 189 S$ 109
      • IAD 08:03
        4h 47m
        1 stop
        MDW 11:50
        Washington D.C. - Chicago | Mon, Oct 26 | Delta Air Lines
        S$ 111 S$ 189
        41% off
        41% off
        S$ 189 S$ 111
      • IAD 07:40
        11h 7m
        1 stop
        MDW 17:47
        Washington D.C. - Chicago | Mon, Nov 2 | Frontier Airlines
        S$ 113 S$ 189
        40% off
        40% off
        S$ 189 S$ 113
      • IAD 12:15
        6h 50m
        1 stop
        MDW 18:05
        Washington D.C. - Chicago | Sat, Oct 17 | Delta Air Lines
        S$ 116
        39% off
        S$ 189 S$ 116
      • IAD 07:00
        4h 58m
        1 stop
        MDW 10:58
        Washington D.C. - Chicago | Wed, Oct 28 | Frontier Airlines
        S$ 118
        38% off
        S$ 189 S$ 118
      • IAD 17:30
        5h 40m
        1 stop
        MDW 22:10
        Washington D.C. - Chicago | Wed, Nov 11 | Delta Air Lines
        S$ 121
        36% off
        S$ 189 S$ 121
      • IAD 06:00
        7h 5m
        1 stop
        MDW 12:05
        Washington D.C. - Chicago | Thu, Nov 12 | Delta Air Lines
        S$ 122
        35% off
        S$ 189 S$ 122
      • IAD 08:05
        10h 42m
        1 stop
        MDW 17:47
        Washington D.C. - Chicago | Tue, Nov 17 | Frontier Airlines
        S$ 135
        28% off
        S$ 189 S$ 135
      • IAD 08:05
        10h 42m
        1 stop
        MDW 17:47
        Washington D.C. - Chicago | Tue, Nov 3 | Frontier Airlines
        S$ 139
        26% off
        S$ 189 S$ 139
      • IAD 08:05
        10h 22m
        1 stop
        MDW 17:27
        Washington D.C. - Chicago | Tue, Oct 27 | Frontier Airlines
        S$ 140
        26% off
        S$ 189 S$ 140
      • IAD 12:20
        6h 40m
        1 stop
        MDW 18:00
        Washington D.C. - Chicago | Sat, Nov 7 | Delta Air Lines
        S$ 143
        24% off
        S$ 189 S$ 143
      • IAD 10:14
        7h
        1 stop
        MDW 16:14
        Washington D.C. - Chicago | Wed, Oct 14 | Delta Air Lines
        S$ 143
        24% off
        S$ 189 S$ 143
      • WAS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Washington D.C. - Chicago | Wed, Oct 7 | Normal Airline
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Flight prices from Dulles International Airport to Chicago Midway International Airport are based on the average fares across airlines for the next three months, based on Trip.com’s latest data.

Which airline offers the cheapest flights from Dulles International Airport to Chicago Midway International Airport?

The cheapest airline flying from Dulles International Airport to Chicago Midway International Airport is Frontier Airlines (from S$ 109) among 4 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From S$ 109
Delta Air Lines
From S$ 111
Porter Airlines
From S$ 273
Air Canada
From S$ 282

Find more flights and airlines

What is the flight schedule from Dulles International Airport to Chicago Midway International Airport?

Check the schedule for flights from Washington D.C. to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL1354

    Dulles International Airport

    07:00

    IAD

    2h

    Direct

    09:00

    ATL

    S M T W T F S
    Search

  2. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00

    ATL

    1h 56m

    Direct

    11:56

    MDW

    S M T W T - S

  3. DL2127

    Dulles International Airport

    06:00

    IAD

    1h 54m

    Direct

    07:54

    ATL

    S M T W T F S
    Search

  4. DL1063

    Hartsfield–Jackson Atlanta International Airport

    09:10

    ATL

    1h 53m

    Direct

    10:03

    MDW

    S M T W T F S

  5. DL3082

    Dulles International Airport

    12:18

    IAD

    1h 32m

    Direct

    13:50

    DTW

    - - - - - F -
    Search

  6. DL4677

    Detroit Metropolitan Wayne County Airport

    18:15

    DTW

    1h 22m

    Direct

    18:37

    MDW

    S M T W T F S

  7. DL1324

    Dulles International Airport

    10:14

    IAD

    1h 50m

    Direct

    12:04

    ATL

    S M T W T F S
    Search

  8. DL1728

    Hartsfield–Jackson Atlanta International Airport

    15:30

    ATL

    1h 55m

    Direct

    16:25

    MDW

    S M T W T F S

  9. DL2327

    Dulles International Airport

    06:00

    IAD

    1h 58m

    Direct

    07:58

    ATL

    S M T W T F S
    Search

  10. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00

    ATL

    1h 56m

    Direct

    11:56

    MDW

    S M T W T - S

  11. F94707

    Dulles International Airport

    07:50

    IAD

    2h 3m

    Direct

    09:53

    ATL

    S M T W T F S
    Search

  12. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:55

    ATL

    1h 56m

    Direct

    17:51

    MDW

    - M T W - - S

  13. F94707

    Dulles International Airport

    07:50

    IAD

    2h 3m

    Direct

    09:53

    ATL

    S M T W T F S
    Search

  14. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:50

    ATL

    1h 53m

    Direct

    23:43

    MDW

    S - - W T F S

  15. F94409

    Dulles International Airport

    21:04

    IAD

    2h 1m

    Direct

    23:05

    ATL

    S M T W T F S
    Search

  16. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:50

    ATL

    1h 53m

    Direct

    23:43

    MDW

    S - - W T F S
Find more flights and airlines

About Dulles International Airport and Chicago Midway International Airport

Learn about Dulles International Airport (IAD) and Chicago Midway International Airport (MDW) — including location, terminals, transportation, and travel tips.

Flight distance 927.54km
Cheapest one-way ticket price S$ 109
Cheapest return ticket price S$ 204

FAQs for Dulles International Airport to Chicago Midway International Airport Flights

  • How many daily flights are there from Dulles International Airport (IAD) to Chicago Midway International Airport (MDW)?

    There are around 2 daily flights from Dulles International Airport (IAD) to Chicago Midway International Airport (MDW).
  • The route from Dulles International Airport (IAD) to Chicago Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around S$ 416 in January, the most expensive month to book this route.
  • The earliest flight departs from Dulles International Airport (IAD) at 06:45 and arrives in Chicago Midway International Airport (MDW) at 07:35.
  • The latest flight departs from Dulles International Airport (IAD) at 20:05 and arrives in Chicago Midway International Airport (MDW) at 21:00.
    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.
  • One-way flights from Dulles International Airport to Chicago Midway International Airport currently start from S$ 109, and round-trip fares start from S$ 204. The current lowest fare is a Frontier Airlines flight departing on Tue, Nov 10; prices may vary depending on availability.
  • Based on Trip.com flight data for departures within the next 30 days with at most one stop, the average one-way price from Dulles International Airport to Chicago Midway International Airport is S$ 223. Prices may vary depending on the departure date, airline, and availability.
  • Enter Dulles International Airport and Chicago Midway International Airport, select your departure date and number of passengers, then compare flights by price, flight duration, and baggage allowance. Once you've chosen a fare, review the change and refund rules, fill in passenger details, and pay to receive your booking confirmation.

Popular Destinations & Recommendations

Note: Prices shown on this page are the lowest estimated prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.