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Midway

$248+ Cheap flights from Duluth (DLH) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
DLH — MDW
Aug 19 — Aug 261
Wed 8/19
Wed 8/26
1 adult, Economy
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2. Select your favorite providers

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Cheap flight deals from Duluth to Midway

Cheapest flights from Duluth to Midway
Explore the most affordable flight options available from Duluth to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 20, 2026.

This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:10 am
DLH
-
MDW
1 stop5h 10m
Delta
Wed 9/232:00 pm
MDW
-
DLH
1 stop5h 25m
Delta
Deal found 7/19$258
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:15 am
DLH
-
MDW
2 stops7h 24m
Delta
Tue 9/227:13 pm
MDW
-
DLH
1 stop3h 22m
Delta
Deal found 7/19$264
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:15 am
DLH
-
MDW
2 stops7h 24m
Delta
Sat 9/199:29 am
MDW
-
DLH
2 stops6h 00m
Delta
Deal found 7/19$269
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:43 am
DLH
-
MDW
1 stop6h 16m
Delta
Wed 9/239:59 am
MDW
-
DLH
1 stop5h 30m
Delta
Deal found 7/19$303
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:10 am
DLH
-
MDW
1 stop3h 39m
Delta
Fri 11/279:30 am
MDW
-
DLH
2 stops6h 14m
Delta
Deal found 7/16$309
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:43 am
DLH
-
MDW
1 stop6h 36m
Delta
Tue 9/229:29 am
MDW
-
DLH
2 stops9h 56m
Delta
Deal found 7/19$342
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:43 am
DLH
-
MDW
1 stop6h 36m
Delta
Tue 9/227:13 pm
MDW
-
DLH
1 stop3h 22m
Delta
Deal found 7/19$358
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:15 am
DLH
-
MDW
2 stops13h 07m
Delta
Tue 9/227:13 pm
MDW
-
DLH
1 stop3h 22m
Delta
Deal found 7/19$362
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:15 am
DLH
-
MDW
2 stops7h 24m
Delta
Mon 9/217:13 pm
MDW
-
DLH
1 stop3h 22m
Delta
Deal found 7/19$364
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1411:41 am
DLH
-
MDW
1 stop6h 20m
Delta
Sun 8/169:59 am
MDW
-
DLH
1 stop5h 32m
Delta
Deal found 7/19$373
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:43 am
DLH
-
MDW
1 stop6h 36m
Delta
Mon 9/211:19 pm
MDW
-
DLH
2 stops9h 16m
Delta
Deal found 7/19$388

Find flight deals from Duluth to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Duluth (DLH) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$258
(Delta)

One-way from

$248
(Delta)

Popular in

August

Cheapest in

April

Average price

$382
Provider with most accurate pricing for Duluth Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Duluth Intl-Chicago Midway flights.
Search Deals
From Duluth Intl to Chicago Midway
Search Deals
One-way flight from Duluth Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Duluth to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 20, 2026.
Use the filters below to find and compare flights from Duluth to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sun 10/4

11:43 am-6:19 pm

1 stop6h 36m

Chicago Midway

Sat 10/10

5:21 pm-10:47 pm

1 stop5h 26m

$258
Quickest round-trip

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 8/15

5:15 am-8:39 am

1 stop3h 24m

Chicago Midway

Sun 8/16

7:25 pm-10:41 pm

1 stop3h 16m

$303

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 9/16

5:15 am-12:39 pm

2 stops7h 24m

Chicago Midway

Mon 9/21

7:13 pm-10:35 pm

1 stop3h 22m

$364

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 9/10

5:15 am-8:48 am

1 stop3h 33m

Chicago Midway

Mon 9/14

1:19 pm-7:25 pm

2 stops6h 06m

$439

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 8/12

5:15 am-8:39 am

1 stop3h 24m

Chicago Midway

Fri 8/14

7:25 pm-10:41 pm

1 stop3h 16m

$496

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 8/21

5:15 am-8:39 am

1 stop3h 24m

Chicago Midway

Mon 8/24

1:51 pm-7:44 pm

1 stop5h 53m

$588

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 7/30

11:50 am-6:18 pm

1 stop6h 28m

Chicago Midway

Sat 8/1

6:55 pm-10:49 pm

1 stop3h 54m

$672
Cheapest one-way

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 9/10

5:15 am-8:48 am

1 stop3h 33m

$248

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 10/8

5:14 am-8:47 am

1 stop3h 33m

$248
Quickest one-way

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 8/14

5:15 am-8:39 am

1 stop3h 24m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/19

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

Compare providers for flights from Duluth to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Duluth to Midway in July.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Duluth-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Duluth-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Duluth-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Duluth-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Duluth-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Duluth to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Duluth with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Duluth to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Duluth to Chicago Midway?

    For a flight from Duluth to Chicago Midway, you will be flying from Duluth Intl. Duluth Intl (DLH) is just 5.8 mi from the center of the city. Duluth Intl is the only Duluth airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Duluth Intl on a regular basis.

  • How long is the flight from Duluth to Chicago Midway Airport?

    Delta can get you from Duluth to Chicago Midway Airport in just under 3h 33m. Your travel time can differ by up to . The distance between Duluth and Chicago Midway Airport is about 412 mi.

  • Can I find deals for flights from Duluth to Midway that include hotel bookings?

    Yes. In addition to deals on Duluth to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Duluth to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Duluth to Midway.

  • Can I find deals for business class flights from Duluth to Midway?

    Yes. Cheapflights offers flight deals from Duluth to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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