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$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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
DLH — MDW
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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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 April 23, 2026.

This Delta deal was found by Cheapflights users on 4/22. 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 5/305:15 am
DLH
-
MDW
1 stop3h 27m
Delta
Sat 6/67:13 pm
MDW
-
DLH
1 stop3h 31m
Delta
Deal found 4/22$258
This Delta deal was found by Cheapflights users on 4/19. 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.
Sun 5/247:58 am
DLH
-
MDW
1 stop5h 21m
Delta
Sat 5/307:13 pm
MDW
-
DLH
1 stop3h 31m
Delta
Deal found 4/19$270
This Delta deal was found by Cheapflights users on 4/20. 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 5/2012:46 pm
DLH
-
MDW
1 stop5h 10m
Delta
Sat 5/231:59 pm
MDW
-
DLH
1 stop5h 32m
Delta
Deal found 4/20$273
This Delta deal was found by Cheapflights users on 4/18. 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 5/165:15 am
DLH
-
MDW
1 stop3h 27m
Delta
Sat 5/231:59 pm
MDW
-
DLH
1 stop5h 32m
Delta
Deal found 4/18$285
This Delta deal was found by Cheapflights users on 4/19. 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.
Thu 8/205:10 am
DLH
-
MDW
1 stop3h 28m
Delta
Mon 8/242:00 pm
MDW
-
DLH
1 stop5h 26m
Delta
Deal found 4/19$300
This Delta deal was found by Cheapflights users on 4/21. 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 5/305:15 am
DLH
-
MDW
2 stops7h 27m
Delta
Wed 6/39:23 am
MDW
-
DLH
1 stop6h 25m
Delta
Deal found 4/21$319
This Delta deal was found by Cheapflights users on 4/20. 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 5/2012:46 pm
DLH
-
MDW
1 stop5h 10m
Delta
Wed 5/279:23 am
MDW
-
DLH
1 stop6h 25m
Delta
Deal found 4/20$327

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 April 23, 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

$208
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. 26% potential increase in price ($140 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 23, 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

Thu 8/20

5:10 am-12:30 pm

2 stops7h 20m

Chicago Midway

Mon 8/24

2:00 pm-7:26 pm

1 stop5h 26m

$291

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 5/30

5:15 am-12:42 pm

2 stops7h 27m

Chicago Midway

Wed 6/3

9:23 am-3:48 pm

1 stop6h 25m

$319

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 5/29

12:46 pm-5:56 pm

1 stop5h 10m

Chicago Midway

Mon 6/1

1:59 pm-7:31 pm

1 stop5h 32m

$327

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 5/28

5:15 am-8:42 am

1 stop3h 27m

Chicago Midway

Mon 6/1

1:59 pm-7:31 pm

1 stop5h 32m

$327

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Tue 5/19

5:15 am-8:42 am

1 stop3h 27m

Chicago Midway

Tue 5/26

9:23 am-3:48 pm

1 stop6h 25m

$359

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 7/10

11:50 am-6:18 pm

1 stop6h 28m

Chicago Midway

Sun 7/12

9:49 am-3:27 pm

1 stop5h 38m

$388
Quickest round-trip

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 5/8

12:46 pm-5:56 pm

1 stop5h 10m

Chicago Midway

Sun 5/10

7:13 pm-10:44 pm

1 stop3h 31m

$543
Cheapest one-way

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sun 6/28

5:05 am-8:37 am

1 stop3h 32m

$248

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 5/30

5:15 am-12:42 pm

2 stops7h 27m

$254

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 5/28

5:15 am-12:42 pm

2 stops7h 27m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 16 resultsSorted by cheapest first
1
2
  • 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 7h 20m. 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
Hammond
Porter

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