$84 Cheap Flights from Duluth (DLH) to Chicago (MDW)

View $84 flight on Tue, Jan 6, 2026Opens in a new window

Popular airlines from Duluth, MN (DLH-Duluth Intl.) to Chicago Midway Airport (MDW)

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Cheap Flights from Duluth to Chicago (DLH-MDW)

Prices were available within the past 7 days and start at $84 for one-way flights and $168 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jan 6 - Thu, Jan 8
DLH
Duluth
MDW
Chicago
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 6 from Duluth to Chicago, returning Thu, Jan 8, priced at $168 found 1 day ago
Delta
Thu, Jan 29 - Wed, Feb 18
DLH
Duluth
MDW
Chicago
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Jan 29 from Duluth to Chicago, returning Wed, Feb 18, priced at $174 found 2 days ago
Delta
Wed, Jan 7 - Sun, Jan 11
DLH
Duluth
MDW
Chicago
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jan 7 from Duluth to Chicago, returning Sun, Jan 11, priced at $183 found 1 day ago
Delta
Tue, Jan 13 - Thu, Jan 29
DLH
Duluth
MDW
Chicago
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jan 13 from Duluth to Chicago, returning Thu, Jan 29, priced at $189 found 2 days ago
Delta
Wed, Oct 29 - Wed, Nov 5
DLH
Duluth
MDW
Chicago
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Oct 29 from Duluth to Chicago, returning Wed, Nov 5, priced at $197 found 4 days ago
Delta
Fri, Jan 9 - Sun, Jan 11
DLH
Duluth
MDW
Chicago
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jan 9 from Duluth to Chicago, returning Sun, Jan 11, priced at $198 found 1 day ago
Delta
Fri, Jan 9 - Thu, Jan 29
DLH
Duluth
MDW
Chicago
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Jan 9 from Duluth to Chicago, returning Thu, Jan 29, priced at $204 found 2 days ago
Delta
Wed, Jan 7 - Thu, Jan 15
DLH
Duluth
MDW
Chicago
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jan 7 from Duluth to Chicago, returning Thu, Jan 15, priced at $213 found 1 day ago
Delta
Tue, Jan 13 - Thu, Jan 15
DLH
Duluth
MDW
Chicago
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jan 13 from Duluth to Chicago, returning Thu, Jan 15, priced at $217 found 3 days ago
Delta
Tue, Jan 20 - Thu, Feb 5
DLH
Duluth
MDW
Chicago
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jan 20 from Duluth to Chicago, returning Thu, Feb 5, priced at $219 found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $269
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $269
Flights from Duluth (DLH) to Chicago (MDW)
Origin airport
Duluth Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$168
Distance
412 mi

Duluth to Chicago Flights

The cheapest times to fly from Duluth to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Duluth to Chicago are during the month of January. You can find some of the cheapest flights from Duluth to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Duluth to Chicago

Sunday is one of the best days to book for cheap flights from Duluth to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Duluth to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Duluth to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $84 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Duluth to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Duluth to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $84 or cheap return flight from $168 from Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW)?
Planning your trip for January is a great way to save, as it's the cheapest month for flights between DLH and MDW. You'll typically find the lowest prices during off-peak months.
What is the cheapest airline that flies from Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest DLH to MDW flight.
How many flights per day from Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW)?
Direct flights from Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from DLH to MDW?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW) route, aim to fly before 3 PM. Departures after this hour have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Duluth Intl. Airport (DLH)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Duluth Intl. Airport (DLH). Browse the available options and discover cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from DLH to MDW just before your trip is usually more expensive. However, if you're flexible with your departure times and dates, you could land a cheap last-minute fare.
Is it cheaper to book a DLH to MDW flight and hotel package?
You'll typically save money by securing a DLH to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After choosing your preferred accommodations and flights, you can add extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Duluth Intl. Airport (DLH) to Midway Intl. Airport (MDW)?
If you booked your DLH to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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*Available to One Key members.