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Cheap flights from Duluth to Chicago from $208

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Duluth to Chicago departing on 4/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Duluth to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:00 am - 8:50 am
DLH
-
MDW
3h 50m
1 stop
Delta Logo
7:20 pm - 10:47 pm
MDW
-
DLH
3h 27m
1 stop
$208Delta
Wed, Apr 1 - Sat, Apr 4
Delta Logo
12:47 pm - 6:36 pm
DLH
-
MDW
5h 49m
1 stop
Delta Logo
7:16 pm - 10:46 pm
MDW
-
DLH
3h 30m
1 stop
$213Delta
Sat, Apr 18 - Mon, Apr 20
Delta Logo
12:15 pm - 6:40 pm
DLH
-
MDW
6h 25m
1 stop
Delta Logo
7:20 pm - 11:55 pm
MDW
-
DLH
4h 35m
1 stop
$223Delta
Wed, Feb 25 - Tue, Mar 3
Delta Logo
12:15 pm - 4:14 pm
DLH
-
MDW
3h 59m
1 stop
Delta Logo
7:20 pm - 11:55 pm
MDW
-
DLH
4h 35m
1 stop
$228Delta
Sat, Feb 28 - Wed, Mar 4
Delta Logo
8:00 am - 5:37 pm
DLH
-
MDW
9h 37m
2 stops
Delta Logo
7:20 pm - 11:55 pm
MDW
-
DLH
4h 35m
1 stop
$229Delta
Wed, Feb 25 - Tue, Mar 3
Delta Logo
12:15 pm - 6:40 pm
DLH
-
MDW
6h 25m
1 stop
Delta Logo
7:20 pm - 11:55 pm
MDW
-
DLH
4h 35m
1 stop
$238Delta
Thu, Feb 26 - Mon, Mar 2
Delta Logo
12:37 pm - 6:40 pm
DLH
-
MDW
6h 03m
1 stop
Delta Logo
2:05 pm - 8:09 pm
MDW
-
DLH
6h 04m
1 stop
$243Delta
Thu, Mar 12 - Thu, Mar 19
Delta Logo
5:00 am - 8:51 am
DLH
-
MDW
3h 51m
1 stop
Delta Logo
7:16 pm - 10:46 pm
MDW
-
DLH
3h 30m
1 stop
$253Delta
Fri, Apr 24 - Mon, Apr 27
Delta Logo
12:37 pm - 6:40 pm
DLH
-
MDW
6h 03m
1 stop
Delta Logo
1:10 pm - 8:09 pm
MDW
-
DLH
6h 59m
2 stops
$259Delta
Wed, Apr 1 - Sat, Apr 4
Delta Logo
12:47 pm - 6:36 pm
DLH
-
MDW
5h 49m
1 stop
Delta Logo
7:16 pm - 10:46 pm
MDW
-
DLH
3h 30m
1 stop
$283Delta
Thu, Apr 30 - Sun, May 3

Delta flights from Duluth to Chicago Midway Airport

Our best Delta deals on Duluth to Chicago Midway Airport flight tickets
Delta
Apr 1
DLH5:00 amDuluth Intl
3h 50m
1 stop
MDW8:50 amChicago Midway
Apr 4
MDW7:20 pmChicago Midway
3h 27m
1 stop
DLH10:47 pmDuluth Intl
$208
Delta
Apr 18
DLH12:47 pmDuluth Intl
5h 49m
1 stop
MDW6:36 pmChicago Midway
Apr 20
MDW7:16 pmChicago Midway
3h 30m
1 stop
DLH10:46 pmDuluth Intl
$213
Delta
Feb 25
DLH12:15 pmDuluth Intl
6h 25m
1 stop
MDW6:40 pmChicago Midway
Mar 3
MDW7:20 pmChicago Midway
4h 35m
1 stop
DLH11:55 pmDuluth Intl
$223

momondo Fare Finder

 
Customize your flight search to find flights from Duluth to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated February 14, 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

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 4/1

5:00 am-8:50 am

1 stop3h 50m

Chicago Midway

Sat 4/4

7:20 pm-10:47 pm

1 stop3h 27m

$208

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 4/18

12:47 pm-6:36 pm

1 stop5h 49m

Chicago Midway

Mon 4/20

7:16 pm-10:46 pm

1 stop3h 30m

$213

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 2/25

12:15 pm-6:40 pm

1 stop6h 25m

Chicago Midway

Tue 3/3

7:20 pm-11:55 pm

1 stop4h 35m

$223

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 2/28

12:15 pm-4:14 pm

1 stop3h 59m

Chicago Midway

Wed 3/4

7:20 pm-11:55 pm

1 stop4h 35m

$228

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 2/25

8:00 am-5:37 pm

2 stops9h 37m

Chicago Midway

Tue 3/3

7:20 pm-11:55 pm

1 stop4h 35m

$229

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 2/26

12:15 pm-6:40 pm

1 stop6h 25m

Chicago Midway

Mon 3/2

7:20 pm-11:55 pm

1 stop4h 35m

$238

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 3/12

12:37 pm-6:40 pm

1 stop6h 03m

Chicago Midway

Thu 3/19

2:05 pm-8:09 pm

1 stop6h 04m

$243

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 4/24

5:00 am-8:51 am

1 stop3h 51m

Chicago Midway

Mon 4/27

7:16 pm-10:46 pm

1 stop3h 30m

$253

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 4/1

12:37 pm-6:40 pm

1 stop6h 03m

Chicago Midway

Sat 4/4

1:10 pm-8:09 pm

2 stops6h 59m

$259

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 4/30

12:47 pm-6:36 pm

1 stop5h 49m

Chicago Midway

Sun 5/3

7:16 pm-10:46 pm

1 stop3h 30m

$283

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Duluth to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Duluth Intl to Chicago Midway?

Delta is the most popular carrier operating from Duluth Intl to Chicago Midway

When to book flights from Duluth to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Duluth to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Duluth to Chicago Midway Airport (DLH to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Duluth to Chicago Midway Airport

Fastest flight time

3h 28m

Direct flights

None
The fastest flight from Duluth to Chicago Midway Airport takes 3h 28m
There are no direct flights from Duluth to Chicago Midway Airport. There are no popular flight routes from Duluth to Chicago Midway Airport.
Search flight deals

  • How far is Duluth Intl to Chicago Midway by plane?

    Chicago Midway is 406.6 mi away from Duluth Intl. 3h 28m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Duluth Intl Airport to Chicago Midway Airport?

    Prices for flights from Duluth Intl Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Duluth Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Duluth Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
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Porter
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Duluth to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Duluth.

Can I find flights from Duluth to Chicago with flexible booking policies on momondo?

All flight searches from Duluth to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Duluth to Chicago?

Once all potential Duluth to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Duluth to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Duluth. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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