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Cheap flights from Duluth to Chicago from $248

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Duluth to Chicago departing on 6/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
12:00 pm - 8:49 am
DLH
-
MDW
20h 49m
1 stop
Delta Logo
12:30 pm - 3:44 pm
MDW
-
DLH
3h 14m
1 stop
$336Delta
Fri, Oct 16 - Mon, Oct 19
Delta Logo
8:18 am - 1:08 pm
DLH
-
MDW
4h 50m
1 stop
Delta Logo
7:25 pm - 10:41 pm
MDW
-
DLH
3h 16m
1 stop
$353Delta
Wed, Aug 19 - Sat, Aug 22
Delta Logo
12:00 pm - 4:50 pm
DLH
-
MDW
4h 50m
1 stop
Delta Logo
12:30 pm - 3:44 pm
MDW
-
DLH
3h 14m
1 stop
$358Delta
Fri, Oct 16 - Sat, Oct 17
Delta Logo
8:18 am - 6:33 pm
DLH
-
MDW
10h 15m
2 stops
Delta Logo
7:25 pm - 10:41 pm
MDW
-
DLH
3h 16m
1 stop
$399Delta
Fri, Aug 21 - Sun, Aug 23
Delta Logo
12:00 pm - 8:49 am
DLH
-
MDW
20h 49m
1 stop
Delta Logo
12:30 pm - 3:44 pm
MDW
-
DLH
3h 14m
1 stop
$405Delta
Thu, Oct 15 - Sat, Oct 17
Delta Logo
11:48 am - 6:18 pm
DLH
-
MDW
6h 30m
1 stop
Delta Logo
7:16 pm - 10:50 pm
MDW
-
DLH
3h 34m
1 stop
$408Delta
Thu, Jun 25 - Wed, Jul 1
Delta Logo
5:15 am - 8:40 am
DLH
-
MDW
3h 25m
1 stop
Delta Logo
7:25 pm - 10:41 pm
MDW
-
DLH
3h 16m
1 stop
$448Delta
Fri, Aug 21 - Sat, Aug 22
Delta Logo
5:15 am - 12:39 pm
DLH
-
MDW
7h 24m
2 stops
Delta Logo
7:25 pm - 10:41 pm
MDW
-
DLH
3h 16m
1 stop
$454Delta
Wed, Aug 19 - Sat, Aug 22
Delta Logo
4:15 pm - 8:49 am
DLH
-
MDW
16h 34m
1 stop
Delta Logo
12:30 pm - 3:44 pm
MDW
-
DLH
3h 14m
1 stop
$486Delta
Wed, Oct 14 - Mon, Oct 19
Delta Logo
5:00 am - 8:37 am
DLH
-
MDW
3h 37m
1 stop
Delta Logo
1:49 pm - 7:24 pm
MDW
-
DLH
5h 35m
1 stop
$488Delta
Fri, Jun 26 - Tue, Jun 30

Delta flights from Duluth to Chicago Midway Airport

Our best Delta deals on Duluth to Chicago Midway Airport flight tickets
Delta
Sep 17
DLH5:10 amDuluth Intl
3h 28m
1 stop
MDW8:38 amChicago Midway
Sep 22
MDW2:00 pmChicago Midway
5h 26m
1 stop
DLH7:26 pmDuluth Intl
$258
Delta
Sep 17
DLH5:10 amDuluth Intl
7h 20m
2 stops
MDW12:30 pmChicago Midway
Sep 22
MDW2:00 pmChicago Midway
5h 26m
1 stop
DLH7:26 pmDuluth Intl
$309
Delta
May 24
DLH7:58 amDuluth Intl
5h 21m
1 stop
MDW1:19 pmChicago Midway
May 30
MDW7:13 pmChicago Midway
3h 31m
1 stop
DLH10:44 pmDuluth Intl
$318

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 May 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

Fri 10/16

12:00 pm-8:49 am

1 stop20h 49m

Chicago Midway

Mon 10/19

12:30 pm-3:44 pm

1 stop3h 14m

$336

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 8/19

8:18 am-1:08 pm

1 stop4h 50m

Chicago Midway

Sat 8/22

7:25 pm-10:41 pm

1 stop3h 16m

$353

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 10/16

12:00 pm-4:50 pm

1 stop4h 50m

Chicago Midway

Sat 10/17

12:30 pm-3:44 pm

1 stop3h 14m

$358

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 8/21

8:18 am-6:33 pm

2 stops10h 15m

Chicago Midway

Sun 8/23

7:25 pm-10:41 pm

1 stop3h 16m

$399

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 10/15

12:00 pm-8:49 am

1 stop20h 49m

Chicago Midway

Sat 10/17

12:30 pm-3:44 pm

1 stop3h 14m

$405

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 6/25

11:48 am-6:18 pm

1 stop6h 30m

Chicago Midway

Wed 7/1

7:16 pm-10:50 pm

1 stop3h 34m

$408
Quickest round-trip

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 8/21

5:15 am-8:40 am

1 stop3h 25m

Chicago Midway

Sat 8/22

7:25 pm-10:41 pm

1 stop3h 16m

$448

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 8/19

5:15 am-12:39 pm

2 stops7h 24m

Chicago Midway

Sat 8/22

7:25 pm-10:41 pm

1 stop3h 16m

$454

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 10/14

4:15 pm-8:49 am

1 stop16h 34m

Chicago Midway

Mon 10/19

12:30 pm-3:44 pm

1 stop3h 14m

$486

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 6/26

5:00 am-8:37 am

1 stop3h 37m

Chicago Midway

Tue 6/30

1:49 pm-7:24 pm

1 stop5h 35m

$488

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 27m

Direct flights

None
The fastest flight from Duluth to Chicago Midway Airport takes 3h 27m
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

Frequently asked questions about flying from Duluth to Chicago Midway Airport

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

    Chicago Midway is 406.6 mi away from Duluth Intl. 3h 27m 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
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Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
Porter
Griffith
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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