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Cheap flights from Duluth to Chicago from $218

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 9/13. 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

Delta Logo
7:50 am - 1:03 pmDLH-MDW
5h 13m1 stop
Delta Logo
3:00 pm - 7:17 pmMDW-DLH
4h 17m1 stop
$228Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
Delta Logo
5:10 am - 12:28 pmDLH-MDW
7h 18m2 stops
Delta Logo
1:43 pm - 7:21 pmMDW-DLH
5h 38m1 stop
$239Delta
Find Deal
Tue, Sep 2 - Sat, Sep 6
Delta Logo
12:02 pm - 5:43 pmDLH-MDW
5h 41m1 stop
Delta Logo
7:10 pm - 11:42 pmMDW-DLH
4h 32m1 stop
$263Delta
Find Deal
Sat, Oct 25 - Tue, Oct 28
Delta Logo
7:50 am - 1:03 pmDLH-MDW
5h 13m1 stop
Delta Logo
7:17 pm - 10:46 pmMDW-DLH
3h 29m1 stop
$268Delta
Find Deal
Thu, Sep 4 - Sat, Sep 6
Delta Logo
7:50 am - 1:03 pmDLH-MDW
5h 13m1 stop
Delta Logo
11:10 am - 7:17 pmMDW-DLH
8h 07m2 stops
$269Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
Delta Logo
7:50 am - 6:35 pmDLH-MDW
10h 45m2 stops
Delta Logo
11:10 am - 7:17 pmMDW-DLH
8h 07m2 stops
$339Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
Delta Logo
7:50 am - 1:08 pmDLH-MDW
5h 18m1 stop
Delta Logo
9:20 am - 3:30 pmMDW-DLH
6h 10m1 stop
$348Delta
Find Deal
Thu, Oct 23 - Sun, Oct 26
Delta Logo
10:55 am - 5:37 pmDLH-MDW
6h 42m1 stop
Delta Logo
1:43 pm - 7:21 pmMDW-DLH
5h 38m1 stop
$388Delta
Find Deal
Tue, Sep 2 - Sat, Sep 6
Delta Logo
5:10 am - 8:53 amDLH-MDW
3h 43m1 stop
Delta Logo
7:10 pm - 11:42 pmMDW-DLH
4h 32m1 stop
$413Delta
Find Deal
Fri, Oct 3 - Mon, Oct 6
Delta Logo
5:10 am - 12:28 pmDLH-MDW
7h 18m2 stops
Delta Logo
9:31 am - 3:39 pmMDW-DLH
6h 08m2 stops
$424Delta
Find Deal
Tue, Sep 2 - Sat, Sep 6

Delta flights from Duluth to Chicago Midway Airport

Our best Delta deals on Duluth to Chicago Midway Airport flight tickets
Delta
Oct 4
DLH7:50 amDuluth Intl
5h 13m
1 stop
MDW1:03 pmChicago Midway
Oct 11
MDW3:00 pmChicago Midway
4h 17m
1 stop
DLH7:17 pmDuluth Intl
$228
Find similar
Delta
Sep 2
DLH5:10 amDuluth Intl
7h 18m
2 stops
MDW12:28 pmChicago Midway
Sep 6
MDW1:43 pmChicago Midway
5h 38m
1 stop
DLH7:21 pmDuluth Intl
$239
Find similar
Delta
Oct 25
DLH12:02 pmDuluth Intl
5h 41m
1 stop
MDW5:43 pmChicago Midway
Oct 28
MDW7:10 pmChicago Midway
4h 32m
1 stop
DLH11:42 pmDuluth Intl
$263
Find similar

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 August 21, 2025.
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

Sat 10/4

7:50 am-1:03 pm

1 stop5h 13m

Chicago Midway

Sat 10/11

3:00 pm-7:17 pm

1 stop4h 17m

$228

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Tue 9/2

5:10 am-12:28 pm

2 stops7h 18m

Chicago Midway

Sat 9/6

1:43 pm-7:21 pm

1 stop5h 38m

$239

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 10/25

12:02 pm-5:43 pm

1 stop5h 41m

Chicago Midway

Tue 10/28

7:10 pm-11:42 pm

1 stop4h 32m

$263

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 9/4

7:50 am-1:03 pm

1 stop5h 13m

Chicago Midway

Sat 9/6

7:17 pm-10:46 pm

1 stop3h 29m

$268

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 10/4

7:50 am-1:03 pm

1 stop5h 13m

Chicago Midway

Sat 10/11

11:10 am-7:17 pm

2 stops8h 07m

$269

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 10/4

7:50 am-6:35 pm

2 stops10h 45m

Chicago Midway

Sat 10/11

11:10 am-7:17 pm

2 stops8h 07m

$339

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 10/23

7:50 am-1:08 pm

1 stop5h 18m

Chicago Midway

Sun 10/26

9:20 am-3:30 pm

1 stop6h 10m

$348

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Tue 9/2

10:55 am-5:37 pm

1 stop6h 42m

Chicago Midway

Sat 9/6

1:43 pm-7:21 pm

1 stop5h 38m

$388

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 10/3

5:10 am-8:53 am

1 stop3h 43m

Chicago Midway

Mon 10/6

7:10 pm-11:42 pm

1 stop4h 32m

$413

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Tue 9/2

5:10 am-12:28 pm

2 stops7h 18m

Chicago Midway

Sat 9/6

9:31 am-3:39 pm

2 stops6h 08m

$424

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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 time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Duluth in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $282 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $335. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Direct flights

None
There are no direct flights from Duluth to Chicago Midway Airport. There are no popular flight routes from Duluth to Chicago Midway Airport.
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  • How far is Duluth Intl to Chicago Midway by plane?

    Chicago Midway is 406.6 mi away from Duluth Intl. 3h 37m 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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.

An easier way to manage your Chicago Midway Airport trip

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