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Cheap flights from Duluth to Chicago from $258

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 9/1. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Duluth to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:41 am - 6:01 pm
DLH
-
MDW
6h 20m
1 stop
Delta Logo
4:52 pm - 10:41 pm
MDW
-
DLH
5h 49m
1 stop
$258Delta
Tue, Sep 1 - Sat, Sep 5
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
$264Delta
Wed, Aug 26 - Mon, Aug 31
Delta Logo
5:15 am - 12:39 pm
DLH
-
MDW
7h 24m
2 stops
Delta Logo
9:24 am - 3:31 pm
MDW
-
DLH
6h 07m
2 stops
$269Delta
Wed, Aug 26 - Wed, Sep 2
Delta Logo
11:41 am - 6:01 pm
DLH
-
MDW
6h 20m
1 stop
Delta Logo
7:25 pm - 10:41 pm
MDW
-
DLH
3h 16m
1 stop
$273Delta
Sat, Aug 15 - Tue, Aug 18
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
$279Delta
Tue, Aug 25 - Mon, Aug 31
Delta Logo
11:41 am - 6:01 pm
DLH
-
MDW
6h 20m
1 stop
Delta Logo
9:59 am - 3:29 pm
MDW
-
DLH
5h 30m
1 stop
$303Delta
Wed, Sep 2 - Fri, Sep 11
Delta Logo
8:18 am - 8:39 am
DLH
-
MDW
24h 21m
1 stop
Delta Logo
7:13 pm - 10:35 pm
MDW
-
DLH
3h 22m
1 stop
$306Delta
Fri, Sep 4 - Wed, Sep 9
Delta Logo
5:15 am - 12:39 pm
DLH
-
MDW
7h 24m
2 stops
Delta Logo
9:59 am - 3:31 pm
MDW
-
DLH
5h 32m
1 stop
$309Delta
Wed, Aug 26 - Tue, Sep 1
Delta Logo
8:18 am - 8:39 am
DLH
-
MDW
24h 21m
1 stop
Delta Logo
9:24 am - 3:31 pm
MDW
-
DLH
6h 07m
2 stops
$312Delta
Fri, Sep 4 - Sun, Sep 6
Delta Logo
5:15 am - 12:39 pm
DLH
-
MDW
7h 24m
2 stops
Delta Logo
9:24 am - 3:31 pm
MDW
-
DLH
6h 07m
2 stops
$314Delta
Sat, Aug 29 - Tue, Sep 1

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Delta flights from Duluth to Chicago Midway Airport

Our best Delta deals on Duluth to Chicago Midway Airport flight tickets
Delta
Sep 1
DLH11:41 amDuluth Intl
6h 20m
1 stop
MDW6:01 pmChicago Midway
Sep 5
MDW4:52 pmChicago Midway
5h 49m
1 stop
DLH10:41 pmDuluth Intl
$258
Delta
Aug 26
DLH5:15 amDuluth Intl
7h 24m
2 stops
MDW12:39 pmChicago Midway
Aug 31
MDW7:25 pmChicago Midway
3h 16m
1 stop
DLH10:41 pmDuluth Intl
$264
Delta
Aug 26
DLH5:15 amDuluth Intl
7h 24m
2 stops
MDW12:39 pmChicago Midway
Sep 2
MDW9:24 amChicago Midway
6h 07m
2 stops
DLH3:31 pmDuluth Intl
$269

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 July 9, 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

Tue 9/1

11:41 am-6:01 pm

1 stop6h 20m

Chicago Midway

Sat 9/5

4:52 pm-10:41 pm

1 stop5h 49m

$258

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 8/26

5:15 am-12:39 pm

2 stops7h 24m

Chicago Midway

Mon 8/31

7:25 pm-10:41 pm

1 stop3h 16m

$264

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 8/26

5:15 am-12:39 pm

2 stops7h 24m

Chicago Midway

Wed 9/2

9:24 am-3:31 pm

2 stops6h 07m

$269
Quickest round-trip

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 8/15

11:41 am-6:01 pm

1 stop6h 20m

Chicago Midway

Tue 8/18

7:25 pm-10:41 pm

1 stop3h 16m

$273

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Tue 8/25

5:15 am-12:39 pm

2 stops7h 24m

Chicago Midway

Mon 8/31

7:25 pm-10:41 pm

1 stop3h 16m

$279

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 9/2

11:41 am-6:01 pm

1 stop6h 20m

Chicago Midway

Fri 9/11

9:59 am-3:29 pm

1 stop5h 30m

$303

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 9/4

8:18 am-8:39 am

1 stop24h 21m

Chicago Midway

Wed 9/9

7:13 pm-10:35 pm

1 stop3h 22m

$306

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 8/26

5:15 am-12:39 pm

2 stops7h 24m

Chicago Midway

Tue 9/1

9:59 am-3:31 pm

1 stop5h 32m

$309

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 9/4

8:18 am-8:39 am

1 stop24h 21m

Chicago Midway

Sun 9/6

9:24 am-3:31 pm

2 stops6h 07m

$312

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 8/29

5:15 am-12:39 pm

2 stops7h 24m

Chicago Midway

Tue 9/1

9:24 am-3:31 pm

2 stops6h 07m

$314

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

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 24m

Direct flights

None
The fastest flight from Duluth to Chicago Midway Airport takes 3h 24m
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 24m 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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