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$191+ Cheap flights from Duluth (DLH) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
DLH — CHI
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap flight deals from Duluth to Chicago

Cheapest flights from Duluth to Chicago
Explore the most affordable flight options available from Duluth to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2026.

This United Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/133:19 pm
DLH
-
ORD
Nonstop1h 46m
United Airlines
Mon 2/168:50 am
ORD
-
DLH
Nonstop1h 53m
United Airlines
Deal found 1/20$191
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:46 pm
DLH
-
MDW
1 stop5h 59m
Delta
Mon 4/202:12 pm
MDW
-
DLH
1 stop5h 49m
Delta
Deal found 1/20$198
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/125:00 am
DLH
-
ORD
1 stop3h 40m
Delta
Mon 2/166:15 am
ORD
-
DLH
1 stop5h 15m
Delta
Deal found 1/20$198
This United Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/183:08 pm
DLH
-
ORD
Nonstop1h 55m
United Airlines
Mon 4/208:12 pm
ORD
-
DLH
Nonstop1h 49m
United Airlines
Deal found 1/20$211
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:46 pm
DLH
-
ORD
1 stop5h 18m
Delta
Mon 4/206:59 pm
ORD
-
DLH
1 stop3h 47m
Delta
Deal found 1/20$213
This United Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:20 am
DLH
-
ORD
Nonstop1h 49m
United Airlines
Fri 3/68:50 am
ORD
-
DLH
Nonstop1h 53m
United Airlines
Deal found 1/20$224
This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/35:00 am
DLH
-
ORD
1 stop3h 40m
Delta
Sat 2/76:15 am
ORD
-
DLH
1 stop4h 56m
Delta
Deal found 1/19$228
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:00 am
DLH
-
ORD
2 stops7h 41m
Delta
Sun 4/198:50 am
ORD
-
DLH
1 stop3h 16m
Delta
Deal found 1/20$249
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:00 am
DLH
-
MDW
1 stop4h 06m
Delta
Fri 3/69:50 am
MDW
-
DLH
1 stop5h 41m
Delta
Deal found 1/20$258
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/315:00 am
DLH
-
ORD
1 stop5h 25m
Delta
Sat 2/76:15 am
ORD
-
DLH
1 stop4h 56m
Delta
Deal found 1/20$258
This United Airlines deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/313:05 pm
DLH
-
ORD
Nonstop2h 05m
United Airlines
Tue 2/38:09 pm
ORD
-
DLH
Nonstop1h 50m
United Airlines
Deal found 1/19$259
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/298:09 am
DLH
-
ORD
2 stops8h 29m
Delta
Thu 2/56:15 am
ORD
-
DLH
1 stop4h 56m
Delta
Deal found 1/20$264

Find flight deals from Duluth to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Duluth (DLH) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$191
(United Airlines)

Popular in

August

Cheapest in

December

Average price

$351

Good round-trip deal

$374 or less

Good one-way deal

$351 or less
Provider with most accurate pricing for Duluth Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Duluth Intl-Chicago (CHI) flights.
Search Deals
From Duluth Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Duluth Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Duluth Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Duluth to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated January 20, 2026.
Use the filters below to find and compare flights from Duluth to Chicago that are best for you.

Fly from

Duluth

Fly to

Chicago

Route

Depart

Return

Price

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 4/18

12:46 pm-6:45 pm

1 stop5h 59m

Chicago Midway

Mon 4/20

2:12 pm-8:01 pm

1 stop5h 49m

$198

DuluthChicago

DLH - ORD

DLHORD

Duluth Intl

Thu 2/12

5:00 am-8:40 am

1 stop3h 40m

Chicago O'Hare Intl

Mon 2/16

6:15 am-11:30 am

1 stop5h 15m

$198

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 5/27

8:05 am-1:07 pm

1 stop5h 02m

Chicago Midway

Sat 5/30

6:45 pm-11:38 pm

1 stop4h 53m

$213

DuluthChicago

DLH - ORD

DLHORD

Duluth Intl

Fri 2/27

11:20 am-1:09 pm

Nonstop1h 49m

Chicago O'Hare Intl

Fri 3/6

8:50 am-10:43 am

Nonstop1h 53m

$224

DuluthChicago

DLH - ORD

DLHORD

Duluth Intl

Tue 2/3

5:00 am-8:40 am

1 stop3h 40m

Chicago O'Hare Intl

Sat 2/7

6:15 am-11:11 am

1 stop4h 56m

$228

DuluthChicago

DLH - ORD

DLHORD

Duluth Intl

Fri 4/17

5:00 am-12:41 pm

2 stops7h 41m

Chicago O'Hare Intl

Sun 4/19

8:50 am-12:06 pm

1 stop3h 16m

$249

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 2/27

5:00 am-9:06 am

1 stop4h 06m

Chicago Midway

Fri 3/6

9:50 am-3:31 pm

1 stop5h 41m

$258

DuluthChicago

DLH - ORD

DLHORD

Duluth Intl

Sat 1/31

5:00 am-10:25 am

1 stop5h 25m

Chicago O'Hare Intl

Sat 2/7

6:15 am-11:11 am

1 stop4h 56m

$258

DuluthChicago

DLH - ORD

DLHORD

Duluth Intl

Sat 1/31

3:05 pm-5:10 pm

Nonstop2h 05m

Chicago O'Hare Intl

Tue 2/3

8:09 pm-9:59 pm

Nonstop1h 50m

$259

DuluthChicago

DLH - ORD

DLHORD

Duluth Intl

Sat 1/31

8:00 am-4:38 pm

2 stops8h 38m

Chicago O'Hare Intl

Thu 2/5

6:15 am-11:11 am

1 stop4h 56m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 27 results
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Compare providers for flights from Duluth to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Duluth to Chicago in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Duluth-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Duluth-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Duluth-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Duluth-Chicago flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Duluth-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Duluth to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Duluth with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Duluth to Chicago

What is the cheapest month to book a flight from Duluth to Chicago?

Currently, October is the cheapest month in which you can book a flight from Duluth to Chicago (average of $158). Flying from Duluth to Chicago in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DLH to CHI?

Find hourly flight availability from Duluth to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 20, 2026.

When flying from Duluth to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Duluth to Chicago

Explore weekly flight availability from Duluth to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 20, 2026.

The most flights from DLH to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated January 20, 2026.
See what other customers who have flown with United Airlines from Duluth to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,183 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,183 reviews
United Airlines
7.4
Good
9,183 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from Duluth to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Duluth to Chicago?

    Duluth Intl (DLH), located 5.8 mi from the city center, is the airport you fly out of when you book flights from Duluth to Chicago. 1 airline have flights from Duluth Intl to Chicago on a regular basis. Booking flights from Duluth Intl to Chicago should not be difficult; the airport handles an average of 6 outbound flights to Chicago per day.

  • How long is the flight from Duluth to Chicago?

    Departing from Duluth to Chicago will take you 1h 49m. The distance from Duluth to Chicago is about 397 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Duluth to Chicago round-trip?

    Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at $209. Users have found that United Airlines is 43% cheaper than the other options available to this destination.

  • What are the most reliable airlines from Duluth to Chicago?

    Consider Copa Airlines (66%), SkyWest Airlines (64%) or United Airlines (64%) when booking your flight. These represent the most reliable airlines when flying from Duluth to Chicago.

  • What are the cheapest flights from Duluth to Chicago?

    Looking at all options, your cheapest flight can be booked for $243. While the most popular route (Duluth Intl - Chicago O'Hare Intl) can be booked for $179 on average, our data indicates $716 when flying from Duluth to Chicago.

  • Can I find deals for flights from Duluth to Chicago that include hotel bookings?

    Yes. In addition to deals on Duluth to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Duluth to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Duluth to Chicago.

  • Can I find deals for business class flights from Duluth to Chicago?

    Yes. Cheapflights offers flight deals from Duluth to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Duluth to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Duluth to Chicago (average of $158). Flying from Duluth to Chicago in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Duluth to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Duluth to Chicago

Discover the top airline that operate flights from Duluth to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$209Average$340FlexibilityNo cancel feeOn-time69%

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