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$198+ Cheap flights from Durango (DRO) 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
DRO — CHI
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Find flight deals from Durango to Chicago

Cheapest flights from Durango to Chicago
Explore the most affordable flight options available from Durango to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2025.

This United Airlines deal was found by Cheapflights users on 11/19. 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.
Fri 12/126:05 pmDRO - ORD
1 stop4h 54mUnited Airlines
Wed 12/171:51 pmORD - DRO
1 stop7h 43mUnited Airlines
Deal found 11/19$248
This United Airlines deal was found by Cheapflights users on 11/18. 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.
Thu 12/186:02 pmDRO - ORD
1 stop4h 57mUnited Airlines
Mon 1/58:45 amORD - DRO
1 stop7h 03mUnited Airlines
Deal found 11/18$267
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 12/115:15 amDRO - ORD
1 stop5h 14mUnited Airlines
Tue 12/166:15 pmORD - DRO
1 stop4h 59mUnited Airlines
Deal found 11/19$276
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/114:30 pmDRO - ORD
1 stop5h 56mAmerican Airlines
Tue 12/165:00 amORD - DRO
1 stop7h 21mAmerican Airlines
Deal found 11/19$304
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Wed 11/261:38 pmDRO - ORD
1 stop6h 20mUnited Airlines
Sun 11/309:30 pmORD - DRO
1 stop4h 38mUnited Airlines
Deal found 11/19$308
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 12/45:15 amDRO - ORD
1 stop5h 14mUnited Airlines
Mon 12/86:15 pmORD - DRO
1 stop4h 59mUnited Airlines
Deal found 11/19$348
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 11/277:00 amDRO - ORD
1 stop6h 48mUnited Airlines
Sun 11/309:30 pmORD - DRO
1 stop4h 38mUnited Airlines
Deal found 11/19$388
This United Airlines deal was found by Cheapflights users on 11/18. 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.
Wed 12/171:39 pmDRO - ORD
1 stop5h 05mUnited Airlines
Sun 12/219:40 pmORD - DRO
1 stop13h 07mUnited Airlines
Deal found 11/18$421
This United Airlines deal was found by Cheapflights users on 11/18. 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 11/221:38 pmDRO - ORD
1 stop6h 20mUnited Airlines
Sun 11/309:30 pmORD - DRO
1 stop4h 38mUnited Airlines
Deal found 11/18$443

Cheap flight deals from Durango to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Durango (DRO) 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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$198
(United Airlines)

Popular in

January

Cheapest in

April

Average price

$511
Provider with most accurate pricing for Durango La Plata County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Durango La Plata County-Chicago (CHI) flights.
Search Deals
From Durango La Plata County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($152 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Durango 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 November 20, 2025.
Use the filters below to find and compare flights from Durango to Chicago that are best for you.

Fly from

Durango

Fly to

Chicago

Route

Depart

Return

Price

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Fri 2/27

1:41 pm-7:40 pm

1 stop4h 59m

Chicago O'Hare Intl

Mon 3/2

2:02 pm-8:51 pm

1 stop7h 49m

$198

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 12/18

6:02 pm-11:59 pm

1 stop4h 57m

Chicago O'Hare Intl

Mon 1/5

8:45 am-2:48 pm

1 stop7h 03m

$267

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 12/11

5:15 am-11:29 am

1 stop5h 14m

Chicago O'Hare Intl

Tue 12/16

6:15 pm-10:14 pm

1 stop4h 59m

$276

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 2/26

1:41 pm-9:29 pm

1 stop6h 48m

Chicago O'Hare Intl

Mon 3/2

2:40 pm-8:51 pm

1 stop7h 11m

$278

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 1/8

3:32 pm-11:58 pm

1 stop7h 26m

Chicago O'Hare Intl

Sat 1/10

8:45 am-12:36 pm

1 stop4h 51m

$278

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 12/11

5:29 am-3:26 pm

1 stop8h 57m

Chicago O'Hare Intl

Tue 12/16

5:00 am-11:21 am

1 stop7h 21m

$304

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Fri 12/12

4:29 pm-11:35 pm

1 stop6h 06m

Chicago O'Hare Intl

Wed 12/17

5:00 am-11:21 am

1 stop7h 21m

$304

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Fri 2/27

6:00 pm-11:59 pm

1 stop4h 59m

Chicago O'Hare Intl

Sun 4/12

7:00 am-12:28 pm

1 stop6h 28m

$324

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Thu 12/4

5:15 am-11:29 am

1 stop5h 14m

Chicago O'Hare Intl

Mon 12/8

6:15 pm-10:14 pm

1 stop4h 59m

$348

DurangoChicago

DRO - ORD

DROORD

Durango La Plata County

Tue 12/23

6:02 pm-11:59 pm

1 stop4h 57m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 16 results
1
2

Compare providers for flights from Durango 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 Durango to Chicago in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars

*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 Durango-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Durango-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Durango-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Durango-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 Durango-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 Durango to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Durango 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 Durango to Chicago

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

Currently, November is the cheapest month in which you can book a flight from Durango to Chicago (average of $262). Flying from Durango to Chicago in March is currently the most expensive (average of $428). 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.

How much does it cost to fly round-trip from Durango to Chicago?

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 November 20, 2025.
Get a feel of what it's like to fly with United Airlines and American Airlines from Durango to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,028 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,028 reviews
United Airlines
7.4
Good
9,028 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,047 reviews
United Airlines
7.4
Good
9,028 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Durango 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 Durango to Chicago?

    Most people fly from Durango La Plata County (DRO) if they book a flight from Durango to Chicago. On average, La Plata County has 0 outbound flights to Chicago per day from 2 airlines. Durango La Plata County is conveniently located just 11.0 mi from Durango’s city center.

  • How long is the flight from Durango to Chicago?

    For as low as $198, United Airlines can have you in Chicago from Durango in 4h 59m. The distance from Durango to Chicago is about 1105 mi.

  • What are the cheapest airlines flying from Durango to Chicago round-trip?

    United Airlines, at $298, was found to be the cheapest airline from Durango to Chicago. An alternate airline flying to your destination would be American Airlines. United Airlines is 31% cheaper than the average price of flights available within the next 90 days to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Durango 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 Durango to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Durango to Chicago (average of $262). Flying from Durango to Chicago in March is currently the most expensive (average of $428). 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
Hammond
Porter
Benton Harbor
Merrillville

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Top 2 airlines flying from Durango to Chicago

Discover the top 2 airlines that operate flights from Durango 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$298Average$536FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$318Average$428FlexibilityNo cancel feeOn-time71%

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