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$298+ Cheap flights from Dubuque (DBQ) 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
DBQ — CHI
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Dubuque to Chicago

Cheapest flights from Dubuque to Chicago
Explore the most affordable flight options available from Dubuque to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This Denver Air Connection deal was found by Cheapflights users on 12/25. 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 Denver Air Connection is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:15 amDBQ - ORD
Nonstop1h 05mDenver Air Connection
Mon 1/57:45 pmORD - DBQ
Nonstop0h 55mDenver Air Connection
Deal found 12/25$338

Find flight deals from Dubuque to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Dubuque (DBQ) 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$298
(Expedia)

One-way from

$139
(Expedia)

Good round-trip deal

$218 or less

Good one-way deal

$108 or less
Provider with most accurate pricing for Dubuque-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Dubuque-Chicago (CHI) flights.
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From Dubuque to Chicago (CHI)
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One-way flight from Dubuque to Chicago (CHI)
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Price to beat on a round-trip flight from Dubuque to Chicago (CHI).
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Price to beat on a one-way flight from Dubuque to Chicago (CHI).
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Dubuque 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 December 28, 2025.
Use the filters below to find and compare flights from Dubuque to Chicago that are best for you.

Fly from

Dubuque

Fly to

Chicago

Route

Depart

Return

Price

DubuqueChicago

DBQ - ORD

DBQORD

Dubuque

Wed 1/7

6:00 am-6:50 am

Nonstop0h 50m

Chicago O'Hare Intl

Sun 1/11

7:45 pm-8:40 pm

Nonstop0h 55m

$298

DubuqueChicago

DBQ - ORD

DBQORD

Dubuque

Thu 1/8

6:00 am-6:50 am

Nonstop0h 50m

Chicago O'Hare Intl

Sun 1/11

7:45 pm-8:40 pm

Nonstop0h 55m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Compare providers for flights from Dubuque 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 Dubuque to Chicago in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust 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 Dubuque-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Dubuque-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Dubuque-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Dubuque-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 Dubuque-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 Dubuque to Chicago

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

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

Currently, October is the cheapest month in which you can book a flight from Dubuque to Chicago (average of $161). Flying from Dubuque to Chicago in April is currently the most expensive (average of $229). 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 DBQ to CHI?

Find hourly flight availability from Dubuque 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 December 28, 2025.

When flying from Dubuque 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.

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 December 28, 2025.
Peruse reviews from past customers who have flown with Denver Air Connection from Dubuque to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Denver Air Connection
8.7
Very good

Entertainment

8.1

Crew

9.4

Overall

8.7

Comfort

8.9

Boarding

8.7

Food

8.4
Denver Air Connection
8.7
Very good
Denver Air Connection
8.7
Very good

Entertainment

8.1

Crew

9.4

Overall

8.7

Comfort

8.9

Boarding

8.7

Food

8.4

Related info for your journey

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

    For a flight from Dubuque to Chicago, you will be flying from Dubuque. Dubuque (DBQ) is just 7.1 mi from the center of the city. Dubuque is the only Dubuque airport and it handles 0 outbound flights to Chicago per day. 1 airline has flights to Chicago from Dubuque on a regular basis.

  • How long is the flight from Dubuque to Chicago?

    A quick flight from Dubuque to Chicago can take about 50m. Denver Air Connection provides one of the quickest options available for as low as $298. Dubuque and Chicago are separated by a distance of 146 mi. All flights are typically nonstop.

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

    Flying on Denver Air Connection is currently your cheapest option to Chicago, with prices starting at $129.

  • What are the cheapest flights from Dubuque to Chicago?

    On average you can expect to pay $189 for a flight from Dubuque to Chicago. The cheapest flight overall is $93 while the most popular route, (Dubuque - Chicago O'Hare Intl) is currently priced at $298.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Dubuque to Chicago (average of $161). Flying from Dubuque to Chicago in April is currently the most expensive (average of $229). 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 Dubuque to Chicago

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Top airline flying from Dubuque to Chicago

Discover the top airline that operate flights from Dubuque 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$129Average$172FlexibilityNo cancel feeOn-timeN/A

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