Cheap Flights from Dubuque (DBQ) to Chicago (MDW)

Popular airlines from Dubuque, IA (DBQ-Dubuque Regional) to Chicago Midway Airport (MDW)

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Frequently asked questions

How much does a flight from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight or cheap return flight from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW)?
The cheapest month to fly from DBQ to MDW is , when demand is low. Off-peak months are usually when better flight deals are available between these airports.
What is the cheapest airline that flies from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest DBQ to MDW flight.
How many flights per day from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way before you know it.
What day of the week has the most flights from DBQ to MDW?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change based on a range of factors, such as the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW)?
Opt for a flight from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of delays and cancellations. Later departures are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Dubuque Regional Airport (DBQ)?
Browse your flight options from Dubuque Regional Airport (DBQ) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW) last-minute?
Last-minute bookings from DBQ to MDW are generally more expensive. For the lowest prices, start looking for flights well in advance. That being said, if you can play around with your travel dates, it's possible to land a cheap ticket right before your trip.
Is it cheaper to book a DBQ to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a DBQ to MDW flight and hotel package with Expedia could result in significant savings. What's more, having everything in one easy place will take the stress out of travel planning. Simply secure your flights and select from our wide range of hotels, then personalize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Dubuque Regional Airport (DBQ) to Midway Intl. Airport (MDW)?
It's usually possible to reschedule or cancel your DBQ to MDW flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
Dubuque Regional
Destination airport
Midway Intl.
Distance
157 mi

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Dubuque to Chicago Flights

The cheapest times to fly from Dubuque to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Dubuque to Chicago are during the month of . You can find some of the cheapest flights from Dubuque to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Dubuque to Chicago

Sunday is one of the best days to book for cheap flights from Dubuque to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Dubuque to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Dubuque to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Dubuque to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Dubuque to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Dubuque to Chicago Flights

*Flight schedules are subject to change.

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