$144 Cheap Flights from Huntsville (HSV) to Chicago (MDW)

View $144 flight on Mon, Nov 24, 2025Opens in a new window

Popular airlines from Huntsville International Airport (HSV) to Chicago Midway Airport (MDW)

Cheap Flights from Huntsville to Chicago (HSV-MDW)

Prices were available within the past 7 days and start at $144 for one-way flights and $229 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Jan 1 - Fri, Jan 2
HSV
Huntsville
MDW
Chicago
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Delta flight, departing Thu, Jan 1 from Huntsville to Chicago, returning Fri, Jan 2, priced at $229 just found
Delta
Sat, Nov 22 - Tue, Nov 25
HSV
Huntsville
MDW
Chicago
$249 Roundtrip, found 1 hour ago
$249
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Nov 22 from Huntsville to Chicago, returning Tue, Nov 25, priced at $249 found 1 hour ago
Delta
Fri, Jan 2 - Mon, Jan 5
HSV
Huntsville
MDW
Chicago
$257 Roundtrip, just found
$257
Roundtrip
just found
Select Delta flight, departing Fri, Jan 2 from Huntsville to Chicago, returning Mon, Jan 5, priced at $257 just found
Delta
Mon, Nov 24 - Mon, Dec 1
HSV
Huntsville
MDW
Chicago
$258 Roundtrip, found 1 hour ago
$258
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Nov 24 from Huntsville to Chicago, returning Mon, Dec 1, priced at $258 found 1 hour ago
Delta
Thu, Nov 13 - Sat, Nov 15
HSV
Huntsville
MDW
Chicago
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 13 from Huntsville to Chicago, returning Sat, Nov 15, priced at $269 found 2 days ago
Delta
Fri, Nov 21 - Wed, Dec 3
HSV
Huntsville
MDW
Chicago
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Nov 21 from Huntsville to Chicago, returning Wed, Dec 3, priced at $277 found 1 day ago
Delta
Sat, Nov 22 - Tue, Nov 25
HSV
Huntsville
MDW
Chicago
$278 Roundtrip, found 1 hour ago
$278
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Nov 22 from Huntsville to Chicago, returning Tue, Nov 25, priced at $278 found 1 hour ago
Delta
Mon, Nov 24 - Mon, Dec 1
HSV
Huntsville
MDW
Chicago
$284 Roundtrip, found 1 hour ago
$284
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Nov 24 from Huntsville to Chicago, returning Mon, Dec 1, priced at $284 found 1 hour ago
Delta
Tue, Dec 30 - Mon, Jan 5
HSV
Huntsville
MDW
Chicago
$285 Roundtrip, just found
$285
Roundtrip
just found
Select Delta flight, departing Tue, Dec 30 from Huntsville to Chicago, returning Mon, Jan 5, priced at $285 just found
Delta
Sat, Nov 22 - Sun, Dec 7
HSV
Huntsville
MDW
Chicago
$286 Roundtrip, found 1 day ago
$286
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 22 from Huntsville to Chicago, returning Sun, Dec 7, priced at $286 found 1 day ago

Find the cheapest month to fly from Huntsville (HSV) to Chicago (MDW)

April is typically the cheapest month to fly

From $186 - $675 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $249
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $249

Frequently asked questions

How much does a flight from Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $144 or cheap return flight from $229 from Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW)?
Planning your getaway for January can help you save, as it's the cheapest month for flights between HSV and MDW. You'll often find the lowest prices during off-peak months.
What is the cheapest airline that flies from Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the cheapest carrier that'll take you from HSV to MDW. Then, sort your results by "Price (lowest to highest)" to snag the best deal available.
How many flights per day from Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights available from Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be on your way in no time at all.
What day of the week has the most flights from HSV to MDW?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change depending on a number of factors, including the season 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 Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) on schedule, opt for a flight that takes off from Huntsville Intl. Airport (HSV) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 Huntsville Intl. Airport (HSV)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Huntsville Intl. Airport (HSV). Browse the options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your trip to book a ticket from HSV to MDW often results in higher prices. While you might find some last-minute offers, they're not always guaranteed. Be flexible with your itinerary for the best chance of landing a bargain.
Is it cheaper to book a HSV to MDW flight and hotel package?
Securing a HSV to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Choose from our impressive range of hotels and then add flights, activities and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW)?
If you booked your HSV to MDW flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

Travel information

Origin airport
Huntsville Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$228
Distance
496 mi

Book with confidence

Huntsville to Chicago Flights

The cheapest times to fly from Huntsville 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 Huntsville to Chicago are during the month of January. You can find some of the cheapest flights from Huntsville to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Huntsville to Chicago

Sunday is one of the best days to book for cheap flights from Huntsville 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 Huntsville 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 Huntsville to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $144 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 Huntsville 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 Huntsville 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.

 

Huntsville to Chicago Flights

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*Available to One Key members.