$224 Cheap Flights from Huntsville (HSV) to Chicago (MDW)

View $224 flight on Wed, Sep 3, 2025Opens in a new window

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

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Cheap Flights from Huntsville to Chicago (HSV-MDW)

Prices were available within the past 7 days and start at $224 for one-way flights and $229 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Nov 5 - Mon, Nov 24
HSV
Huntsville
MDW
Chicago
$229 Roundtrip, found 6 hours ago
$229
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Nov 5 from Huntsville to Chicago, returning Mon, Nov 24, priced at $229 found 6 hours ago
Delta
Tue, Aug 12 - Tue, Aug 19
HSV
Huntsville
MDW
Chicago
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 12 from Huntsville to Chicago, returning Tue, Aug 19, priced at $239 found 1 day ago
Delta
Wed, Aug 13 - Sat, Aug 16
HSV
Huntsville
MDW
Chicago
$249 Roundtrip, found 7 hours ago
$249
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Aug 13 from Huntsville to Chicago, returning Sat, Aug 16, priced at $249 found 7 hours ago
Delta
Fri, Oct 17 - Tue, Oct 21
HSV
Huntsville
MDW
Chicago
$264 Roundtrip, found 13 hours ago
$264
Roundtrip
found 13 hours ago
Select Delta flight, departing Fri, Oct 17 from Huntsville to Chicago, returning Tue, Oct 21, priced at $264 found 13 hours ago
Delta
Tue, Oct 7 - Tue, Oct 21
HSV
Huntsville
MDW
Chicago
$267 Roundtrip, found 6 days ago
$267
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Oct 7 from Huntsville to Chicago, returning Tue, Oct 21, priced at $267 found 6 days ago
Delta
Wed, Nov 5 - Sat, Nov 22
HSV
Huntsville
MDW
Chicago
$274 Roundtrip, found 6 hours ago
$274
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Nov 5 from Huntsville to Chicago, returning Sat, Nov 22, priced at $274 found 6 hours ago
Delta
Sat, Aug 2 - Wed, Aug 6
HSV
Huntsville
MDW
Chicago
$279 Roundtrip, found 15 hours ago
$279
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Aug 2 from Huntsville to Chicago, returning Wed, Aug 6, priced at $279 found 15 hours ago
Delta
Fri, Aug 1 - Sat, Aug 16
HSV
Huntsville
MDW
Chicago
$285 Roundtrip, found 3 days ago
$285
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Aug 1 from Huntsville to Chicago, returning Sat, Aug 16, priced at $285 found 3 days ago
Delta
Tue, Sep 23 - Mon, Oct 6
HSV
Huntsville
MDW
Chicago
$287 Roundtrip, found 4 days ago
$287
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 23 from Huntsville to Chicago, returning Mon, Oct 6, priced at $287 found 4 days ago
Delta
Fri, Aug 22 - Sun, Aug 24
HSV
Huntsville
MDW
Chicago
$289 Roundtrip, found 18 hours ago
$289
Roundtrip
found 18 hours ago
Select Delta flight, departing Fri, Aug 22 from Huntsville to Chicago, returning Sun, Aug 24, priced at $289 found 18 hours ago

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

April is typically the cheapest month to fly

From $186 - $678 per traveler.

Graph displaying average flight prices per month

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. Average driving time to city center is 23 minutes. Flights from $229
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $229
Flights from Huntsville (HSV) to Chicago (MDW)
Origin airport
Huntsville Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$228
Distance
496 mi

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 November. 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 $224 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.

 

Frequently asked questions

How much does a flight from Huntsville Intl. Airport (HSV) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from HSV to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from HSV to MDW?
The cheapest flights from HSV to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from HSV to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from HSV to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
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.

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Chicago nearby Airports

Chicago

Huntsville to O'Hare Intl.
$208.96
*Available to One Key members.