$142 Cheap Flights from Harrisburg (MDT) to Chicago (MDW)

View $142 flight on Sun, Mar 1, 2026Opens in a new window

Popular airlines from Harrisburg Intl. Airport (MDT) to Chicago Midway Airport (MDW)

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Cheap Flights from Harrisburg to Chicago (MDT-MDW)

Prices were available within the past 7 days and start at $142 for one-way flights and $168 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, Oct 24 - Fri, Oct 31
MDT
Harrisburg
MDW
Chicago
$168 Roundtrip, found 6 hours ago
$168
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Oct 24 from Harrisburg to Chicago, returning Fri, Oct 31, priced at $168 found 6 hours ago
Frontier Airlines
Fri, Oct 17 - Fri, Oct 31
MDT
Harrisburg
MDW
Chicago
$205 Roundtrip, found 20 hours ago
$205
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Fri, Oct 17 from Harrisburg to Chicago, returning Fri, Oct 31, priced at $205 found 20 hours ago
Frontier Airlines
Fri, Oct 17 - Sun, Oct 19
MDT
Harrisburg
MDW
Chicago
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 17 from Harrisburg to Chicago, returning Sun, Oct 19, priced at $220 found 1 day ago
Delta
Wed, Nov 5 - Sat, Nov 8
MDT
Harrisburg
MDW
Chicago
$229 Roundtrip, found 1 hour ago
$229
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Nov 5 from Harrisburg to Chicago, returning Sat, Nov 8, priced at $229 found 1 hour ago
Frontier Airlines
Fri, Oct 17 - Sun, Oct 26
MDT
Harrisburg
MDW
Chicago
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 17 from Harrisburg to Chicago, returning Sun, Oct 26, priced at $234 found 1 day ago
Delta
Tue, Nov 11 - Mon, Nov 17
MDT
Harrisburg
MDW
Chicago
$239 Roundtrip, found 3 hours ago
$239
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Nov 11 from Harrisburg to Chicago, returning Mon, Nov 17, priced at $239 found 3 hours ago
Delta
Fri, Jan 9 - Sun, Jan 11
MDT
Harrisburg
MDW
Chicago
$249 Roundtrip, found 12 hours ago
$249
Roundtrip
found 12 hours ago
Select Delta flight, departing Fri, Jan 9 from Harrisburg to Chicago, returning Sun, Jan 11, priced at $249 found 12 hours ago
Delta
Wed, Oct 22 - Mon, Oct 27
MDT
Harrisburg
MDW
Chicago
$265 Roundtrip, found 9 hours ago
$265
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Oct 22 from Harrisburg to Chicago, returning Mon, Oct 27, priced at $265 found 9 hours ago
Delta
Fri, Oct 24 - Mon, Oct 27
MDT
Harrisburg
MDW
Chicago
$269 Roundtrip, found 4 hours ago
$269
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Oct 24 from Harrisburg to Chicago, returning Mon, Oct 27, priced at $269 found 4 hours ago
Frontier Airlines
Fri, Oct 17 - Sun, Oct 19
MDT
Harrisburg
MDW
Chicago
$271 Roundtrip, found 20 hours ago
$271
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Fri, Oct 17 from Harrisburg to Chicago, returning Sun, Oct 19, priced at $271 found 20 hours ago

Find the cheapest month to fly from Harrisburg (MDT) to Chicago (MDW)

June is typically the cheapest month to fly

From $215 - $658 per traveler.
Flights from Harrisburg (MDT) to Chicago (MDW)
Origin airport
Harrisburg Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$168
Distance
582 mi

Harrisburg to Chicago Flights

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

 

The best time to book a flight from Harrisburg to Chicago

Sunday is one of the best days to book for cheap flights from Harrisburg 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 Harrisburg 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 Harrisburg to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $142 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 Harrisburg 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 Harrisburg 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 Harrisburg Intl. Airport (MDT) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $142 or cheap return flight from $168 from Harrisburg Intl. Airport (MDT) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Harrisburg Intl. Airport (MDT) to Midway Intl. Airport (MDW)?
Planning your trip for October may help you find better deals, as it's the cheapest month for flights between MDT and MDW. You'll often find the lowest fares during the off-season.
What is the cheapest airline that flies from Harrisburg Intl. Airport (MDT) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest MDT to MDW flight.
How many flights per day from Harrisburg Intl. Airport (MDT) to Midway Intl. Airport (MDW)?
Nonstop flights from Harrisburg Intl. Airport (MDT) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDT to MDW?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change depending on a number of factors, such as 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 Harrisburg Intl. Airport (MDT) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) on schedule, book a flight that takes off from Harrisburg Intl. Airport (MDT) before 3 PM. The likelihood 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 Harrisburg Intl. Airport (MDT)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Harrisburg Intl. Airport (MDT). Explore the options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Harrisburg Intl. Airport (MDT) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from MDT to MDW right before your trip is generally more expensive. However, if you're flexible with your travel times and dates, you could snag a cheap last-minute fare.
Is it cheaper to book a MDT to MDW flight and hotel package?
Booking a MDT to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Select from our wide range of hotels and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Harrisburg Intl. Airport (MDT) to Midway Intl. Airport (MDW)?
Typically, it's possible to reschedule or cancel your MDT 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 information on our Customer Service portal.

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*Available to One Key members.