$179 Cheap Flights from Ithaca (ITH) to Chicago (MDW)

View $179 flight on Sat, Oct 25, 2025Opens in a new window

Popular airlines from Ithaca, NY (ITH-Tompkins Regional) to Chicago Midway Airport (MDW)

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Cheap Flights from Ithaca to Chicago (ITH-MDW)

Prices were available within the past 7 days and start at $179 for one-way flights and $259 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Nov 1 - Mon, Nov 10
ITH
Ithaca
MDW
Chicago
$259 Roundtrip, found 4 days ago
$259
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 1 from Ithaca to Chicago, returning Mon, Nov 10, priced at $259 found 4 days ago
Delta
Wed, Nov 5 - Mon, Nov 10
ITH
Ithaca
MDW
Chicago
$282 Roundtrip, found 4 days ago
$282
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov 5 from Ithaca to Chicago, returning Mon, Nov 10, priced at $282 found 4 days ago
Delta
Sat, Nov 1 - Sat, Nov 8
ITH
Ithaca
MDW
Chicago
$312 Roundtrip, found 4 days ago
$312
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 1 from Ithaca to Chicago, returning Sat, Nov 8, priced at $312 found 4 days ago
Delta
Sat, Nov 1 - Sun, Nov 9
ITH
Ithaca
MDW
Chicago
$332 Roundtrip, found 4 days ago
$332
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 1 from Ithaca to Chicago, returning Sun, Nov 9, priced at $332 found 4 days ago
Delta
Wed, Nov 5 - Sat, Nov 8
ITH
Ithaca
MDW
Chicago
$336 Roundtrip, found 4 days ago
$336
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov 5 from Ithaca to Chicago, returning Sat, Nov 8, priced at $336 found 4 days ago
Delta
Tue, Nov 4 - Mon, Nov 10
ITH
Ithaca
MDW
Chicago
$342 Roundtrip, found 4 days ago
$342
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Nov 4 from Ithaca to Chicago, returning Mon, Nov 10, priced at $342 found 4 days ago
Delta
Wed, Nov 5 - Sun, Nov 9
ITH
Ithaca
MDW
Chicago
$356 Roundtrip, found 4 days ago
$356
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Nov 5 from Ithaca to Chicago, returning Sun, Nov 9, priced at $356 found 4 days ago
Delta
Fri, Nov 7 - Mon, Nov 10
ITH
Ithaca
MDW
Chicago
$367 Roundtrip, found 4 days ago
$367
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Nov 7 from Ithaca to Chicago, returning Mon, Nov 10, priced at $367 found 4 days ago
Delta
Sat, Nov 1 - Thu, Nov 6
ITH
Ithaca
MDW
Chicago
$372 Roundtrip, found 4 days ago
$372
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 1 from Ithaca to Chicago, returning Thu, Nov 6, priced at $372 found 4 days ago
Delta
Sat, Nov 1 - Fri, Nov 7
ITH
Ithaca
MDW
Chicago
$382 Roundtrip, found 4 days ago
$382
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 1 from Ithaca to Chicago, returning Fri, Nov 7, priced at $382 found 4 days ago

Frequently asked questions

How much does a flight from Tompkins Regional Airport (ITH) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $179 or cheap return flight from $259 from Tompkins Regional Airport (ITH) 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 Tompkins Regional Airport (ITH) to Midway Intl. Airport (MDW)?
The cheapest month to fly from ITH to MDW is November, when demand is low. Off-peak season is typically when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Tompkins Regional Airport (ITH) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest ITH to MDW flight.
How many flights per day from Tompkins Regional Airport (ITH) to Midway Intl. Airport (MDW)?
You'll need to catch a flight with a layover when traveling from Tompkins Regional Airport (ITH) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from ITH to MDW?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change depending on various 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 Tompkins Regional Airport (ITH) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) on time, select a flight that leaves Tompkins Regional Airport (ITH) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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.
Is it cheaper to buy a plane ticket from Tompkins Regional Airport (ITH) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from ITH to MDW are typically more expensive. To secure the cheapest rates, start searching for flights as early as possible. That being said, if you're flexible with your travel dates, you may land a cheap fare right before you leave.
Is it cheaper to book an ITH to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking an ITH to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one easy place takes the hassle out of planning your trip. Just secure your flights and choose from our wide range of stays, then customize your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Tompkins Regional Airport (ITH) to Midway Intl. Airport (MDW)?
Typically, it's possible to cancel or reschedule your ITH 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 further details on our Customer Service portal.

Travel information

Travel information

Origin airport
Tompkins Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$259
Distance
579 mi

Book with confidence

Book with confidence

Ithaca to Chicago Flights

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

 

The best time to book a flight from Ithaca to Chicago

Sunday is one of the best days to book for cheap flights from Ithaca 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 Ithaca 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 Ithaca to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $179 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 Ithaca 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 Ithaca 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.

 

Ithaca to Chicago Flights

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*Available to One Key members.