$220 Cheap Flights from Ithaca (ITH) to Chicago (ORD)

View $220 flight on Mon, Aug 25, 2025Opens in a new window

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Cheap Flights from Ithaca to Chicago (ITH-ORD)

Prices were available within the past 7 days and start at $220 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, May 28 - Sat, May 31
ITH
Ithaca
ORD
Chicago
$249 Roundtrip, just found
$249
Roundtrip
just found
Select Delta flight, departing Wed, May 28 from Ithaca to Chicago, returning Sat, May 31, priced at $249 just found
United
Mon, May 5 - Mon, May 12
ITH
Ithaca
ORD
Chicago
$254 Roundtrip, found 3 days ago
$254
Roundtrip
found 3 days ago
Select United flight, departing Mon, May 5 from Ithaca to Chicago, returning Mon, May 12, priced at $254 found 3 days ago
Delta
Wed, May 28 - Sat, Jun 7
ITH
Ithaca
ORD
Chicago
$254 Roundtrip, just found
$254
Roundtrip
just found
Select Delta flight, departing Wed, May 28 from Ithaca to Chicago, returning Sat, Jun 7, priced at $254 just found
Delta
Wed, May 7 - Tue, May 13
ITH
Ithaca
ORD
Chicago
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 7 from Ithaca to Chicago, returning Tue, May 13, priced at $259 found 1 day ago
Delta
Sat, May 10 - Wed, May 14
ITH
Ithaca
ORD
Chicago
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 10 from Ithaca to Chicago, returning Wed, May 14, priced at $259 found 1 day ago
Delta
Sat, May 10 - Tue, May 13
ITH
Ithaca
ORD
Chicago
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 10 from Ithaca to Chicago, returning Tue, May 13, priced at $264 found 1 day ago
United
Tue, Jul 1 - Tue, Jul 8
ITH
Ithaca
ORD
Chicago
$279 Roundtrip, found 3 days ago
$279
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jul 1 from Ithaca to Chicago, returning Tue, Jul 8, priced at $279 found 3 days ago
United
Tue, Jul 1 - Tue, Jul 8
ITH
Ithaca
ORD
Chicago
$280 Roundtrip, found 3 days ago
$280
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jul 1 from Ithaca to Chicago, returning Tue, Jul 8, priced at $280 found 3 days ago
Delta
Tue, May 6 - Tue, May 13
ITH
Ithaca
ORD
Chicago
$284 Roundtrip, found 1 day ago
$284
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, May 6 from Ithaca to Chicago, returning Tue, May 13, priced at $284 found 1 day ago
Delta
Sun, Jun 15 - Fri, Jul 4
ITH
Ithaca
ORD
Chicago
$284 Roundtrip, found 22 hours ago
$284
Roundtrip
found 22 hours ago
Select Delta flight, departing Sun, Jun 15 from Ithaca to Chicago, returning Fri, Jul 4, priced at $284 found 22 hours ago
Flights from Ithaca (ITH) to Chicago (ORD)
Origin airport
Tompkins Regional
Destination airport
O'Hare Intl.
Airlines serving
Delta, United
Roundtrip price
$248
Distance
586 mi

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 May. 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 $220 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.

Frequently asked questions

How much does a flight from Tompkins Regional Airport (ITH) to O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from ITH to ORD 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 ITH to ORD?
The cheapest flights from ITH to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Tompkins Regional Airport (ITH) to O'Hare Intl. Airport (ORD)?
You can’t fly direct to O’Hare Intl. Airport (ORD) from Ithaca, NY (ITH-Tompkins Regional). However, you can seamlessly travel to Chicago without any layovers by departing from Hancock Intl. Airport (SYR).
What is the cheapest airline that flies from ITH to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ITH to ORD. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Tompkins Regional Airport (ITH) to O'Hare Intl. Airport (ORD)?
You’ll need to take a flight with a layover if you’re traveling from Tompkins Regional Airport (ITH) to O’Hare Intl. Airport (ORD). Direct flights don’t operate daily on this route. However, just filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from ITH to ORD?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change based on various factors, such as the time of year and carrier.*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 O'Hare Intl. Airport (ORD)?
Select a flight from Tompkins Regional Airport (ITH) to O’Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures later than this have a 22% higher chance of being canceled, on average.**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 O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your departure to book a ticket from ITH to ORD often results in higher prices. While you may find some last-minute offers, there’s no guarantee. Be flexible with your travel plans for a better chance of landing a bargain.
Is it cheaper to book an ITH to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking an ITH to ORD flight and hotel package with Expedia could result in significant savings. Better still, managing everything in one place will take the hassle out of planning your trip. Simply secure your flights and choose from our extensive 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 Tompkins Regional Airport (ITH) to O'Hare Intl. Airport (ORD)?
It’s usually possible to cancel or reschedule your ITH to ORD flight. However, if it’s been more than 24 hours since booking, additional fees 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.