$132 Cheap Flights from Rochester (ROC) to Chicago (MDW)

View $132 flight on Thu, Dec 25, 2025Opens in a new window

Popular airlines from Greater Rochester Intl. Airport (ROC) to Chicago Midway Airport (MDW)

Cheap Flights from Rochester to Chicago (ROC-MDW)

Prices were available within the past 7 days and start at $132 for one-way flights and $273 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Dec 13 - Mon, Dec 15
ROC
Rochester
MDW
Chicago
$273 Roundtrip, found 9 hours ago
$273
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Rochester to Chicago, returning Mon, Dec 15, priced at $273 found 9 hours ago
Southwest Airlines
Thu, Dec 11 - Sat, Dec 13
ROC
Rochester
MDW
Chicago
$283 Roundtrip, found 9 hours ago
$283
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Thu, Dec 11 from Rochester to Chicago, returning Sat, Dec 13, priced at $283 found 9 hours ago
Delta
Mon, Dec 15 - Wed, Dec 17
ROC
Rochester
MDW
Chicago
$283 Roundtrip, found 5 hours ago
$283
Roundtrip
found 5 hours ago
Select Delta flight, departing Mon, Dec 15 from Rochester to Chicago, returning Wed, Dec 17, priced at $283 found 5 hours ago
Delta
Thu, Dec 4 - Sat, Dec 6
ROC
Rochester
MDW
Chicago
$286 Roundtrip, found 6 hours ago
$286
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Dec 4 from Rochester to Chicago, returning Sat, Dec 6, priced at $286 found 6 hours ago
Southwest Airlines
Sat, Dec 6 - Tue, Dec 9
ROC
Rochester
MDW
Chicago
$288 Roundtrip, found 11 hours ago
$288
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Rochester to Chicago, returning Tue, Dec 9, priced at $288 found 11 hours ago
Southwest Airlines
Tue, Jan 27 - Tue, Feb 3
ROC
Rochester
MDW
Chicago
$291 Roundtrip, found 2 days ago
$291
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Jan 27 from Rochester to Chicago, returning Tue, Feb 3, priced at $291 found 2 days ago
Southwest Airlines
Tue, Jan 27 - Tue, Feb 3
ROC
Rochester
MDW
Chicago
$301 Roundtrip, found 2 days ago
$301
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Jan 27 from Rochester to Chicago, returning Tue, Feb 3, priced at $301 found 2 days ago
Delta
Tue, Jan 27 - Sat, Feb 14
ROC
Rochester
MDW
Chicago
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 27 from Rochester to Chicago, returning Sat, Feb 14, priced at $305 found 1 day ago
Southwest Airlines
Tue, Jan 27 - Tue, Feb 3
ROC
Rochester
MDW
Chicago
$306 Roundtrip, found 2 days ago
$306
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Jan 27 from Rochester to Chicago, returning Tue, Feb 3, priced at $306 found 2 days ago
Delta
Sun, Dec 21 - Mon, Jan 19
ROC
Rochester
MDW
Chicago
$308 Roundtrip, found 9 hours ago
$308
Roundtrip
found 9 hours ago
Select Delta flight, departing Sun, Dec 21 from Rochester to Chicago, returning Mon, Jan 19, priced at $308 found 9 hours ago

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 $201
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $201
0
Flights from Rochester (ROC) to Chicago (MDW)
Origin airport
Greater Rochester Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$273
Distance
521 mi

Rochester to Chicago Flights

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

 

The best time to book a flight from Rochester to Chicago

Sunday is one of the best days to book for cheap flights from Rochester 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 Rochester 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 Rochester to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $132 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 Rochester 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 Rochester 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 Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $132 or cheap return flight from $273 from Greater Rochester Intl. Airport (ROC) 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 Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW)?
Traveling in December may help you find better deals, as it's the cheapest month for flights between ROC and MDW. You'll often find the lowest prices during the off-season.
What is the cheapest airline that flies from Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll take you from ROC to MDW. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW)?
You'll need to take a flight with a layover when traveling from Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from ROC to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Later flights have a 22% higher chance of cancellation.**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 Greater Rochester Intl. Airport (ROC)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Greater Rochester Intl. Airport (ROC). Explore the options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW) last-minute?
Waiting until right before your break to book a ticket from ROC to MDW often results in higher prices. While you might find some last-minute discounts, there's no guarantee. Allow some flexibility in your schedule for a better chance of landing a bargain.
Is it cheaper to book a ROC to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a ROC to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one convenient place will take the hassle out of travel planning. Simply secure your flights and select from our wide range of hotels, then tailor your trip with extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW)?
If you booked your ROC to MDW flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

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*Available to One Key members.