$146 Cheap Flights from Rochester (ROC) to Chicago (MDW)

View $146 flight on Tue, Jan 27, 2026Opens in a new window

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

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Cheap Flights from Rochester to Chicago (ROC-MDW)

Prices were available within the past 7 days and start at $146 for one-way flights and $291 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Jan 27 - Tue, Feb 3
ROC
Rochester
MDW
Chicago
$291 Roundtrip, found 11 hours ago
$291
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Jan 27 from Rochester to Chicago, returning Tue, Feb 3, priced at $291 found 11 hours ago
Southwest Airlines
Tue, Jan 27 - Tue, Feb 3
ROC
Rochester
MDW
Chicago
$301 Roundtrip, found 11 hours ago
$301
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Jan 27 from Rochester to Chicago, returning Tue, Feb 3, priced at $301 found 11 hours ago
Delta
Tue, Feb 3 - Tue, Feb 10
ROC
Rochester
MDW
Chicago
$305 Roundtrip, just found
$305
Roundtrip
just found
Select Delta flight, departing Tue, Feb 3 from Rochester to Chicago, returning Tue, Feb 10, priced at $305 just found
Southwest Airlines
Tue, Jan 27 - Tue, Feb 3
ROC
Rochester
MDW
Chicago
$306 Roundtrip, found 11 hours ago
$306
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Jan 27 from Rochester to Chicago, returning Tue, Feb 3, priced at $306 found 11 hours ago
Southwest Airlines
Tue, Jan 20 - Mon, Jan 26
ROC
Rochester
MDW
Chicago
$315 Roundtrip, found 6 days ago
$315
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Jan 20 from Rochester to Chicago, returning Mon, Jan 26, priced at $315 found 6 days ago
Delta
Mon, Nov 24 - Wed, Dec 3
ROC
Rochester
MDW
Chicago
$317 Roundtrip, found 6 days ago
$317
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Nov 24 from Rochester to Chicago, returning Wed, Dec 3, priced at $317 found 6 days ago
Southwest Airlines
Tue, Dec 16 - Wed, Jan 7
ROC
Rochester
MDW
Chicago
$319 Roundtrip, found 11 hours ago
$319
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Rochester to Chicago, returning Wed, Jan 7, priced at $319 found 11 hours ago
Delta
Wed, Dec 17 - Wed, Dec 24
ROC
Rochester
MDW
Chicago
$322 Roundtrip, found 1 day ago
$322
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 17 from Rochester to Chicago, returning Wed, Dec 24, priced at $322 found 1 day ago
Delta
Tue, Jan 27 - Tue, Feb 3
ROC
Rochester
MDW
Chicago
$327 Roundtrip, found 11 hours ago
$327
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jan 27 from Rochester to Chicago, returning Tue, Feb 3, priced at $327 found 11 hours ago
Southwest Airlines
Tue, Dec 16 - Wed, Jan 7
ROC
Rochester
MDW
Chicago
$329 Roundtrip, found 11 hours ago
$329
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Rochester to Chicago, returning Wed, Jan 7, priced at $329 found 11 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 $359
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $359

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 $146 or cheap return flight from $291 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 January 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.

Travel information

0
Origin airport
Greater Rochester Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$291
Distance
521 mi

Book with confidence

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 January. 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 $146 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.

 

Rochester to Chicago Flights

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*Available to One Key members.