$119 Cheap Flights from Rochester (ROC) to Chicago (MDW)

View $119 flight on Sun, Sep 14, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

Cheap Flights from Rochester to Chicago (ROC-MDW)

Prices were available within the past 7 days and start at $119 for one-way flights and $273 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Aug 30 - Wed, Sep 3
ROC
Rochester
MDW
Chicago
$273 Roundtrip, found 4 days ago
$273
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 30 from Rochester to Chicago, returning Wed, Sep 3, priced at $273 found 4 days ago
Southwest Airlines
Tue, Jul 1 - Sat, Jul 5
ROC
Rochester
MDW
Chicago
$279 Roundtrip, found 4 hours ago
$279
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Jul 1 from Rochester to Chicago, returning Sat, Jul 5, priced at $279 found 4 hours ago
Southwest Airlines
Thu, Jun 5 - Tue, Jun 10
ROC
Rochester
MDW
Chicago
$286 Roundtrip, found 9 hours ago
$286
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Thu, Jun 5 from Rochester to Chicago, returning Tue, Jun 10, priced at $286 found 9 hours ago
Southwest Airlines
Tue, May 13 - Wed, May 14
ROC
Rochester
MDW
Chicago
$289 Roundtrip, found 5 days ago
$289
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, May 13 from Rochester to Chicago, returning Wed, May 14, priced at $289 found 5 days ago
Delta
Wed, Jun 11 - Tue, Jul 1
ROC
Rochester
MDW
Chicago
$289 Roundtrip, found 2 days ago
$289
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 11 from Rochester to Chicago, returning Tue, Jul 1, priced at $289 found 2 days ago
Southwest Airlines
Tue, Jul 1 - Thu, Jul 3
ROC
Rochester
MDW
Chicago
$294 Roundtrip, found 3 hours ago
$294
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Jul 1 from Rochester to Chicago, returning Thu, Jul 3, priced at $294 found 3 hours ago
Southwest Airlines
Thu, Jul 3 - Tue, Jul 8
ROC
Rochester
MDW
Chicago
$296 Roundtrip, just found
$296
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Jul 3 from Rochester to Chicago, returning Tue, Jul 8, priced at $296 just found
Southwest Airlines
Thu, Jun 5 - Tue, Jun 10
ROC
Rochester
MDW
Chicago
$301 Roundtrip, found 9 hours ago
$301
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Thu, Jun 5 from Rochester to Chicago, returning Tue, Jun 10, priced at $301 found 9 hours ago
Southwest Airlines
Mon, Jun 9 - Wed, Jun 11
ROC
Rochester
MDW
Chicago
$303 Roundtrip, found 1 day ago
$303
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Jun 9 from Rochester to Chicago, returning Wed, Jun 11, priced at $303 found 1 day ago
Southwest Airlines
Tue, May 13 - Wed, May 14
ROC
Rochester
MDW
Chicago
$306 Roundtrip, found 5 days ago
$306
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, May 13 from Rochester to Chicago, returning Wed, May 14, priced at $306 found 5 days ago

Frequently asked questions

How much does a flight from Greater Rochester Intl. Airport (ROC) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from ROC to MDW 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 ROC to MDW?
The cheapest flights from ROC to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ROC to MDW?
Right now, the cheapest airline offering one-way flights from ROC to MDW is Southwest Airlines. You can book a seat on this route from $152. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ROC on June 5 2025. Prices were last updated on April 23 2025 and have not changed since.
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.
*Available to One Key members.