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Midway

$107+ Cheap flights from Rochester (ROC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — MDW
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Rochester to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Rochester (ROC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 18, 2025.

Round-trip from

$279
(Delta)

One-way from

$107
(Kiwi.com)

Popular in

October

Cheapest in

January

Average price

$332

Good round-trip deal

$266 or less

Good one-way deal

$183 or less
From Rochester Greater Rochester Intl to Chicago Midway
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One-way flight from Rochester Greater Rochester Intl to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Rochester Greater Rochester Intl to Chicago Midway.
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Price to beat on a one-way flight from Rochester Greater Rochester Intl to Chicago Midway.
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Find flight deals from Rochester to Midway

Cheapest flights from Rochester to Midway
Explore the most affordable flight options available from Rochester to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:13 pmROC - MDW
1 stop20h 19mMultiple Airlines
Mon 11/179:32 amMDW - ROC
1 stop25h 45mMultiple Airlines
Deal found 8/18$222
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/412:30 pmROC - MDW
1 stop6h 55mDelta
Tue 11/111:00 pmMDW - ROC
1 stop8h 52mDelta
Deal found 8/17$279
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/99:00 amROC - MDW
Nonstop1h 50mSouthwest
Thu 9/116:55 pmMDW - ROC
Nonstop1h 40mSouthwest
Deal found 8/17$283
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:14 pmROC - MDW
1 stop5h 00mDelta
Tue 11/119:30 amMDW - ROC
1 stop12h 22mDelta
Deal found 8/17$288
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:55 amROC - MDW
Nonstop1h 50mSouthwest
Mon 10/276:55 pmMDW - ROC
Nonstop1h 35mSouthwest
Deal found 8/17$289
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/412:30 pmROC - MDW
1 stop6h 55mDelta
Sat 11/86:23 pmMDW - ROC
1 stop14h 23mDelta
Deal found 8/17$292
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/179:00 amROC - MDW
Nonstop1h 50mSouthwest
Sat 9/209:35 amMDW - ROC
1 stop4h 25mSouthwest
Deal found 8/18$293
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:00 amROC - MDW
1 stop4h 40mDelta
Wed 9/246:00 amMDW - ROC
1 stop4h 48mDelta
Deal found 8/18$297
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:25 pmROC - MDW
Nonstop1h 55mSouthwest
Mon 11/179:20 amMDW - ROC
1 stop4h 55mSouthwest
Deal found 8/18$299
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:14 pmROC - MDW
1 stop5h 00mDelta
Sat 11/86:23 pmMDW - ROC
1 stop14h 23mDelta
Deal found 8/17$301
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/106:00 amROC - MDW
1 stop4h 34mDelta
Sat 9/136:00 amMDW - ROC
1 stop6h 03mDelta
Deal found 8/18$303

Cheapflights Fare Finder

 
Customize your flight search to find flights from Rochester to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
Use the filters below to find and compare flights from Rochester to Chicago Midway Airport that are best for you.

Fly from

Rochester

Fly to

Midway

Route

Depart

Return

Price

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Thu 11/13

1:13 pm-8:32 am

1 stop20h 19m

Chicago Midway

Mon 11/17

9:32 am-12:17 pm

1 stop25h 45m

$222

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Tue 11/4

12:30 pm-6:25 pm

1 stop6h 55m

Chicago Midway

Tue 11/11

1:00 pm-10:52 pm

1 stop8h 52m

$279

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Tue 9/9

9:00 am-9:50 am

Nonstop1h 50m

Chicago Midway

Thu 9/11

6:55 pm-9:35 pm

Nonstop1h 40m

$283

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Tue 10/7

6:45 pm-7:35 pm

Nonstop1h 50m

Chicago Midway

Sat 10/11

5:30 pm-8:05 pm

Nonstop1h 35m

$283

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Wed 9/17

9:00 am-9:50 am

Nonstop1h 50m

Chicago Midway

Sat 9/20

4:45 pm-7:20 pm

Nonstop1h 35m

$283

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Sat 10/18

5:30 pm-6:25 pm

Nonstop1h 55m

Chicago Midway

Wed 10/22

6:10 pm-8:45 pm

Nonstop1h 35m

$283

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Wed 11/5

6:14 pm-10:14 pm

1 stop5h 00m

Chicago Midway

Tue 11/11

9:30 am-10:52 pm

1 stop12h 22m

$288

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Wed 12/31

12:06 pm-4:23 pm

1 stop5h 17m

Chicago Midway

Tue 1/6

1:00 pm-10:57 pm

1 stop8h 57m

$288

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Thu 10/23

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Mon 10/27

6:55 pm-9:30 pm

Nonstop1h 35m

$289

RochesterChicago

ROC - MDW

ROCMDW

Rochester Greater Rochester Intl

Thu 9/11

7:50 am-8:45 am

Nonstop1h 55m

Chicago Midway

Mon 9/15

6:55 pm-9:35 pm

Nonstop1h 40m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 17 results
1
2

Best time to book a flight from Rochester to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Rochester with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Rochester to Chicago Midway Airport

What is the cheapest month to book a flight from Rochester to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Rochester to Chicago Midway Airport (average of $160). Flying from Rochester to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ROC to MDW?

Find hourly flight availability from Rochester to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

When flying from Rochester to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 27% versus a flight at noon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated August 18, 2025.
Read reviews from past customers who have flown Southwest from Rochester to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Rochester to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Rochester to Chicago Midway?

    Located just 3.8 mi from the city center, Rochester Greater Rochester Intl is the airport most travelers will use when flying to Chicago Midway from Rochester. Booking flights from Greater Rochester Intl (ROC) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 1 airline.

  • How long is the flight from Rochester to Chicago Midway Airport?

    A quick flight from Rochester to Chicago Midway Airport can take about 1h 50m. Delta provides one of the quickest options available for as low as $283. The distance from Rochester to Chicago Midway Airport is about 521 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Rochester to Chicago Midway Airport round-trip?

    According to our current data, Southwest ($287), offers the cheapest pricing from Rochester to Chicago Midway Airport. This flight start at 25% lower than the current average price 3 months from now.

  • What are the cheapest flights from Rochester to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $108. While the most popular route (Rochester Greater Rochester Intl - Chicago Midway) can be booked for $283 on average our data indicates $277 when flying from Rochester to Chicago Midway Airport.

  • Can I find deals for flights from Rochester to Midway that include hotel bookings?

    Yes. In addition to deals on Rochester to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Rochester to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Rochester to Midway.

  • Can I find deals for business class flights from Rochester to Midway?

    Yes. Cheapflights offers flight deals from Rochester to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Rochester to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Rochester to Chicago Midway Airport (average of $160). Flying from Rochester to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Rochester to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Rochester to Midway

Discover the top airline that operate flights from Rochester to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$287Average$378FlexibilityNo cancel feeOn-time63%

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