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Midway

$198+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — MDW
Jun 24 — Jul 11
Wed 6/24
Wed 7/1
1 adult, Economy
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Cheap 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 May 25, 2026.

This Southwest deal was found by Cheapflights users on 5/24. 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 7/217:05 pm
ROC
-
MDW
Nonstop1h 45m
Southwest
Tue 8/115:55 pm
MDW
-
ROC
Nonstop1h 40m
Southwest
Deal found 5/24$395
This Southwest deal was found by Cheapflights users on 5/20. 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.
Mon 7/207:35 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Wed 7/226:30 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 5/20$403
This Southwest deal was found by Cheapflights users on 5/24. 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 6/167:05 pm
ROC
-
MDW
Nonstop1h 45m
Southwest
Tue 6/2312:05 pm
MDW
-
ROC
1 stop5h 20m
Southwest
Deal found 5/24$405
This Southwest deal was found by Cheapflights users on 5/20. 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.
Fri 7/177:35 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Mon 7/206:50 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 5/20$411
This Southwest deal was found by Cheapflights users on 5/20. 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 8/116:20 pm
ROC
-
MDW
Nonstop1h 45m
Southwest
Fri 8/1411:25 am
MDW
-
ROC
1 stop5h 40m
Southwest
Deal found 5/20$413
This Southwest deal was found by Cheapflights users on 5/23. 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.
Sat 6/138:25 am
ROC
-
MDW
Nonstop1h 45m
Southwest
Tue 6/166:30 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 5/23$414
This Delta deal was found by Cheapflights users on 5/24. 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 6/176:10 am
ROC
-
MDW
1 stop4h 04m
Delta
Tue 6/239:17 am
MDW
-
ROC
1 stop5h 31m
Delta
Deal found 5/24$415
This Southwest deal was found by Cheapflights users on 5/22. 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.
Sat 8/157:50 am
ROC
-
MDW
Nonstop1h 40m
Southwest
Sun 8/166:25 pm
MDW
-
ROC
Nonstop1h 40m
Southwest
Deal found 5/22$419
This Southwest deal was found by Cheapflights users on 5/22. 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.
Mon 6/227:35 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Thu 6/2511:00 am
MDW
-
ROC
1 stop7h 00m
Southwest
Deal found 5/22$421

Find 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 May 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$395
(Southwest)

One-way from

$198
(Southwest)

Popular in

February

Cheapest in

September

Average price

$452

Good round-trip deal

$413 or less

Good one-way deal

$220 or less
Provider with most accurate pricing for Greater Rochester Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greater Rochester Intl-Chicago Midway flights.
Search Deals
From Greater Rochester Intl to Chicago Midway
Search Deals
One-way flight from Greater Rochester Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Greater Rochester Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Greater Rochester Intl to Chicago Midway.
Search Deals

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 May 25, 2026.
Use the filters below to find and compare flights from Rochester to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sun 7/19

7:45 pm-8:35 pm

Nonstop1h 50m

Chicago Midway

Tue 7/21

6:30 pm-9:10 pm

Nonstop1h 40m

$403

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Tue 6/16

7:05 pm-7:50 pm

Nonstop1h 45m

Chicago Midway

Tue 6/23

12:05 pm-6:25 pm

1 stop5h 20m

$405
Quickest round-trip

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 6/22

7:35 pm-8:25 pm

Nonstop1h 50m

Chicago Midway

Mon 6/29

6:50 pm-9:25 pm

Nonstop1h 35m

$411

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 7/29

2:15 pm-10:00 pm

1 stop8h 45m

Chicago Midway

Sat 8/1

6:50 pm-9:25 pm

Nonstop1h 35m

$413

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 8/1

6:30 pm-7:15 pm

Nonstop1h 45m

Chicago Midway

Tue 8/4

12:45 pm-5:30 pm

1 stop3h 45m

$413

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 6/17

6:10 am-9:14 am

1 stop4h 04m

Chicago Midway

Tue 6/23

9:17 am-3:48 pm

1 stop5h 31m

$415

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sun 10/11

7:15 pm-8:05 pm

Nonstop1h 50m

Chicago Midway

Wed 10/14

2:50 pm-10:20 pm

2 stops6h 30m

$418

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 8/27

6:45 pm-7:35 pm

Nonstop1h 50m

Chicago Midway

Mon 8/31

11:25 am-6:05 pm

1 stop5h 40m

$421

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 7/17

12:55 pm-5:10 pm

1 stop5h 15m

Chicago Midway

Mon 7/20

6:50 pm-9:25 pm

Nonstop1h 35m

$421

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 8/12

6:00 am-9:59 am

1 stop4h 59m

Chicago Midway

Fri 8/14

10:54 am-5:20 pm

1 stop5h 26m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Rochester to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Rochester to Midway in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Rochester-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Rochester-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Rochester-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Rochester-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Rochester-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 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 May 25, 2026.

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 44% 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 May 25, 2026.
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
7.9
Good
4,270 reviews

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,270 reviews
Southwest
7.9
Good
4,270 reviews

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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, 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 is 1 daily outbound flight 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. Southwest provides one of the quickest options available for as low as $403. The distance from Rochester to Chicago Midway Airport is about 521 mi. All flights are typically nonstop.

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

    According to our current data, Southwest ($305), offers the cheapest pricing from Rochester to Chicago Midway Airport.

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

    Looking at all options, your cheapest flight can be booked for $173. While the most popular route (Greater Rochester Intl - Chicago Midway) can be booked for $395 on average, our data indicates $378 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.

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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 May 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$305Average$411FlexibilityNo cancel feeOn-time63%

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