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Midway

$86+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — MDW
Mar 28 — Apr 41
Sat 3/28
Sat 4/4
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 February 26, 2026.

This Southwest deal was found by Cheapflights users on 2/22. 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.
Wed 5/64:05 pm
ROC
-
MDW
1 stop4h 25m
Southwest
Mon 5/113:50 pm
MDW
-
ROC
2 stops6h 20m
Southwest
Deal found 2/22$321
This Southwest deal was found by Cheapflights users on 2/24. 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 3/246:50 pm
ROC
-
MDW
Nonstop1h 55m
Southwest
Wed 3/253:35 pm
MDW
-
ROC
1 stop6h 05m
Southwest
Deal found 2/24$322
This Southwest deal was found by Cheapflights users on 2/24. 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.
Wed 5/66:40 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Fri 5/86:45 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 2/24$323
This Southwest deal was found by Cheapflights users on 2/23. 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.
Mon 4/204:00 pm
ROC
-
MDW
1 stop5h 20m
Southwest
Wed 4/2212:45 pm
MDW
-
ROC
2 stops8h 20m
Southwest
Deal found 2/23$326
This Southwest deal was found by Cheapflights users on 2/22. 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.
Wed 5/136:35 am
ROC
-
MDW
2 stops8h 30m
Southwest
Sat 5/165:25 pm
MDW
-
ROC
1 stop4h 45m
Southwest
Deal found 2/22$328
This Southwest deal was found by Cheapflights users on 2/25. 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 3/218:10 am
ROC
-
MDW
Nonstop2h 00m
Southwest
Tue 3/246:10 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 2/25$331
This Southwest deal was found by Cheapflights users on 2/25. 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 4/156:40 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Fri 4/1711:45 am
MDW
-
ROC
1 stop3h 50m
Southwest
Deal found 2/25$333
This Southwest deal was found by Cheapflights users on 2/23. 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.
Tue 3/246:50 pm
ROC
-
MDW
Nonstop1h 55m
Southwest
Thu 3/267:40 pm
MDW
-
ROC
Nonstop1h 35m
Southwest
Deal found 2/23$334
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/236:16 pm
ROC
-
MDW
1 stop5h 15m
Delta
Mon 3/306:07 pm
MDW
-
ROC
1 stop4h 52m
Delta
Deal found 2/22$335
This Delta deal was found by Cheapflights users on 2/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:16 pm
ROC
-
MDW
1 stop5h 15m
Delta
Fri 4/109:35 am
MDW
-
ROC
1 stop5h 07m
Delta
Deal found 2/23$336
This Southwest deal was found by Cheapflights users on 2/23. 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.
Wed 4/226:40 pm
ROC
-
MDW
Nonstop1h 50m
Southwest
Sat 4/253:35 pm
MDW
-
ROC
Nonstop1h 30m
Southwest
Deal found 2/23$337

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 February 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$321
(Southwest)

One-way from

$86
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$435

Good round-trip deal

$391 or less

Good one-way deal

$189 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. 13% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 26, 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

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 5/6

4:05 pm-7:30 pm

1 stop4h 25m

Chicago Midway

Mon 5/11

3:50 pm-11:10 pm

2 stops6h 20m

$321

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 5/13

6:35 am-2:05 pm

2 stops8h 30m

Chicago Midway

Sat 5/16

5:25 pm-11:10 pm

1 stop4h 45m

$328

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 4/1

10:09 am-12:29 pm

1 stop3h 20m

Chicago Midway

Sun 4/5

9:35 am-3:42 pm

1 stop5h 07m

$354

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 4/23

7:50 pm-8:40 pm

Nonstop1h 50m

Chicago Midway

Mon 4/27

11:45 am-4:35 pm

1 stop3h 50m

$365

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 5/22

7:50 pm-8:40 pm

Nonstop1h 50m

Chicago Midway

Mon 5/25

6:45 pm-9:20 pm

Nonstop1h 35m

$391

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 3/14

6:16 pm-10:31 pm

1 stop5h 15m

Chicago Midway

Tue 3/24

6:34 pm-10:59 pm

1 stop3h 25m

$393

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 4/17

7:50 pm-8:40 pm

Nonstop1h 50m

Chicago Midway

Sun 4/19

6:45 pm-9:20 pm

Nonstop1h 35m

$398

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 4/15

12:35 pm-4:15 pm

1 stop4h 40m

Chicago Midway

Fri 4/17

3:50 pm-11:10 pm

2 stops6h 20m

$398

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 8/21

11:35 am-4:15 pm

1 stop5h 40m

Chicago Midway

Tue 8/25

5:55 pm-8:35 pm

Nonstop1h 40m

$401

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 8/1

6:00 am-1:10 pm

2 stops8h 10m

Chicago Midway

Sat 8/8

9:05 am-11:45 am

Nonstop1h 40m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/25

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 February.
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 February 26, 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 17% 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 February 26, 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
8.0
Very good
4,301 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
8.0
Very good
4,301 reviews
Southwest
8.0
Very good
4,301 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 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 3h 20m. Southwest provides one of the quickest options available for as low as $354. 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 ($303), 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 $129. While the most popular route (Greater Rochester Intl - Chicago Midway) can be booked for $272 on average, our data indicates $357 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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 February 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$303Average$391FlexibilityNo cancel feeOn-time63%

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