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$116+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
ROC — MDW
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$318
(Kiwi.com)

One-way from

$116
(Kiwi.com)

Popular in

September

Cheapest in

November

Average price

$283

Good round-trip deal

$367 or less

Good one-way deal

$156 or less
Provider with most accurate pricing for Greater Rochester Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Greater Rochester Intl-Chicago Midway flights.
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From Greater Rochester Intl to Chicago Midway
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One-way flight from Greater Rochester Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Greater Rochester Intl to Chicago Midway.
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Price to beat on a one-way flight from 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 November 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:00 pmROC - MDW
1 stop28h 04mMultiple Airlines
Wed 12/246:12 amMDW - ROC
2 stops9h 43mMultiple Airlines
Deal found 11/24$318
This Delta deal was found by Cheapflights users on 11/24. 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.
Mon 12/156:00 amROC - MDW
1 stop6h 55mDelta
Wed 1/146:45 amMDW - ROC
1 stop5h 28mDelta
Deal found 11/24$351
This Southwest deal was found by Cheapflights users on 11/24. 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.
Sun 12/143:25 pmROC - MDW
Nonstop1h 55mSouthwest
Wed 12/173:15 pmMDW - ROC
Nonstop1h 35mSouthwest
Deal found 11/24$366
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:15 amROC - MDW
1 stop3h 34mDelta
Sat 12/276:08 pmMDW - ROC
1 stop3h 58mDelta
Deal found 11/25$375
This Delta deal was found by Cheapflights users on 11/24. 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.
Tue 12/166:00 amROC - MDW
1 stop6h 55mDelta
Tue 12/165:39 pmMDW - ROC
1 stop5h 15mDelta
Deal found 11/24$379
This Southwest deal was found by Cheapflights users on 11/25. 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.
Thu 12/256:25 pmROC - MDW
Nonstop1h 55mSouthwest
Thu 1/12:30 pmMDW - ROC
2 stops7h 00mSouthwest
Deal found 11/25$382
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:15 amROC - MDW
1 stop3h 34mDelta
Wed 12/246:08 pmMDW - ROC
1 stop3h 58mDelta
Deal found 11/25$386
This Southwest deal was found by Cheapflights users on 11/24. 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.
Thu 12/183:25 pmROC - MDW
Nonstop1h 55mSouthwest
Sat 12/205:40 amMDW - ROC
1 stop8h 50mSouthwest
Deal found 11/24$388

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 November 26, 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

Greater Rochester Intl

Sat 12/20

6:00 pm-9:04 pm

1 stop28h 04m

Chicago Midway

Wed 12/24

6:12 am-4:55 pm

2 stops9h 43m

$318

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 1/1

6:25 pm-7:20 pm

Nonstop1h 55m

Chicago Midway

Mon 1/5

7:30 pm-10:05 pm

Nonstop1h 35m

$343

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 12/15

6:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Wed 1/14

6:45 am-1:13 pm

1 stop5h 28m

$351

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 2/25

3:40 pm-7:00 pm

1 stop4h 20m

Chicago Midway

Fri 2/27

11:10 am-1:45 pm

Nonstop1h 35m

$365

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sun 12/14

3:25 pm-4:20 pm

Nonstop1h 55m

Chicago Midway

Wed 12/17

3:15 pm-5:50 pm

Nonstop1h 35m

$366

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Sat 12/20

3:10 pm-9:00 pm

1 stop6h 50m

Chicago Midway

Wed 12/24

3:10 pm-5:45 pm

Nonstop1h 35m

$376

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Fri 1/23

6:10 am-7:25 am

Nonstop2h 15m

Chicago Midway

Mon 1/26

6:50 am-3:00 pm

1 stop7h 10m

$377

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Thu 1/1

6:00 pm-1:21 pm

2 stops20h 21m

Chicago Midway

Mon 1/5

3:10 pm-4:55 pm

1 stop24h 45m

$380

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Mon 1/26

6:50 pm-12:05 pm

2 stops18h 15m

$123

RochesterChicago

ROC - MDW

ROCMDW

Greater Rochester Intl

Wed 1/21

4:32 pm-10:19 pm

2 stops30h 47m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 16 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Rochester-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 month to book a flight from Rochester to Chicago Midway Airport?

Currently, October is the cheapest month in which you can book a flight from Rochester to Chicago Midway Airport (average of $157). Flying from Rochester to Chicago Midway Airport in December is currently the most expensive (average of $336). 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 November 26, 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 23% 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 November 26, 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
4,254 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 1h 55m. Southwest provides one of the quickest options available for as low as $343. 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. This flight start at 20% 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 $111. While the most popular route (Greater Rochester Intl - Chicago Midway) can be booked for $331 on average, our data indicates $334 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, October is the cheapest month in which you can book a flight from Rochester to Chicago Midway Airport (average of $157). Flying from Rochester to Chicago Midway Airport in December is currently the most expensive (average of $336). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$303Average$393FlexibilityNo cancel feeOn-time63%

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